NO325530B1 - Bisyklopyrazoler som er aktive som kinaseinhibitorer, fremgangsmate for deres fremstilling og farmasoytiske preparater som inneholder slike forbindelser - Google Patents
Bisyklopyrazoler som er aktive som kinaseinhibitorer, fremgangsmate for deres fremstilling og farmasoytiske preparater som inneholder slike forbindelser Download PDFInfo
- Publication number
- NO325530B1 NO325530B1 NO20030381A NO20030381A NO325530B1 NO 325530 B1 NO325530 B1 NO 325530B1 NO 20030381 A NO20030381 A NO 20030381A NO 20030381 A NO20030381 A NO 20030381A NO 325530 B1 NO325530 B1 NO 325530B1
- Authority
- NO
- Norway
- Prior art keywords
- pyrazol
- dihydropyrrolo
- urea
- acetyl
- tetrahydropyridin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 190
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 28
- 230000008569 process Effects 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 102000001253 Protein Kinase Human genes 0.000 claims abstract description 24
- 108060006633 protein kinase Proteins 0.000 claims abstract description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 201000010099 disease Diseases 0.000 claims abstract description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 1072
- 239000004202 carbamide Substances 0.000 claims description 707
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 573
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 377
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 149
- -1 carbonylamino, formylamino Chemical group 0.000 claims description 144
- 239000001257 hydrogen Substances 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 92
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 63
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 54
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 50
- 229940080818 propionamide Drugs 0.000 claims description 33
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 29
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- 230000000694 effects Effects 0.000 claims description 28
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 230000005764 inhibitory process Effects 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052705 radium Inorganic materials 0.000 claims description 17
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 14
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 14
- 239000004305 biphenyl Substances 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 14
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 14
- 125000001041 indolyl group Chemical group 0.000 claims description 14
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 13
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 13
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 13
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 13
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 13
- 125000005110 aryl thio group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 13
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 13
- 125000004986 diarylamino group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 13
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000004793 Polystyrene Substances 0.000 claims description 8
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 8
- 229920002223 polystyrene Polymers 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 229920005990 polystyrene resin Polymers 0.000 claims description 7
- 239000000126 substance 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
- IWYRNSNSGTZSKM-QXMHVHEDSA-N (z)-n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1\C=C/C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 IWYRNSNSGTZSKM-QXMHVHEDSA-N 0.000 claims description 6
- BRAPWNJIQFCXTK-UHFFFAOYSA-N 4-tert-butyl-n-[5-(2-thiophen-2-ylacetyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=C2CN(C(=O)CC=3SC=CC=3)CC2=NN1 BRAPWNJIQFCXTK-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- JTILILYPQUDTDO-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2,5-dimethoxybenzamide Chemical compound COC1=CC=C(OC)C(C(=O)NC2=C3CN(CC3=NN2)S(=O)(=O)CC=2C=CC=CC=2)=C1 JTILILYPQUDTDO-UHFFFAOYSA-N 0.000 claims description 6
- MNPYFYHKJQJXNK-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-(2-fluorophenyl)acetamide Chemical compound FC1=CC=CC=C1CC(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 MNPYFYHKJQJXNK-UHFFFAOYSA-N 0.000 claims description 6
- QEKQHVDPIMZCGU-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-(3-methylphenyl)acetamide Chemical compound CC1=CC=CC(CC(=O)NC2=C3CN(CC3=NN2)S(=O)(=O)CC=2C=CC=CC=2)=C1 QEKQHVDPIMZCGU-UHFFFAOYSA-N 0.000 claims description 6
- VKLBTPGVGJYVCV-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-chlorobenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 VKLBTPGVGJYVCV-UHFFFAOYSA-N 0.000 claims description 6
- QNFCOBYEOQUHPP-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 QNFCOBYEOQUHPP-UHFFFAOYSA-N 0.000 claims description 6
- MBVBOIITVKQSRR-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 MBVBOIITVKQSRR-UHFFFAOYSA-N 0.000 claims description 6
- VMNXIBZQKUTSTO-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-methylpropanamide Chemical compound C1C2=C(NC(=O)C(C)C)NN=C2CN1S(=O)(=O)CC1=CC=CC=C1 VMNXIBZQKUTSTO-UHFFFAOYSA-N 0.000 claims description 6
- VVZMNSXOCXGCOV-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-naphthalen-1-ylacetamide Chemical compound C=1C=CC2=CC=CC=C2C=1CC(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 VVZMNSXOCXGCOV-UHFFFAOYSA-N 0.000 claims description 6
- TWGOCDQQNLEMGQ-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-phenylacetamide Chemical compound N1N=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=C1NC(=O)CC1=CC=CC=C1 TWGOCDQQNLEMGQ-UHFFFAOYSA-N 0.000 claims description 6
- BWTPWCXRJHBZJC-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-2-phenylpropanamide Chemical compound C=1C=CC=CC=1C(C)C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 BWTPWCXRJHBZJC-UHFFFAOYSA-N 0.000 claims description 6
- CLHBVCHJXQHPED-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3,4-dimethoxybenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 CLHBVCHJXQHPED-UHFFFAOYSA-N 0.000 claims description 6
- GSJAVESYLZFMHC-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3,5-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC(C(=O)NC2=C3CN(CC3=NN2)S(=O)(=O)CC=2C=CC=CC=2)=C1 GSJAVESYLZFMHC-UHFFFAOYSA-N 0.000 claims description 6
- AFIUWLJTRGNSRB-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-cyanobenzamide Chemical compound C=1C=CC(C#N)=CC=1C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 AFIUWLJTRGNSRB-UHFFFAOYSA-N 0.000 claims description 6
- AVRXFSGRXPSFKL-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-piperidin-1-ylpropanamide Chemical compound N1N=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=C1NC(=O)CCN1CCCCC1 AVRXFSGRXPSFKL-UHFFFAOYSA-N 0.000 claims description 6
- CVFSIYAIYXQIOK-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 CVFSIYAIYXQIOK-UHFFFAOYSA-N 0.000 claims description 6
- DFDKSQFNTVGTQP-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-thiophen-2-ylprop-2-enamide Chemical compound C=1C=CSC=1C=CC(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 DFDKSQFNTVGTQP-UHFFFAOYSA-N 0.000 claims description 6
- PLDOPWDWLKBXEF-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-thiophen-2-ylpropanamide Chemical compound N1N=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=C1NC(=O)CCC1=CC=CS1 PLDOPWDWLKBXEF-UHFFFAOYSA-N 0.000 claims description 6
- XYXLPZXXRHKCOO-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-4-cyanobenzamide Chemical compound C=1C=C(C#N)C=CC=1C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 XYXLPZXXRHKCOO-UHFFFAOYSA-N 0.000 claims description 6
- OVJOPVXRAZIXQW-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 OVJOPVXRAZIXQW-UHFFFAOYSA-N 0.000 claims description 6
- UDSAYXMHOGIZIA-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-4-oxo-4-phenylbutanamide Chemical compound N1N=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=C1NC(=O)CCC(=O)C1=CC=CC=C1 UDSAYXMHOGIZIA-UHFFFAOYSA-N 0.000 claims description 6
- NLQORGSESUCNJI-UHFFFAOYSA-N n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-4-oxo-4-thiophen-2-ylbutanamide Chemical compound N1N=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=C1NC(=O)CCC(=O)C1=CC=CS1 NLQORGSESUCNJI-UHFFFAOYSA-N 0.000 claims description 6
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- 230000002062 proliferating effect Effects 0.000 claims description 6
- IWYRNSNSGTZSKM-VAWYXSNFSA-N (e)-n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)-3-phenylprop-2-enamide Chemical compound C=1C=CC=CC=1/C=C/C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)CC1=CC=CC=C1 IWYRNSNSGTZSKM-VAWYXSNFSA-N 0.000 claims description 5
- KKAZXCCMAQLUHV-UHFFFAOYSA-N 4-acetamido-n-(5-benzylsulfonyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC1=C2CN(S(=O)(=O)CC=3C=CC=CC=3)CC2=NN1 KKAZXCCMAQLUHV-UHFFFAOYSA-N 0.000 claims description 5
- QQRXUKGHFOTONV-UHFFFAOYSA-N 4-tert-butyl-n-[5-(3-methylbutyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]benzamide Chemical compound C=12CN(CCC(C)C)CC2=NNC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 QQRXUKGHFOTONV-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
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- YKQNLWSSRMMFFE-UHFFFAOYSA-N n-[5-(3-methylbutanoyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide Chemical compound C=12CN(C(=O)CC(C)C)CC2=NNC=1NC(=O)C(C=C1)=CC=C1N1CCN(C)CC1 YKQNLWSSRMMFFE-UHFFFAOYSA-N 0.000 claims description 2
- WRSXCTFLOVZOKD-UHFFFAOYSA-N n-[5-(4-chloro-2,5-difluorobenzoyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-2-naphthalen-2-ylacetamide Chemical compound C1=C(Cl)C(F)=CC(C(=O)N2CC3=C(NC(=O)CC=4C=C5C=CC=CC5=CC=4)NN=C3C2)=C1F WRSXCTFLOVZOKD-UHFFFAOYSA-N 0.000 claims description 2
- PMKUWBBADZBMDB-UHFFFAOYSA-N n-[5-(4-fluorobenzoyl)-6,6-dimethyl-1,4-dihydropyrrolo[3,4-c]pyrazol-3-yl]cyclopropanecarboxamide Chemical compound N1N=C2C(C)(C)N(C(=O)C=3C=CC(F)=CC=3)CC2=C1NC(=O)C1CC1 PMKUWBBADZBMDB-UHFFFAOYSA-N 0.000 claims description 2
- RFDPNNFLQOIUSS-UHFFFAOYSA-N n-[5-(4-imidazol-1-ylbenzoyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-2-naphthalen-2-ylacetamide Chemical compound C=1C=C2C=CC=CC2=CC=1CC(=O)NC(=C1C2)NN=C1CN2C(=O)C(C=C1)=CC=C1N1C=CN=C1 RFDPNNFLQOIUSS-UHFFFAOYSA-N 0.000 claims description 2
- CVNZGKMLINKIEJ-UHFFFAOYSA-N n-[5-(benzenesulfonyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-2-(4-pyrrolidin-1-ylphenyl)propanamide Chemical compound C=1C=C(N2CCCC2)C=CC=1C(C)C(=O)NC(=C1C2)NN=C1CN2S(=O)(=O)C1=CC=CC=C1 CVNZGKMLINKIEJ-UHFFFAOYSA-N 0.000 claims description 2
- ZRUCHNFMDLHPHC-UHFFFAOYSA-N n-[5-(benzenesulfonyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=C2CN(S(=O)(=O)C=3C=CC=CC=3)CC2=NN1 ZRUCHNFMDLHPHC-UHFFFAOYSA-N 0.000 claims description 2
- YLVQSPBRNXKUMS-UHFFFAOYSA-N n-[5-(butylcarbamoylamino)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-2-pyridin-4-ylacetamide Chemical compound C=12CN(NC(=O)NCCCC)CC2=NNC=1NC(=O)CC1=CC=NC=C1 YLVQSPBRNXKUMS-UHFFFAOYSA-N 0.000 claims description 2
- RUJAQNGTGYTPFI-UHFFFAOYSA-N n-[5-(butylcarbamoylamino)-4-(4-pyrrolidin-1-ylphenyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]acetamide Chemical compound CCCCNC(=O)NN1CC2=NNC(NC(C)=O)=C2C1C(C=C1)=CC=C1N1CCCC1 RUJAQNGTGYTPFI-UHFFFAOYSA-N 0.000 claims description 2
- BDBVDELNYFYOKG-UHFFFAOYSA-N n-[5-(butylcarbamoylamino)-6,6-dimethyl-1,4-dihydropyrrolo[3,4-c]pyrazol-3-yl]-2-phenylacetamide Chemical compound N1N=C2C(C)(C)N(NC(=O)NCCCC)CC2=C1NC(=O)CC1=CC=CC=C1 BDBVDELNYFYOKG-UHFFFAOYSA-N 0.000 claims description 2
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- QLHXPAUBTKZRQO-UHFFFAOYSA-N n-[5-(furan-2-carbonyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-3-yl]-2-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]acetamide Chemical compound N1N=C2CN(C(=O)C=3OC=CC=3)CC2=C1NC(=O)CC(C=C1)=CC=C1N1CCOC1=O QLHXPAUBTKZRQO-UHFFFAOYSA-N 0.000 claims description 2
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- WRLVNJCUDLSWPR-UHFFFAOYSA-N n-[6,6-dimethyl-5-(2-thiophen-2-ylacetyl)-1,4-dihydropyrrolo[3,4-c]pyrazol-3-yl]-4-fluorobenzamide Chemical compound N1N=C2C(C)(C)N(C(=O)CC=3SC=CC=3)CC2=C1NC(=O)C1=CC=C(F)C=C1 WRLVNJCUDLSWPR-UHFFFAOYSA-N 0.000 claims description 2
- ZNKDULITOCQBFB-UHFFFAOYSA-N n-[6,6-dimethyl-5-(2-thiophen-2-ylacetyl)-1,4-dihydropyrrolo[3,4-c]pyrazol-3-yl]cyclopropanecarboxamide Chemical compound N1N=C2C(C)(C)N(C(=O)CC=3SC=CC=3)CC2=C1NC(=O)C1CC1 ZNKDULITOCQBFB-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C40—COMBINATORIAL TECHNOLOGY
- C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
- C40B40/00—Libraries per se, e.g. arrays, mixtures
Landscapes
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- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US63591400A | 2000-08-10 | 2000-08-10 | |
PCT/EP2001/008639 WO2002012242A2 (en) | 2000-08-10 | 2001-07-25 | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
Publications (3)
Publication Number | Publication Date |
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NO20030381D0 NO20030381D0 (no) | 2003-01-24 |
NO20030381L NO20030381L (no) | 2003-02-24 |
NO325530B1 true NO325530B1 (no) | 2008-06-09 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO20030381A NO325530B1 (no) | 2000-08-10 | 2003-01-24 | Bisyklopyrazoler som er aktive som kinaseinhibitorer, fremgangsmate for deres fremstilling og farmasoytiske preparater som inneholder slike forbindelser |
Country Status (29)
Country | Link |
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US (3) | US7541354B2 (ko) |
EP (1) | EP1320531B1 (ko) |
JP (2) | JP4555547B2 (ko) |
KR (1) | KR100904157B1 (ko) |
CN (2) | CN102060857A (ko) |
AR (1) | AR034137A1 (ko) |
AT (1) | ATE480539T1 (ko) |
AU (2) | AU8765401A (ko) |
BR (1) | BR0113176A (ko) |
CA (1) | CA2416527C (ko) |
CY (1) | CY1110914T1 (ko) |
CZ (1) | CZ2003591A3 (ko) |
DE (1) | DE60143041D1 (ko) |
DK (1) | DK1320531T3 (ko) |
EA (1) | EA006381B1 (ko) |
EE (1) | EE05405B1 (ko) |
ES (1) | ES2349762T3 (ko) |
HU (1) | HU229824B1 (ko) |
IL (2) | IL153997A0 (ko) |
MX (1) | MXPA03001169A (ko) |
MY (1) | MY148632A (ko) |
NO (1) | NO325530B1 (ko) |
NZ (1) | NZ524475A (ko) |
PE (1) | PE20020274A1 (ko) |
PL (1) | PL213199B1 (ko) |
PT (1) | PT1320531E (ko) |
SK (1) | SK1882003A3 (ko) |
WO (1) | WO2002012242A2 (ko) |
ZA (1) | ZA200301813B (ko) |
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AU8765401A (en) * | 2000-08-10 | 2002-02-18 | Pharmacia Italia Spa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation andpharmaceutical compositions comprising them |
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BR0311291A (pt) * | 2002-05-17 | 2005-03-29 | Pharmacia Italia Spa | Derivados de aminoindazol ativos como inibidores da cinase, processo para sua preparação e composições farmacêuticas compreendendo os mesmos |
ES2304531T3 (es) * | 2002-07-17 | 2008-10-16 | Pfizer Italia S.R.L. | Derivados heterobiciclicos de pirazol como inhibidores de quinasa. |
MXPA05000947A (es) * | 2002-07-25 | 2005-05-16 | Pharmacia Italia Spa | Biciclo-pirazoles activos como inhibidores de cinasa, procedimiento para su preparacion y composiciones farmaceuticas que los contienen. |
CA2493680C (en) * | 2002-07-25 | 2010-09-07 | Pharmacia Italia S.P.A. | Condensed heterocyclic pyrazole derivatives as kinase inhibitors |
BR0312913A (pt) * | 2002-07-25 | 2005-07-12 | Pharmacia Italia Spa | Ativo de biciclo-pirazóis como inibidores de cinase, processo para sua preparação e composições farmacêuticas compreendendo o mesmo |
UA81790C2 (uk) | 2002-12-19 | 2008-02-11 | Фармация Италия С.П.А. | Заміщені піролопіразольні похідні як інгібітори кінази |
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