Oxygen/nitrogen heterocycle inhibitors of tyrosine phosphatases
First Claim
Patent Images
1. A compound having the formula:
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or a pharmaceutically acceptable salt thereof, wherein;
L1, L2 , and L3 are each, independently, a bond or (CH2), where s is 1-3;
X is CR7 or N, wherein R7 is H or C1-C3 alkyl;
G1 is H or a phenyl ring, wherein the phenyl ring is optionally substituted with one or more moieties selected from the group consisting of;
phosphonodifluoromethyl, phosphonodifluoromethyl monoethyl ester, phosphonodifluoromethyl monomethyl ester, phosphonodifluoromethyl diethyl ester, phosphonodifluoromethyl mono-acyloxyalkyl ester, where acyl is C2-C7 alkanoyl or C4-C7 cycloalkanoyl, phosphonodifluoromethyl mono-alkoxycarbonyloxyalkyl ester, where alkoxy is C1-C6 or C3-C6 cycloalkoxy, phosphonodifluoromethyl mono-alkoxyalkyl ester, where alkoxy is C15-C22, phosphonodifluoromethyl mono-amide, 2-carboxyethenyl optionally substituted with 1-2 fluorines or methyl groups, carboxymethoxy, carboxy —
C2-C4-alkyl optionally further substituted with 1-4 halogen atoms or 1-4 methyl groups, Cl, Br, F, CN, OH, CH3 , and ethynyl;
G2 is H, C1-C3 alkyl, or a phenyl or pyridyl ring, wherein the alkyl, phenyl or pyridyl group is optionally and independently substituted with 1, 2, or 3 of the following moieties;
Cl, F, Br, carboxy, methoxycarbonyl, OCH3, OCF3, OCHF2, C1-C3 alkyl, and C1-C3-alkylsulfonyl;
G3 is H, C1-C3 alkyl, or a phenyl or pyridyl ring, wherein the phenyl or pyridyl ring is optionally substituted with;
(i) F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, CF2P(═
O)(OR)(OR1);
(ii) phenyl, wherein said phenyl is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CH2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
(iii) phenoxy, wherein said phenoxy is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
or (iv) benzyloxy, wherein said benzyloxy is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
wherein m=0 to 6 and n=0 to 2;
wherein R and R1 are independently selected from hydrogen, an alkyl group of 1 to 6 carbon atoms, wherein the alkyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1 , Y2 , and Y3 , an aryl group, wherein the aryl group is unsubstituted or mono-, di- or tri- substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , —
OC(R2 R3)OC(═
O)R4, and —
OC(R2 R3)OC(═
O)OR4, or R and R1 are joined to form a 4-8 membered cycloalkyl, cycloalkenyl, cycloalkynyl, or heterocyclic ring;
wherein R2, R3 and R4 are independently selected from (i) and (ii) as follows;
(i) H, C1-C7 alkyl, alkenyl of 2 to 6 carbon atoms, wherein the alkenyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , alkynyl of 2 to 6 carbon atoms, wherein the alkynyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , cycloalkyl of 3 to 8 carbon atoms, wherein the cycloalkyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , aryl of 6 to 14 carbon atoms, wherein the aryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , linked biaryl or heterobiaryl groups of 10 to 20 atoms featuring two aromatic or heteroaromatic ring systems linked through a single bond, with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, and wherein the linked biaryl or heterobiaryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , aralkyl of 7 to 16 carbon atoms, wherein the aralkyl is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , monocyclic-heteroaryl or bicyclic-heteroaryl having 5 to 14 ring atoms with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, and wherein the monocyclic-heteroaryl or bicyclic heteroaryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , and a heteroaralkyl group of 5 to 14 ring atoms with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, wherein the heteroaralkyl is unsubstituted or substituted on the alkyl chain and which is unsubstituted on the ring or mono-, di- or tri-substituted on the ring with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 ;
or (ii) R2 and R3, and/or R3 and R4, and/or R2 and R4 are joined to form a 4-8-membered cycloalkyl, cycloalkenyl, cycloalkynyl, or heterocyclic ring, and the other of R2, R3, and R4, when not joined in a ring, is selected as in (i) above;
and wherein Y1, Y2, and Y3 are each, independently, selected from (i) or (ii) as follows;
(i) R5, (CR5 R6)nOR5, OH, (CR5 R6)nNR5R6, C(=NR5)NR5R6, C(═
NOR5)NR5R6, halogen (F, Cl, Br, I), cyano, nitro, CF3, CF2CF3, CH2CF3, CH(CF3)2, C(OH)(CF3)2, OCHCl2, OCF3, OCF2H, OCF2CF3, OCH2CF3, (CR5R6)nOC(═
O)NR5R6, (CR5R6)nNHC(═
O)C(═
O)OR5, (CR5R6)nNHC(═
O)NR5SO2(Me, CF3), (CR5R6)nNHSO2(Me, CF3), (CR5R6)nNHSO2NR5R6, NHSO2NR5C(═
O)(Me, CF3), (CR5R6)nNHC(═
O)R5, (CR5R6)nNHC(═
O)NR5R6, C(═
O)OH, (CR5R6)nC(═
O)OH, C(═
O)OR5, C(═
O)O(CR5R6)OC(═
O)R5, C(═
O)O(CR5R6)OC(═
O)OR5, C(═
O)R5,—
(CR5R6)nC(═
O)R5, (CF2)nC(═
O)R5, (CFR5) nC(═
O)R5, tetrazolyl (Tzl), (CR5R6)nTzl, (CF2)nTzl, (CFR5)nTzl, (CR5R6)nC(═
O)OR5, (CR5R6)nC(═
O)NH2, (CR5R6)nC(═
O)NR5R6, (CR5R6)nC(═
O)C(═
O)OR5, (CR5R6)nCH(OR5)C(═
O)OR5, (CF2)nC(═
O)OH, (CF2)nC(═
O)OR5, (CF2)nC(═
O)NH2, (CF2)nC(═
O)NR5R6, 017121-025999 (CR5R6)nC(═
O)C(═
O)OR5, (CR5R6)nCH(OR5)C(═
O)OR5, C(R5)=C(R6), C(═
O)OR5, C(R5)=C(R6)-Tzl, (CR5R6)nP(═
O)(OH)2, (CR5R6)nP(═
O)(OR5)(OR6), P(═
O)(OR5)[(OCR5R6)OC(═
O)R5], P(═
O)(OR5)[(OCR5R6)OC(═
O)OR5], P(═
O) [(OCR5R6)OC(═
O)R5)] [(OCR5R6)OC(═
O)R5], P(═
O)[(OCR5R6)OC(═
O)OR5)] [(OCR5R6)OC(═
O)OR5], (CR5R6)nP(═
O)(Me)(OR5), (CR5R6)nP(═
O)(CF3)(OR5), (CF2)nP(═
O)(OR5)(OR6), (CF2)nP(═
O)(Me)(OR5), (CF2)nP(═
O)(CF3)(OR5), (CFR5)nP(═
O)(OR5)(OR6), CR5═
CR5-P(═
O)(OR5)(OR6), CR5═
CR5-P(═
O)(Me)(OR5), CC-P(═
O)(OR5)(OR6), (C═
O)P(═
O)(OR5)(OR6), (C═
O)P(═
O)(Me)(OR5), (C═
O)P(═
O)(CF3)(0 R5), (CR5 OR6)nP(═
O)(OR5)(OR6), (CR5 OR6)nP(═
O)(Me)(OR5), (CR5 OR6)nP(═
O)(CF3)(OR5), O(CR5R6)nC(═
O)OR5, O(CF2)nC(═
O)OR5, OC(═
O)R5, OCH[C(═
O)OR5]2, O(CR5R6),CH[C(═
O)OR5]2, OCF [C(═
O)OR5]2, O(CR5R6)nC(═
O)C(═
O)OR5, O(CF2)nC(═
O)C(═
O)OR5, O(CR5R6)nTzl, O(CF2)nTzl, OCH(Tzl)2, O(CF2)nP(═
O)(OR5)(OR6), O(CF2)nP(═
O)(Me)(OR5), O(CF2)nP(═
O)(CF3)(OR5), O(CFR5)nP(═
O)(OR5)(OR6), O(CFR5)nP(═
O)(Me)(OR5), O(CFR5)nP(═
O)(CF3)(OR5), (CR5R6)nP(═
O)(OR5)(OR6), O(CR5R6)nP(═
O)(Me)(OR5), O(CR5R6)nP(═
O)(CF3)(OR5), OCF [P(═
O)(Me)(OR5)]2, SO3 H, —
(CR5R6)nSO3 H, S(O), R5, SCF3, SCHF2, SO2 CF3, SO2 Ph, (CR5R6)nS(O)nR5, (CR5R6)nS (0)2 CF3, (CR5R6)nSO2 NR5R6, (CR5R6)nSO2 NR5 C(═
O)(Me, CF3), (CF2)nSO3 H, (CFR5)nSO3 H, and (CF2)nSO2 NR5R6, wherein n=0-2, and wherein R5 and R6 are each independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, a C3-C8 cycloalkyl ring, or a 5-7 membered heterocyclic ring;
or (ii) Y1 and Y2, and/or Y1 and Y3 , and/or Y2 and Y3 are selected together to be (CR5R6)2-6, —
O[C(R8)(R9)]rO—
or —
O[C(R8)(R9)]r+1—
, wherein r is an integer from 1 to 4 and R8 and R9 are independently selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, heteroaryl of 5 to 14 ring atoms, aralkyl of 7 to 15 carbon atoms, and heteroarylalkyl of 5 to 14 ring atoms, and the other of Y1, Y2, and Y3, when not selected as in (ii), is selected as in (i) above.
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Accused Products
Abstract
Compounds, pharmaceutical compositions, and methods for treating, preventing, or ameliorating symptoms associated with diseases such as diabetes, cancer, neurodegenerative diseases, and obesity are provided. The compounds and compositions inhibit protein tyrosine phosphatase enzymes, e.g., PTP-1B.
83 Citations
27 Claims
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1. A compound having the formula:
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or a pharmaceutically acceptable salt thereof, wherein;
L1, L2 , and L3 are each, independently, a bond or (CH2), where s is 1-3;
X is CR7 or N, wherein R7 is H or C1-C3 alkyl;
G1 is H or a phenyl ring, wherein the phenyl ring is optionally substituted with one or more moieties selected from the group consisting of;
phosphonodifluoromethyl, phosphonodifluoromethyl monoethyl ester, phosphonodifluoromethyl monomethyl ester, phosphonodifluoromethyl diethyl ester, phosphonodifluoromethyl mono-acyloxyalkyl ester, where acyl is C2-C7 alkanoyl or C4-C7 cycloalkanoyl, phosphonodifluoromethyl mono-alkoxycarbonyloxyalkyl ester, where alkoxy is C1-C6 or C3-C6 cycloalkoxy, phosphonodifluoromethyl mono-alkoxyalkyl ester, where alkoxy is C15-C22, phosphonodifluoromethyl mono-amide, 2-carboxyethenyl optionally substituted with 1-2 fluorines or methyl groups, carboxymethoxy, carboxy —
C2-C4-alkyl optionally further substituted with 1-4 halogen atoms or 1-4 methyl groups, Cl, Br, F, CN, OH, CH3 , and ethynyl;
G2 is H, C1-C3 alkyl, or a phenyl or pyridyl ring, wherein the alkyl, phenyl or pyridyl group is optionally and independently substituted with 1, 2, or 3 of the following moieties;
Cl, F, Br, carboxy, methoxycarbonyl, OCH3, OCF3, OCHF2, C1-C3 alkyl, and C1-C3-alkylsulfonyl;
G3 is H, C1-C3 alkyl, or a phenyl or pyridyl ring, wherein the phenyl or pyridyl ring is optionally substituted with;
(i) F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, CF2P(═
O)(OR)(OR1);
(ii) phenyl, wherein said phenyl is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CH2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
(iii) phenoxy, wherein said phenoxy is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
or(iv) benzyloxy, wherein said benzyloxy is optionally further substituted with F, Cl, Br, CF3, OR, methoxycarbonyl, carboxy, (CRR1)nCO2R, CF2CO2R, O(CRR1)CO2R, CH═
CHCO2R, tetrazolyl (Tzl), NRR1, NRC(═
O)OR1, OC(═
O)NRR1, C(═
O)NRR1, NRC(═
O)C(═
O)OR1, SO2NRR1, S(O)m(CRR1)CO2R, S(O)m(CRR1)CONRR1, SO2NRR1, C1-C3-alkylsulfonyl, or CF2P(═
O)(OR)(OR1);
wherein m=0 to 6 and n=0 to 2;
wherein R and R1 are independently selected from hydrogen, an alkyl group of 1 to 6 carbon atoms, wherein the alkyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1 , Y2 , and Y3 , an aryl group, wherein the aryl group is unsubstituted or mono-, di- or tri- substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , —
OC(R2 R3)OC(═
O)R4, and —
OC(R2 R3)OC(═
O)OR4, or R and R1 are joined to form a 4-8 membered cycloalkyl, cycloalkenyl, cycloalkynyl, or heterocyclic ring;
wherein R2, R3 and R4 are independently selected from (i) and (ii) as follows;
(i) H, C1-C7 alkyl, alkenyl of 2 to 6 carbon atoms, wherein the alkenyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , alkynyl of 2 to 6 carbon atoms, wherein the alkynyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , cycloalkyl of 3 to 8 carbon atoms, wherein the cycloalkyl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , aryl of 6 to 14 carbon atoms, wherein the aryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , linked biaryl or heterobiaryl groups of 10 to 20 atoms featuring two aromatic or heteroaromatic ring systems linked through a single bond, with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, and wherein the linked biaryl or heterobiaryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , aralkyl of 7 to 16 carbon atoms, wherein the aralkyl is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , monocyclic-heteroaryl or bicyclic-heteroaryl having 5 to 14 ring atoms with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, and wherein the monocyclic-heteroaryl or bicyclic heteroaryl group is unsubstituted or mono-, di- or tri-substituted with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 , and a heteroaralkyl group of 5 to 14 ring atoms with the ring atoms selected from carbon and heteroatoms, wherein the heteroatoms are selected from oxygen, nitrogen, and sulfur, wherein the heteroaralkyl is unsubstituted or substituted on the alkyl chain and which is unsubstituted on the ring or mono-, di- or tri-substituted on the ring with 1 to 3 substituents selected from the group consisting of Y1, Y2 , and Y3 ;
or(ii) R2 and R3, and/or R3 and R4, and/or R2 and R4 are joined to form a 4-8-membered cycloalkyl, cycloalkenyl, cycloalkynyl, or heterocyclic ring, and the other of R2, R3, and R4, when not joined in a ring, is selected as in (i) above;
and wherein Y1, Y2, and Y3 are each, independently, selected from (i) or (ii) as follows;
(i) R5, (CR5 R6)nOR5, OH, (CR5 R6)nNR5R6, C(=NR5)NR5R6, C(═
NOR5)NR5R6, halogen (F, Cl, Br, I), cyano, nitro, CF3, CF2CF3, CH2CF3, CH(CF3)2, C(OH)(CF3)2, OCHCl2, OCF3, OCF2H, OCF2CF3, OCH2CF3, (CR5R6)nOC(═
O)NR5R6, (CR5R6)nNHC(═
O)C(═
O)OR5, (CR5R6)nNHC(═
O)NR5SO2(Me, CF3), (CR5R6)nNHSO2(Me, CF3), (CR5R6)nNHSO2NR5R6, NHSO2NR5C(═
O)(Me, CF3), (CR5R6)nNHC(═
O)R5, (CR5R6)nNHC(═
O)NR5R6, C(═
O)OH, (CR5R6)nC(═
O)OH, C(═
O)OR5, C(═
O)O(CR5R6)OC(═
O)R5, C(═
O)O(CR5R6)OC(═
O)OR5, C(═
O)R5,—
(CR5R6)nC(═
O)R5, (CF2)nC(═
O)R5, (CFR5) nC(═
O)R5, tetrazolyl (Tzl), (CR5R6)nTzl, (CF2)nTzl, (CFR5)nTzl, (CR5R6)nC(═
O)OR5, (CR5R6)nC(═
O)NH2, (CR5R6)nC(═
O)NR5R6, (CR5R6)nC(═
O)C(═
O)OR5, (CR5R6)nCH(OR5)C(═
O)OR5, (CF2)nC(═
O)OH, (CF2)nC(═
O)OR5, (CF2)nC(═
O)NH2, (CF2)nC(═
O)NR5R6, 017121-025999 (CR5R6)nC(═
O)C(═
O)OR5, (CR5R6)nCH(OR5)C(═
O)OR5, C(R5)=C(R6), C(═
O)OR5, C(R5)=C(R6)-Tzl, (CR5R6)nP(═
O)(OH)2, (CR5R6)nP(═
O)(OR5)(OR6), P(═
O)(OR5)[(OCR5R6)OC(═
O)R5], P(═
O)(OR5)[(OCR5R6)OC(═
O)OR5], P(═
O) [(OCR5R6)OC(═
O)R5)] [(OCR5R6)OC(═
O)R5], P(═
O)[(OCR5R6)OC(═
O)OR5)] [(OCR5R6)OC(═
O)OR5], (CR5R6)nP(═
O)(Me)(OR5), (CR5R6)nP(═
O)(CF3)(OR5), (CF2)nP(═
O)(OR5)(OR6), (CF2)nP(═
O)(Me)(OR5), (CF2)nP(═
O)(CF3)(OR5), (CFR5)nP(═
O)(OR5)(OR6), CR5═
CR5-P(═
O)(OR5)(OR6), CR5═
CR5-P(═
O)(Me)(OR5), CC-P(═
O)(OR5)(OR6), (C═
O)P(═
O)(OR5)(OR6), (C═
O)P(═
O)(Me)(OR5), (C═
O)P(═
O)(CF3)(0 R5), (CR5 OR6)nP(═
O)(OR5)(OR6), (CR5 OR6)nP(═
O)(Me)(OR5), (CR5 OR6)nP(═
O)(CF3)(OR5), O(CR5R6)nC(═
O)OR5, O(CF2)nC(═
O)OR5, OC(═
O)R5, OCH[C(═
O)OR5]2, O(CR5R6),CH[C(═
O)OR5]2, OCF [C(═
O)OR5]2, O(CR5R6)nC(═
O)C(═
O)OR5, O(CF2)nC(═
O)C(═
O)OR5, O(CR5R6)nTzl, O(CF2)nTzl, OCH(Tzl)2, O(CF2)nP(═
O)(OR5)(OR6), O(CF2)nP(═
O)(Me)(OR5), O(CF2)nP(═
O)(CF3)(OR5), O(CFR5)nP(═
O)(OR5)(OR6), O(CFR5)nP(═
O)(Me)(OR5), O(CFR5)nP(═
O)(CF3)(OR5), (CR5R6)nP(═
O)(OR5)(OR6), O(CR5R6)nP(═
O)(Me)(OR5), O(CR5R6)nP(═
O)(CF3)(OR5), OCF [P(═
O)(Me)(OR5)]2, SO3 H, —
(CR5R6)nSO3 H, S(O), R5, SCF3, SCHF2, SO2 CF3, SO2 Ph, (CR5R6)nS(O)nR5, (CR5R6)nS (0)2 CF3, (CR5R6)nSO2 NR5R6, (CR5R6)nSO2 NR5 C(═
O)(Me, CF3), (CF2)nSO3 H, (CFR5)nSO3 H, and (CF2)nSO2 NR5R6, wherein n=0-2, and wherein R5 and R6 are each independently H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, a C3-C8 cycloalkyl ring, or a 5-7 membered heterocyclic ring;
or(ii) Y1 and Y2, and/or Y1 and Y3 , and/or Y2 and Y3 are selected together to be (CR5R6)2-6, —
O[C(R8)(R9)]rO—
or —
O[C(R8)(R9)]r+1—
, wherein r is an integer from 1 to 4 and R8 and R9 are independently selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, heteroaryl of 5 to 14 ring atoms, aralkyl of 7 to 15 carbon atoms, and heteroarylalkyl of 5 to 14 ring atoms, and the other of Y1, Y2, and Y3, when not selected as in (ii), is selected as in (i) above.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27)
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- 16. A pharmaceutical composition comprising the compound of claim I and a pharmaceutically acceptable carrier.
Specification
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Current AssigneeMetabasis Therapeutics, Inc. (Ligand Pharmaceuticals, Inc.), Cengent Therapeutics, Inc. (Long-E International, Inc.)
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Original AssigneeMetabasis Therapeutics, Inc. (Ligand Pharmaceuticals, Inc.)
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InventorsWang, Jing, Cheruvallath, Zacharia S., Semple, Joseph E., Mylvaganam, Shankari, Nutt, Ruth F.
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Application NumberUS11/177,539Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/92CPC Class CodesA61K 31/4245 OxadiazolesA61P 25/28 for treating neurodegenerat...A61P 3/04 Anorexiants; Antiobesity ag...A61P 3/10 for hyperglycaemia, e.g. an...A61P 35/00 Antineoplastic agentsA61P 43/00 Drugs for specific purposes...C07D 263/48 Nitrogen atoms not forming ...C07D 271/07 with oxygen, sulfur or nitr...C07D 413/10 linked by a carbon chain co...C07F 9/653 Five-membered ringsC07F 9/65312 having the two nitrogen ato...C07F 9/65583 each of the hetero rings co...
