ZA200103610B - Tricyclic pyrazole derivatives. - Google Patents
Tricyclic pyrazole derivatives. Download PDFInfo
- Publication number
- ZA200103610B ZA200103610B ZA200103610A ZA200103610A ZA200103610B ZA 200103610 B ZA200103610 B ZA 200103610B ZA 200103610 A ZA200103610 A ZA 200103610A ZA 200103610 A ZA200103610 A ZA 200103610A ZA 200103610 B ZA200103610 B ZA 200103610B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- group
- optionally substituted
- alkyl
- dihydroindeno
- Prior art date
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- 150000003217 pyrazoles Chemical class 0.000 title description 3
- -1 tri-substituted phenyl Chemical group 0.000 claims description 512
- 125000000217 alkyl group Chemical group 0.000 claims description 320
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 316
- 229910052799 carbon Inorganic materials 0.000 claims description 180
- 125000003545 alkoxy group Chemical group 0.000 claims description 163
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 150
- 229910052739 hydrogen Inorganic materials 0.000 claims description 133
- 125000005843 halogen group Chemical group 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 95
- 150000002431 hydrogen Chemical class 0.000 claims description 83
- 125000003277 amino group Chemical group 0.000 claims description 78
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 70
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 229910052760 oxygen Inorganic materials 0.000 claims description 57
- 125000004076 pyridyl group Chemical group 0.000 claims description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000001544 thienyl group Chemical group 0.000 claims description 36
- 125000002541 furyl group Chemical group 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 25
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 22
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 21
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 108091008598 receptor tyrosine kinases Proteins 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 102000027426 receptor tyrosine kinases Human genes 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 102000001253 Protein Kinase Human genes 0.000 claims description 13
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 13
- 108060006633 protein kinase Proteins 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 102000004190 Enzymes Human genes 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 230000033115 angiogenesis Effects 0.000 claims description 9
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 claims description 9
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 101100381481 Caenorhabditis elegans baz-2 gene Proteins 0.000 claims description 7
- 101100372762 Rattus norvegicus Flt1 gene Proteins 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 108091000080 Phosphotransferase Proteins 0.000 claims description 5
- 102000020233 phosphotransferase Human genes 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 3
- 206010030113 Oedema Diseases 0.000 claims description 3
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 3
- 208000002780 macular degeneration Diseases 0.000 claims description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 3
- 206010003445 Ascites Diseases 0.000 claims description 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 206010063045 Effusion Diseases 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 230000029663 wound healing Effects 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 45
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 28
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 21
- 125000003342 alkenyl group Chemical group 0.000 claims 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 20
- 125000003282 alkyl amino group Chemical group 0.000 claims 19
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 15
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 14
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 14
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 14
- 125000003368 amide group Chemical group 0.000 claims 14
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 13
- 125000001624 naphthyl group Chemical group 0.000 claims 13
- 125000005554 pyridyloxy group Chemical group 0.000 claims 13
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims 13
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical group CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 0.000 claims 12
- 125000000304 alkynyl group Chemical group 0.000 claims 11
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 10
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 10
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 9
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 8
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 8
- 239000004202 carbamide Substances 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 8
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 7
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 7
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 7
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 7
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 7
- 125000004104 aryloxy group Chemical group 0.000 claims 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 229910052740 iodine Inorganic materials 0.000 claims 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 7
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 7
- 150000003536 tetrazoles Chemical class 0.000 claims 7
- 150000003852 triazoles Chemical class 0.000 claims 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 6
- 230000005764 inhibitory process Effects 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 claims 3
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- ZJZNZNMPNRNCLA-UHFFFAOYSA-N 2-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]ethanol Chemical compound OCCOC1=CC=CC(C=2C3=C(C4=CC=CC=C4C3)NN=2)=C1 ZJZNZNMPNRNCLA-UHFFFAOYSA-N 0.000 claims 2
- BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical compound NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 claims 2
- DEQJKZRYMLWJBH-UHFFFAOYSA-N 3-phenyl-1h-[1]benzothiolo[3,2-c]pyrazole Chemical compound C1=CC=CC=C1C1=NNC2=C1SC1=CC=CC=C12 DEQJKZRYMLWJBH-UHFFFAOYSA-N 0.000 claims 2
- JONNOQBWAKYHJE-UHFFFAOYSA-N 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4C3)NN=2)C=CC=1C(=O)NCCN1CCOCC1 JONNOQBWAKYHJE-UHFFFAOYSA-N 0.000 claims 2
- MRDKBCGWHNPOFW-UHFFFAOYSA-N 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=NNC2=C1CC1=CC=CC=C21 MRDKBCGWHNPOFW-UHFFFAOYSA-N 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims 2
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- WTNAMXIGHPHQLL-UHFFFAOYSA-N n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)acetamide Chemical compound C=1C(NC(=O)C)=CC=C2C=1CC1=C2NN=C1C1=CC=CC=C1 WTNAMXIGHPHQLL-UHFFFAOYSA-N 0.000 claims 2
- OLBCBJLTUPNFPS-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide Chemical compound C1=CC(C(=O)NCCN(CC)CC)=CC=C1C1=NNC2=C1CC1=CC=CC=C21 OLBCBJLTUPNFPS-UHFFFAOYSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RHWVVGJOLLGHPM-UHFFFAOYSA-N 1-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]-1-(2-morpholin-4-ylethyl)urea Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4C3)NN=2)C=CC=1N(C(=O)N)CCN1CCOCC1 RHWVVGJOLLGHPM-UHFFFAOYSA-N 0.000 claims 1
- IFPJOYYOWRGVSW-UHFFFAOYSA-N 1-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]-3-(2-piperidin-1-ylethyl)urea;urea Chemical compound NC(N)=O.C=1C=C(C=2C3=C(C4=CC=CC=C4C3)NN=2)C=CC=1NC(=O)NCCN1CCCCC1 IFPJOYYOWRGVSW-UHFFFAOYSA-N 0.000 claims 1
- CICIXNWIIGJYFK-UHFFFAOYSA-N 1-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]-3-(pyridin-4-ylmethyl)urea Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4C3)NN=2)C=CC=1NC(=O)NCC1=CC=NC=C1 CICIXNWIIGJYFK-UHFFFAOYSA-N 0.000 claims 1
- KAUABWYBFARJAF-UHFFFAOYSA-N 1h-pyrazol-4-ol Chemical compound OC=1C=NNC=1 KAUABWYBFARJAF-UHFFFAOYSA-N 0.000 claims 1
- NEYLQPUBSGXTBO-UHFFFAOYSA-N 2-(1,4-diazepan-1-yl)-n-[4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]acetamide Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4C3)NN=2)C=CC=1NC(=O)CN1CCCNCC1 NEYLQPUBSGXTBO-UHFFFAOYSA-N 0.000 claims 1
- PIPBEWHETLVUCG-UHFFFAOYSA-N 2-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]-n-(2-morpholin-4-ylethyl)acetamide Chemical compound C=1C=CC(C=2C3=C(C4=CC=CC=C4C3)NN=2)=CC=1OCC(=O)NCCN1CCOCC1 PIPBEWHETLVUCG-UHFFFAOYSA-N 0.000 claims 1
- WOWVOEVNUNJEHD-UHFFFAOYSA-N 2-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(C=2C3=C(C4=CC=CC=C4C3)NN=2)=C1 WOWVOEVNUNJEHD-UHFFFAOYSA-N 0.000 claims 1
- JPULUQHTUYCRCO-UHFFFAOYSA-N 2-amino-2-ethyl-n-phenylbutanamide Chemical compound CCC(N)(CC)C(=O)NC1=CC=CC=C1 JPULUQHTUYCRCO-UHFFFAOYSA-N 0.000 claims 1
- XZUCBHPUPYFPNV-UHFFFAOYSA-N 2-chloro-4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol Chemical compound C1=C(Cl)C(O)=CC=C1C1=NNC2=C1CC1=CC=CC=C21 XZUCBHPUPYFPNV-UHFFFAOYSA-N 0.000 claims 1
- GVQMFFMYOWZTFS-UHFFFAOYSA-N 2-ethyl-n-(3-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-6-yl)butanamide Chemical compound C=1C(NC(=O)C(CC)CC)=CC=C(C=2NN=3)C=1CC=2C=3C1=CC=CC=C1 GVQMFFMYOWZTFS-UHFFFAOYSA-N 0.000 claims 1
- FKVIYERFOLSTTM-UHFFFAOYSA-N 2-fluoro-n-phenylacetamide Chemical compound FCC(=O)NC1=CC=CC=C1 FKVIYERFOLSTTM-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (1)
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| US6462036B1 (en) * | 1998-11-06 | 2002-10-08 | Basf Aktiengesellschaft | Tricyclic pyrazole derivatives |
| BR0009322A (pt) * | 1999-03-26 | 2002-04-30 | Euro Celtique Sa | Pirazóis, imidazóis, oxazóis, tiazóis e pirróis substituìdos com arila e o uso dos mesmos |
| US6297238B1 (en) | 1999-04-06 | 2001-10-02 | Basf Aktiengesellschaft | Therapeutic agents |
| DK1165544T3 (da) * | 1999-04-06 | 2003-12-01 | Abbott Gmbh & Co Kg | Substituerede 1,4-dihydroindeno[1,2-c]pyrazoler som inhibitorer af tyrosinkinase |
| US20040048844A1 (en) | 1999-10-20 | 2004-03-11 | Bristol-Myers Squibb Pharma Company | Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents |
| US6291504B1 (en) | 1999-10-20 | 2001-09-18 | Dupont Pharmaceuticals Company | Acylsemicarbazides and their uses |
| DE60125543T2 (de) | 2000-04-05 | 2007-10-04 | Zymogenetics, Inc., Seattle | Löslicher zytokinrezeptor zalpha11 |
| US6723730B2 (en) | 2000-07-20 | 2004-04-20 | Neurogen Corporation | Capsaicin receptor ligands |
| ATE295354T1 (de) | 2000-08-18 | 2005-05-15 | Agouron Pharma | Heterozyklische-hydroximino-fluorene und ihre verwendung zur inhibierung von proteinkinasen |
| US6849631B2 (en) | 2000-12-08 | 2005-02-01 | Bristol Myers Squibb Pharma Company | Semicarbazides and their uses |
| WO2003024935A2 (en) | 2001-09-19 | 2003-03-27 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| US6849653B2 (en) | 2001-09-19 | 2005-02-01 | Pharmacia Corporation | Substituted pyrazolyl benzenesulfamide compounds for the treatment of inflammation |
| MXPA04008680A (es) * | 2002-02-19 | 2004-12-06 | Pharmacia Italia Spa | Derivados de pirazol triciclicos, procedimientos para su preparacion y su uso como agentes anti-tumorales. |
| CA2516254A1 (en) * | 2003-02-17 | 2004-08-26 | Pharmacia Italia S.P.A. | Tetracyclic pyrazole derivatives as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| US7456169B2 (en) | 2003-02-27 | 2008-11-25 | Abbott Laboratories Inc. | Heterocyclic kinase inhibitors |
| JP2006520400A (ja) * | 2003-03-07 | 2006-09-07 | アボット・ラボラトリーズ | 縮合三および四環式ピラゾールキナーゼ阻害剤 |
| US7320986B2 (en) | 2003-03-07 | 2008-01-22 | Abbott Labortories | Fused tri and tetra-cyclic pyrazole kinase inhibitors |
| WO2004092139A2 (en) * | 2003-04-07 | 2004-10-28 | Gpc Biotech, Inc. | Inhibitors of cyclin-dependent kinases, compositions and uses related thereto |
| AR045037A1 (es) | 2003-07-10 | 2005-10-12 | Aventis Pharma Sa | Tetrahidro-1h-pirazolo [3,4-c] piridinas sustituidas, composiciones que las contienen y su utilizacion. |
| GB0326601D0 (en) * | 2003-11-14 | 2003-12-17 | Novartis Ag | Organic compounds |
| EP1740579B1 (en) | 2004-03-24 | 2015-08-19 | AbbVie Inc. | Tricyclic pyrazole kinase inhibitors |
| WO2005118543A1 (ja) * | 2004-06-03 | 2005-12-15 | Ono Pharmaceutical Co., Ltd. | キナーゼ阻害薬およびその用途 |
| PT3424932T (pt) | 2005-02-16 | 2021-05-19 | Anacor Pharmaceuticals Inc | Boronoftalidas para utilização terapêutica |
| JP2009519974A (ja) * | 2005-12-16 | 2009-05-21 | ジェネンテック・インコーポレーテッド | 四環系キナーゼ阻害剤 |
| RU2008131324A (ru) | 2005-12-30 | 2010-02-10 | Анакор Фармасьютикалз, Инк. (Us) | Борсодержащие малые молекулы |
| ES2728455T3 (es) | 2006-02-16 | 2019-10-24 | Anacor Pharmaceuticals Inc | Moléculas pequeñas que contienen boro como agentes antiinflamatorios |
| WO2007132307A1 (en) | 2006-05-09 | 2007-11-22 | Pfizer Products Inc. | Cycloalkylamino acid derivatives and pharmaceutical compositions thereof |
| KR101672511B1 (ko) | 2008-03-06 | 2016-11-03 | 아나코르 파마슈티칼스 인코포레이티드 | 소염제로써 붕소가 함유된 소분자 |
| WO2010028005A1 (en) | 2008-09-04 | 2010-03-11 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| EP2348863A4 (en) | 2008-09-04 | 2012-03-07 | Anacor Pharmaceuticals Inc | BORN SMALL MOLECULES |
| WO2011049971A1 (en) | 2009-10-20 | 2011-04-28 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as antiprotozoal agents |
| EP2597089A1 (en) * | 2009-10-29 | 2013-05-29 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds |
| WO2011060199A1 (en) | 2009-11-11 | 2011-05-19 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules |
| WO2011116348A1 (en) | 2010-03-19 | 2011-09-22 | Anacor Pharmaceuticals, Inc. | Boron-containing small molecules as anti-protozoal agent |
| EP2613788B1 (en) | 2010-09-07 | 2017-06-21 | Anacor Pharmaceuticals, Inc. | Benzoxaborole derivatives for treating bacterial infections |
| US8853207B2 (en) | 2012-04-12 | 2014-10-07 | Development Center For Biotechnology | Heterocyclic pyrazole compounds, method for preparing the same and use thereof |
| CN102675326B (zh) * | 2012-04-26 | 2014-08-20 | 华东理工大学 | 3,4-二氢苯并吡喃[3,4-c]吡唑类三环化合物的制备方法 |
| EP2909212B1 (en) | 2012-09-07 | 2017-02-22 | Takeda Pharmaceutical Company Limited | Substituted 1,4-dihydropyrazolo[4,3-b]indoles |
| JP2016529234A (ja) * | 2013-07-15 | 2016-09-23 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 殺有害生物化合物 |
| WO2016113261A1 (en) * | 2015-01-13 | 2016-07-21 | Basf Se | Fused tricyclic compounds, compositions comprising these compounds and their use for con-trolling invertebrate pests |
| CN105884828A (zh) | 2015-02-16 | 2016-08-24 | 上海迪诺医药科技有限公司 | 多环化合物、其药物组合物及应用 |
| CN110234633A (zh) | 2016-09-02 | 2019-09-13 | 百时美施贵宝公司 | 取代的三环杂环化合物 |
| US11225470B2 (en) | 2016-11-28 | 2022-01-18 | Sumitomo Chemical Company, Limited | Tetrazolinone compounds and its use as pest control agents |
| WO2019032631A1 (en) | 2017-08-09 | 2019-02-14 | Bristol-Myers Squibb Company | OXIME ETHER COMPOUNDS |
| WO2019032632A1 (en) | 2017-08-09 | 2019-02-14 | Bristol-Myers Squibb Company | ALKYLPHENYL COMPOUNDS |
| WO2021115560A1 (en) * | 2019-12-09 | 2021-06-17 | Rottapharm Biotech S.R.L. | New fyn and vegfr2 kinase inhibitors |
| CN113773258B (zh) * | 2020-06-09 | 2023-08-25 | 兰州大学 | 人源lrrk2蛋白小分子抑制剂及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843665A (en) * | 1973-04-11 | 1974-10-22 | Sandoz Ag | Process for preparing substituted indeno,naphtho and cyclohepta pyrazoles |
| JPS60130521A (ja) * | 1983-12-19 | 1985-07-12 | Morishita Seiyaku Kk | 抗癌剤 |
| AU706262B2 (en) * | 1995-10-23 | 1999-06-10 | Osteoscreen, Inc. | Compositions and methods for treating bone deficit conditions |
| EP1021182A1 (en) * | 1997-10-06 | 2000-07-26 | Basf Aktiengesellschaft | Indeno[1,2-c] pyrazole derivatives for inhibiting tyrosine kinase activity |
| CN1278725A (zh) * | 1997-10-06 | 2001-01-03 | 巴斯福股份公司 | 茚并[1,2－c]－、萘并[1,2－c]－和苯并[6,7]芳庚并[1,2－c]吡唑类衍生物 |
-
1999
- 1999-11-04 CN CN99814744A patent/CN1335836A/zh active Pending
- 1999-11-04 PL PL99348210A patent/PL348210A1/xx not_active Application Discontinuation
- 1999-11-04 SK SK528-2001A patent/SK5282001A3/sk unknown
- 1999-11-04 BR BR9915132-4A patent/BR9915132A/pt not_active IP Right Cessation
- 1999-11-04 WO PCT/US1999/026105 patent/WO2000027822A2/en not_active Application Discontinuation
- 1999-11-04 IL IL14258499A patent/IL142584A0/xx unknown
- 1999-11-04 ID IDW00200101001A patent/ID30132A/id unknown
- 1999-11-04 TR TR2001/02277T patent/TR200102277T2/xx unknown
- 1999-11-04 CA CA002350235A patent/CA2350235A1/en not_active Abandoned
- 1999-11-04 AU AU19091/00A patent/AU762992B2/en not_active Ceased
- 1999-11-04 HU HU0200310A patent/HUP0200310A3/hu unknown
- 1999-11-04 KR KR1020017005726A patent/KR20010086005A/ko not_active Application Discontinuation
- 1999-11-04 EP EP99962700A patent/EP1127051A2/en not_active Withdrawn
- 1999-11-04 JP JP2000581002A patent/JP2003517447A/ja active Pending
- 1999-11-04 CZ CZ20011563A patent/CZ20011563A3/cs unknown
-
2001
- 2001-04-27 BG BG105481A patent/BG105481A/xx unknown
- 2001-05-04 ZA ZA200103610A patent/ZA200103610B/en unknown
- 2001-05-04 NO NO20012219A patent/NO20012219L/no not_active Application Discontinuation
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2002
- 2002-05-31 HK HK02104091.8A patent/HK1042895A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010086005A (ko) | 2001-09-07 |
| HUP0200310A3 (en) | 2002-12-28 |
| NO20012219D0 (no) | 2001-05-04 |
| WO2000027822A2 (en) | 2000-05-18 |
| CA2350235A1 (en) | 2000-05-18 |
| TR200102277T2 (tr) | 2002-01-21 |
| SK5282001A3 (en) | 2002-01-07 |
| JP2003517447A (ja) | 2003-05-27 |
| AU762992B2 (en) | 2003-07-10 |
| AU1909100A (en) | 2000-05-29 |
| ID30132A (id) | 2001-11-08 |
| WO2000027822A3 (en) | 2000-08-10 |
| IL142584A0 (en) | 2002-03-10 |
| CN1335836A (zh) | 2002-02-13 |
| HUP0200310A2 (hu) | 2002-11-28 |
| HK1042895A1 (zh) | 2002-08-30 |
| EP1127051A2 (en) | 2001-08-29 |
| BR9915132A (pt) | 2001-08-07 |
| BG105481A (en) | 2001-12-29 |
| NO20012219L (no) | 2001-06-13 |
| PL348210A1 (en) | 2002-05-06 |
| CZ20011563A3 (cs) | 2003-02-12 |
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