KR20110044304A - 치료에 유용한 아마이드 화합물 - Google Patents

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Publication number

KR20110044304A

KR20110044304A KR1020117006161A KR20117006161A KR20110044304A KR 20110044304 A KR20110044304 A KR 20110044304A KR 1020117006161 A KR1020117006161 A KR 1020117006161A KR 20117006161 A KR20117006161 A KR 20117006161A KR 20110044304 A KR20110044304 A KR 20110044304A

Authority

KR

South Korea

Prior art keywords

pyrazole

carboxamide

cyanophenyl

isopropyl

cyclopropyl

Prior art date

2008-09-18

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.)

Ceased

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• Global Dossier
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• 238000011282 treatment Methods 0.000 title claims abstract description 45
• -1 Amide Compounds Chemical class 0.000 title claims description 150
• 150000001875 compounds Chemical class 0.000 claims abstract description 590
• 238000000034 method Methods 0.000 claims abstract description 357
• 239000000203 mixture Substances 0.000 claims abstract description 134
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 92
• 150000003839 salts Chemical class 0.000 claims abstract description 62
• 201000010260 leiomyoma Diseases 0.000 claims abstract description 39
• 239000012453 solvate Substances 0.000 claims abstract description 39
• 201000009273 Endometriosis Diseases 0.000 claims abstract description 37
• 125000001424 substituent group Chemical group 0.000 claims abstract description 31
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
• 150000002367 halogens Chemical class 0.000 claims abstract description 26
• 206010046798 Uterine leiomyoma Diseases 0.000 claims abstract description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract description 8
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 26
• 208000024891 symptom Diseases 0.000 claims description 26
• 208000000450 Pelvic Pain Diseases 0.000 claims description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 206010006187 Breast cancer Diseases 0.000 claims description 17
• 208000026310 Breast neoplasm Diseases 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 15
• 102000003998 progesterone receptors Human genes 0.000 claims description 15
• 108090000468 progesterone receptors Proteins 0.000 claims description 15
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 12
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 11
• 230000001684 chronic effect Effects 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 230000001568 sexual effect Effects 0.000 claims description 11
• 208000003200 Adenoma Diseases 0.000 claims description 10
• 206010001233 Adenoma benign Diseases 0.000 claims description 10
• 206010033128 Ovarian cancer Diseases 0.000 claims description 10
• 239000003085 diluting agent Substances 0.000 claims description 10
• 210000000481 breast Anatomy 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 230000033001 locomotion Effects 0.000 claims description 9
• 230000002611 ovarian Effects 0.000 claims description 9
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 8
• 208000007106 menorrhagia Diseases 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 208000022168 hypermenorrhea Diseases 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 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 description 6
• 206010014733 Endometrial cancer Diseases 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 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 description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000002950 monocyclic group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
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• 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 description 3
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