Bicyclic androgen and progesterone receptor modulator compounds and methods
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Abstract
The present invention is directed to compounds, pharmaceutical compositions, and methods for modulating processes mediated by AR and PR. More particularly, the invention relates to nonsteroidal compounds and compositions that are high affinity, high specificity agonists, partial agonists (i.e., partial activators and/or tissue-specific activators) and antagonists for AR and PR. Also provided are methods of making such compounds and pharmaceutical compositions, as well as critical intermediates used in their synthesis.
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Citations
41 Claims
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1. 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, 34, 35, 38, 39)
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2. A compound of claim 1, wherein:
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R3 and R4 are each independently hydrogen or optionally substituted C1-C6 alkyl;
R3A is optionally substituted aryl or heteroaryl;
R5 is selected from the group of hydrogen, halogen and optionally substituted C1-C6 alkyl;
R7 and R8 are each independently hydrogen or halogen; and
R9 is hydrogen or halogen.
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3. A compound of claim 2, wherein:
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R11 is selected form the group of halogen, CN, NO2 and optionally substituted C1-C6 haloalkyl;
R12 is halogen or optionally substituted haloalkyl;
R13 is selected from the group of hydrogen, halogen, C1-C6 alkyl and C1-C6 heteroalkyl, wherein said C1-C6 alkyl and C1-C6 heteroalkyl are optionally substituted;
R15 is halogen or OR16; and
R18 and R19 are each independently optionally substituted C1-C6 alkyl;
orR18 and R19 taken together form a five- to six-membered ring.
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4. A compound of claim 3, wherein:
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R22 and R23 are each independently hydrogen or optionally substituted C1-C6 alkyl;
orR22 and R23 taken together form a three- to seven-membered ring;
R25 through R30 are each independently hydrogen, C1-C6 alkyl, or C1-C6 haloalkyl, wherein said C1-C6 alkyl and C1-C6 haloalkyl are optionally substituted. Y is selected from the group of O, S, and NOR3; and
m is 1 to 3
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5. A compound of claim 1, wherein:
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R1 and R2 are each independently selected from the group of COR3, CSR3, SO2R3, NO, NR3R4, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C1-C8 heteroalkyl, C2-C8 heteroalkenyl, C2-C8 heteroalkynyl, (CH2)nR3A, aryl, and heteroaryl, wherein the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, aryl, and heteroaryl are optionally substituted with F, Cl, Br, I, OR3, NR3R4, CN, NO2, SR3, SOR3, SO2R3, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 heteroalkyl;
R3 and R4 are each independently hydrogen or optionally substituted C1-C6 alkyl;
R3A is optionally substituted aryl or heteroaryl;
R5 is selected from the group of hydrogen, halogen and optionally substituted C1-C6 alkyl;
R7 and R8 are each independently hydrogen or halogen;
R9 is hydrogen or halogen. R11 is selected form the group of halogen, CN, NO2 and optionally substituted C1-C6 haloalkyl;
R12 is halogen or optionally substituted haloalkyl;
R13 is selected from the group of hydrogen, halogen, C1-C6 alkyl and C1-C6 heteroalkyl, wherein said C1-C6 alkyl and C1-C6 heteroalkyl are optionally substituted;
R15 is halogen or OR16;
R18 and R19 are each independently optionally substituted C1-C6 alkyl;
orR18 and R19 taken together form a five- to six-membered ring;
R22 and R23 are each independently hydrogen or optionally substituted C1-C6 alkyl;
orR22 and R23 together form a three- to seven-membered ring;
R25 through R30 are each independently hydrogen, C1-C6 alkyl, or C1-C6 haloalkyl, wherein said C1-C6 alkyl and C1-C6 haloalkyl are optionally substituted;
Y is selected from the group of O, S, and NOR3; and
m is 1 to 3.
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6. A compound of claim 1, wherein:
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R1 and R2 taken together form a three- to nine-membered alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring, wherein the alkyl, alkenyl, heteroalkyl, or heteroalkenyl ring are optionally substituted with F, Cl, Br, I, OR3, NR3R4, C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 heteroalkyl;
R3 and R4 are each independently hydrogen or optionally substituted C1-C6 alkyl;
R3A is optionally substituted aryl or heteroaryl;
R5 is selected from the group of hydrogen, halogen and optionally substituted C1-C6 alkyl;
R7 and R8 are each independently hydrogen or halogen;
R9 is hydrogen or halogen;
R11 is selected form the group of halogen, CN, NO2 and optionally substituted C1-C6 haloalkyl;
R12 is halogen or optionally substituted haloalkyl;
R13 is selected from the group of hydrogen, halogen, C1-C6 alkyl and C1-C6 heteroalkyl, wherein said C1-C6 alkyl and C1-C6 heteroalkyl are optionally substituted;
R15 is halogen or OR16;
R18 and R19 are each independently optionally substituted C1-C6 alkyl;
orR18 and R19 taken together form a five- to six-membered ring;
R22 and R23 are each independently hydrogen or optionally substituted C1-C6 alkyl;
orR22 and R23 together form a three- to seven-membered ring;
R25 through R30 are each independently hydrogen, C1-C6 alkyl, or C1-C6 haloalkyl, wherein said C1-C6 alkyl and C1-C6 haloalkyl are optionally substituted;
Y is selected from the group of O, S, and NOR3; and
m is 1 to 3.
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7. A compound of claim 1, wherein:
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R1 and R2 taken together form one of;
R3 and R4 are each independently hydrogen or optionally substituted C1-C6 alkyl;
R3A is optionally substituted aryl or heteroaryl;
R5 is selected from the group of hydrogen, halogen and optionally substituted C1-C6 alkyl;
R7 and R8 are each independently hydrogen or halogen;
R9 is hydrogen or halogen;
R11 is selected form the group of halogen, CN, NO2 and optionally substituted C1-C6 haloalkyl;
R12 is halogen or optionally substituted haloalkyl;
R13 is selected from the group of hydrogen, halogen, C1-C6 alkyl and C1-C6 heteroalkyl, wherein said C1-C6 alkyl and C1-C6 heteroalkyl are optionally substituted;
R15 is halogen or OR16;
R18 and R19 are each independently optionally substituted C1-C6 alkyl;
orR18 and R19 taken together form a five- to six-membered ring;
R22 and R23 are each independently hydrogen or optionally substituted C1-C6 alkyl;
orR22 and R23 together form a three- to seven-membered ring;
R25 through R30 are each independently hydrogen, C1-C6 alkyl, or C1-C6 haloalkyl, wherein said C1-C6 alkyl and C1-C6 haloalkyl are optionally substituted;
Y is selected from the group of O, S, and NOR3; and
m is 1 to 3.
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8. A compound of claim 1, wherein:
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R1 and R2 are each independently selected from the group of COR3, CSR3, SO2R3, C1-C8 alkyl, C2-C8 alkenyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C1-C8 heteroalkyl, C2-C8 heteroalkenyl, CH2R3A, aryl and heteroaryl, wherein the aryl or heteroaryl are optionally substituted with F, Cl, Br, CN, NO2, OR3, NR3R4, SR3, COMe, COCF3, C1-C4 alkyl, or C1-C4 haloalkyl;
orR1 and R2 are taken together to form one of;
R3 and R4 are each independently selected from the group of hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C1-C8 haloalkyl, and C1-C8 heteroalkyl;
R3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, OMe, SMe, C1-C4 alkyl, or C1-C4 haloalkyl;
R5 is selected from the group of hydrogen, F, Cl, Br, OH, OMe, C1-C4 alkyl, and C1-C4 haloalkyl;
R6 is selected from the group of F, Cl, Br, CH3, CF3, CHF2, CFH2, CN, CF2C1, CF2OR3, OR3, SR3, NR3R4, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C1-C4 heteroalkyl, and C2-C4 heteroalkenyl;
R7 and R8 are each independently selected from the group of hydrogen, F, Cl, Br, OR3, NR3R4, SR3, C1-C8 alkyl, C1-C8 haloalkyl, and C1-C8 heteroalkyl;
R9 is selected from the group of hydrogen, F, Br, C1, OR3, NR3R4, SR3, C1-C4 alkyl, and C1-C4 haloalkyl;
R10 is selected from the group of;
R11 is selected from the group of F, Br, Cl, I, C1-C6 alkyl, C1-C6 haloalkyl, NO2, CN, CF3, OH, OMe, NR3R4, and SR3;
R12 is selected from the group of F, Br, Cl, and C1-C4 haloalkyl;
R13 is selected from the group of hydrogen, F, Cl, Br, I, CN, OR3, NR3R4, SR3, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C1-C8 heteroalkyl, and CH2R3A;
R13A is NHR1 or heteroaryl, wherein the heteroaryl is optionally substituted with F, Cl, Br, CN, NMe2, NO2, CF3, Me, or OMe;
R14 is selected from the group of F, Br, C1, CF3, CHF2, CH2F, CF2Cl, or CF2OMe;
R15 is selected from the group of F, Br, Cl, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 heteroalkyl, OR16, NR16R4, and SR16;
R16 is selected from the group of hydrogen, C1-C alkyl, C1-C8 haloalkyl, C1-C8 heteroalkyl, COR17, CO2R17, and CONR17R17;
R17 is selected from the group of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 heteroalkyl;
R18 and R19 are each independently selected from the group of C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 heteroalkyl;
orR18 and R19 are taken together to form a four- to seven-membered ring;
R20 is aryl or heteroaryl, optionally substituted with F, Cl, Br, CN, NO2, CF3, or C1-C4 alkyl;
R21 is selected from the group of C2-C8 alkyl, C2-C8 haloalkyl, or C2-C8 heteroalkyl;
R22 and R23 are each independently selected from the group of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl and C1-C6 heteroalkyl;
orR22 and R23 are taken together to form a three- to seven-membered ring;
R24 is hydrogen or OR3;
R25 through R30 are each independently selected from the group of hydrogen, F, Cl, Br, OR3, NR3R4, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 heteroalkyl and C2-C6 alkenyl, wherein the alkyl, haloalkyl, heteroalkyl, and alkenyl are optionally substituted with F, Cl, Br, OR3, NR3R4, aryl or heteroaryl, and wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, CN, NO2, OH, OCH3, CF3 or C1-C6 alkyl;
any two of R25, R26, R27, R28, R29 and R30 taken together form a three to seven-membered alkyl or alkenyl or heteroalkyl ring;
orany four of R25, R26, R27, R28, R29 and R3 taken together form a fused aromatic ring;
X is S;
Y is selected from the group of O, S, NR3, and NOR3;
Z is selected from the group of O, S, NR3, and CR25R26, or Z is two hydrogens;
n is 1 or 2; and
m is 1 to 4.
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9. A compound of claim 1, wherein said compound is represented by any one of formula I through formula VIII:
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R1 and R2 are each independently selected from the group of COR3, C1-C8 alkyl, C2-C8 alkenyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C1-C8 heteroalkyl, CH2R3A, aryl, and heteroaryl, wherein the aryl and heteroaryl are optionally substituted with F, Cl, Br, OH, OMe, SH, OMe, SMe, CN, NO2, CF3, Me, COMe, or COCF3;
orR1 and R2 are taken together to form;
R3 and R4 are each independently selected from the group of hydrogen, C1-C6 alkyl, and C1-C6 haloalkyl;
R3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, OMe, C1-C4 alkyl, or C1-C4 haloalkyl;
R5 is selected from the group of hydrogen, F, Cl, OH, OMe, C1-C4 alkyl, and CF3;
R6 is selected from the group of F, Cl, Br, C1-C4 alkyl, CF3, CHF2, CFH2, CN, CF2C1, CF2OMe, and OMe;
R7 is selected from the group of hydrogen, F, Cl, Me, OMe, and CF3;
R8 is selected from the group of hydrogen, F, Cl, Br, OR3, NR3R4, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 heteroalkyl;
R9 is selected from the group of hydrogen, F, Cl, OH, Me, OMe, and CF3;
R10 is selected from the group of;
R11 is selected from the group of F, Br, C1, C1-C6 alkyl, NO2, CN, CF3, OH, and OMe;
R12 is selected from the group of F, Cl, CF3, CF2H, and CFH2;
R13 is selected from the group of hydrogen, F, Cl, Br, OR3, SR3, C1-C8 alkyl, C2-C8 alkenyl, and C1-C8 haloalkyl;
R3A is NHR1;
R14 is selected from the group of F, Cl, CF3, CHF2, CH2F, and CF2Cl;
R15 is selected from the group of F, Cl, CN, CF3, OR16, and SR16;
R16 is selected from the group of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, COR17, CO2R17, and CONR17R17;
R17 is selected from the group of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 heteroalkyl;
R18 and R19 are each independently selected from the group of C1-C6 alkyl, C1-C6 haloalkyl;
orR18 and R19 taken together form a five- to six-membered ring;
R21 is C2-C8 alkyl or C2-C8 haloalkyl;
R22 and R23 are each independently selected from the group of hydrogen, C1-C6 alkyl, and C1-C6 haloalkyl;
orR22 and R23 taken together form a four- to six-membered ring;
R24 is hydrogen or OH;
R25 through R30 are each independently selected from the group of hydrogen, F, Cl, OH, OMe, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 heteroalkyl and C2-C6 alkenyl;
orAny two of R25, R26, R27, R28R29 and R30 taken together form a four to six-membered alkyl or alkenyl ring;
orAny four of R25, R26, R27, R28, R29 and R30 taken together form a fused aromatic ring;
V is selected from the group of CR22R23, CR3R4O, and CR3R4S;
W is O or CR3R4;
X is O or NR16;
Y is selected from the group of O, S, and NOR3;
Z is O or CR25R26;
orZ is two hydrogens;
n is 1 or 2; and
m is 1 to 3.
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10. A compound of claim 1, wherein said compound is represented by any one of formula I, III, IV and VI-VIII, and wherein:
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R1 and R2 are each independently selected from the group of C1-C8 alkyl, C2-C8 alkenyl, C1-C8 haloalkyl, C1-C8 heteroalkyl, and CH2R3A;
orR1 and R2 are taken together to form;
R3 and R4 are each independently selected from the group of hydrogen, C1-C6 alkyl, and C1-C6 haloalkyl;
R3A is heteroaryl or aryl, wherein the heteroaryl and aryl are optionally substituted with F, Cl, Br, CN, CF3, OMe, or C1-C4 alkyl;
R5 is selected from the group of hydrogen, F, Cl, OMe, and Me;
R6 is selected from the group of F, Cl, C1-C4 alkyl, CF3, CHF2, CFH2, CF2C1, CF2OMe, and OMe;
R7 is selected from the group of hydrogen, F, Cl, Me, OMe;
R8 is selected from the group of hydrogen, F, Cl, Br, OR3, NR3R4, C1-C6 alkyl, C1-C6 haloalkyl;
R9 is selected from the group of hydrogen, F, Cl, Me, OMe, CF3;
R10 is selected from the group of;
R13 is selected from the group of hydrogen, F, Cl, Br, C1-C4 alkyl, C2-C4 alkenyl, and C1-C8 haloalkyl;
R13A is NHR1;
R14 is selected from the group of C1, CF3, CHF2, CH2F, and CF2Cl;
R15 is selected from the group of Cl, OR16 and SR16;
R16 is selected from the group of hydrogen, C1-C6 alkyl, COR17, CO2R17, and CONR17R17;
R17 is selected from the group of C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 heteroalkyl;
R18 and R19 are each independently C1-C4 alkyl or C1-C4 haloalkyl;
orR18 and R19 are taken together to form a five- to six-membered ring;
R21 is selected from the group of C2-C8 alkyl, C2-C8 haloalkyl, and C2-C8 heteroalkyl;
R24 is hydrogen or OH;
R25 through R30 are each independently selected from the group of hydrogen, F, Cl, OH, OMe, C1-C4 alkyl, and C1-C4 haloalkyl;
W is O;
X is NR16;
Y is O or S;
Z is two hydrogens; and
n is 1 or 2.
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11. A compound of claim 1, wherein R10 is represented by the formula:
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12. A compound of claim 1, wherein R10 is represented by the formula:
- R3OH
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13. A compound of claim 1, wherein R10 is represented by the formula:
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14. A compound according to claim 1, wherein the compound is an androgen receptor modulator.
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15. A compound according to claim 14, wherein the compound is an androgen receptor antagonist.
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16. A compound according to claim 14, wherein the compound is an androgen receptor agonist.
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17. A compound according to claim 14, wherein the compound is an androgen receptor partial agonist.
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18. A compound according to claim 1, wherein the compound is a progesterone receptor modulator.
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19. A compound according to claim 18, wherein the compound is a progesterone receptor antagonist
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20. A compound according to claim 18, wherein the compound is a progesterone receptor agonist.
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21. A compound according to claim 18, wherein the compound is a progesterone receptor partial agonist.
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22. A compound according to claim 1, wherein the compound is selected from the group of:
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6-(bis-2,2,2-Trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
474);
(±
)-3,4-Dihydro-6-(bis-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
476);
6-(2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
477);
6-(N-Isopropyl-N-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
478);
6-N-Isobutylamino-4-trifluoromethylcoumarin (Compound
479);
6-N,N-Diethylamino-4-trifluoromethylcoumarin (Compound
480);
6-N,N-Dipropylamino-4-trifluoromethylcoumarin (Compound
481)6-N-Propylamino-4-trifluoromethylcoumarin (Compound
482);
6-(N-Isobutyl-N-propylamino)-4-trifluoromethylcoumarin (Compound
483);
6-(N-2,2,2-Trifluoroethyl-N-propylamino)-4-trifluoromethylcoumarin (Compound
484);
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34. A method for affecting androgen receptor activity in a mammal, comprising administering to said mammal a compound according to claim 1.
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35. A method for affecting progesterone receptor activity in a mammal, comprising administering to said mammal a compound according to claim 1.
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38. A method for modulating a process in a mammal mediated by androgen receptors, comprising administering to a mammal a pharmaceutically effective amount of a compound according to claim 1.
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39. A method for modulating a process in a mammal mediated by progesterone receptors, comprising administering to a mammal a pharmaceutically effective amount of a compound according to claim 1.
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2. A compound of claim 1, wherein:
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23. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of the formula:
- View Dependent Claims (24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 36, 37, 40, 41)
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24. A pharmaceutical composition according to claim 23, wherein the compound is an androgen receptor modulator.
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25. A pharmaceutical composition according to claim 24, wherein the compound is an androgen receptor antagonist.
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26. A pharmaceutical composition according to claim 24, wherein the compound is an androgen receptor agonist.
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27. A pharmaceutical composition according to claim 24, wherein the compound is an androgen receptor partial agonist.
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28. A pharmaceutical composition according to claim 23, wherein the compound is a progesterone receptor modulator.
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29. A pharmaceutical composition according to claim 28, wherein the compound is a progesterone receptor antagonist.
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30. A pharmaceutical composition according to claim 28, wherein the compound is a progesterone receptor agonist.
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31. A pharmaceutical composition according to claim 28, wherein the compound is a progesterone receptor partial agonist.
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32. A pharmaceutical composition according to claim 28, wherein the composition comprises one or more compounds selected from the group of:
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6-(bis-2,2,2-Trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
474);
6-Amino-4-trifluoromethylcoumarin (Compound
475);
(±
)-3,4-Dihydro-6-(bis-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
476);
6-(2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
477);
6-(N-Isopropyl-N-2,2,2-trifluoroethyl)amino-4-trifluoromethylcoumarin (Compound
478);
6-N-Isobutylamino-4-trifluoromethylcoumarin (Compound
479);
6-N,N-Diethylamino-4-trifluoromethylcoumarin (Compound
480);
6-N,N-Dipropylamino-4-trifluoromethylcoumarin (Compound
481);
6-N-Propylamino-4-trifluoromethylcoumarin (Compound
482);
6-(N-Isobutyl-N-propylamino)-4-trifluoromethylcoumarin (Compound
483);
6-(N-2,2,2-Trifluoroethyl-N-propylamino)-4-trifluoromethylcoumarin (Compound
484); and
1,4-Dihydro-4,4-dimethyl-6-methylamino-1,3-benzo[d]oxazin-2-one (Compound
485).
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33. A pharmaceutical composition according to claim 23, wherein the composition is formulated for oral, topical, intravenous, suppository or parenteral administration.
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36. A method for affecting androgen receptor activity in a mammal, comprising administering to said mammal a compound according to claim 23.
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37. A method for affecting progesterone receptor activity in a mammal, comprising administering to said mammal a compound according to claim 23.
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40. A method of modulating a process in a mammal mediated by androgen receptors, comprising administering to a mammal a pharmaceutically effective amount of a composition according to claim 23.
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41. A method of modulating a process in a mammal mediated by progesterone receptors, comprising administering to a mammal a pharmaceutically effective amount of a composition according to claim 23.
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24. A pharmaceutical composition according to claim 23, wherein the compound is an androgen receptor modulator.
Specification
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Current AssigneeLigand Pharmaceuticals, Inc.
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Original AssigneeLigand Pharmaceuticals, Inc.
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InventorsMartinborough, Esther, Zhi, Lin, Van Oeveren, Cornelis Arjan
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current514/397
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CPC Class CodesA61P 13/08 of the prostateA61P 15/00 Drugs for genital or sexual...A61P 15/04 for inducing labour or abor...A61P 15/08 for gonadal disorders or fo...A61P 15/10 for impotenceA61P 15/16 Masculine contraceptivesA61P 15/18 Feminine contraceptivesA61P 17/10 Anti-acne agentsA61P 17/14 for baldness or alopeciaA61P 35/00 Antineoplastic agentsA61P 43/00 Drugs for specific purposes...A61P 5/24 of the sex hormonesA61P 5/26 AndrogensA61P 5/28 AntiandrogensA61P 5/34 GestagensA61P 5/36 AntigestagensA61P 7/04 Antihaemorrhagics; Procoagu...A61P 7/06 AntianaemicsC07D 209/34 in position 2C07D 209/96 Spiro-condensed ring systemsC07D 215/227 : only one oxygen atom which ...C07D 215/36 : Sulfur atoms C07D215/24 tak...C07D 215/38 : Nitrogen atoms nitro radica...C07D 239/80 : Oxygen atomsC07D 265/18 : with hetero atoms directly ...C07D 265/36 : condensed with one six-memb...C07D 277/68 : with hetero atoms or with c...C07D 311/14 : substituted in position 6 a...C07D 311/20 : hydrogenated in the hetero ...C07D 401/04 : directly linked by a ring-m...C07D 401/12 : linked by a chain containin...C07D 405/04 : directly linked by a ring-m...C07D 405/12 : linked by a chain containin...C07D 409/04 : directly linked by a ring-m...C07D 409/12 : linked by a chain containin...C07D 413/04 : directly linked by a ring-m...C07D 417/04 : directly linked by a ring-m...