EA018268B1 - Аналоги пиридона и пиридазона как модуляторы gpr119 - Google Patents
Аналоги пиридона и пиридазона как модуляторы gpr119 Download PDFInfo
- Publication number
- EA018268B1 EA018268B1 EA201100210A EA201100210A EA018268B1 EA 018268 B1 EA018268 B1 EA 018268B1 EA 201100210 A EA201100210 A EA 201100210A EA 201100210 A EA201100210 A EA 201100210A EA 018268 B1 EA018268 B1 EA 018268B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- yloxy
- oxo
- dihydropyridazin
- piperidin
- phenyl
- Prior art date
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- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- -1 trans-tert-butyl-2-methyl-4- (1- (4- (methylsulfonyl) phenyl) -2-oxo-1,2-dihydropyridin-4-yloxy) piperidine Chemical compound 0.000 claims 6
- 125000005605 benzo group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- FNOIIWTWYBZNFY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-[1-(5-iodopyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(I)=CN=2)C(C#N)=N1 FNOIIWTWYBZNFY-UHFFFAOYSA-N 0.000 claims 1
- ZJSNRQKZPQHAFS-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-6-oxo-4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridazine-3-carbonitrile Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=C(Cl)C(Cl)=CC=2)C#N)CC1 ZJSNRQKZPQHAFS-UHFFFAOYSA-N 0.000 claims 1
- DDJDIHFWRKTLPW-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-4-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carbonitrile Chemical compound FC1=CC(Br)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(Cl)=CN=2)C(C#N)=N1 DDJDIHFWRKTLPW-UHFFFAOYSA-N 0.000 claims 1
- FYRNKUJPCREPGA-UHFFFAOYSA-N 1-(4-bromo-3-fluorophenyl)-4-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carbonitrile Chemical compound C1=C(Br)C(F)=CC(N2C(C=C(OC3CCN(CC3)C=3N=CC(Cl)=CN=3)C(C#N)=N2)=O)=C1 FYRNKUJPCREPGA-UHFFFAOYSA-N 0.000 claims 1
- ZTKCFYYPXNYKQS-UHFFFAOYSA-N 1-(4-cyano-3-fluorophenyl)-4-[1-(5-iodopyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=CC(N2C(C=C(OC3CCN(CC3)C=3N=CC(I)=CN=3)C(C#N)=N2)=O)=C1 ZTKCFYYPXNYKQS-UHFFFAOYSA-N 0.000 claims 1
- BGXDSPPKIWTZCM-UHFFFAOYSA-N 1-(4-cyano-3-fluorophenyl)-6-oxo-4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridazine-3-carbonitrile Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=C(F)C(C#N)=CC=2)C#N)CC1 BGXDSPPKIWTZCM-UHFFFAOYSA-N 0.000 claims 1
- RLJXSSOXMQLDDJ-UHFFFAOYSA-N 1-(4-cyano-3-fluorophenyl)-6-oxo-4-[1-[5-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl]oxypyridazine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=CC(N2C(C=C(OC3CCN(CC3)C=3N=CC(=CN=3)C(F)(F)F)C(C#N)=N2)=O)=C1 RLJXSSOXMQLDDJ-UHFFFAOYSA-N 0.000 claims 1
- NHPKODRMSBRNNL-UHFFFAOYSA-N 1-(4-methylsulfonylphenyl)-6-oxo-4-[1-[5-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl]oxypyridazine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(=CN=2)C(F)(F)F)C(C#N)=N1 NHPKODRMSBRNNL-UHFFFAOYSA-N 0.000 claims 1
- SYPMUXPBRUFPPP-UHFFFAOYSA-N 1-(6-cyanopyridin-3-yl)-4-[1-(5-iodopyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carbonitrile Chemical compound N1=CC(I)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=NC(=CC=2)C#N)C#N)CC1 SYPMUXPBRUFPPP-UHFFFAOYSA-N 0.000 claims 1
- SIWDJNIVGMMYEZ-UHFFFAOYSA-N 1-(6-cyanopyridin-3-yl)-6-oxo-4-[1-[5-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl]oxypyridazine-3-carbonitrile Chemical compound N1=CC(C(F)(F)F)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=NC(=CC=2)C#N)C#N)CC1 SIWDJNIVGMMYEZ-UHFFFAOYSA-N 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- HULUTEQBGKOKRV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridazin-3-one Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC2=CC(=O)N(C=3C=C(Cl)C(Cl)=CC=3)N=C2)CC1 HULUTEQBGKOKRV-UHFFFAOYSA-N 0.000 claims 1
- LNIWLXPXHIGJEE-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-5-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridazin-3-one Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC2=CC(=O)N(C=3C=CC(=CC=3)S(C)(=O)=O)N=C2)CC1 LNIWLXPXHIGJEE-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- DAUWKSLHXXOBIL-GHTZIAJQSA-N 4-[(2s,4r)-2-methyl-1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)pyridin-2-one Chemical compound N1=CC(CCC)=CN=C1N1[C@@H](C)C[C@H](OC2=CC(=O)N(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2)CC1 DAUWKSLHXXOBIL-GHTZIAJQSA-N 0.000 claims 1
- KMSLMPXQCNNBIW-UHFFFAOYSA-N 4-[1-(5-bromopyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-cyano-3-fluorophenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=CC(N2C(C=C(OC3CCN(CC3)C=3N=CC(Br)=CN=3)C(C#N)=N2)=O)=C1 KMSLMPXQCNNBIW-UHFFFAOYSA-N 0.000 claims 1
- DNBBZWRLTMJLIU-UHFFFAOYSA-N 4-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]oxy-1-(3,4-dichlorophenyl)-6-oxopyridazine-3-carbonitrile Chemical compound N1=CC(Cl)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=C(Cl)C(Cl)=CC=2)C#N)CC1 DNBBZWRLTMJLIU-UHFFFAOYSA-N 0.000 claims 1
- QEPMGKHRJDRKRA-UHFFFAOYSA-N 4-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(Cl)=CN=2)C(C#N)=N1 QEPMGKHRJDRKRA-UHFFFAOYSA-N 0.000 claims 1
- CEFBJQIWTVXQOY-UHFFFAOYSA-N 4-[1-(5-cyanopyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(=CN=2)C#N)C(C#N)=N1 CEFBJQIWTVXQOY-UHFFFAOYSA-N 0.000 claims 1
- VPMFWUORLQIHSU-UHFFFAOYSA-N 4-[1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl]oxy-1-(3,4-dichlorophenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(=CN=2)C2CC2)C(C#N)=N1 VPMFWUORLQIHSU-UHFFFAOYSA-N 0.000 claims 1
- MJRDPBMJYROUDG-UHFFFAOYSA-N 4-[1-(5-iodopyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(I)=CN=2)C(C#N)=N1 MJRDPBMJYROUDG-UHFFFAOYSA-N 0.000 claims 1
- HNNCJYMFLNBDFO-UHFFFAOYSA-N 4-[1-[5-(difluoromethoxy)pyrimidin-2-yl]piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)-6-oxopyridazine-3-carbonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(OC(F)F)=CN=2)C(C#N)=N1 HNNCJYMFLNBDFO-UHFFFAOYSA-N 0.000 claims 1
- PUVAOZONWHKKLZ-UHFFFAOYSA-N 4-[5-chloro-4-[1-(5-cyclopropylpyrimidin-2-yl)-3-methylpiperidin-4-yl]oxy-2-oxopyridin-1-yl]-2-fluorobenzonitrile Chemical class CC1CN(C=2N=CC(=CN=2)C2CC2)CCC1OC(C(=C1)Cl)=CC(=O)N1C1=CC=C(C#N)C(F)=C1 PUVAOZONWHKKLZ-UHFFFAOYSA-N 0.000 claims 1
- YBXXGIAOCOLCOU-UHFFFAOYSA-N 5-[1-(5-acetylpyrimidin-2-yl)piperidin-4-yl]oxy-2-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound N1=CC(C(=O)C)=CN=C1N1CCC(OC2=CC(=O)N(C=3C=CC(=CC=3)S(C)(=O)=O)N=C2)CC1 YBXXGIAOCOLCOU-UHFFFAOYSA-N 0.000 claims 1
- OLRSIDWVXJFEEO-UHFFFAOYSA-N 5-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]oxy-6-(hydroxymethyl)-2-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(Cl)=CN=2)C(CO)=N1 OLRSIDWVXJFEEO-UHFFFAOYSA-N 0.000 claims 1
- ODXRUCYUIVSMNG-UHFFFAOYSA-N 5-[1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl]oxy-2-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C=C(OC2CCN(CC2)C=2N=CC(=CN=2)C2CC2)C=N1 ODXRUCYUIVSMNG-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- MQJITIGDPCCLDU-UHFFFAOYSA-N methyl 1-(3,4-dichlorophenyl)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(Cl)C(Cl)=C1 MQJITIGDPCCLDU-UHFFFAOYSA-N 0.000 claims 1
- AFTKQMWKIBEUJR-UHFFFAOYSA-N methyl 1-(4-bromo-2-fluorophenyl)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(Br)C=C1F AFTKQMWKIBEUJR-UHFFFAOYSA-N 0.000 claims 1
- CELDTPDTZVSCII-UHFFFAOYSA-N methyl 1-(4-bromo-3-fluorophenyl)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(Br)C(F)=C1 CELDTPDTZVSCII-UHFFFAOYSA-N 0.000 claims 1
- SLGBFOWTQHIJRF-UHFFFAOYSA-N methyl 1-(4-cyano-3-fluorophenyl)-4-[1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C=2N=CC(=CN=2)C2CC2)C(C(=O)OC)=NN1C1=CC=C(C#N)C(F)=C1 SLGBFOWTQHIJRF-UHFFFAOYSA-N 0.000 claims 1
- DCNVSQXLNAHFAQ-UHFFFAOYSA-N methyl 1-(4-cyano-3-fluorophenyl)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(C#N)C(F)=C1 DCNVSQXLNAHFAQ-UHFFFAOYSA-N 0.000 claims 1
- HYBNUZOBDYVJED-UHFFFAOYSA-N methyl 1-(4-cyano-3-fluorophenyl)-6-oxo-4-[1-(5-propylpyrimidin-2-yl)piperidin-4-yl]oxypyridazine-3-carboxylate Chemical compound N1=CC(CCC)=CN=C1N1CCC(OC=2C(=NN(C(=O)C=2)C=2C=C(F)C(C#N)=CC=2)C(=O)OC)CC1 HYBNUZOBDYVJED-UHFFFAOYSA-N 0.000 claims 1
- UOGQMLHJEKQHBF-UHFFFAOYSA-N methyl 1-(6-cyanopyridin-3-yl)-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(C#N)N=C1 UOGQMLHJEKQHBF-UHFFFAOYSA-N 0.000 claims 1
- XHLFLSLERBBNAO-UHFFFAOYSA-N methyl 4-[1-(5-bromopyrimidin-2-yl)piperidin-4-yl]oxy-1-(4-cyano-3-fluorophenyl)-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C=2N=CC(Br)=CN=2)C(C(=O)OC)=NN1C1=CC=C(C#N)C(F)=C1 XHLFLSLERBBNAO-UHFFFAOYSA-N 0.000 claims 1
- WZJOXQAKEPZYCW-UHFFFAOYSA-N methyl 4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]oxy-1-(4-methylsulfonylphenyl)-6-oxopyridazine-3-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)OC)=NN1C1=CC=C(S(C)(=O)=O)C=C1 WZJOXQAKEPZYCW-UHFFFAOYSA-N 0.000 claims 1
- 230000008520 organization Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- CSTCILFMBXQPJD-UHFFFAOYSA-N propan-2-yl 4-[3-cyano-1-(4-cyano-3-fluorophenyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1OC1=CC(=O)N(C=2C=C(F)C(C#N)=CC=2)N=C1C#N CSTCILFMBXQPJD-UHFFFAOYSA-N 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- LUIXGNGNSSPHFL-AUUYWEPGSA-N tert-butyl (3R,4R)-4-[5-chloro-1-(4-cyano-3-fluorophenyl)-2-oxopyridin-4-yl]oxy-3-methylpiperidine-1-carboxylate Chemical compound ClC=1C(=CC(N(C=1)C1=CC(=C(C=C1)C#N)F)=O)O[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)C LUIXGNGNSSPHFL-AUUYWEPGSA-N 0.000 claims 1
- FUGDVSJDCRANNE-UHFFFAOYSA-N tert-butyl 4-[1-(3,4-dichlorophenyl)-3-(hydroxymethyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(Cl)C(Cl)=CC=2)N=C1CO FUGDVSJDCRANNE-UHFFFAOYSA-N 0.000 claims 1
- UXHILQKQEWHAQW-UHFFFAOYSA-N tert-butyl 4-[1-(3,4-dichlorophenyl)-3-(methylcarbamoyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound O=C1C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C(=O)NC)=NN1C1=CC=C(Cl)C(Cl)=C1 UXHILQKQEWHAQW-UHFFFAOYSA-N 0.000 claims 1
- UYTNZSDSABMCHU-UHFFFAOYSA-N tert-butyl 4-[1-(4-bromo-2-fluorophenyl)-3-cyano-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C(=CC(Br)=CC=2)F)N=C1C#N UYTNZSDSABMCHU-UHFFFAOYSA-N 0.000 claims 1
- SZNLDAZJQJQFCI-UHFFFAOYSA-N tert-butyl 4-[1-(4-bromo-3-fluorophenyl)-3-cyano-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(F)C(Br)=CC=2)N=C1C#N SZNLDAZJQJQFCI-UHFFFAOYSA-N 0.000 claims 1
- OPTVONFAMRBUCB-UHFFFAOYSA-N tert-butyl 4-[1-(4-cyano-3-fluorophenyl)-3-(hydroxymethyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(F)C(C#N)=CC=2)N=C1CO OPTVONFAMRBUCB-UHFFFAOYSA-N 0.000 claims 1
- JYTJDHKQPSVOHF-UHFFFAOYSA-N tert-butyl 4-[1-[(4-methoxyphenyl)methyl]-6-oxo-3-phenylpyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C=C(OC2CCN(CC2)C(=O)OC(C)(C)C)C(C=2C=CC=CC=2)=N1 JYTJDHKQPSVOHF-UHFFFAOYSA-N 0.000 claims 1
- ZHKCHUVVMYBSFO-UHFFFAOYSA-N tert-butyl 4-[3-amino-1-(3,4-dichlorophenyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(Cl)C(Cl)=CC=2)N=C1N ZHKCHUVVMYBSFO-UHFFFAOYSA-N 0.000 claims 1
- WIELFKWIAJKOFN-UHFFFAOYSA-N tert-butyl 4-[3-carbamoyl-1-(3,4-dichlorophenyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(Cl)C(Cl)=CC=2)N=C1C(N)=O WIELFKWIAJKOFN-UHFFFAOYSA-N 0.000 claims 1
- CHRXBUUZORBWNY-UHFFFAOYSA-N tert-butyl 4-[3-cyano-1-(3,4-dichlorophenyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=C(Cl)C(Cl)=CC=2)N=C1C#N CHRXBUUZORBWNY-UHFFFAOYSA-N 0.000 claims 1
- YZGVNJPJZKQJBH-UHFFFAOYSA-N tert-butyl 4-[3-cyano-1-(4-methylsulfonylphenyl)-6-oxopyridazin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(=O)N(C=2C=CC(=CC=2)S(C)(=O)=O)N=C1C#N YZGVNJPJZKQJBH-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 abstract 4
- 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 abstract 4
- 229940075993 receptor modulator Drugs 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 3
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| PCT/US2009/050618 WO2010009183A1 (en) | 2008-07-16 | 2009-07-15 | Pyridone and pyridazone analogues as gpr119 modulators |
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| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US8481731B2 (en) | 2009-06-24 | 2013-07-09 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical composition and methods relating thereto |
| US8293729B2 (en) | 2009-06-24 | 2012-10-23 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical composition and methods relating thereto |
| WO2011030139A1 (en) | 2009-09-11 | 2011-03-17 | Astrazeneca Ab | 4- (pyrimidin-2-yl) -piperazine and 4- (pyrimidin-2-yl) -piperidine derivatives as gpr119 modulators |
| US20130109703A1 (en) | 2010-03-18 | 2013-05-02 | Boehringer Ingelheim International Gmbh | Combination of a GPR119 Agonist and the DPP-IV Inhibitor Linagliptin for Use in the Treatment of Diabetes and Related Conditions |
| PH12012501853A1 (en) | 2010-04-08 | 2013-01-07 | Bristol Myers Squibb Co | Pyrimidinylpiperidinyloxypyridinone analogues as gpr119 modulators |
| EA201270778A1 (ru) | 2010-05-06 | 2013-04-30 | Бристол-Майерс Сквибб Компани | Бициклические гетероарильные аналоги в качестве модуляторов рецептора gpr119 |
| WO2011140161A1 (en) | 2010-05-06 | 2011-11-10 | Bristol-Myers Squibb Company | Benzofuranyl analogues as gpr119 modulators |
| CN103080101A (zh) | 2010-05-17 | 2013-05-01 | 阵列生物制药公司 | 作为gpr119调节剂的哌啶基取代的内酰胺 |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| PH12013500671A1 (en) | 2010-10-08 | 2018-04-11 | Cadila Healthcare Ltd | Novel gpr 119 agonists |
| WO2012170867A1 (en) | 2011-06-09 | 2012-12-13 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of gpr-119 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9174965B2 (en) | 2012-05-16 | 2015-11-03 | Bristol-Myers Squibb Company | Pyrimidinylpiperidinyloxypyridone analogues as GPR119 modulators |
| EP2872127A1 (en) | 2012-07-11 | 2015-05-20 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| AU2013203000B9 (en) | 2012-08-10 | 2017-02-02 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| CN103664795B (zh) * | 2012-09-06 | 2017-10-03 | 华东理工大学 | 哒嗪酮类化合物及其用途 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9499553B2 (en) | 2013-03-13 | 2016-11-22 | Chugai Seiyaku Kabushiki Kaisha | Dihydropyridazine-3,5-dione derivative and pharmaceuticals containing the same |
| HUE050577T2 (hu) * | 2013-03-13 | 2020-12-28 | Chugai Pharmaceutical Co Ltd | Dihidropiridazin-3,5-dion-származék |
| NO2986357T3 (enExample) | 2013-04-18 | 2018-07-14 | ||
| WO2014175621A1 (en) * | 2013-04-25 | 2014-10-30 | Yuhan Corporation | Novel triazolone derivatives or salts thereof and pharmaceutical composition comprising the same |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
| CN104370806B (zh) * | 2014-06-17 | 2017-07-07 | 中国海洋大学 | 一种吡啶酮生物碱类化合物及其制备方法和用途 |
| EA202092269A1 (ru) * | 2018-03-23 | 2020-12-14 | Кармот Терапьютикс, Инк. | Модуляторы сопряженных с g-белком рецепторов |
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- 2009-07-15 US US13/003,914 patent/US8372837B2/en active Active
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- 2009-07-15 DK DK09790426.2T patent/DK2313395T3/da active
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- 2009-07-15 JP JP2011518862A patent/JP2011528362A/ja active Pending
- 2009-07-15 CN CN2009801362083A patent/CN102159566A/zh active Pending
- 2009-07-15 PL PL09790426T patent/PL2313395T3/pl unknown
- 2009-07-15 BR BRPI0915918A patent/BRPI0915918A2/pt not_active IP Right Cessation
- 2009-07-15 EP EP09790426A patent/EP2313395B1/en not_active Not-in-force
- 2009-07-15 ES ES09790426T patent/ES2400587T3/es active Active
- 2009-07-15 MX MX2011000394A patent/MX2011000394A/es active IP Right Grant
- 2009-07-15 AR ARP090102687A patent/AR073254A1/es not_active Application Discontinuation
- 2009-07-15 SI SI200930537T patent/SI2313395T1/sl unknown
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2013
- 2013-01-18 US US13/744,604 patent/US20130131074A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| CN102159566A (zh) | 2011-08-17 |
| TW201006821A (en) | 2010-02-16 |
| BRPI0915918A2 (pt) | 2018-07-10 |
| DK2313395T3 (da) | 2013-03-18 |
| EA201100210A1 (ru) | 2011-08-30 |
| EP2313395B1 (en) | 2012-12-19 |
| US20130131074A1 (en) | 2013-05-23 |
| US8372837B2 (en) | 2013-02-12 |
| CY1113715T1 (el) | 2016-06-22 |
| MX2011000394A (es) | 2011-03-01 |
| EP2313395A1 (en) | 2011-04-27 |
| SI2313395T1 (sl) | 2013-04-30 |
| US20110263548A1 (en) | 2011-10-27 |
| AR073254A1 (es) | 2010-10-28 |
| SMT201300040B (it) | 2013-05-06 |
| CA2730929A1 (en) | 2010-01-21 |
| WO2010009183A1 (en) | 2010-01-21 |
| ES2400587T3 (es) | 2013-04-10 |
| PT2313395E (pt) | 2013-03-07 |
| PL2313395T3 (pl) | 2013-05-31 |
| JP2011528362A (ja) | 2011-11-17 |
| HRP20130120T1 (hr) | 2013-03-31 |
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