JP2012502975A5 - - Google Patents
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- JP2012502975A5 JP2012502975A5 JP2011527444A JP2011527444A JP2012502975A5 JP 2012502975 A5 JP2012502975 A5 JP 2012502975A5 JP 2011527444 A JP2011527444 A JP 2011527444A JP 2011527444 A JP2011527444 A JP 2011527444A JP 2012502975 A5 JP2012502975 A5 JP 2012502975A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazole
- carboxamide
- cyanophenyl
- isopropyl
- cyclopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 3-tetrahydrofuranyl Chemical group 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 24
- 239000012453 solvate Substances 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- YIAGHWLJXSQTNF-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC(C)C)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 YIAGHWLJXSQTNF-UHFFFAOYSA-N 0.000 claims 2
- VDSNWLNCUOGZBC-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 VDSNWLNCUOGZBC-UHFFFAOYSA-N 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- LRRUUZSCDWDGOP-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-4-cyclopropyl-n-[2-(methylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C(C)=CC=1C1=NN(C(C)C)C(C(=O)NCC(=O)NC)=C1C1CC1 LRRUUZSCDWDGOP-UHFFFAOYSA-N 0.000 claims 2
- BGJBWNKGIONRMZ-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-(2-hydroxy-2-methylpropyl)-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC1=C(C(=O)NCC(C)(C)O)N(C(C)C)N=C1C1=CC=C(C#N)C(C)=C1 BGJBWNKGIONRMZ-UHFFFAOYSA-N 0.000 claims 2
- HSPGZCZZFFLAIW-ZDUSSCGKSA-N 5-(4-cyano-3-methylphenyl)-n-[(2s)-2-hydroxypropyl]-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@@H](O)C)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 HSPGZCZZFFLAIW-ZDUSSCGKSA-N 0.000 claims 2
- VCVJJXWOLOJNJU-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-hydroxy-2-methylpropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 VCVJJXWOLOJNJU-UHFFFAOYSA-N 0.000 claims 2
- WZKANHVIGHAWDK-IBGZPJMESA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3s)-1-propanoylpyrrolidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(=O)CC)CC[C@@H]1NC(=O)C(N(N=C1C=2C=CC(=CC=2)C#N)C(C)C)=C1C1CC1 WZKANHVIGHAWDK-IBGZPJMESA-N 0.000 claims 2
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- SDZICSPVYMXOSB-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-(2-hydroxy-2-methylpropyl)pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NCC(C)(C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 SDZICSPVYMXOSB-UHFFFAOYSA-N 0.000 claims 1
- QMOWKNTVESEZCI-ARLHGKGLSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[(2r)-2-hydroxypropyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC[C@@H](C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 QMOWKNTVESEZCI-ARLHGKGLSA-N 0.000 claims 1
- QMOWKNTVESEZCI-KZUDCZAMSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[(2s)-2-hydroxypropyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC[C@H](C)O)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 QMOWKNTVESEZCI-KZUDCZAMSA-N 0.000 claims 1
- OTODJUJPEZDJAD-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-[2-(methylamino)-2-oxoethyl]pyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NCC(=O)NC)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 OTODJUJPEZDJAD-UHFFFAOYSA-N 0.000 claims 1
- FFPYOXYDFNUAFY-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-methylpyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 FFPYOXYDFNUAFY-UHFFFAOYSA-N 0.000 claims 1
- ITEZWOJCRBHRKD-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-4-ethyl-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC1=C(C(=O)NC(C)C)N(C(C)CC)N=C1C1=CC=C(C#N)C=C1 ITEZWOJCRBHRKD-UHFFFAOYSA-N 0.000 claims 1
- XRKVQHBODOBNNB-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-n-(cyclopropylmethyl)-4-ethylpyrazole-3-carboxamide Chemical compound CCC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(CC)=C1C(=O)NCC1CC1 XRKVQHBODOBNNB-UHFFFAOYSA-N 0.000 claims 1
- COQQZKHXBCBTTJ-UHFFFAOYSA-N 2-butan-2-yl-5-(4-cyanophenyl)-n-cyclopropyl-4-ethylpyrazole-3-carboxamide Chemical compound CCC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(CC)=C1C(=O)NC1CC1 COQQZKHXBCBTTJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- IEOCDBZXUUPNPG-UHFFFAOYSA-N 4-benzyl-5-(4-cyanophenyl)-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC(C)C)=C1CC1=CC=CC=C1 IEOCDBZXUUPNPG-UHFFFAOYSA-N 0.000 claims 1
- LGAQXDXWEYTAGV-UHFFFAOYSA-N 4-benzyl-5-(4-cyanophenyl)-n-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1CC1=CC=CC=C1 LGAQXDXWEYTAGV-UHFFFAOYSA-N 0.000 claims 1
- OSKNGWSQLJMACL-UHFFFAOYSA-N 4-benzyl-5-(4-cyanophenyl)-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC)=C1CC1=CC=CC=C1 OSKNGWSQLJMACL-UHFFFAOYSA-N 0.000 claims 1
- RRSUQXDTEZPRMH-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-(cyclopropylmethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(C#N)=C1C(=O)NCC1CC1 RRSUQXDTEZPRMH-UHFFFAOYSA-N 0.000 claims 1
- YEWVTHULFRGMBO-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=CC(=CC=2)C#N)C(C#N)=C1C(=O)NC1CC1 YEWVTHULFRGMBO-UHFFFAOYSA-N 0.000 claims 1
- XBTGKQAYTSXSFW-UHFFFAOYSA-N 4-cyano-5-(4-cyanophenyl)-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=C(C#N)C(C=2C=CC(=CC=2)C#N)=N1 XBTGKQAYTSXSFW-UHFFFAOYSA-N 0.000 claims 1
- QYDGVWGFJZRANB-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-4-methyl-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC(C)C)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 QYDGVWGFJZRANB-UHFFFAOYSA-N 0.000 claims 1
- RSLGKBCEJSCKQG-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-4-methyl-n-[2-(methylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC(=O)NC)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 RSLGKBCEJSCKQG-UHFFFAOYSA-N 0.000 claims 1
- KTWAYRSCWRZRGZ-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n,4-dimethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 KTWAYRSCWRZRGZ-UHFFFAOYSA-N 0.000 claims 1
- ZLLBZXOYDXZIBB-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-(cyclopropylmethyl)-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=C(C)C(C#N)=CC=2)C(C)=C1C(=O)NCC1CC1 ZLLBZXOYDXZIBB-UHFFFAOYSA-N 0.000 claims 1
- HSPGZCZZFFLAIW-CYBMUJFWSA-N 5-(4-cyano-3-methylphenyl)-n-[(2r)-2-hydroxypropyl]-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@H](O)C)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 HSPGZCZZFFLAIW-CYBMUJFWSA-N 0.000 claims 1
- QVADJKYRFUVAIF-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-cyclopropyl-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1N=C(C=2C=C(C)C(C#N)=CC=2)C(C)=C1C(=O)NC1CC1 QVADJKYRFUVAIF-UHFFFAOYSA-N 0.000 claims 1
- LZIQYEQHLHOHMT-UHFFFAOYSA-N 5-(4-cyano-3-methylphenyl)-n-ethyl-4-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC)=C(C)C(C=2C=C(C)C(C#N)=CC=2)=N1 LZIQYEQHLHOHMT-UHFFFAOYSA-N 0.000 claims 1
- YVAATYQYZGXYHX-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-4-methyl-n-[2-(methylamino)-2-oxoethyl]pyrazole-3-carboxamide Chemical compound CNC(=O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 YVAATYQYZGXYHX-UHFFFAOYSA-N 0.000 claims 1
- UWCYXOGMFRIUGH-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n,4-dimethylpyrazole-3-carboxamide Chemical compound CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UWCYXOGMFRIUGH-UHFFFAOYSA-N 0.000 claims 1
- TZPWEISEDROZNX-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-(2-hydroxy-2-methylpropyl)-4-methylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 TZPWEISEDROZNX-UHFFFAOYSA-N 0.000 claims 1
- YOQBZXHUZVMUNY-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-(cyclopropylmethyl)-4-methylpyrazole-3-carboxamide Chemical compound C1CC1CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 YOQBZXHUZVMUNY-UHFFFAOYSA-N 0.000 claims 1
- UMIUTNHZINBZSD-GFCCVEGCSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-[(2r)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UMIUTNHZINBZSD-GFCCVEGCSA-N 0.000 claims 1
- UMIUTNHZINBZSD-LBPRGKRZSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-[(2s)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 UMIUTNHZINBZSD-LBPRGKRZSA-N 0.000 claims 1
- QCNXVNKVIAVYEC-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclobutyl-n-cyclopropyl-4-methylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCC1 QCNXVNKVIAVYEC-UHFFFAOYSA-N 0.000 claims 1
- SIVWFSCCEFCZGK-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-4-methyl-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 SIVWFSCCEFCZGK-UHFFFAOYSA-N 0.000 claims 1
- RDPAMRISSWIKCD-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n,4-dimethylpyrazole-3-carboxamide Chemical compound CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 RDPAMRISSWIKCD-UHFFFAOYSA-N 0.000 claims 1
- FBYQOMWMZAJYSY-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-(2-hydroxy-2-methylpropyl)-4-methylpyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 FBYQOMWMZAJYSY-UHFFFAOYSA-N 0.000 claims 1
- WJTRCVPTGKYBLV-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-(cyclopropylmethyl)-4-methylpyrazole-3-carboxamide Chemical compound C1CC1CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 WJTRCVPTGKYBLV-UHFFFAOYSA-N 0.000 claims 1
- MPOJUMRSSPODEY-LLVKDONJSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-[(2r)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 MPOJUMRSSPODEY-LLVKDONJSA-N 0.000 claims 1
- MPOJUMRSSPODEY-NSHDSACASA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-[(2s)-2-hydroxypropyl]-4-methylpyrazole-3-carboxamide Chemical compound C[C@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 MPOJUMRSSPODEY-NSHDSACASA-N 0.000 claims 1
- UKMMKUYMOZCEHR-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-cyclopropyl-n-ethyl-4-methylpyrazole-3-carboxamide Chemical compound CCNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 UKMMKUYMOZCEHR-UHFFFAOYSA-N 0.000 claims 1
- PHTWLGFHZKPPSJ-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-(3,3-difluorocyclobutyl)-n-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC)=C1C1CC(F)(F)C1 PHTWLGFHZKPPSJ-UHFFFAOYSA-N 0.000 claims 1
- VQECVCDXYDUCNV-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-(3,3-difluorocyclobutyl)-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC)=C1C1CC(F)(F)C1 VQECVCDXYDUCNV-UHFFFAOYSA-N 0.000 claims 1
- YPYBHGOWHLTPSH-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-(1-pyrazol-1-ylpropan-2-yl)pyrazole-3-carboxamide Chemical compound C1CC1C=1C(C=2C=CC(=CC=2)C#N)=NN(C(C)C)C=1C(=O)NC(C)CN1C=CC=N1 YPYBHGOWHLTPSH-UHFFFAOYSA-N 0.000 claims 1
- OACGSIMESQKOCL-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-(2,2,2-trifluoroethyl)pyrazole-3-carboxamide Chemical compound FC(F)(F)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 OACGSIMESQKOCL-UHFFFAOYSA-N 0.000 claims 1
- WHUHOJGJYFZXDS-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-(3,3,3-trifluoropropyl)pyrazole-3-carboxamide Chemical compound FC(F)(F)CCNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 WHUHOJGJYFZXDS-UHFFFAOYSA-N 0.000 claims 1
- BJRLXZSHCGSCEJ-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-(pyrimidin-4-ylmethyl)pyrazole-3-carboxamide Chemical compound C=1C=NC=NC=1CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 BJRLXZSHCGSCEJ-UHFFFAOYSA-N 0.000 claims 1
- BQROTUNVXNXQFO-QGZVFWFLSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-[(3r)-pyrrolidin-3-yl]pyrazole-3-carboxamide Chemical compound N([C@H]1CNCC1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 BQROTUNVXNXQFO-QGZVFWFLSA-N 0.000 claims 1
- BQROTUNVXNXQFO-KRWDZBQOSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-[(3s)-pyrrolidin-3-yl]pyrazole-3-carboxamide Chemical compound N([C@@H]1CNCC1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 BQROTUNVXNXQFO-KRWDZBQOSA-N 0.000 claims 1
- VCFGQSOYEVGCLF-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-yl-n-propylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCCC)=C1C1CC1 VCFGQSOYEVGCLF-UHFFFAOYSA-N 0.000 claims 1
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- XKBWGFIBNCHSGP-UHFFFAOYSA-N n-(azetidin-3-yl)-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1NCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 XKBWGFIBNCHSGP-UHFFFAOYSA-N 0.000 claims 1
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- SBGVKFIPMHCOIC-AWEZNQCLSA-N n-[(2s)-butan-2-yl]-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)N[C@@H](C)CC)=C1C1CC1 SBGVKFIPMHCOIC-AWEZNQCLSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 201000004228 ovarian endometrial cancer Diseases 0.000 claims 1
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- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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| CA2831338C (en) * | 2011-04-21 | 2018-07-17 | Orion Corporation | Androgen receptor modulating carboxamides |
| CA2842360C (en) * | 2011-07-21 | 2020-07-07 | The Regents Of The University Of California | Targeting gli proteins in human cancer by small molecules |
| ES2733750T3 (es) | 2012-02-17 | 2019-12-02 | Eisai R&D Man Co Ltd | Métodos y compuestos útiles en la síntesis de antagonistas del receptor de orexina-2 |
| EP2700635A1 (en) | 2012-08-20 | 2014-02-26 | Basf Se | 5-Trifluoromethylpyrazole amides having herbicidal activity |
| ES3007293T3 (en) | 2013-01-23 | 2025-03-19 | Univ California | Targeting gli proteins in human cancer by small molecules |
| EP3290421B1 (en) | 2013-02-22 | 2019-01-02 | Pfizer Inc | Combination of pyrrolo [2, 3 -d]pyrimidine derivatives with one or more additional agents as inhibitors of janus- related kinases (jak) |
| WO2014143617A1 (en) * | 2013-03-14 | 2014-09-18 | Teva Women's Health, Inc. | Deuterium-enriched tanaproget and processes for its preparation |
| JP6585158B2 (ja) | 2014-08-12 | 2019-10-02 | ファイザー・インク | ヤヌスキナーゼの阻害に有用なピロロ［２，３−ｄ］ピリミジン誘導体 |
| US20190321363A1 (en) * | 2016-06-20 | 2019-10-24 | Dr. Reddy's Laboratories Limited | Process for the preparation of elagolix sodium and its polymorph |
| CN108623446A (zh) * | 2017-03-24 | 2018-10-09 | 北京艾德旺科技发展有限公司 | 一种合成3，3-二氟环丁烷甲酸的方法 |
| EP3946606B1 (en) | 2019-03-27 | 2025-01-01 | Insilico Medicine IP Limited | Bicyclic jak inhibitors and uses thereof |
| AU2020373913B2 (en) * | 2019-10-28 | 2024-04-18 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Five-membered heterocyclic oxocarboxylic acid compound and medical use thereof |
| CN118660877A (zh) * | 2022-05-12 | 2024-09-17 | 西北农林科技大学 | 二苯基吡唑类化合物的制备方法 |
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| EP1874732A1 (en) * | 2005-04-20 | 2008-01-09 | Pfizer Limited | Pyrazole derivatives as progesterone receptor antagonists |
| EP1932833B1 (en) * | 2005-10-07 | 2012-08-01 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
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2012
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