RU2015144193A - Галогенпиразолы в качестве ингибиторов тромбина - Google Patents
Галогенпиразолы в качестве ингибиторов тромбина Download PDFInfo
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- RU2015144193A RU2015144193A RU2015144193A RU2015144193A RU2015144193A RU 2015144193 A RU2015144193 A RU 2015144193A RU 2015144193 A RU2015144193 A RU 2015144193A RU 2015144193 A RU2015144193 A RU 2015144193A RU 2015144193 A RU2015144193 A RU 2015144193A
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- substituted
- unsubstituted
- fluoro
- chlorothiophen
- methyl
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- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 50
- 125000003118 aryl group Chemical group 0.000 claims 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 238000000034 method Methods 0.000 claims 13
- -1 5 - [(5-chlorothiophen-2-yl) methyl] amino-4-fluoro-3- (oxan-4-yl) -1H-pyrazol-1-yl Chemical group 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000001544 thienyl group Chemical group 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 9
- 208000007536 Thrombosis Diseases 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 125000003566 oxetanyl group Chemical group 0.000 claims 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims 5
- 125000004474 heteroalkylene group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- 206010014513 Embolism arterial Diseases 0.000 claims 2
- 206010014522 Embolism venous Diseases 0.000 claims 2
- 208000001435 Thromboembolism Diseases 0.000 claims 2
- 230000001269 cardiogenic effect Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 208000004043 venous thromboembolism Diseases 0.000 claims 2
- VVVRDPJUHPXOME-UHFFFAOYSA-N 1-[4-[5-[(5-chlorothiophen-2-yl)methylamino]-1-(2,3-dihydro-1,4-benzodioxine-5-carbonyl)-4-fluoropyrazol-3-yl]phenyl]pyrrolidin-2-one Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)N1N=C(C=2C=CC(=CC=2)N2C(CCC2)=O)C(F)=C1NCC1=CC=C(Cl)S1 VVVRDPJUHPXOME-UHFFFAOYSA-N 0.000 claims 1
- GKYCDIHRVHGHIP-UHFFFAOYSA-N 1-[4-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-1-(2-methoxybenzoyl)pyrazol-3-yl]phenyl]pyrrolidin-2-one Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C=2C=CC(=CC=2)N2C(CCC2)=O)=N1 GKYCDIHRVHGHIP-UHFFFAOYSA-N 0.000 claims 1
- HHGALJPSBFASOJ-UHFFFAOYSA-N 1-[5-(benzylamino)-4-fluoro-3-phenylpyrazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=CC=C1 HHGALJPSBFASOJ-UHFFFAOYSA-N 0.000 claims 1
- JYCHAIMVFMTDKR-UHFFFAOYSA-N 1-[5-(benzylamino)-4-fluoro-3-pyridin-2-ylpyrazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2N=CC=CC=2)C(F)=C1NCC1=CC=CC=C1 JYCHAIMVFMTDKR-UHFFFAOYSA-N 0.000 claims 1
- HRLKXNFBOABUKO-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-3-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4-fluoropyrazol-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)N(CC1)CCC1C(C=1F)=NN(C(=O)C(C)(C)CO)C=1NCC1=CC=C(Cl)S1 HRLKXNFBOABUKO-UHFFFAOYSA-N 0.000 claims 1
- LUDFIQPKZDFJEM-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C=C3CCCC(O)C3=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 LUDFIQPKZDFJEM-UHFFFAOYSA-N 0.000 claims 1
- KEJQPLBDPVKEMM-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound FC1=C(NCC=2SC(Cl)=CC=2)N(C(=O)C(C)(CO)C)N=C1C1CCOCC1 KEJQPLBDPVKEMM-UHFFFAOYSA-N 0.000 claims 1
- HMNBVVOSLOHPOL-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-3-methoxy-2,2-dimethylpropan-1-one Chemical compound FC1=C(NCC=2SC(Cl)=CC=2)N(C(=O)C(C)(C)COC)N=C1C1CCOCC1 HMNBVVOSLOHPOL-UHFFFAOYSA-N 0.000 claims 1
- YKXZEZIMLOLTLH-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 YKXZEZIMLOLTLH-UHFFFAOYSA-N 0.000 claims 1
- YNSLDHRLLMPSNB-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-2-hydroxy-2-methylpropan-1-one Chemical compound CC(C)(O)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 YNSLDHRLLMPSNB-UHFFFAOYSA-N 0.000 claims 1
- JPIBTSRVHVXZBN-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-2-methoxy-2-methylpropan-1-one Chemical compound COC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 JPIBTSRVHVXZBN-UHFFFAOYSA-N 0.000 claims 1
- QILSBTDHXMFDCU-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-3-(2-methoxyethoxy)-2,2-dimethylpropan-1-one Chemical compound COCCOCC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 QILSBTDHXMFDCU-UHFFFAOYSA-N 0.000 claims 1
- YMUNSTMHICDGNC-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound OCC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 YMUNSTMHICDGNC-UHFFFAOYSA-N 0.000 claims 1
- SWTDJZNFPFJRQP-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-3-methoxy-2,2-dimethylpropan-1-one Chemical compound COCC(C)(C)C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 SWTDJZNFPFJRQP-UHFFFAOYSA-N 0.000 claims 1
- OUSJHIBXTVEEFG-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-2-methoxy-2-methylpropan-1-one Chemical compound FC1=C(NCC=2SC(Cl)=CC=2)N(C(=O)C(C)(C)OC)N=C1C1CCNCC1 OUSJHIBXTVEEFG-UHFFFAOYSA-N 0.000 claims 1
- DJVJRNGBPQDBJO-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-3-hydroxy-2,2-dimethylpropan-1-one Chemical compound FC1=C(NCC=2SC(Cl)=CC=2)N(C(=O)C(C)(CO)C)N=C1C1CCNCC1 DJVJRNGBPQDBJO-UHFFFAOYSA-N 0.000 claims 1
- UMADNIUGPMKADU-UHFFFAOYSA-N 1-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-3-methoxy-2,2-dimethylpropan-1-one Chemical compound FC1=C(NCC=2SC(Cl)=CC=2)N(C(=O)C(C)(C)COC)N=C1C1CCNCC1 UMADNIUGPMKADU-UHFFFAOYSA-N 0.000 claims 1
- DRULVWVSZKGIIH-UHFFFAOYSA-N 6-[5-[(5-chlorothiophen-2-yl)methylamino]-1-(2,2-dimethylpropanoyl)-4-fluoropyrazol-3-yl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C=C3CCCC(=O)C3=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 DRULVWVSZKGIIH-UHFFFAOYSA-N 0.000 claims 1
- CFYNRMPDOAJILH-UHFFFAOYSA-N 6-[5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-1-(2-methoxybenzoyl)pyrazol-3-yl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C=2C=C3CCCC(=O)C3=CC=2)=N1 CFYNRMPDOAJILH-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- JTVDTAQXPNXTGX-UHFFFAOYSA-N [3-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-5-(oxan-4-yl)pyrazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=3OCCOC=3C=CC=2)C(C2CCOCC2)=C(F)C=1NCC1=CC=C(Cl)S1 JTVDTAQXPNXTGX-UHFFFAOYSA-N 0.000 claims 1
- JJYAQOXBURBKGN-UHFFFAOYSA-N [3-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-5-(oxan-4-yl)pyrazol-1-yl]-(2,4-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1C(C2CCOCC2)=C(F)C(NCC=2SC(Cl)=CC=2)=N1 JJYAQOXBURBKGN-UHFFFAOYSA-N 0.000 claims 1
- AQWRTUWBEIODPC-UHFFFAOYSA-N [3-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-5-(oxan-4-yl)pyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(C2CCOCC2)=C(F)C(NCC=2SC(Cl)=CC=2)=N1 AQWRTUWBEIODPC-UHFFFAOYSA-N 0.000 claims 1
- NWSTZAZCBVHZCY-UHFFFAOYSA-N [3-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-5-(oxan-4-yl)pyrazol-1-yl]-phenylmethanone Chemical compound N=1N(C(=O)C=2C=CC=CC=2)C(C2CCOCC2)=C(F)C=1NCC1=CC=C(Cl)S1 NWSTZAZCBVHZCY-UHFFFAOYSA-N 0.000 claims 1
- WVWCTFWUTCJOFM-UHFFFAOYSA-N [3-[(5-chlorothiophen-2-yl)methylamino]-5-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4-fluoropyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(C2CCN(CC2)S(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)=C(F)C(NCC=2SC(Cl)=CC=2)=N1 WVWCTFWUTCJOFM-UHFFFAOYSA-N 0.000 claims 1
- RFJMJKBGUAGIFO-UHFFFAOYSA-N [4-[3-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-1h-pyrazol-5-yl]piperidin-1-yl]-(1-hydroxycyclopropyl)methanone Chemical compound C1CC(C2=C(C(NCC=3SC(Cl)=CC=3)=NN2)F)CCN1C(=O)C1(O)CC1 RFJMJKBGUAGIFO-UHFFFAOYSA-N 0.000 claims 1
- VQFCADVXAYMBNM-UHFFFAOYSA-N [5-(benzylamino)-4-fluoro-3-phenylpyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2C=CC=CC=2)=C(F)C(C=2C=CC=CC=2)=N1 VQFCADVXAYMBNM-UHFFFAOYSA-N 0.000 claims 1
- ZSASFIQLWSZLFG-UHFFFAOYSA-N [5-(benzylamino)-4-fluoro-3-pyridin-2-ylpyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2C=CC=CC=2)=C(F)C(C=2N=CC=CC=2)=N1 ZSASFIQLWSZLFG-UHFFFAOYSA-N 0.000 claims 1
- RERBYEJMKXCEAV-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-3-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4-fluoropyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCN(CC2)S(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)=N1 RERBYEJMKXCEAV-UHFFFAOYSA-N 0.000 claims 1
- WNLXJTRUJQCYRU-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)N1N=C(C2CCOCC2)C(F)=C1NCC1=CC=C(Cl)S1 WNLXJTRUJQCYRU-UHFFFAOYSA-N 0.000 claims 1
- YYNNIVLDVFDWTL-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(2,4-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCOCC2)=N1 YYNNIVLDVFDWTL-UHFFFAOYSA-N 0.000 claims 1
- LMEURFSIHPOQNR-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCOCC2)=N1 LMEURFSIHPOQNR-UHFFFAOYSA-N 0.000 claims 1
- ZDXDVCZQVQEJMG-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(4-methyloxan-4-yl)methanone Chemical compound N1=C(C2CCOCC2)C(F)=C(NCC=2SC(Cl)=CC=2)N1C(=O)C1(C)CCOCC1 ZDXDVCZQVQEJMG-UHFFFAOYSA-N 0.000 claims 1
- PLCIVTUFAXTGQS-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)N1N=C(C2CCOCC2)C(F)=C1NCC1=CC=C(Cl)S1 PLCIVTUFAXTGQS-UHFFFAOYSA-N 0.000 claims 1
- YDQDBKJMDXVZLY-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-(furan-3-yl)methanone Chemical compound C1=COC=C1C(=O)N1N=C(C2CCOCC2)C(F)=C1NCC1=CC=C(Cl)S1 YDQDBKJMDXVZLY-UHFFFAOYSA-N 0.000 claims 1
- YIEMZHOIAYJNHX-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-[1-(hydroxymethyl)cyclopropyl]methanone Chemical compound N1=C(C2CCOCC2)C(F)=C(NCC=2SC(Cl)=CC=2)N1C(=O)C1(CO)CC1 YIEMZHOIAYJNHX-UHFFFAOYSA-N 0.000 claims 1
- PWWFYQHPSAIRTE-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-[4-(2-methoxyethoxy)phenyl]methanone Chemical compound C1=CC(OCCOC)=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCOCC2)=N1 PWWFYQHPSAIRTE-UHFFFAOYSA-N 0.000 claims 1
- GIGLTYCAUZBJQL-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)N1N=C(C2CCOCC2)C(F)=C1NCC1=CC=C(Cl)S1 GIGLTYCAUZBJQL-UHFFFAOYSA-N 0.000 claims 1
- ABLJXAXKFVPREL-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-(oxan-4-yl)pyrazol-1-yl]-thiophen-3-ylmethanone Chemical compound C1=CSC=C1C(=O)N1N=C(C2CCOCC2)C(F)=C1NCC1=CC=C(Cl)S1 ABLJXAXKFVPREL-UHFFFAOYSA-N 0.000 claims 1
- RSNNCZRERIBJKL-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-[4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]pyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C=2C=CC(=CC=2)C(O)C(F)(F)F)=N1 RSNNCZRERIBJKL-UHFFFAOYSA-N 0.000 claims 1
- LMRZEDUBKCAKCP-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 LMRZEDUBKCAKCP-UHFFFAOYSA-N 0.000 claims 1
- YNDMMARFYKNMPF-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-(2,4-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C=2C=CC=CC=2)=N1 YNDMMARFYKNMPF-UHFFFAOYSA-N 0.000 claims 1
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- VYZHLHQLGSVAFG-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-(4-methyloxan-4-yl)methanone Chemical compound N1=C(C=2C=CC=CC=2)C(F)=C(NCC=2SC(Cl)=CC=2)N1C(=O)C1(C)CCOCC1 VYZHLHQLGSVAFG-UHFFFAOYSA-N 0.000 claims 1
- BHUNAZGKKNUSFE-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-(furan-3-yl)methanone Chemical compound C1=COC=C1C(=O)N1N=C(C=2C=CC=CC=2)C(F)=C1NCC1=CC=C(Cl)S1 BHUNAZGKKNUSFE-UHFFFAOYSA-N 0.000 claims 1
- LKRDVTZSHQESMB-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-phenylpyrazol-1-yl]-[1-(hydroxymethyl)cyclopropyl]methanone Chemical compound N1=C(C=2C=CC=CC=2)C(F)=C(NCC=2SC(Cl)=CC=2)N1C(=O)C1(CO)CC1 LKRDVTZSHQESMB-UHFFFAOYSA-N 0.000 claims 1
- QTJPWWUOGPZHSV-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-5-yl)methanone Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)N1N=C(C2CCNCC2)C(F)=C1NCC1=CC=C(Cl)S1 QTJPWWUOGPZHSV-UHFFFAOYSA-N 0.000 claims 1
- DHRNXXUANUPUQS-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-(2,4-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCNCC2)=N1 DHRNXXUANUPUQS-UHFFFAOYSA-N 0.000 claims 1
- NMRQZCFRTDOLDV-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C2CCNCC2)=N1 NMRQZCFRTDOLDV-UHFFFAOYSA-N 0.000 claims 1
- TUPUIJGMMTYCQZ-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-piperidin-4-ylpyrazol-1-yl]-(furan-3-yl)methanone Chemical compound C1=COC=C1C(=O)N1N=C(C2CCNCC2)C(F)=C1NCC1=CC=C(Cl)S1 TUPUIJGMMTYCQZ-UHFFFAOYSA-N 0.000 claims 1
- MVTNAJPKGNDKOB-UHFFFAOYSA-N [5-[(5-chlorothiophen-2-yl)methylamino]-4-fluoro-3-pyridin-2-ylpyrazol-1-yl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1C(NCC=2SC(Cl)=CC=2)=C(F)C(C=2N=CC=CC=2)=N1 MVTNAJPKGNDKOB-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361789358P | 2013-03-15 | 2013-03-15 | |
| US61/789,358 | 2013-03-15 | ||
| US201361899588P | 2013-11-04 | 2013-11-04 | |
| US61/899,588 | 2013-11-04 | ||
| PCT/US2014/000058 WO2014149139A2 (en) | 2013-03-15 | 2014-03-17 | Halogenopyrazoles as inhibitors of thrombin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2015144193A true RU2015144193A (ru) | 2017-04-24 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2015144193A RU2015144193A (ru) | 2013-03-15 | 2014-03-17 | Галогенпиразолы в качестве ингибиторов тромбина |
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| Country | Link |
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| US (2) | US9951025B2 (enExample) |
| EP (1) | EP2970141B1 (enExample) |
| JP (3) | JP6479749B2 (enExample) |
| KR (1) | KR20150130405A (enExample) |
| CN (2) | CN110423221A (enExample) |
| AU (2) | AU2014238478B2 (enExample) |
| BR (1) | BR112015023214A8 (enExample) |
| CA (1) | CA2902431A1 (enExample) |
| ES (1) | ES2791749T3 (enExample) |
| HK (1) | HK1214252A1 (enExample) |
| IL (1) | IL240763B (enExample) |
| MX (1) | MX373646B (enExample) |
| RU (1) | RU2015144193A (enExample) |
| SG (2) | SG10201707486XA (enExample) |
| WO (2) | WO2014149139A2 (enExample) |
| ZA (1) | ZA201506440B (enExample) |
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| ES2853483T3 (es) | 2013-03-15 | 2021-09-16 | Verseon Int Corporation | Compuestos aromáticos multisustituidos como inhibidores de la serina proteasa |
| ES2791749T3 (es) | 2013-03-15 | 2020-11-05 | Verseon Corp | Halogenopirazoles como inhibidores de la trombina |
| HK1246164A1 (zh) * | 2015-02-27 | 2018-09-07 | Verseon Corporation | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| SG11202110406SA (en) | 2019-04-11 | 2021-10-28 | Angion Biomedica Corp | Solid forms of (e)-3-[2-(2-thienyl)vinyl]-1h-pyrazole |
| CN112062692A (zh) * | 2019-06-11 | 2020-12-11 | 太仓市茜泾化工有限公司 | 一种乙氧甲叉氰基乙酸乙酯的制备方法 |
| CN112986065B (zh) * | 2021-02-08 | 2021-08-31 | 杭州同创医学检验实验室有限公司 | 一种用于血细胞分析仪的全血质控品及其制备方法 |
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- 2014-03-17 KR KR1020157027980A patent/KR20150130405A/ko not_active Ceased
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| CA2902431A1 (en) | 2014-09-25 |
| CN110423221A (zh) | 2019-11-08 |
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| AU2018250514A1 (en) | 2018-11-15 |
| JP6479749B2 (ja) | 2019-03-06 |
| IL240763A0 (en) | 2015-10-29 |
| BR112015023214A2 (pt) | 2017-07-18 |
| MX2015011567A (es) | 2016-04-25 |
| AU2014238478A1 (en) | 2015-09-10 |
| US20180186751A1 (en) | 2018-07-05 |
| EP2970141A4 (en) | 2016-08-31 |
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| MX373646B (es) | 2020-04-02 |
| CN105209440A (zh) | 2015-12-30 |
| SG11201506757TA (en) | 2015-09-29 |
| KR20150130405A (ko) | 2015-11-23 |
| EP2970141B1 (en) | 2020-02-26 |
| CN105209440B (zh) | 2019-07-23 |
| SG10201707486XA (en) | 2017-10-30 |
| JP2019081782A (ja) | 2019-05-30 |
| US9951025B2 (en) | 2018-04-24 |
| JP2016512243A (ja) | 2016-04-25 |
| AU2014238478B2 (en) | 2018-07-19 |
| WO2014146059A1 (en) | 2014-09-18 |
| BR112015023214A8 (pt) | 2019-12-24 |
| EP2970141A2 (en) | 2016-01-20 |
| HK1214252A1 (zh) | 2016-07-22 |
| WO2014149139A2 (en) | 2014-09-25 |
| IL240763B (en) | 2019-11-28 |
| WO2014149139A3 (en) | 2014-11-27 |
| ES2791749T3 (es) | 2020-11-05 |
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