Compounds, compositions, and methods for preventing metastasis of cancer cells
First Claim
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1. A method for treating a subject with cancer, comprisingadministering to the subject and effective amount of a compound having the formula:
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Abstract
Disclosed are methods for preventing metastasis of cancer cells. The disclosed compounds can be used to prevent the spread of tumor or other types of cancer cells.
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Citations
52 Claims
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1. A method for treating a subject with cancer, comprising
administering to the subject and effective amount of a compound having the formula: - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52)
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2. The method according to claim 1, further comprising administering one or more chemotherapeutic agents.
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3. The method according to claim 2, wherein the chemotherapeutic agent is chosen from vincristine, vinblastine, vindesine, vinorelbine-5′
- -noranhydroblastine, irinotecan, topotecan, cisplatin, cyclophosphamide, nitrogen mustard, trimethylene thiophosphoramide, carmustine, busulfan, chlorambucil, belustine, chlomaphazin, dacarbazine, cytosine arabinoside, fluorouracil, methotrexate, mercaptopurine, azathioprime, procarbazine, doxorubicin, bleomycin, dactinomycin, daunorubicin, mithramycin, mitomycin, mytomycin C, daunomycin, azacytidine, amsacrine, melphalan, ifosfamide, mitoxantrone, cis-platin, etoposide, taxol, acivicin;
aclarubicin;
acodazole hydrochloride;
acronine;
adozelesin;
aldesleukin;
altretamine;
ambomycin;
ametantrone acetate;
aminoglutethimide;
anastrozole;
anthramycin;
asperlin;
azacitidine;
azetepa;
azotomycin;
batimastat;
benzodepa;
bicalutamide;
bisantrene hydrochloride;
bisnafide dimesylate;
bizelesin;
brequinar sodium;
bropirimine;
cactinomycin;
calusterone;
caracemide;
carbetimer;
carboplatin;
carubicin hydrochloride;
carzelesin;
cedefingol;
cirolemycin;
cladribine;
crisnatol mesylate;
cytarabine;
decitabine;
dexormaplatin;
dezaguanine;
diaziquone;
docetaxel;
droloxifene;
duazomycin;
edatrexate;
eflornithine hydrochloride;
elsamitrucin;
enloplatin;
enpromate;
epipropidine;
epirubicin hydrochloride;
erbulozole;
esorubicin hydrochloride;
estramustine;
etanidazole;
etoprine;
fadrozole hydrochloride;
fazarabine;
fenretinide;
floxuridine;
fludarabine phosphate;
fluorocitabine;
fosquidone;
fostriecin sodium;
gemcitabine;
hydroxyurea;
idarubicin hydrochloride;
ilmofosine;
interleukin II interferon alfa-2a;
interferon alfa-2b;
interferon alfa-n1;
interferon alfa-n3;
interferon beta-I a;
interferon gamma-I b;
iproplatin;
lanreotide acetate;
letrozole;
leuprolide acetate;
liarozole hydrochloride;
lometrexol sodium;
lomustine;
losoxantrone hydrochloride;
masoprocol;
maytansine;
mechlorethamine hydrochloride;
megestrol acetate;
melengestrol acetate;
menogaril;
metoprine;
meturedepa;
mitindomide;
mitocarcin;
mitocromin;
mitogillin;
mitomalcin;
mitosper;
mitotane;
mycophenolic acid;
nocodazole;
nogalamycin;
ormaplatin;
oxisuran;
paclitaxel;
pegaspargase;
peliomycin;
pentamustine;
peplomycin sulfate;
perfosfamide;
pipobroman;
piposulfan;
piroxantrone hydrochloride;
plicamycin;
plomestane;
porfimer sodium;
porfiromycin;
prednimustine;
puromycin;
pyrazofurin;
riboprine;
rogletimide;
safingol;
semustine;
simtrazene;
sparfosate sodium;
sparsomycin;
spirogermanium hydrochloride;
spiromustine;
spiroplatin;
streptonigrin;
streptozocin;
sulofenur;
talisomycin;
tecogalan sodium;
tegafur;
teloxantrone hydrochloride;
temoporfin;
teniposide;
teroxirone;
testolactone;
thiamiprine;
thioguanine;
thiotepa;
tiazofurin;
tirapazamine;
toremifene citrate;
trestolone acetate;
triciribine phosphate;
trimetrexate;
triptorelin;
tubulozole hydrochloride;
uredepa;
vapreotide;
verteporfin;
vinepidine sulfate;
vinglycinate sulfate;
vinleurosine sulfate;
vinrosidine sulfate;
vinzolidine sulfate;
vorozole;
zeniplatin;
zinostatin; and
zorubicin hydrochloride.
- -noranhydroblastine, irinotecan, topotecan, cisplatin, cyclophosphamide, nitrogen mustard, trimethylene thiophosphoramide, carmustine, busulfan, chlorambucil, belustine, chlomaphazin, dacarbazine, cytosine arabinoside, fluorouracil, methotrexate, mercaptopurine, azathioprime, procarbazine, doxorubicin, bleomycin, dactinomycin, daunorubicin, mithramycin, mitomycin, mytomycin C, daunomycin, azacytidine, amsacrine, melphalan, ifosfamide, mitoxantrone, cis-platin, etoposide, taxol, acivicin;
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4. The method according to claim 2, wherein the chemotherapeutic agent is chosen from taxol, IL-2, gemcitabine, erlotinib, doxil, irinortecan, and bevacizumab.
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5. The method according to claim 2 wherein the compound is administered prior to administration of the chemotherapeutic agent.
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6. The method according to claim 2 wherein the compound is administered together with each administration of the chemotherapeutic agent.
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7. The method according to claim 2, wherein the compound is administered each time the chemotherapeutic agent is administered and between administrations of the chemotherapeutic agent.
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8. The method according to claim 1, wherein the method further comprises radiation therapy.
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9. The method according to claim 8, wherein the compound is administered at the time of radiation therapy.
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10. The method according to claim 8, wherein the compound is administered prior to the onset of radiation therapy.
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11. The method according to claim 8, wherein the compound is administered after radiation therapy.
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12. The method according to claim 8, wherein the compound is administered at the time of each radiation therapy and between each subsequent administration of radiation therapy.
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13. The method according to claim 1, wherein R has the formula:
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14. The method according to claim 1, wherein R2 is chosen from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl;
- and R3 is hydrogen.
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15. A method according to claim 1, wherein R2 is an alkyl unit wherein one or more hydrogen atoms are substituted with one or more substitutions chosen from:
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i) halogen; ii) —
N(R11)2; andiii) —
OR11;wherein each R11 is independently hydrogen or C1-C4 linear or branched alkyl.
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16. The method according to claim 1, wherein R2 is substituted or unsubstituted phenyl and R3 is hydrogen.
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17. The method according to claim 1, wherein R2 is substituted or unsubstituted heteroaryl and R3 is hydrogen.
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18. The method according to claim 1, wherein R2 is a heteroaryl unit chosen from 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, [1,2,3]triazol-4-yl, [1,2,3]triazol-5-yl, [1,2,4]triazol-4-yl, [1,2,4]triazol-5-yl, imidazol-2-yl, imidazol-4-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, [1,2,4]oxadiazol-3-yl, [1,2,4]oxadiazol-5-yl, [1,3,4]oxadiazol-2-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, [1,2,4]thiadiazol-3-yl, [1,2,4]thiadiazol-5-yl, or [1,3,4]thiadiazol-2-yl.
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19. The method according to claim 1, wherein R2 is thiophen-2-yl or thiophen-3-yl.
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20. The method according to claim 1, wherein R has the formula:
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21. The method according to claim 1, wherein R4 is hydrogen or substituted or unsubstituted C1-C6 linear, branched, or cyclic alkyl.
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22. The method according to claim 1, wherein R4 is chosen from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl;
- and R3 is hydrogen.
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23. The method according to claim 1, wherein R4 is substituted or unsubstituted phenyl and R3 is hydrogen.
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24. The method according to claim 1, wherein R4 is an alkyl unit wherein one or more hydrogen atoms are substituted with one or more substitutions chosen from:
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i) halogen; ii) —
N(R11)2; andiii) —
OR1;wherein each R11 is independently hydrogen or C1-C4 linear or C3-C4 branched alkyl.
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25. The method according to claim 1, wherein R4 is substituted or unsubstituted heteroaryl.
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26. The method according to claim 1, wherein R4 is a heteroaryl unit chosen from 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, [1,2,3]triazol-4-yl, [1,2,3]triazol-5-yl, [1,2,4]triazol-4-yl, [1,2,4]triazol-5-yl, imidazol-2-yl, imidazol-4-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, [1,2,4]oxadiazol-3-yl, [1,2,4]oxadiazol-5-yl, [1,3,4]oxadiazol-2-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, [1,2,4]thiadiazol-3-yl, [1,2,4]thiadiazol-5-yl, and [1,3,4]thiadiazol-2-yl.
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27. The method according to claim 1, wherein R4 is thiophen-2-yl or thiophen-3-yl.
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28. The method according to claim 1, wherein R1 is hydrogen, methyl, ethyl, tert-butyl, or methyl substituted with phenyl.
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29. The method according to claim 1, wherein L has the formula:
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—
C(O)[C(R5aR5b)]xNHC(O)—R5a is hydrogen, substituted or unsubstituted phenyl, and substituted or unsubstituted heteroaryl;
the index x is 1 or 2.
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30. The method according to claim 1, wherein L has the formula chosen from:
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i) —
C(O)[C(R5aH)]NHC(O)O—
;ii) —
C(O)[C(R5aH)][CH2]NHC(O)O—
;ii) —
C(O)[CH2][C(R5aH)]NHC(O)O—
;iv) —
C(O)[C(R5aH)]NHC(O)—
;v) —
C(O)[C(R5aH)][CH2]NHC(O)—
;
orvi) —
C(O)[CH2][C(R5aH)]NHC(O)—
;wherein R5a is; i) hydrogen; ii) methyl; iii) ethyl; iv) isopropyl; v) phenyl; vi) benzyl; vii) 4-hydroxybenzyl; viii) hydroxymethyl;
orix) 1-hydroxyethyl.
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31. The method according to claim 1, wherein R1 is chosen from phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,3-dimethoxyphenyl, 3,4-dimethoxyphenyl, and 3,5-dimethoxyphenyl.
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32. The method according to claim 1, wherein R2 is methyl or ethyl, R3 is hydrogen, and L has the formula —
- C(O)CH2—
.
- C(O)CH2—
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33. The method according to claim 1, wherein R2 is methyl or ethyl, R3 is hydrogen, and L has the formula —
- C(O)CH2CH2—
.
- C(O)CH2CH2—
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34. The method according to claim 3, wherein R1 is a substituted or unsubstituted heteroaryl unit, said substitutions chosen from:
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i) C1-C6 linear, C3-C6 branched, and C3-C6 cyclic alkyl; ii) substituted or unsubstituted phenyl and benzyl; iii) substituted of unsubstituted heteroaryl; iv) —
C(O)R9;
orv) —
NHC(O)R9;R9 is C1-C6 linear or C3-C6 branched alkyl;
C1-C6 linear or C3-C6 branched alkoxy;
or —
NHCH2C(O)R10;
R10 is chosen from hydrogen, methyl, ethyl, or tert-butyl.
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35. The method according to claim 1, wherein R1 is a heteroaryl unit substituted by an alkyl unit chosen from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or tert-butyl.
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36. The method according to claim 1, wherein R1 is a heteroaryl unit substituted by a carboxy unit having the formula —
- NHC(O)R9;
R9 is chosen from methyl, methoxy, ethyl, ethoxy, tert-butyl, and tert-butoxy.
- NHC(O)R9;
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37. The method according to claim 1, wherein the compound has the formula:
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38. The method according to claim 1, wherein the compound has the formula:
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39. The method according to claim 1, wherein the compound has the formula:
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40. The method according to claim 1, wherein the compound has the formula:
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41. The method according to claim 1, wherein R1 is a substituted or unsubstituted heteroaryl unit chosen from:
i) 1,2,3,4-tetrazol-1-yl and 1,2,3,4-tetrazol-5-yl having the respective formulae;
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42. The method according to claim 1, wherein the compound is chosen from:
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(S)-4-[2-Benzamido-2-(4-ethylthiazol-2-yl)ethyl]phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(2-fluorophenyl)acetamido]ethyl}phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(2-(3-fluorophenyl)acetamido)ethyl)phenylsulfamic acid; (S)-4-(2-(2-(2,3-Difluorophenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)phenyl-sulfamic acid; (S)-4-(2-(2-(3,4-Difluorophenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)phenyl-sulfamic acid; (S)-4-(2-(2-(2-Chlorophenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)phenylsulfamic acid; (S)-4-(2-(2-(3-Chlorophenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(2-(3-hydroxyphenyl)acetamido)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(2-(2-methoxyphenyl)acetamido)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(2-(3-methoxyphenyl)acetamido)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(3-phenylpropanamido)ethyl)phenylsulfamic acid; (S)-4-(2-(2-(3,4-Dimethoxyphenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)-phenylsulfamic acid; (S)-4-(2-(2-(2,3-Dimethoxyphenyl)acetamido)-2-(4-ethylthiazol-2-yl)ethyl)-phenylsulfamic acid; (S)-4-(2-(3-(3-Chlorophenyl)propanamido)-2-(4-ethylthiazol-2-yl)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(3-(2-methoxyphenyl)propanamido)ethyl)phenyl-sulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(3-(3-methoxyphenyl)propanamido)ethyl)pheny-lsulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(3-(4-methoxyphenyl)propanamido)ethyl)phenyl-sulfamic acid; (S)-4-{2-[2-(4-Ethyl-2,3-dioxopiperazin-1-yl)acetamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamide]ethyl}phenylsulfamic acid; (S)-4-[2-(Benzo[d][1,3]dioxole-5-carboxamido)-2-(4-ethylthiazol-2-yl)ethyl]-phenylsulfamic acid; 4-((S)-2-(2-(2-Chlorophenyl)acetamido)-2-(2-(thiophene2-yl)thiazol-4-yl)ethyl)-phenylsulfamic acid; 4-((S)-2-(2-(3-Methoxyphenyl)acetamido)-2-(2-(thiophene2-yl)thiazol-4-yl)ethyl)-phenylsulfamic acid; 4-{(S)-2-(3-Phenylpropanamido)-2-[2-(thiophene2-yl)thiazol-4-yl]ethyl}phenyl-sulfamic acid; 4-{(S)-2-(3-(3-Chlorophenyl)propanamido)-2-[2-(thiophene2-yl)thiazol-4-yl]ethyl}-phenylsulfamic acid; 4-{(S)-2-[2-(3-Fluorophenyl)acetamide]-2-[2-(thiophene2-yl)thiazol-4-yl]ethyl}-phenylsulfamic acid; (S)-4-{2-[2-(2,5-Dimethylthiazol-4-yl)acetamide]-2-(4-ethylthiazol-2-yl]ethyl}-phenylsulfamic acid; (S)-4-{2-[2-(2,4-Dimethylthiazol-5-yl)acetamide]-2-(4-methylthiazol-2-ylethyl}-phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[3-(thiazol-2-yl)propanamido]ethyl}phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(4-ethylthiazol-2-yl)acetamide]ethyl}phenyl-sulfamic acid; (S)-4-{2-[2-(3-Methyl-1,2,4-oxadiazol-5-yl)acetamide]-2-(2-phenylthiazol-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[2-(4-Ethyl-2,3-dioxopiperazin-1-yl)acetamide]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; (S)-4-(2-(2,3-Diphenylpropanamido)-2-(4-ethylthiazol-2-yl)ethyl)phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(2-methoxyphenyl)-3-phenylpropanamido]-ethyl)phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(3-fluorophenyl)-3-phenylpropanamido]-ethyl}phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(3-methoxyphenyl)-3-phenylpropanamido]-ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-3-phenylpropanamido]ethyl}phenylsulfamic acid; (S)-4-[2-(4-Ethylthiazol-2-yl)-2-(4-oxo-4-phenylbutanamido)-ethyl]phenylsulfamic acid; (S)-4-(2-(4-Ethylthiazol-2-yl)-2-(5-methyl-4-oxohexanamido)ethyl)phenylsulfamic acid; (S)-4-{2-[4-(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-4-oxobutanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; (S)-4-{2-[4-(2,3-Dimethoxyphenyl)-4-oxobutanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[4-oxo-4-(pyridin-2-yl)butanamido]ethyl}phenyl-sulfamic acid; (S)-4-{2-[4-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-4-oxobutanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; (S)-4-[2-(4-tert-Butoxy-4-oxobutanamido)-2-(4-ethylthiazol-2-yl)ethyl]phenyl-sulfamic acid; (S)-4-[2-(4-Ethoxy-4-oxobutanamido)-2-(4-ethylthiazol-2-yl)ethyl]phenylsulfamic acid; (S)-4-(2-(3-Benzylureido)-2-(4-ethylthiazol-2-yl)ethyl)phenylsulfamic acid; 4-{[(S)-2-(2-Ethylthiazol-4-yl)-2-(3-(R)-1 methoxy-1-oxo-3-phenylpropan-2-yl)ureido]ethyl}phenylsulfamic acid; 4-{(S)-2-(3-Benzylureido)-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; {4-(S)-[2-Phenylmethanesulfonylamino-2-(2-thiophen-2-ylthiazol-4-yl)ethyl]-phenylsulfamic acid; 4-{(S)-2-[(2-Methylthiazol-4-yl)methylsulfonamido]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; {4-(S)-[2-Phenylmethanesulfonylamino-2-(2-ethylthiazol-4-yl)ethyl]phenyl}-sulfamic acid; {4-(S)-[2-(3-Methoxyphenyl)methanesulfonylamino-2-(2-ethylthiazol-4-yl)ethyl]phenyl}sulfamic acid; (S)-4-{[1-(2-Ethylthiazol-4-yl)-2-(4-sulfoaminophenyl)ethylsulfamoyl]methyl}-benzoic acid methyl ester; (S)-4-[2-(2-Ethylthiazol-4-yl)-2-(1-methyl-1H-imidazol-4-sulfonamido)ethyl]-phenylsulfamic acid; 4-{(S)-2-[2-(Thiophen-2-yl)thiazol-4-yl]-2-(2,2,2-trifluoroethylsulfonamido)-ethyl}phenylsulfamic acid; {4-(S)-[2-(Phenylethanesulfonylamino)-2-(2thiophen-2-ylthiazol-4-yl)ethyl]-phenyl}sulfamic acid; {4-(S)-[3-(Phenylpropanesulfonylamino)-2-(2thiophen-2-ylthiazol-4-yl)ethyl]-phenyl}sulfamic acid; (S)-{4-[2-(4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-7-sulfonylamino)-2-(2-thiophen-2-ylthiazol-4-yl)ethyl]phenyl}sulfamic acid; 4-{(S)-2-(4-Acetamidophenylsulfonamido)-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-(2-cyclopropylthiazol-4-yl)-2-[4-(3-methoxyphenyl)-thiazol-2-ylamino]ethyl}phenylsulfamic acid; (S)-4-(2-(4-((2-Methoxy-2-oxoethyl)carbamoyl)thiazole-5-ylamino)-2-(2-ethylthiazole-4-yl)ethyl)phenylsulfamic acid; 4-((S)-2-(5-(1-N-(2-Methoxy-2-oxoethyl)-1-H-indol-3-yl)oxazole-2-ylamino)-2-(2-methylthiazol-4-yl)ethyl))phenylsulfamic acid; 4-((S)-2-(5-(2-Methoxyphenyl)oxazol-2-ylamino)-2-(2-methylthiazol-4-yl)ethyl)-phenylsulfamic acid; 4-((S)-2-(5-((S)-1-(tert-Butoxycarbonyl)-2-phenylethyl)oxazole-2-ylamino)-2-(2-methylthiazole-4-yl)ethyl)phenylsulfamic acid; (S)-4-(2-(5-(4-Methoxycarbonyl)phenyl)oxazole-2-ylamino)-2-(2-methylthiazole-4-yl)ethyl)phenylsulfamic acid; (S)-4-(2-(5-(3-Methoxybenzyl)oxazole-2-ylamino)-2-(2-methylthiazole-4-yl)ethyl)-phenylsulfamic acid; (S)-4-(2-(2-Methylthiazole-4-yl)-2-(5-phenyloxazole-2-ylamino)ethyl)phenyl-sulfamic acid; 4-((S)-2-(2-Cyclopropylthiazol-4-yl)-2-(4-(3-methoxyphenyl)thiazol-2-ylamino)-ethyl)phenylsulfamic acid; (S)-4-(2-(2-cyclopropylthiazol-4-yl)-2-(4-(4-fluorophenyl)thiazol-2-ylamino)ethyl)-phenylsulfamic acid; 4-((S)-2-(2-cyclopropylthiazol-4-yl)-2-(4-(2-methoxyphenyl)thiazol-2-ylamino)-ethyl)phenylsulfamic acid; 4-((S)-2-(2-cyclopropylthiazol-4-yl)-2-(4-(2,4-difluorophenyl)thiazol-2-ylamino)-ethyl)phenylsulfamic acid; (S)-4-(2-(4-(3-methoxybenzyl)thiazol-2-ylamino)-2-(2-cyclopropylthiazol-4-yl)ethyl)phenylsulfamic acid; (S)-{5-[1-(2-Ethylthiazol-4-yl)-2-(4-sulfoaminophenyl)ethylamino]-2-methyl-2H-[1,2,4]triazole-3-yl}carbamic acid methyl ester; 4-{(S)-2-[4-(2-Methoxyphenyl)thiazol-2-ylamino)-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[5-(3-Methoxyphenyl)oxazole-2-ylamino]-2-(2-phenylthiazole-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(2,4-Difluorophenyl)thiazol-2-ylamino]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; (S)-4-{2-[4-(Ethoxycarbonyl)thiazol-2-ylamino]-2-(2-phenylthiazol-4-yl)ethyl}-phenylsulfamic acid; (S)-4-{2-[4-(2-Ethoxy-2-oxoethyl)thiazol-2-ylamino]-2-(2-phenylthiazol-4-yl)ethyl}phenylsulfamic acid; (S)-4-{2-[4-(4-Acetamidophenyl)thiazol-2-ylamino]-2-(2-phenylthiazol-4-yl)ethyl}phenylsulfamic acid; (S)-4-[2-(4-Phenylthiazol-2-ylamino)-2-(2-phenylthiazol-4-yl)ethyl]phenylsulfamic acid; (S)-4-{2-[4-(4-(Methoxycarbonyl)phenyl)thiazol-2-ylamino]-2-(2-phenylthiazol-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(Ethoxycarbonyl)thiazol-2-ylamino]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; (S)-4-[2-(4-(Methoxycarbonyl)thiazol-5-ylamino)-2-(2-phenylthiazole-4-yl)ethyl]-phenylsulfamic acid; (S)-4-[2-(5-Phenyloxazole-2-ylamino)]-2-(2-phenylthiazole-4-yl)phenylsulfamic acid; (S)-4-{2-[5-(4-Acetamidophenyl)oxazole-2-ylamino]-2-(2-phenylthiazole-4-yl)ethyl}phenylsufamic acid; 4-((S)-2-(5-(2,4-Difluorophenyl)oxazole-2-ylamino)-2-(2-phenylthiazole-4-yl)ethyl)phenylsulfamic acid; 4-{(S)-2-[5-(3-Methoxyphenyl)oxazol-2-ylamino]-2-[(2-thiophen-2-yl)thiazole-4-yl]ethyl}phenylsulfamic acid; (S)-4-[2-(4,6-Dimethylpyrimidene-2-ylamino)-2-(2-methylthiazole-4-yl)ethyl]-phenylsulfamic acid; (S)-4-[2-(4-Hydroxy-6-methylpyrimidine-2-ylamino)-2-(2-methylthiazole-4-yl)ethyl]phenylsulfamic acid;
4-{(S)-2-[(S)-2-(tert-Butoxycarbonylamino)-3-phenylpropanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid;4-{(S)-2-[(R)-2-(tert-Butoxycarbonylamino)-3-phenylpropanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; {1-[1-(5-Ethylthiazol-2-yl)-(S)-2-(4-sulfoaminophenyl)ethylcarbamoyl]-(S)-2-phenylethyl}methyl carbamic acid tert-butyl ester; {(S)-2-Phenyl-1-[1-(4-phenylthiazol-2-yl)-(S)-2-(4-sulfoaminophenyl)ethyl-carbamoyl]ethyl}carbamic acid tert-butyl ester; 4-{(S)-2-(S)-2-(tert-Butoxycarbonylamino)-3-phenylpropaneamido-2-(2-phenylthiazole-4-yl)}phenylsulfamic acid; 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(thiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(4-methylthiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(4-propylthiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-(4-tert-Butylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Cyclopropylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Cyclohexylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-(4,5-Dimethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-Phenyl-1-[1-(2-phenylthiazol-4-yl)-(S)-2-(4-sulfoaminophenyl)ethyl-carbamoyl]ethyl}carbamic acid tert-butyl ester; 4-{(S)-2-(4-Ethyl-5-methylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[4-(2,2,2-trifluoroethyl)thiazol-2-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido)-2-[4-(3,3,3-trifluoropropyl)thiazol-2-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(2,2-Difluorocyclopropyl)thiazol-2-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[4-(methoxy-methyl)thiazol-2-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-(4-(Ethoxycarbonylamino)thiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(5-phenylthiazol-2-yl))ethyl}phenylsulfamic acid; 4-{(S)-2-(4-tert-Butylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Ethyl-5-phenylthiazol-2-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(3,4-Dimethylphenyl)thiazol-2-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(4-phenylthiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[4-(thiophen-2-yl)thiazol-2-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[4-(thiophen-3-yl)thiazol-2-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbinyl)-3-phenylpropion-amido]ethyl}phenylsulfamic acid; 4-{(S)-2-(5,6-Dihydro-4H-cyclopenta[d]thiazol-2-yl)-2-[(S)-2-(methoxy-carbonyl)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[4-(5-Chlorothiophen-2-yl)thiazol-2-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Ethoxycarbonylamino)-3-phenylpropanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(2-ethylthiazol-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(2-methyl-thiazol-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-(2-Ethylthiazole-4-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropan-amido]ethyl}phenylsulfamic acid; 4-{(S)-2-(2-Isopropylthiazol-4-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propan-amido]ethyl}phenylsulfamic acid; 4-{(S)-2-(2-Cyclopropylthiazol-4-yl)-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-{2-[(4-Chlorophenylsulfonyl)methyl]thiazol-4-yl}-2-[(S)-2-(methoxy-carbonyl)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[2-(tert-Butylsulfonylmethyl)thiazol-4-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropionamido]-2-(2-phenyl-thiazole-4-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[2-(3-Chlorothiophen-2-yl)thiazol-4-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenylpropanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[2-(3-methylthiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{[(S)-2-(2-(Furan-2-yl)thiazol-4-yl]-2-[(S)-2-(methoxycarbonylamino)-3-phenyl-propanamido]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[2-(2-methylthiazole-4-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-(2-pyrazine-2-yl)thiazole-4-yl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonylamino)-3-phenylpropanamido]-2-[2-(6-methylpyridin-3-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-[(S)-2-((S)-2-Acetamido-3-phenylpropanamido)-2-(4-ethylthiazol-2-yl)ethyl]-phenylsulfamic acid; 4-[(S)-2-((S)-2-Acetamido-3-phenylpropanamido)-2-(4-tert-butylthiazol-2-yl)ethyl]-phenylsulfamic acid; 4-{(S)-2-((S)-2-Acetamido-3-phenylpropanamido)-2-[4-(thiophen-3-yl)thiazol-2-yl]ethyl)phenylsulfamic acid; 4-{(S)-2-[(S)-2-(tert-Butoxycarbonyl)-3-methylbutanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; (S)-4-{2-[2-(tert-Butoxycarbonyl)acetamide]-2-(4-ethylthiazol-2-yl)ethyl}phenyl-sulfamic acid; (S)-4-{2-(4-Ethylthiazol-2-yl)-2-[2-(methoxycarbonyl)acetamido]ethyl}phenyl-sulfamic acid; 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonyl)-3-methylbutanamido]-ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(tert-Butoxycarbonyl)-4-methylpentanamido]-2-(4-ethylthiazol-2-yl)ethyl}phenylsulfamic acid; 4-{(S)-2-(4-Ethylthiazol-2-yl)-2-[(S)-2-(methoxycarbonyl)-4-methylpentan-amido]ethyl}phenylsulfamic acid; 4-((S)-2-(4-Ethylthiazol-2-yl)-2-{(S)-2-[2-(methoxycarbonyl)acetamide]-3-phenylpropanamido}ethyl)phenylsulfamic acid; 4-{(S)-2-[(S)-2-(tert-Butoxycarbonyl)-4-methylpentanamido]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; 4-{(S)-2-[(S)-2-(Methoxycarbonyl)-4-methylpentanamido]-2-[2-(thiophen-2-yl)thiazol-4-yl]ethyl}phenylsulfamic acid; and (S)-4-{2-[2-(tert-Butoxycarbonyl)acetamide]-2-(4-ethylthiazol-2-yl)ethyl}-phenylsulfamic acid.
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43. The method according to claim 1, wherein the compound has the formula:
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44. The method according to claim 43, wherein the method further comprises radiation therapy.
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45. The method according to claim 1, wherein the compound has the formula:
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46. The method according to claim 45, wherein the method further comprises radiation therapy.
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47. The method according to claim 1, wherein the compound has the formula:
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48. The method according to claim 1, wherein the method further comprises radiation therapy.
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49. The method according to claim 1, wherein the compound has the formula:
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50. The method according to claim 49, wherein the method further comprises radiation therapy.
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51. The method according to claim 1, wherein the cancer is chosen from Acute Lymphoblastic;
- Acute Myeloid Leukemia;
Adrenocortical Carcinoma;
Adrenocortical Carcinoma, Childhood;
Appendix Cancer;
Basal Cell Carcinoma;
Bile Duct Cancer, Extrahepatic;
Bladder Cancer;
Bone Cancer;
Osteosarcoma and Malignant Fibrous Histiocytoma;
Brain Stem Glioma, Childhood;
Brain Tumor, Adult;
Brain Tumor, Brain Stem Glioma, Childhood;
Brain Tumor, Central Nervous System Atypical Teratoid/Rhabdoid Tumor, Childhood;
Central Nervous System Embryonal Tumors;
Cerebellar Astrocytoma;
Cerebral Astrocytoma/Malignant Glioma;
Craniopharyngioma;
Ependymoblastoma;
Ependymoma;
Medulloblastoma;
Medulloepithelioma;
Pineal Parenchymal Tumors of Intermediate Differentiation;
Supratentorial Primitive Neuroectodermal Tumors and Pineoblastoma;
Visual Pathway and Hypothalamic Glioma;
Brain and Spinal Cord Tumors;
Breast Cancer;
Bronchial Tumors;
Burkitt Lymphoma;
Carcinoid Tumor;
Carcinoid Tumor, Gastrointestinal;
Central Nervous System Atypical Teratoid/Rhabdoid Tumor;
Central Nervous System Embryonal Tumors;
Central Nervous System Lymphoma;
Cerebellar Astrocytoma;
Cerebral Astrocytoma/Malignant Glioma, Childhood;
Cervical Cancer;
Chordoma, Childhood;
Chronic Lymphocytic Leukemia;
Chronic Myelogenous Leukemia;
Chronic Myeloproliferative Disorders;
Colon Cancer;
Colorectal Cancer;
Craniopharyngioma;
Cutaneous T-Cell Lymphoma;
Esophageal Cancer;
Ewing Family of Tumors;
Extragonadal Germ Cell Tumor;
Extrahepatic Bile Duct Cancer;
Eye Cancer, Intraocular Melanoma;
Eye Cancer, Retinoblastoma;
Gallbladder Cancer;
Gastric (Stomach) Cancer;
Gastrointestinal Carcinoid Tumor;
Gastrointestinal Stromal Tumor (GIST);
Germ Cell Tumor, Extracranial;
Germ Cell Tumor, Extragonadal;
Germ Cell Tumor, Ovarian;
Gestational Trophoblastic Tumor;
Glioma;
Glioma, Childhood Brain Stem;
Glioma, Childhood Cerebral Astrocytoma;
Glioma, Childhood Visual Pathway and Hypothalamic;
Hairy Cell Leukemia;
Head and Neck Cancer;
Hepatocellular (Liver) Cancer;
Histiocytosis, Langerhans Cell;
Hodgkin Lymphoma;
Hypopharyngeal Cancer;
Hypothalamic and Visual Pathway Glioma;
Intraocular Melanoma;
Islet Cell Tumors;
Kidney (Renal Cell) Cancer;
Langerhans Cell Histiocytosis;
Laryngeal Cancer;
Leukemia, Acute Lymphoblastic;
Leukemia, Acute Myeloid;
Leukemia, Chronic Lymphocytic;
Leukemia, Chronic Myelogenous;
Leukemia, Hairy Cell;
Lip and Oral Cavity Cancer;
Liver Cancer;
Lung Cancer, Non-Small Cell;
Lung Cancer, Small Cell;
Lymphoma, AIDS-Related;
Lymphoma, Burkitt;
Lymphoma, Cutaneous T-Cell;
Lymphoma, Hodgkin;
Lymphoma, Non-Hodgkin;
Lymphoma, Primary Central Nervous System;
Macroglobulinemia, Waldenstrom;
Malignant Fibrous Histiocytoma of Bone and Osteosarcoma;
Medulloblastoma;
Melanoma;
Melanoma, Intraocular (Eye);
Merkel Cell Carcinoma;
Mesothelioma;
Metastatic Squamous Neck Cancer with Occult Primary;
Mouth Cancer;
Multiple Endocrine Neoplasia Syndrome, (Childhood);
Multiple Myeloma/Plasma Cell Neoplasm;
Mycosis Fungoides;
Myelodysplastic Syndromes;
Myelodysplastic/Myeloproliferative Diseases;
Myelogenous Leukemia, Chronic;
Myeloid Leukemia, Adult Acute;
Myeloid Leukemia, Childhood Acute;
Myeloma, Multiple;
Myeloproliferative Disorders, Chronic;
Nasal Cavity and Paranasal Sinus Cancer;
Nasopharyngeal Cancer;
Neuroblastoma;
Non-Small Cell Lung Cancer;
Oral Cancer;
Oral Cavity Cancer;
Oropharyngeal Cancer;
Osteosarcoma and Malignant Fibrous Histiocytoma of Bone;
Ovarian Cancer;
Ovarian Epithelial Cancer;
Ovarian Germ Cell Tumor;
Ovarian Low Malignant Potential Tumor;
Pancreatic Cancer;
Pancreatic Cancer, Islet Cell Tumors;
Papillomatosis;
Parathyroid Cancer;
Penile Cancer;
Pharyngeal Cancer;
Pheochromocytoma;
Pineal Parenchymal Tumors of Intermediate Differentiation;
Pineoblastoma and Supratentorial Primitive Neuroectodermal Tumors;
Pituitary Tumor;
Plasma Cell Neoplasm/Multiple Myeloma;
Pleuropulmonary Blastoma;
Primary Central Nervous System Lymphoma;
Prostate Cancer;
Rectal Cancer;
Renal Cell (Kidney) Cancer;
Renal Pelvis and Ureter, Transitional Cell Cancer;
Respiratory Tract Carcinoma Involving the NUT Gene on Chromosome 15;
Retinoblastoma;
Rhabdomyosarcoma;
Salivary Gland Cancer;
Sarcoma, Ewing Family of Tumors;
Sarcoma, Kaposi;
Sarcoma, Soft Tissue;
Sarcoma, Uterine;
S6zary Syndrome;
Skin Cancer (Nonmelanoma);
Skin Cancer (Melanoma);
Skin Carcinoma, Merkel Cell;
Small Cell Lung Cancer;
Small Intestine Cancer;
Soft Tissue Sarcoma;
Squamous Cell Carcinoma, Squamous Neck Cancer with Occult Primary, Metastatic;
Stomach (Gastric) Cancer;
Supratentorial Primitive Neuroectodermal Tumors;
T-Cell Lymphoma, Cutaneous;
Testicular Cancer;
Throat Cancer;
Thymoma and Thymic Carcinoma;
Thyroid Cancer;
Transitional Cell Cancer of the Renal Pelvis and Ureter;
Trophoblastic Tumor, Gestational;
Urethral Cancer;
Uterine Cancer, Endometrial;
Uterine Sarcoma;
Vaginal Cancer;
Vulvar Cancer;
Waldenstrom Macroglobulinemia;
or Wilms Tumor.
- Acute Myeloid Leukemia;
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52. The method according to claim 1, wherein the cancer is chosen from renal cell carcinoma, lung cancer, malignant melanoma, or pancreatic cancer.
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2. The method according to claim 1, further comprising administering one or more chemotherapeutic agents.
Specification
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Current AssigneeEyePoint Pharmaceuticals, Inc.
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Original AssigneeAerpio Therapeutics Incorporated (Aadi Bioscience, Inc.)
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InventorsShalwitz, Robert, Peters, Kevin Gene
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Primary Examiner(s)LEWIS, PATRICK T
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Application NumberUS13/783,311Publication NumberTime in Patent Office618 DaysField of SearchNoneUS Class Current514/365CPC Class CodesA61K 31/4245 OxadiazolesA61K 31/426 1,3-ThiazolesA61K 31/427 not condensed and containin...A61K 31/428 condensed with carbocyclic ...A61K 31/433 ThidiazolesA61K 31/4439 containing a five-membered ...A61K 31/497 containing further heterocy...A61K 31/506 not condensed and containin...A61K 31/513 having oxo groups directly ...A61K 31/538 ortho- or peri-condensed wi...A61K 31/7068 having oxo groups directly ...A61K 45/06 Mixtures of active ingredie...C07D 277/28 Radicals substituted by nit...C07D 277/60 condensed with carbocyclic ...C07D 277/64 with only hydrocarbon or su...C07D 417/04 directly linked by a ring-m...C07D 417/12 linked by a chain containin...C07D 417/14 containing three or more he...