HRP20020128A2 - 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents - Google Patents
3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents Download PDFInfo
- Publication number
- HRP20020128A2 HRP20020128A2 HR20020128A HRP20020128A HRP20020128A2 HR P20020128 A2 HRP20020128 A2 HR P20020128A2 HR 20020128 A HR20020128 A HR 20020128A HR P20020128 A HRP20020128 A HR P20020128A HR P20020128 A2 HRP20020128 A2 HR P20020128A2
- Authority
- HR
- Croatia
- Prior art keywords
- cyclopropyl
- pyrazol
- acetamide
- phenyl
- biphenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 40
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000002246 antineoplastic agent Substances 0.000 title claims description 5
- 230000008569 process Effects 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 189
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 89
- -1 β-naphthyl Chemical group 0.000 claims description 80
- 238000006243 chemical reaction Methods 0.000 claims description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 46
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 235000010290 biphenyl Nutrition 0.000 claims description 22
- 239000004305 biphenyl Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 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 13
- 230000000694 effects Effects 0.000 claims description 13
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 102000016736 Cyclin Human genes 0.000 claims description 12
- 108050006400 Cyclin Proteins 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 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 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 108091000080 Phosphotransferase Proteins 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- 102000020233 phosphotransferase Human genes 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 8
- 239000003814 drug Substances 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
- 239000002253 acid Substances 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
- 201000011510 cancer Diseases 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- 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 6
- 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 6
- 230000022131 cell cycle Effects 0.000 claims description 6
- 230000004663 cell proliferation Effects 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
- 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 6
- 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 6
- WQWWGFZSXJKBLV-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(4-pyridin-2-ylphenyl)acetamide Chemical compound C1=C(C2CC2)NN=C1NC(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 WQWWGFZSXJKBLV-UHFFFAOYSA-N 0.000 claims description 6
- BMHKQQMFMAIHFX-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(4-ethylphenyl)phenyl]acetamide Chemical compound C1=CC(CC)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 BMHKQQMFMAIHFX-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- ZNDCZISSHFJHSI-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 ZNDCZISSHFJHSI-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 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
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 238000002512 chemotherapy Methods 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 230000001419 dependent effect 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
- QOANGDYWJQUHJE-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2,5-dimethyl-1-(thiophen-2-ylmethyl)pyrrole-3-carboxamide Chemical compound CC=1N(CC=2SC=CC=2)C(C)=CC=1C(=O)NC(=NN1)C=C1C1CC1 QOANGDYWJQUHJE-UHFFFAOYSA-N 0.000 claims description 5
- SUINGYZBGJLPCS-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(4-methylsulfonylphenyl)acetamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 SUINGYZBGJLPCS-UHFFFAOYSA-N 0.000 claims description 5
- CDEWMDQJPNQZPX-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(4-fluorophenyl)phenyl]acetamide Chemical compound C1=CC(F)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 CDEWMDQJPNQZPX-UHFFFAOYSA-N 0.000 claims description 5
- 238000001959 radiotherapy Methods 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
- DPJRDLPFUUALSA-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=CC(CN)=CC=C1CC(=O)NC1=CC(C2CC2)=NN1 DPJRDLPFUUALSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 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
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl 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
- 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
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 229940079593 drug 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
- 125000006517 heterocyclyl carbonyl group Chemical group 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
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- RXIOHFVHNCXMDS-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[2,2-difluoro-3-(3-fluorophenyl)cyclopropyl]acetamide Chemical compound FC1=CC=CC(C2C(C2CC(=O)NC=2NN=C(C=2)C2CC2)(F)F)=C1 RXIOHFVHNCXMDS-UHFFFAOYSA-N 0.000 claims description 4
- CDEPAFPYGGSMBI-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(4-formylphenyl)phenyl]acetamide Chemical compound C1=CC(C=O)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 CDEPAFPYGGSMBI-UHFFFAOYSA-N 0.000 claims description 4
- ZJYFOLIAAGTQAF-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(4-hydroxyphenyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 ZJYFOLIAAGTQAF-UHFFFAOYSA-N 0.000 claims description 4
- JARUZUKIBXAGQY-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(methanesulfonamido)phenyl]acetamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 JARUZUKIBXAGQY-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
- YNHUQERRJJWIPY-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)quinoxaline-2-carboxamide Chemical compound C=1N=C2C=CC=CC2=NC=1C(=O)NC(NN=1)=CC=1C1CC1 YNHUQERRJJWIPY-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 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
- OOJJENKEQWHNPR-CYBMUJFWSA-N (2r)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-(3-fluoro-4-phenylphenyl)propanamide Chemical compound O=C([C@H](C)C=1C=C(F)C(=CC=1)C=1C=CC=CC=1)NC(NN=1)=CC=1C1CC1 OOJJENKEQWHNPR-CYBMUJFWSA-N 0.000 claims description 3
- IKTSXTHXYZRAPU-CQSZACIVSA-N (2r)-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-CQSZACIVSA-N 0.000 claims description 3
- FBXNIBPDLWTKJM-FQEVSTJZSA-N (2s)-2-amino-3-[5-[4-[2-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-oxoethyl]phenyl]-1h-indol-3-yl]propanoic acid Chemical compound C1=C2C(C[C@H](N)C(O)=O)=CNC2=CC=C1C(C=C1)=CC=C1CC(=O)NC(=NN1)C=C1C1CC1 FBXNIBPDLWTKJM-FQEVSTJZSA-N 0.000 claims description 3
- KTHMSZIGCQCCFJ-ZDUSSCGKSA-N (2s)-2-amino-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-phenylacetamide Chemical compound O=C([C@@H](N)C=1C=CC=CC=1)NC(=NN1)C=C1C1CC1 KTHMSZIGCQCCFJ-ZDUSSCGKSA-N 0.000 claims description 3
- YTASAQPFUKRKQU-QMMMGPOBSA-N (2s)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2,5-dihydro-1h-pyrrole-2-carboxamide Chemical compound O=C([C@@H]1C=CCN1)NC(NN=1)=CC=1C1CC1 YTASAQPFUKRKQU-QMMMGPOBSA-N 0.000 claims description 3
- OUFGAEIXDBKNPC-AWEZNQCLSA-N (2s)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanamide Chemical compound O=C([C@@H](C)C=1C=CC(=CC=1)N1C(C2=CC=CC=C2C1)=O)NC(=NN1)C=C1C1CC1 OUFGAEIXDBKNPC-AWEZNQCLSA-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
- AUXVMZOJPIFVLU-HNNXBMFYSA-N (2s)-n-(5-cyclopropyl-1h-pyrazol-3-yl)-3,3,3-trifluoro-2-methoxy-2-phenylpropanamide Chemical compound O=C([C@@](OC)(C=1C=CC=CC=1)C(F)(F)F)NC(NN=1)=CC=1C1CC1 AUXVMZOJPIFVLU-HNNXBMFYSA-N 0.000 claims description 3
- BCSDSLYDNHZRFR-IZZDOVSWSA-N (e)-3-[3-[4-[2-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-oxoethyl]phenyl]phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C=2C=CC(CC(=O)NC3=NNC(=C3)C3CC3)=CC=2)=C1 BCSDSLYDNHZRFR-IZZDOVSWSA-N 0.000 claims description 3
- ZZFJSNWWKACXIB-LFYBBSHMSA-N (e)-3-[4-[4-[2-[(5-cyclopropyl-1h-pyrazol-3-yl)amino]-2-oxoethyl]phenyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=C1)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 ZZFJSNWWKACXIB-LFYBBSHMSA-N 0.000 claims description 3
- IUQZEGBBRAMGIZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)cyclopentane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)NC2=NNC(=C2)C2CC2)CCCC1 IUQZEGBBRAMGIZ-UHFFFAOYSA-N 0.000 claims description 3
- WHAHMWYRGQQNHC-UHFFFAOYSA-N 2,4-dichloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)-5-fluorobenzamide Chemical compound C1=C(Cl)C(F)=CC(C(=O)NC2=NNC(=C2)C2CC2)=C1Cl WHAHMWYRGQQNHC-UHFFFAOYSA-N 0.000 claims description 3
- DJJJZOBCIZIFJT-UHFFFAOYSA-N 2,5-dichloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)thiophene-3-carboxamide Chemical compound S1C(Cl)=CC(C(=O)NC=2NN=C(C=2)C2CC2)=C1Cl DJJJZOBCIZIFJT-UHFFFAOYSA-N 0.000 claims description 3
- DYPLZZPUFHEBRR-UHFFFAOYSA-N 2,6-dichloro-n-(5-cyclopropyl-1h-pyrazol-3-yl)benzamide Chemical compound ClC1=CC=CC(Cl)=C1C(=O)NC1=NNC(C2CC2)=C1 DYPLZZPUFHEBRR-UHFFFAOYSA-N 0.000 claims description 3
- NAJKFIAJCUNNLM-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C=1SC2=CC=CC=C2C=1CC(=O)NC(NN=1)=CC=1C1CC1 NAJKFIAJCUNNLM-UHFFFAOYSA-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
- KJBKTMDKDKUOLO-UHFFFAOYSA-N 2-(3-bromo-4-methoxyphenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=C(Br)C(OC)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 KJBKTMDKDKUOLO-UHFFFAOYSA-N 0.000 claims description 3
- JMIYBRNRWDGDDI-UHFFFAOYSA-N 2-(3-bromophenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound BrC1=CC=CC(CC(=O)NC2=NNC(=C2)C2CC2)=C1 JMIYBRNRWDGDDI-UHFFFAOYSA-N 0.000 claims description 3
- QSHOXMGRRYCAAC-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-(5-cyclopropyl-1h-pyrazol-3-yl)acetamide Chemical compound C1=C(Cl)C(O)=CC=C1CC(=O)NC1=NNC(C2CC2)=C1 QSHOXMGRRYCAAC-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
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- DQZIKEQUAGVICW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-(5-cyclopropyl-1h-pyrazol-3-yl)pyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1OC1=NC=CC=C1C(=O)NC1=CC(C2CC2)=NN1 DQZIKEQUAGVICW-UHFFFAOYSA-N 0.000 claims description 3
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- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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- 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
- C07D231/16—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)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (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)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Virology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US37283199A | 1999-08-12 | 1999-08-12 | |
PCT/US2000/006699 WO2001012189A1 (en) | 1999-08-12 | 2000-05-05 | 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents |
Publications (1)
Publication Number | Publication Date |
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HRP20020128A2 true HRP20020128A2 (en) | 2003-04-30 |
Family
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HR20020128A HRP20020128A2 (en) | 1999-08-12 | 2002-02-12 | 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents |
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US (2) | US7034049B1 (de) |
EP (1) | EP1202733B1 (de) |
JP (1) | JP2003507329A (de) |
KR (1) | KR20020060160A (de) |
CN (1) | CN1373662A (de) |
AP (1) | AP2002002442A0 (de) |
AR (1) | AR026122A1 (de) |
AT (1) | ATE305782T1 (de) |
AU (1) | AU4971400A (de) |
BG (1) | BG106480A (de) |
BR (1) | BR0013143A (de) |
CA (1) | CA2383555C (de) |
CZ (1) | CZ2002422A3 (de) |
DE (1) | DE60023012T2 (de) |
DK (1) | DK1202733T3 (de) |
EA (1) | EA005373B1 (de) |
EE (1) | EE200200065A (de) |
ES (1) | ES2249270T3 (de) |
GE (1) | GEP20053476B (de) |
HK (1) | HK1046866A1 (de) |
HR (1) | HRP20020128A2 (de) |
HU (1) | HUP0203542A3 (de) |
IL (1) | IL147923A0 (de) |
IS (1) | IS6265A (de) |
MA (1) | MA25493A1 (de) |
MX (1) | MXPA02001498A (de) |
NO (1) | NO20020684L (de) |
NZ (1) | NZ517237A (de) |
OA (1) | OA12046A (de) |
PE (1) | PE20010130A1 (de) |
PL (1) | PL353455A1 (de) |
SK (1) | SK1812002A3 (de) |
WO (1) | WO2001012189A1 (de) |
YU (1) | YU9602A (de) |
ZA (1) | ZA200201511B (de) |
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