OA12046A - 3(5)-Amino-pyrazole derivatives, process for theirpreparation and their use as antitumor agents. - Google Patents
3(5)-Amino-pyrazole derivatives, process for theirpreparation and their use as antitumor agents. Download PDFInfo
- 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
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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
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- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 3
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Classifications
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
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- Physical Education & Sports Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
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US37283199A | 1999-08-12 | 1999-08-12 |
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OA1200200051A OA12046A (en) | 1999-08-12 | 2000-05-05 | 3(5)-Amino-pyrazole derivatives, process for theirpreparation and their use as antitumor agents. |
Country Status (35)
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US (2) | US7034049B1 (fr) |
EP (1) | EP1202733B1 (fr) |
JP (1) | JP2003507329A (fr) |
KR (1) | KR20020060160A (fr) |
CN (1) | CN1373662A (fr) |
AP (1) | AP2002002442A0 (fr) |
AR (1) | AR026122A1 (fr) |
AT (1) | ATE305782T1 (fr) |
AU (1) | AU4971400A (fr) |
BG (1) | BG106480A (fr) |
BR (1) | BR0013143A (fr) |
CA (1) | CA2383555C (fr) |
CZ (1) | CZ2002422A3 (fr) |
DE (1) | DE60023012T2 (fr) |
DK (1) | DK1202733T3 (fr) |
EA (1) | EA005373B1 (fr) |
EE (1) | EE200200065A (fr) |
ES (1) | ES2249270T3 (fr) |
GE (1) | GEP20053476B (fr) |
HK (1) | HK1046866A1 (fr) |
HR (1) | HRP20020128A2 (fr) |
HU (1) | HUP0203542A3 (fr) |
IL (1) | IL147923A0 (fr) |
IS (1) | IS6265A (fr) |
MA (1) | MA25493A1 (fr) |
MX (1) | MXPA02001498A (fr) |
NO (1) | NO20020684L (fr) |
NZ (1) | NZ517237A (fr) |
OA (1) | OA12046A (fr) |
PE (1) | PE20010130A1 (fr) |
PL (1) | PL353455A1 (fr) |
SK (1) | SK1812002A3 (fr) |
WO (1) | WO2001012189A1 (fr) |
YU (1) | YU9602A (fr) |
ZA (1) | ZA200201511B (fr) |
Families Citing this family (157)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9901691D0 (en) | 1999-01-26 | 1999-03-17 | Cerebrus Ltd | Chemical compounds |
JP2003507329A (ja) * | 1999-08-12 | 2003-02-25 | フアルマシア・イタリア・エツセ・ピー・アー | 3(5)−アミノ−ピラゾール誘導体、それらの製造方法および抗腫瘍薬としてのそれらの使用 |
AU2972701A (en) | 2000-02-07 | 2001-08-14 | Bristol Myers Squibb Co | 3-aminopyrazole inhibitors of cyclin dependent kinases |
JP2004507455A (ja) | 2000-04-25 | 2004-03-11 | ブリストル−マイヤーズ スクイブ カンパニー | サイクリン依存性キナーゼ阻害剤としての、5−チオ−、スルフィニル−およびスルホニルピラゾロ[3,4−b]−ピリジンの用途 |
DE10037310A1 (de) | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
AU2001280009A1 (en) * | 2000-08-31 | 2002-03-13 | Pfizer Products Inc. | Pyrazole derivatives and their use as protein kinase inhibitors |
US20020103185A1 (en) * | 2000-08-31 | 2002-08-01 | Sanner Mark A. | Pyrazole derivatives |
AU2002215053A1 (en) * | 2000-11-27 | 2002-06-24 | Pharmacia Italia S.P.A. | Phenylacetamido- pyrazole derivatives and their use as antitumor agents |
US6455559B1 (en) * | 2001-07-19 | 2002-09-24 | Pharmacia Italia S.P.A. | Phenylacetamido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
EP1379524A2 (fr) * | 2001-01-26 | 2004-01-14 | Pharmacia Italia S.p.A. | Derives de chromane, procede de preparation et d'utilisation de ces derives en tant qu'agents antitumoraux |
DE60210058T2 (de) * | 2001-03-02 | 2006-11-09 | F. Hoffmann-La Roche Ag | Alkoxycarbonylamino-heteroaryl-carbonsäurederivate als ip-antagonisten |
SE0100903D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
US6787555B2 (en) | 2001-04-30 | 2004-09-07 | The Procter & Gamble Company | Triazole compounds useful in treating diseases associated with unwanted cytokine activity |
US6727364B2 (en) | 2001-04-30 | 2004-04-27 | The Procter & Gamble Company | Triazole compounds useful in treating diseases associated with unwanted cytokine activity |
JP2004535411A (ja) | 2001-05-25 | 2004-11-25 | ブリストルーマイヤーズ スクイブ カンパニー | マトリックスメタロプロテナーゼ及び/またはTNF−α転換酵素(TACE)の阻害剤としてのヒダントイン及び関連複素環化合物 |
DE10148617A1 (de) * | 2001-09-25 | 2003-04-24 | Schering Ag | Substituierte N-(1,4,5,6-Tetrahydro-cyclopentapyrazol-3-yl)-Derivate, deren Herstellung und Verwendung als Arzneimittel |
DE10148618B4 (de) * | 2001-09-25 | 2007-05-03 | Schering Ag | Substituierte N-(1,4,5,6-Tetrahydro-cyclopentapyrazol-3-yl)-Derivate, deren Herstellung und Verwendung als Arzneimittel |
DE60233420D1 (de) * | 2001-09-27 | 2009-10-01 | Equispharm Co Ltd | Fumagillolderivate und verfahren zu deren herstellung |
SE0103710D0 (sv) | 2001-11-07 | 2001-11-07 | Astrazeneca Ab | Compounds |
AU2002362030A1 (en) * | 2001-11-27 | 2003-06-10 | Fred Hutchinson Cancer Research Center | Methods for inhibiting deacetylase activity |
SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
GB0221246D0 (en) * | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
US6593477B1 (en) | 2002-10-29 | 2003-07-15 | Eastman Kodak Company | Synthesis of 3-acylaminopyrazoles |
CA2508990C (fr) * | 2002-12-10 | 2013-05-28 | Virochem Pharma Inc. | Composes et procedes de traitement ou de prevention d'infections a flavivirus |
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- 2000-05-05 JP JP2001516535A patent/JP2003507329A/ja not_active Withdrawn
- 2000-05-05 IL IL14792300A patent/IL147923A0/xx unknown
- 2000-05-05 CN CN00812732A patent/CN1373662A/zh active Pending
- 2000-05-05 KR KR1020027001857A patent/KR20020060160A/ko not_active Application Discontinuation
- 2000-05-05 EP EP00931906A patent/EP1202733B1/fr not_active Expired - Lifetime
- 2000-05-05 AP APAP/P/2002/002442A patent/AP2002002442A0/en unknown
- 2000-05-05 CA CA002383555A patent/CA2383555C/fr not_active Expired - Fee Related
- 2000-05-05 DE DE60023012T patent/DE60023012T2/de not_active Expired - Fee Related
- 2000-05-05 MX MXPA02001498A patent/MXPA02001498A/es active IP Right Grant
- 2000-05-05 ES ES00931906T patent/ES2249270T3/es not_active Expired - Lifetime
- 2000-05-05 EA EA200200248A patent/EA005373B1/ru not_active IP Right Cessation
- 2000-05-05 AU AU49714/00A patent/AU4971400A/en not_active Abandoned
- 2000-05-05 HU HU0203542A patent/HUP0203542A3/hu unknown
- 2000-05-05 NZ NZ517237A patent/NZ517237A/xx unknown
- 2000-05-05 SK SK181-2002A patent/SK1812002A3/sk unknown
- 2000-05-05 DK DK00931906T patent/DK1202733T3/da active
- 2000-05-05 PL PL00353455A patent/PL353455A1/xx not_active Application Discontinuation
- 2000-05-05 YU YU9602A patent/YU9602A/sh unknown
- 2000-05-05 BR BR0013143-1A patent/BR0013143A/pt not_active Application Discontinuation
- 2000-05-05 GE GE4758A patent/GEP20053476B/en unknown
- 2000-05-05 CZ CZ2002422A patent/CZ2002422A3/cs unknown
- 2000-05-05 AT AT00931906T patent/ATE305782T1/de not_active IP Right Cessation
- 2000-05-05 EE EEP200200065A patent/EE200200065A/xx unknown
- 2000-05-05 US US10/048,486 patent/US7034049B1/en not_active Expired - Fee Related
- 2000-05-05 WO PCT/US2000/006699 patent/WO2001012189A1/fr active IP Right Grant
- 2000-05-05 OA OA1200200051A patent/OA12046A/en unknown
- 2000-05-15 PE PE2000000453A patent/PE20010130A1/es not_active Application Discontinuation
- 2000-05-16 AR ARP000102347A patent/AR026122A1/es unknown
- 2000-09-22 US US09/667,603 patent/US6218418B1/en not_active Expired - Fee Related
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2002
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- 2002-02-12 HR HR20020128A patent/HRP20020128A2/hr not_active Application Discontinuation
- 2002-02-22 ZA ZA200201511A patent/ZA200201511B/xx unknown
- 2002-03-05 BG BG06480A patent/BG106480A/xx unknown
- 2002-03-11 MA MA26549A patent/MA25493A1/fr unknown
- 2002-11-26 HK HK02108532.6A patent/HK1046866A1/zh unknown
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