OA12046A - 3(5)-Amino-pyrazole derivatives, process for theirpreparation and their use as antitumor agents. - Google Patents

Info

Publication number

OA12046A

OA12046A OA1200200051A OA1200200051A OA12046A OA 12046 A OA12046 A OA 12046A OA 1200200051 A OA1200200051 A OA 1200200051A OA 1200200051 A OA1200200051 A OA 1200200051A OA 12046 A OA12046 A OA 12046A

Authority

OA

OAPI

Prior art keywords

cyclopropyl

pyrazol

acetamide

phenyl

biphenyl

Prior art date

1999-08-12

Links

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• Global Dossier
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• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title claims abstract description 27
• 238000000034 method Methods 0.000 title claims description 38
• 239000002246 antineoplastic agent Substances 0.000 title claims description 11
• 230000008569 process Effects 0.000 title claims description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 174
• 125000003118 aryl group Chemical group 0.000 claims abstract description 26
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• 208000035475 disorder Diseases 0.000 claims abstract description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
• 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 9
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 7
• 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 4
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
• 208000036142 Viral infection Diseases 0.000 claims abstract description 4
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 4
• 230000009385 viral infection Effects 0.000 claims abstract description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 530
• 239000004305 biphenyl Substances 0.000 claims description 187
• -1 aiyl Chemical group 0.000 claims description 125
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 67
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 50
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 40
• 235000010290 biphenyl Nutrition 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 20
• 229920000642 polymer Polymers 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 108091000080 Phosphotransferase Proteins 0.000 claims description 11
• 102000020233 phosphotransferase Human genes 0.000 claims description 11
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 230000003301 hydrolyzing effect Effects 0.000 claims description 8
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 8
• RWWLLDRWXRZEPB-UHFFFAOYSA-N 2-(4-bromophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(Br)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 RWWLLDRWXRZEPB-UHFFFAOYSA-N 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• CSHGNXKXFVXVSH-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-1-phenylcyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)NC(NN=1)=CC=1C1CC1 CSHGNXKXFVXVSH-UHFFFAOYSA-N 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 230000022131 cell cycle Effects 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• ZRKZVQWEOWMPPZ-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NNC(=C2)C2CC2)=C1 ZRKZVQWEOWMPPZ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
• SASTXGCBTVYEKG-UHFFFAOYSA-N 2-[4-(5-acetylthiophen-2-yl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound S1C(C(=O)C)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 SASTXGCBTVYEKG-UHFFFAOYSA-N 0.000 claims description 4
• WCLJSIGYSOSTDV-UHFFFAOYSA-N 3-chloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)thiophene-2-carboxamide Chemical compound C1=CSC(C(=O)NC=2NN=C(C=2)C2CC2)=C1Cl WCLJSIGYSOSTDV-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 229940127089 cytotoxic agent Drugs 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 201000005787 hematologic cancer Diseases 0.000 claims description 4
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• DDFSJDKEEMGHMO-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(2-fluorophenyl)acetamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=CC(C2CC2)=NN1 DDFSJDKEEMGHMO-UHFFFAOYSA-N 0.000 claims description 4
• UYBHLRTZCZUGGN-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(3-formylthiophen-2-yl)phenyl]acetamide Chemical compound C1=CSC(C=2C=CC(CC(=O)NC3=NNC(=C3)C3CC3)=CC=2)=C1C=O UYBHLRTZCZUGGN-UHFFFAOYSA-N 0.000 claims description 4
• BOQUQUULEJPJNK-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-thiophen-2-ylacetamide Chemical compound C1=C(C2CC2)NN=C1NC(=O)CC1=CC=CS1 BOQUQUULEJPJNK-UHFFFAOYSA-N 0.000 claims description 4
• IBKDCAPTVXKXES-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-4-(4-fluorobenzoyl)-1h-pyrrole-2-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)C1=CNC(C(=O)NC=2NN=C(C=2)C2CC2)=C1 IBKDCAPTVXKXES-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 238000001959 radiotherapy Methods 0.000 claims description 4
• 208000037803 restenosis Diseases 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 210000001685 thyroid gland Anatomy 0.000 claims description 4
• 230000002792 vascular Effects 0.000 claims description 4
• LAXIFYBTVBLPOV-QWHCGFSZSA-N (1r,2r)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](C1)C=1C=CC=CC=1)NC(NN=1)=CC=1C1CC1 LAXIFYBTVBLPOV-QWHCGFSZSA-N 0.000 claims description 3
• KRHNLFKGPKBLOS-ZDUSSCGKSA-N (2s)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-hydroxy-2-phenylacetamide Chemical compound O=C([C@@H](O)C=1C=CC=CC=1)NC(=NN1)C=C1C1CC1 KRHNLFKGPKBLOS-ZDUSSCGKSA-N 0.000 claims description 3
• IKTSXTHXYZRAPU-AWEZNQCLSA-N (2s)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-methoxy-2-phenylacetamide Chemical compound O=C([C@@H](OC)C=1C=CC=CC=1)NC(=NN1)C=C1C1CC1 IKTSXTHXYZRAPU-AWEZNQCLSA-N 0.000 claims description 3
• NLKKXCDIGUOEIV-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound FC1=CC=CC(Cl)=C1CC(=O)NC1=NNC(C2CC2)=C1 NLKKXCDIGUOEIV-UHFFFAOYSA-N 0.000 claims description 3
• FQMAZZSFSGDAMX-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound ClC1=CC=CC=C1CC(=O)NC1=CC(C2CC2)=NN1 FQMAZZSFSGDAMX-UHFFFAOYSA-N 0.000 claims description 3
• OWUDYKIZSZRBFC-UHFFFAOYSA-N 2-(3-aminonaphthalen-2-yl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound NC1=CC2=CC=CC=C2C=C1CC(=O)NC(=NN1)C=C1C1CC1 OWUDYKIZSZRBFC-UHFFFAOYSA-N 0.000 claims description 3
• SQOFSKOJGKPQKN-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound ClC1=CC=CC(CC(=O)NC=2NN=C(C=2)C2CC2)=C1 SQOFSKOJGKPQKN-UHFFFAOYSA-N 0.000 claims description 3
• WOYWARLAWHTBQY-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CC(=O)NC1=CC(C2CC2)=NN1 WOYWARLAWHTBQY-UHFFFAOYSA-N 0.000 claims description 3
• LWLAERTXSWJYBG-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound BrC1=CN=CC(CC(=O)NC2=NNC(=C2)C2CC2)=C1 LWLAERTXSWJYBG-UHFFFAOYSA-N 0.000 claims description 3
• MWERTZXXSXAQLE-UHFFFAOYSA-N 2-[3-(2-amino-2-oxoethoxy)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound NC(=O)COC1=CC=CC(CC(=O)NC2=NNC(=C2)C2CC2)=C1 MWERTZXXSXAQLE-UHFFFAOYSA-N 0.000 claims description 3
• TXOFRUXRKZVNSG-UHFFFAOYSA-N 2-[4-(2-amino-6-methyl-4-oxo-1h-pyrimidin-5-yl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound CC1=NC(N)=NC(O)=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 TXOFRUXRKZVNSG-UHFFFAOYSA-N 0.000 claims description 3
• GDRUMFJEBYVIAZ-UHFFFAOYSA-N 2-[4-(4-cyanophenyl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=C(C2CC2)NN=C1NC(=O)CC(C=C1)=CC=C1C1=CC=C(C#N)C=C1 GDRUMFJEBYVIAZ-UHFFFAOYSA-N 0.000 claims description 3
• QWUVWONWOMUHAF-UHFFFAOYSA-N 2-[4-(bromomethyl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(CBr)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 QWUVWONWOMUHAF-UHFFFAOYSA-N 0.000 claims description 3
• LNBBKCQRUKPHJK-UHFFFAOYSA-N 2-[4-(carbamoylamino)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(NC(=O)N)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 LNBBKCQRUKPHJK-UHFFFAOYSA-N 0.000 claims description 3
• HLRFWZRMUGGJHI-UHFFFAOYSA-N 2-[5-[4-[2-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-oxoethyl]phenyl]-1h-indol-3-yl]acetic acid Chemical compound C1=C2C(CC(=O)O)=CNC2=CC=C1C(C=C1)=CC=C1CC(=O)NC(=NN1)C=C1C1CC1 HLRFWZRMUGGJHI-UHFFFAOYSA-N 0.000 claims description 3
• SQORFVOAWZIVLS-UHFFFAOYSA-N 2-chloro-2,2-bis(2-chlorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C(=CC=CC=1)Cl)C(=O)NC1=NNC(C2CC2)=C1 SQORFVOAWZIVLS-UHFFFAOYSA-N 0.000 claims description 3
• IRLQHXQBCHTZPD-UHFFFAOYSA-N 2-cyclohexyl-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-phenylacetamide Chemical compound C1CCCCC1C(C=1C=CC=CC=1)C(=O)NC(NN=1)=CC=1C1CC1 IRLQHXQBCHTZPD-UHFFFAOYSA-N 0.000 claims description 3
• BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 claims description 3
• RZZOQMRNGZYSME-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)prop-2-enamide Chemical compound ClC1=CC=CC=C1C=CC(=O)NC1=CC(C2CC2)=NN1 RZZOQMRNGZYSME-UHFFFAOYSA-N 0.000 claims description 3
• WGKZZCPNRPJVPY-UHFFFAOYSA-N 3-chloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)-4-methylsulfonylthiophene-2-carboxamide Chemical compound CS(=O)(=O)C1=CSC(C(=O)NC2=NNC(=C2)C2CC2)=C1Cl WGKZZCPNRPJVPY-UHFFFAOYSA-N 0.000 claims description 3
• CWTPGQGJXRTOTH-UHFFFAOYSA-N 3-chloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)-4-propan-2-ylsulfonylthiophene-2-carboxamide Chemical compound CC(C)S(=O)(=O)C1=CSC(C(=O)NC2=NNC(=C2)C2CC2)=C1Cl CWTPGQGJXRTOTH-UHFFFAOYSA-N 0.000 claims description 3
• VZQVEDSPJWSGNE-UHFFFAOYSA-N 3-chloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)benzamide Chemical compound ClC1=CC=CC(C(=O)NC2=NNC(=C2)C2CC2)=C1 VZQVEDSPJWSGNE-UHFFFAOYSA-N 0.000 claims description 3
• HOGSTXUBWWWSLQ-UHFFFAOYSA-N 3-cyano-n-(5-cyclopropyl-1h-pyrazol-3-yl)benzamide Chemical compound C=1C=CC(C#N)=CC=1C(=O)NC(NN=1)=CC=1C1CC1 HOGSTXUBWWWSLQ-UHFFFAOYSA-N 0.000 claims description 3
• RZDRNGFJYRPHOW-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NC=2NN=C(C=2)C2CC2)=CC=C1OC1=CC=C(Cl)C=C1 RZDRNGFJYRPHOW-UHFFFAOYSA-N 0.000 claims description 3
• SXLSCHBWYJQWOF-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-(5-cyclopropyl-1h-pyrazol-3-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C(=O)NC=2NN=C(C=2)C2CC2)C=C1 SXLSCHBWYJQWOF-UHFFFAOYSA-N 0.000 claims description 3
• JVPDRXUYMJRVTI-UHFFFAOYSA-N 4-(cyclohexanecarbonyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-1h-pyrrole-2-carboxamide Chemical compound C=1C(C(=O)C2CCCCC2)=CNC=1C(=O)NC(NN=1)=CC=1C1CC1 JVPDRXUYMJRVTI-UHFFFAOYSA-N 0.000 claims description 3
• IFWRXHDSVNMZIT-UHFFFAOYSA-N 4-bromo-n-(5-cyclobutyl-1h-pyrazol-3-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=NNC(C2CCC2)=C1 IFWRXHDSVNMZIT-UHFFFAOYSA-N 0.000 claims description 3
• KTIAVDWJHSVFJO-UHFFFAOYSA-N 4-bromo-n-(5-cyclopentyl-1h-pyrazol-3-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=NNC(C2CCCC2)=C1 KTIAVDWJHSVFJO-UHFFFAOYSA-N 0.000 claims description 3
• WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 3
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
• 208000031481 Pathologic Constriction Diseases 0.000 claims description 3
• 201000010208 Seminoma Diseases 0.000 claims description 3
• 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 3
• 210000003169 central nervous system Anatomy 0.000 claims description 3
• 208000022605 chemotherapy-induced alopecia Diseases 0.000 claims description 3
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 3
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
• 125000004986 diarylamino group Chemical group 0.000 claims description 3
• 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 230000003325 follicular Effects 0.000 claims description 3
• WHUUTDBJXJRKMK-UHFFFAOYSA-L glutamate(2-) Chemical compound [O-]C(=O)C(N)CCC([O-])=O WHUUTDBJXJRKMK-UHFFFAOYSA-L 0.000 claims description 3
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
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• 230000001590 oxidative effect Effects 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims 6
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