JP2012502975A5 - - Google Patents
Download PDFInfo
- Publication number
- 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- Withdrawn
Links
- -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
- LSKWDBADKXIQFN-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-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)=C1C1CC1 LSKWDBADKXIQFN-UHFFFAOYSA-N 0.000 claims 1
- SBTLHVUCPBSIBT-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(1-hydroxy-2-methylpropan-2-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound OCC(C)(C)NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 SBTLHVUCPBSIBT-UHFFFAOYSA-N 0.000 claims 1
- ZPSGDVZKRMFCMX-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(1-methyl-6-oxopiperidin-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC(=O)N(C)CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 ZPSGDVZKRMFCMX-UHFFFAOYSA-N 0.000 claims 1
- ZZWKFOCGDWCDDX-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(1-methylsulfonylazetidin-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(S(C)(=O)=O)CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 ZZWKFOCGDWCDDX-UHFFFAOYSA-N 0.000 claims 1
- JBODGSANAKZLOE-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(1-propanoylazetidin-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(=O)CC)CC1NC(=O)C(N(N=C1C=2C=CC(=CC=2)C#N)C(C)C)=C1C1CC1 JBODGSANAKZLOE-UHFFFAOYSA-N 0.000 claims 1
- UBXGKYILYOCVGB-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2,2-dimethylpropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)(C)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 UBXGKYILYOCVGB-UHFFFAOYSA-N 0.000 claims 1
- WCXVUYXIGPFOGB-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-cyclopropylethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1CCNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 WCXVUYXIGPFOGB-UHFFFAOYSA-N 0.000 claims 1
- WUSZRFPVDRBEDT-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-methoxyethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCCOC)=C1C1CC1 WUSZRFPVDRBEDT-UHFFFAOYSA-N 0.000 claims 1
- KBORPXVRRGHOJB-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(2-oxopropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(=O)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 KBORPXVRRGHOJB-UHFFFAOYSA-N 0.000 claims 1
- VJQZKDYGAKVNHM-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(3-methoxypropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCCCOC)=C1C1CC1 VJQZKDYGAKVNHM-UHFFFAOYSA-N 0.000 claims 1
- OIAAHTXRBGPLJC-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(cyclopropylmethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 OIAAHTXRBGPLJC-UHFFFAOYSA-N 0.000 claims 1
- PNXMWRMYLRHPOU-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(cyclopropylmethyl)-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CC1CN(C)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 PNXMWRMYLRHPOU-UHFFFAOYSA-N 0.000 claims 1
- PUHTUSWAWVREGY-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(oxan-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CCOCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 PUHTUSWAWVREGY-UHFFFAOYSA-N 0.000 claims 1
- GDFKDZQZHHFAQS-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(oxan-4-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1COCCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 GDFKDZQZHHFAQS-UHFFFAOYSA-N 0.000 claims 1
- DYTPNQVJXMKNGA-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(oxolan-2-ylmethyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CCOC1CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 DYTPNQVJXMKNGA-UHFFFAOYSA-N 0.000 claims 1
- PMFFJQNIINPWNE-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-(oxolan-3-yl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1COCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 PMFFJQNIINPWNE-UHFFFAOYSA-N 0.000 claims 1
- RWJUUZFBLRWHGJ-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(1-methylpyrazol-4-yl)methyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1=NN(C)C=C1CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 RWJUUZFBLRWHGJ-UHFFFAOYSA-N 0.000 claims 1
- PEWNLSMMUUAIKA-CYBMUJFWSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(2r)-2-hydroxypropyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC[C@H](O)C)=C1C1CC1 PEWNLSMMUUAIKA-CYBMUJFWSA-N 0.000 claims 1
- PEWNLSMMUUAIKA-ZDUSSCGKSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(2s)-2-hydroxypropyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC[C@@H](O)C)=C1C1CC1 PEWNLSMMUUAIKA-ZDUSSCGKSA-N 0.000 claims 1
- UDVMXBBSEPROLV-HXUWFJFHSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(=O)C(C)C)CC[C@H]1NC(=O)C(N(N=C1C=2C=CC(=CC=2)C#N)C(C)C)=C1C1CC1 UDVMXBBSEPROLV-HXUWFJFHSA-N 0.000 claims 1
- FEDQYUGKJRIKKB-GOSISDBHSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3r)-1-methylsulfonylpyrrolidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound N([C@H]1CN(CC1)S(C)(=O)=O)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 FEDQYUGKJRIKKB-GOSISDBHSA-N 0.000 claims 1
- HHYYYIJQMLJIAH-MRXNPFEDSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3r)-5-oxopyrrolidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound N([C@@H]1CC(=O)NC1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 HHYYYIJQMLJIAH-MRXNPFEDSA-N 0.000 claims 1
- UDVMXBBSEPROLV-FQEVSTJZSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3s)-1-(2-methylpropanoyl)pyrrolidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(=O)C(C)C)CC[C@@H]1NC(=O)C(N(N=C1C=2C=CC(=CC=2)C#N)C(C)C)=C1C1CC1 UDVMXBBSEPROLV-FQEVSTJZSA-N 0.000 claims 1
- QXYUZNJWZVXGOS-INIZCTEOSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(3s)-2-oxooxolan-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound N([C@@H]1C(OCC1)=O)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 QXYUZNJWZVXGOS-INIZCTEOSA-N 0.000 claims 1
- UMPUBZWZIUDOOM-GOSISDBHSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(6r)-6,7-dihydro-5h-pyrrolo[1,2-a]imidazol-6-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound N([C@H]1CN2C=CN=C2C1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 UMPUBZWZIUDOOM-GOSISDBHSA-N 0.000 claims 1
- UMPUBZWZIUDOOM-SFHVURJKSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[(6s)-6,7-dihydro-5h-pyrrolo[1,2-a]imidazol-6-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound N([C@@H]1CN2C=CN=C2C1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 UMPUBZWZIUDOOM-SFHVURJKSA-N 0.000 claims 1
- QSMVRLNQTWKTDV-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[1-(1-methylpyrazol-4-yl)ethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1=NN(C)C=C1C(C)NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 QSMVRLNQTWKTDV-UHFFFAOYSA-N 0.000 claims 1
- OOJXSVJVUKKWLL-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[1-(2-methylpropanoyl)azetidin-3-yl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(=O)C(C)C)CC1NC(=O)C(N(N=C1C=2C=CC(=CC=2)C#N)C(C)C)=C1C1CC1 OOJXSVJVUKKWLL-UHFFFAOYSA-N 0.000 claims 1
- VZMRCHJLDZYEIR-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[2-(ethylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC(=O)NCC)=C1C1CC1 VZMRCHJLDZYEIR-UHFFFAOYSA-N 0.000 claims 1
- JMXMTVLYFLKDNA-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[2-(methylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NCC(=O)NC)=C1C1CC1 JMXMTVLYFLKDNA-UHFFFAOYSA-N 0.000 claims 1
- VBPZGYPGYXZUHA-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[3-(2-oxopyrrolidin-1-yl)propyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CCC(=O)N1CCCNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 VBPZGYPGYXZUHA-UHFFFAOYSA-N 0.000 claims 1
- DYTPNQVJXMKNGA-GOSISDBHSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[[(2r)-oxolan-2-yl]methyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C([C@@H]1OCCC1)NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 DYTPNQVJXMKNGA-GOSISDBHSA-N 0.000 claims 1
- DYTPNQVJXMKNGA-SFHVURJKSA-N 5-(4-cyanophenyl)-4-cyclopropyl-n-[[(2s)-oxolan-2-yl]methyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C([C@H]1OCCC1)NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 DYTPNQVJXMKNGA-SFHVURJKSA-N 0.000 claims 1
- AOHXXMCSOZRHPR-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-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)=C1C1CC1 AOHXXMCSOZRHPR-UHFFFAOYSA-N 0.000 claims 1
- JHNKPVKQRMPQAS-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-cyclopropyl-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)=C1C1CC1 JHNKPVKQRMPQAS-UHFFFAOYSA-N 0.000 claims 1
- FCLJBNPOXFMTPP-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-ethyl-n,2-di(propan-2-yl)pyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC(C)C)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 FCLJBNPOXFMTPP-UHFFFAOYSA-N 0.000 claims 1
- PEZVHKVTOBJLHW-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-ethyl-n-(2-hydroxy-2-methylpropyl)-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC(C)(C)O)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 PEZVHKVTOBJLHW-UHFFFAOYSA-N 0.000 claims 1
- AIUUGQUUYHIIFP-CYBMUJFWSA-N 5-(4-cyanophenyl)-4-ethyl-n-[(2r)-2-hydroxypropyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@@H](C)O)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 AIUUGQUUYHIIFP-CYBMUJFWSA-N 0.000 claims 1
- AIUUGQUUYHIIFP-ZDUSSCGKSA-N 5-(4-cyanophenyl)-4-ethyl-n-[(2s)-2-hydroxypropyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC[C@H](C)O)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 AIUUGQUUYHIIFP-ZDUSSCGKSA-N 0.000 claims 1
- IEAYDBOPDLXDKO-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-ethyl-n-[2-(methylamino)-2-oxoethyl]-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC(=O)NC)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 IEAYDBOPDLXDKO-UHFFFAOYSA-N 0.000 claims 1
- ABHXMAYIJUGROV-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-ethyl-n-methyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 ABHXMAYIJUGROV-UHFFFAOYSA-N 0.000 claims 1
- MKDVQMOTGWFXAS-UHFFFAOYSA-N 5-(4-cyanophenyl)-4-methyl-2-(oxolan-3-yl)-n-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCOC1 MKDVQMOTGWFXAS-UHFFFAOYSA-N 0.000 claims 1
- QPVDZLPTLGDRPO-UHFFFAOYSA-N 5-(4-cyanophenyl)-n,2-dicyclopropyl-4-methylpyrazole-3-carboxamide Chemical compound C1CC1NC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CC1 QPVDZLPTLGDRPO-UHFFFAOYSA-N 0.000 claims 1
- FCDGFMMLLIREBJ-UHFFFAOYSA-N 5-(4-cyanophenyl)-n,4-dicyclopropyl-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=1C1CC1 FCDGFMMLLIREBJ-UHFFFAOYSA-N 0.000 claims 1
- YZDIBZSBRCJEEL-UHFFFAOYSA-N 5-(4-cyanophenyl)-n,4-diethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NCC)=C(CC)C(C=2C=CC(=CC=2)C#N)=N1 YZDIBZSBRCJEEL-UHFFFAOYSA-N 0.000 claims 1
- VKBOJTQZXPRWSY-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(2-hydroxy-2-methylpropyl)-4-methyl-2-(oxolan-3-yl)pyrazole-3-carboxamide Chemical compound CC(O)(C)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCOC1 VKBOJTQZXPRWSY-UHFFFAOYSA-N 0.000 claims 1
- RDCCZYHLSAKEIS-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-(cyclopropylmethyl)-4-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC=1C(C=2C=CC(=CC=2)C#N)=NN(C(C)C)C=1C(=O)NCC1CC1 RDCCZYHLSAKEIS-UHFFFAOYSA-N 0.000 claims 1
- RURICRZQHKXBKR-ZGTOLYCTSA-N 5-(4-cyanophenyl)-n-[(2r)-2-hydroxypropyl]-4-methyl-2-(oxolan-3-yl)pyrazole-3-carboxamide Chemical compound C[C@@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCOC1 RURICRZQHKXBKR-ZGTOLYCTSA-N 0.000 claims 1
- RURICRZQHKXBKR-HKALDPMFSA-N 5-(4-cyanophenyl)-n-[(2s)-2-hydroxypropyl]-4-methyl-2-(oxolan-3-yl)pyrazole-3-carboxamide Chemical compound C[C@H](O)CNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCOC1 RURICRZQHKXBKR-HKALDPMFSA-N 0.000 claims 1
- OZSSUUDDOJZMMU-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-cyclobutyl-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1CCC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 OZSSUUDDOJZMMU-UHFFFAOYSA-N 0.000 claims 1
- NNJMDXQZFHKCMQ-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-cyclopropyl-4-(3,3-difluorocyclobutyl)-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=1C1CC(F)(F)C1 NNJMDXQZFHKCMQ-UHFFFAOYSA-N 0.000 claims 1
- WHQQUTRCBTUYPN-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-cyclopropyl-4-ethyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CCC=1C(C=2C=CC(=CC=2)C#N)=NN(C(C)C)C=1C(=O)NC1CC1 WHQQUTRCBTUYPN-UHFFFAOYSA-N 0.000 claims 1
- HFPWGPXJTGLOSR-UHFFFAOYSA-N 5-(4-cyanophenyl)-n-ethyl-4-methyl-2-(oxolan-3-yl)pyrazole-3-carboxamide Chemical compound CCNC(=O)C1=C(C)C(C=2C=CC(=CC=2)C#N)=NN1C1CCOC1 HFPWGPXJTGLOSR-UHFFFAOYSA-N 0.000 claims 1
- 208000005641 Adenomyosis Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- DIJUWBLZTLVHSX-CALCHBBNSA-N N([C@H]1C[C@@H](O)C1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 Chemical compound N([C@H]1C[C@@H](O)C1)C(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 DIJUWBLZTLVHSX-CALCHBBNSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000000450 Pelvic Pain Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 201000009274 endometriosis of uterus Diseases 0.000 claims 1
- 208000007106 menorrhagia Diseases 0.000 claims 1
- DCJDJSMLHVXBHF-UHFFFAOYSA-N methyl 2-[[5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carbonyl]amino]-2-methylpropanoate Chemical compound C=1C=C(C#N)C=CC=1C1=NN(C(C)C)C(C(=O)NC(C)(C)C(=O)OC)=C1C1CC1 DCJDJSMLHVXBHF-UHFFFAOYSA-N 0.000 claims 1
- 208000017708 myomatous neoplasm Diseases 0.000 claims 1
- 210000000754 myometrium Anatomy 0.000 claims 1
- BYHDNQBLRHQLBA-UHFFFAOYSA-N n-(1-acetylazetidin-3-yl)-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound C1N(C(C)=O)CC1NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 BYHDNQBLRHQLBA-UHFFFAOYSA-N 0.000 claims 1
- HOUFMPAPOZWTOF-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(N)(C)CNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 HOUFMPAPOZWTOF-UHFFFAOYSA-N 0.000 claims 1
- QQTZVXXMBPURRW-UHFFFAOYSA-N n-(2-aminoethyl)-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound NCCNC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 QQTZVXXMBPURRW-UHFFFAOYSA-N 0.000 claims 1
- 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
- SBGVKFIPMHCOIC-CQSZACIVSA-N n-[(2r)-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-CQSZACIVSA-N 0.000 claims 1
- 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
- WJAXQXCFEZCZRA-UHFFFAOYSA-N n-tert-butyl-5-(4-cyanophenyl)-4-cyclopropyl-2-propan-2-ylpyrazole-3-carboxamide Chemical compound CC(C)(C)NC(=O)C=1N(C(C)C)N=C(C=2C=CC(=CC=2)C#N)C=1C1CC1 WJAXQXCFEZCZRA-UHFFFAOYSA-N 0.000 claims 1
- 201000004228 ovarian endometrial cancer Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 102000003998 progesterone receptors Human genes 0.000 claims 1
- 108090000468 progesterone receptors Proteins 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9790208P | 2008-09-18 | 2008-09-18 | |
| US61/097,902 | 2008-09-18 | ||
| PCT/IB2009/054038 WO2010032200A1 (en) | 2008-09-18 | 2009-09-16 | Amide compounds useful in therapy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012502975A JP2012502975A (ja) | 2012-02-02 |
| JP2012502975A5 true JP2012502975A5 (OSRAM) | 2012-10-25 |
Family
ID=41269630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011527444A Withdrawn JP2012502975A (ja) | 2008-09-18 | 2009-09-16 | 治療において有用なアミド化合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US8232269B2 (OSRAM) |
| EP (1) | EP2350017A1 (OSRAM) |
| JP (1) | JP2012502975A (OSRAM) |
| KR (1) | KR20110044304A (OSRAM) |
| CN (1) | CN102159548A (OSRAM) |
| AP (1) | AP2011005611A0 (OSRAM) |
| AU (1) | AU2009294290B2 (OSRAM) |
| BR (1) | BRPI0918935A2 (OSRAM) |
| CA (1) | CA2735931A1 (OSRAM) |
| CL (1) | CL2011000570A1 (OSRAM) |
| CO (1) | CO6351734A2 (OSRAM) |
| DO (1) | DOP2011000083A (OSRAM) |
| EA (1) | EA201100368A1 (OSRAM) |
| EC (1) | ECSP11010901A (OSRAM) |
| IL (1) | IL211479A0 (OSRAM) |
| MA (1) | MA32642B1 (OSRAM) |
| MX (1) | MX2011002899A (OSRAM) |
| PE (1) | PE20110793A1 (OSRAM) |
| WO (1) | WO2010032200A1 (OSRAM) |
| ZA (1) | ZA201102690B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013026905B1 (pt) * | 2011-04-21 | 2021-09-14 | Orion Corporation | Compostos de carboxamida moduladora do receptor de andrógeno e seu uso no tratamento e prevenção de câncer de próstata, bem como composições farmacêuticas compreendendo os ditos compostos |
| EP2734042B1 (en) * | 2011-07-21 | 2017-02-01 | The Regents Of The University Of California | Targeting gli proteins in human cancer by small molecules |
| CA2861493C (en) | 2012-02-17 | 2019-09-24 | Eisai R&D Management Co., Ltd. | Methods and compounds useful in the synthesis of orexin-2 receptor antagonists |
| EP2700635A1 (en) | 2012-08-20 | 2014-02-26 | Basf Se | 5-Trifluoromethylpyrazole amides having herbicidal activity |
| WO2014116651A1 (en) | 2013-01-23 | 2014-07-31 | The Regents Of The University Of California | Targeting gli proteins in human cancer by small molecules |
| MY177476A (en) | 2013-02-22 | 2020-09-16 | Pfizer | Pyrrolo [2,3-d]pyrimidine derivatives as inhibitors of janus kinases (jak) |
| WO2014143617A1 (en) * | 2013-03-14 | 2014-09-18 | Teva Women's Health, Inc. | Deuterium-enriched tanaproget and processes for its preparation |
| EP3180344B1 (en) | 2014-08-12 | 2019-09-18 | Pfizer Inc | Pyrrolo[2,3-d]pyrimidine derivatives useful for inhibiting janus kinase |
| 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 |
| CN113993585B (zh) | 2019-03-27 | 2024-10-01 | 英矽智能科技知识产权有限公司 | 双环jak抑制剂及其用途 |
| CN114829357A (zh) * | 2019-10-28 | 2022-07-29 | 中国科学院上海药物研究所 | 五元杂环氧代羧酸类化合物及其医药用途 |
| WO2023217203A2 (zh) * | 2022-05-12 | 2023-11-16 | 西北农林科技大学 | 二苯基吡唑类化合物的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006111856A1 (en) * | 2005-04-20 | 2006-10-26 | Pfizer Limited | Pyrazole derivatives as progesterone receptor antagonists |
| WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
-
2009
- 2009-09-16 CA CA2735931A patent/CA2735931A1/en not_active Abandoned
- 2009-09-16 BR BRPI0918935A patent/BRPI0918935A2/pt not_active IP Right Cessation
- 2009-09-16 AP AP2011005611A patent/AP2011005611A0/xx unknown
- 2009-09-16 WO PCT/IB2009/054038 patent/WO2010032200A1/en not_active Ceased
- 2009-09-16 KR KR1020117006161A patent/KR20110044304A/ko not_active Ceased
- 2009-09-16 EP EP09787204A patent/EP2350017A1/en not_active Withdrawn
- 2009-09-16 JP JP2011527444A patent/JP2012502975A/ja not_active Withdrawn
- 2009-09-16 AU AU2009294290A patent/AU2009294290B2/en not_active Expired - Fee Related
- 2009-09-16 MX MX2011002899A patent/MX2011002899A/es not_active Application Discontinuation
- 2009-09-16 EA EA201100368A patent/EA201100368A1/ru unknown
- 2009-09-16 PE PE2011000628A patent/PE20110793A1/es not_active Application Discontinuation
- 2009-09-16 CN CN2009801364939A patent/CN102159548A/zh active Pending
- 2009-09-17 US US12/561,398 patent/US8232269B2/en not_active Expired - Fee Related
-
2011
- 2011-02-28 IL IL211479A patent/IL211479A0/en unknown
- 2011-03-17 DO DO2011000083A patent/DOP2011000083A/es unknown
- 2011-03-17 CL CL2011000570A patent/CL2011000570A1/es unknown
- 2011-03-17 EC EC2011010901A patent/ECSP11010901A/es unknown
- 2011-03-18 MA MA33710A patent/MA32642B1/fr unknown
- 2011-03-25 CO CO11036952A patent/CO6351734A2/es not_active Application Discontinuation
- 2011-04-11 ZA ZA2011/02690A patent/ZA201102690B/en unknown
-
2012
- 2012-06-18 US US13/525,893 patent/US20120316150A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012502975A5 (OSRAM) | ||
| AU2018360854B2 (en) | Modulators of the integrated stress pathway | |
| KR102566924B1 (ko) | 케모카인 수용체 조절제 및 이의 용도 | |
| CN109641854B (zh) | 整合应激通路的调节剂 | |
| JP6556146B2 (ja) | 複素環化合物 | |
| JP2013516415A5 (OSRAM) | ||
| JP6914933B2 (ja) | ヤヌスキナーゼ、並びにその組成物及びその使用 | |
| JP2014511869A5 (OSRAM) | ||
| KR20120062839A (ko) | 단백질 키나제 억제제로서의 화합물 및 조성물 | |
| RU2016112952A (ru) | Производные индола и индазола | |
| JP2020503299A5 (OSRAM) | ||
| RU2018127315A (ru) | Индуцирующие апоптоз средства для лечения злокачественной опухоли и иммунологических и аутоиммунных заболеваний | |
| JP2004502642A5 (OSRAM) | ||
| JP2014139226A5 (OSRAM) | ||
| RU2011125314A (ru) | Новое производное пиразол-3-карбоксамида, обладающее антагонистической активностью в отношении рецептора 5-нт2в | |
| JP2010514689A5 (OSRAM) | ||
| JP2011524363A5 (OSRAM) | ||
| JPWO2015016206A1 (ja) | 複素環化合物 | |
| JP2012525431A5 (OSRAM) | ||
| JP2016510035A5 (OSRAM) | ||
| JP2019504901A5 (OSRAM) | ||
| RU2007100136A (ru) | Соединения и композиции в качестве ингибиторов протеинкиназы | |
| JP2016518434A (ja) | スルファモイルピロールアミド誘導体およびｂ型肝炎を処置するための医薬品としてのその使用 | |
| RU2666730C2 (ru) | Диазольные лактамы | |
| JP6900491B2 (ja) | ピラゾロピリミジン化合物及びその使用方法 |