SK12752000A3 - Inhibítory fosfolipázových enzýmov, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Inhibítory fosfolipázových enzýmov, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK12752000A3 SK12752000A3 SK1275-2000A SK12752000A SK12752000A3 SK 12752000 A3 SK12752000 A3 SK 12752000A3 SK 12752000 A SK12752000 A SK 12752000A SK 12752000 A3 SK12752000 A3 SK 12752000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- cooh
- phenyl
- indol
- benzyl
- Prior art date
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- 108010064785 Phospholipases Proteins 0.000 title claims description 48
- 102000015439 Phospholipases Human genes 0.000 title claims description 48
- 239000003112 inhibitor Substances 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 230000004968 inflammatory condition Effects 0.000 claims abstract description 4
- 241000124008 Mammalia Species 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 395
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 265
- 125000003545 alkoxy group Chemical group 0.000 claims description 249
- -1 -O-phenyl Chemical group 0.000 claims description 189
- 229910052736 halogen Inorganic materials 0.000 claims description 186
- 150000002367 halogens Chemical class 0.000 claims description 186
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 164
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 115
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 113
- 125000001424 substituent group Chemical group 0.000 claims description 111
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 89
- 229910052757 nitrogen Inorganic materials 0.000 claims description 78
- 125000000623 heterocyclic group Chemical group 0.000 claims description 76
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 75
- 229910052760 oxygen Inorganic materials 0.000 claims description 75
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 69
- 229910052717 sulfur Inorganic materials 0.000 claims description 69
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 64
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 64
- 125000005842 heteroatom Chemical group 0.000 claims description 63
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 51
- 150000003536 tetrazoles Chemical class 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 38
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000004076 pyridyl group Chemical group 0.000 claims description 37
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 36
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 36
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 35
- 125000002541 furyl group Chemical group 0.000 claims description 35
- 229940124530 sulfonamide Drugs 0.000 claims description 35
- 125000001544 thienyl group Chemical group 0.000 claims description 35
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 claims description 34
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 34
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 34
- 125000002619 bicyclic group Chemical group 0.000 claims description 33
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 33
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 32
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 32
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 30
- 239000002532 enzyme inhibitor Substances 0.000 claims description 28
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 22
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 18
- 229930192474 thiophene Natural products 0.000 claims description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 16
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000006413 ring segment Chemical group 0.000 claims description 16
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 15
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 15
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 13
- 125000005647 linker group Chemical group 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 11
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 239000003981 vehicle Substances 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 5
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- MRJQDVAHZBEXLG-UHFFFAOYSA-N 2-[5-bromo-1-(cyclopropylmethyl)indol-3-yl]acetic acid Chemical compound C12=CC=C(Br)C=C2C(CC(=O)O)=CN1CC1CC1 MRJQDVAHZBEXLG-UHFFFAOYSA-N 0.000 claims description 3
- OITCGBQODCHTHA-UHFFFAOYSA-N 4-[[5-(cyclopentyloxycarbonylamino)-1-(cyclopropylmethyl)indol-3-yl]methyl]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1CC(C1=CC(NC(=O)OC2CCCC2)=CC=C11)=CN1CC1CC1 OITCGBQODCHTHA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- SKCWSWIRXLRPRW-NTCAYCPXSA-N (e)-3-(1-benzhydryl-5-nitroindol-3-yl)-n-methylsulfonylprop-2-enamide Chemical compound C12=CC=C([N+]([O-])=O)C=C2C(/C=C/C(=O)NS(=O)(=O)C)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 SKCWSWIRXLRPRW-NTCAYCPXSA-N 0.000 claims description 2
- KUJRDHRZOUGACY-OBGWFSINSA-N (e)-3-[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]prop-2-enoic acid Chemical compound C12=CC=C(NC(=O)C3CCCC3)C=C2C(/C=C/C(=O)O)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 KUJRDHRZOUGACY-OBGWFSINSA-N 0.000 claims description 2
- OKXPHWVWNVANJN-KPKJPENVSA-N (e)-4-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]phenoxy]but-2-enoic acid Chemical compound C1=CC(OC/C=C/C(=O)O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OKXPHWVWNVANJN-KPKJPENVSA-N 0.000 claims description 2
- AUHQIFNCMAADGL-UHFFFAOYSA-N 1-[[2,4-bis(trifluoromethyl)phenyl]methyl]-2-methyl-5-phenylmethoxyindole-3-carboxylic acid Chemical compound C=1C=C2N(CC=3C(=CC(=CC=3)C(F)(F)F)C(F)(F)F)C(C)=C(C(O)=O)C2=CC=1OCC1=CC=CC=C1 AUHQIFNCMAADGL-UHFFFAOYSA-N 0.000 claims description 2
- VGYJHLMIQHFBHG-UHFFFAOYSA-N 1-benzhydryl-5-(cyclopentanecarbonylamino)-n-(2-methylphenyl)sulfonylindole-3-carboxamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)C(C1=CC(NC(=O)C2CCCC2)=CC=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 VGYJHLMIQHFBHG-UHFFFAOYSA-N 0.000 claims description 2
- MTNBXMUURNBCCC-UHFFFAOYSA-N 1-benzyl-2-methyl-5-phenylmethoxyindole-3-carboxylic acid Chemical compound C=1C=C2N(CC=3C=CC=CC=3)C(C)=C(C(O)=O)C2=CC=1OCC1=CC=CC=C1 MTNBXMUURNBCCC-UHFFFAOYSA-N 0.000 claims description 2
- QRUPUESEDLSKNZ-UHFFFAOYSA-N 2-(1-benzyl-5-phenylindol-3-yl)acetic acid Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C(CC(=O)O)=CN1CC1=CC=CC=C1 QRUPUESEDLSKNZ-UHFFFAOYSA-N 0.000 claims description 2
- OUNSVKRIQBEBLA-UHFFFAOYSA-N 2-[(1-benzhydryl-5,6-dichloroindol-3-yl)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CC(C1=CC(Cl)=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OUNSVKRIQBEBLA-UHFFFAOYSA-N 0.000 claims description 2
- INBVWZTWWJQLFY-UHFFFAOYSA-N 2-[(1-benzhydryl-6-chloro-5-fluoroindol-3-yl)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CC(C1=CC(F)=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 INBVWZTWWJQLFY-UHFFFAOYSA-N 0.000 claims description 2
- FXSNEPOFZPJJHR-UHFFFAOYSA-N 2-[(1-benzhydryl-6-chloroindol-3-yl)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FXSNEPOFZPJJHR-UHFFFAOYSA-N 0.000 claims description 2
- BKRFANMAHKRHLR-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-5-[3-(trifluoromethyl)phenyl]indol-3-yl]acetic acid Chemical compound C12=CC=C(C=3C=C(C=CC=3)C(F)(F)F)C=C2C(CC(=O)O)=CN1CC1CC1 BKRFANMAHKRHLR-UHFFFAOYSA-N 0.000 claims description 2
- JYHJHUAYWPUVQI-UHFFFAOYSA-N 2-[1-(cyclopropylmethyl)-5-thiophen-2-ylindol-3-yl]acetic acid Chemical compound C12=CC=C(C=3SC=CC=3)C=C2C(CC(=O)O)=CN1CC1CC1 JYHJHUAYWPUVQI-UHFFFAOYSA-N 0.000 claims description 2
- ULUHREPKBPSKFD-UHFFFAOYSA-N 2-[1-[(4-benzylphenyl)methyl]-5-phenylmethoxyindol-3-yl]-2-oxoacetic acid Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C(=O)O)=CN1CC(C=C1)=CC=C1CC1=CC=CC=C1 ULUHREPKBPSKFD-UHFFFAOYSA-N 0.000 claims description 2
- KXTJXZMSZIHMEL-UHFFFAOYSA-N 2-[1-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]methyl]-3-oxopiperazin-2-yl]acetic acid Chemical compound C1CNC(=O)C(CC(=O)O)N1CC(C1=CC(NC(=O)C2CCCC2)=CC=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 KXTJXZMSZIHMEL-UHFFFAOYSA-N 0.000 claims description 2
- NNQKGFIGZVFBHS-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]-2,6-dimethylphenoxy]acetic acid Chemical compound CC1=C(OCC(O)=O)C(C)=CC(CC=2C3=CC=C(Cl)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 NNQKGFIGZVFBHS-UHFFFAOYSA-N 0.000 claims description 2
- QVWZMYOFHCPAET-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]-2-methoxyphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(OC)=CC(CC=2C3=CC=C(Cl)C=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 QVWZMYOFHCPAET-UHFFFAOYSA-N 0.000 claims description 2
- WMWOHFWKPACPEF-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]-3-chlorophenoxy]acetic acid Chemical compound ClC1=CC(OCC(=O)O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 WMWOHFWKPACPEF-UHFFFAOYSA-N 0.000 claims description 2
- ALYNEIFZQLBPJV-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]-3-methoxyphenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ALYNEIFZQLBPJV-UHFFFAOYSA-N 0.000 claims description 2
- MEFQVOHQYGAFNI-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]anilino]-2-oxoacetic acid Chemical compound C1=CC(NC(=O)C(=O)O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MEFQVOHQYGAFNI-UHFFFAOYSA-N 0.000 claims description 2
- WQRVNEKJFAPVSI-UHFFFAOYSA-N 2-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 WQRVNEKJFAPVSI-UHFFFAOYSA-N 0.000 claims description 2
- VAHVXORJLVCFCT-UHFFFAOYSA-N 2-[5-(1-benzofuran-2-yl)-1-benzylindol-3-yl]acetic acid Chemical compound C12=CC=C(C=3OC4=CC=CC=C4C=3)C=C2C(CC(=O)O)=CN1CC1=CC=CC=C1 VAHVXORJLVCFCT-UHFFFAOYSA-N 0.000 claims description 2
- SQDDMBXFDLJDAI-UHFFFAOYSA-N 2-[[1-[bis(4-hydroxyphenyl)methyl]-6-chloroindol-3-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 SQDDMBXFDLJDAI-UHFFFAOYSA-N 0.000 claims description 2
- ABGMKCKXJOOUHG-UHFFFAOYSA-N 2-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]methylamino]-3-hydroxypropanoic acid Chemical compound C12=CC=C(NC(=O)C3CCCC3)C=C2C(CNC(CO)C(O)=O)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ABGMKCKXJOOUHG-UHFFFAOYSA-N 0.000 claims description 2
- ZZFHRCKGDQIYCF-UHFFFAOYSA-N 2-[[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]-3-methoxybenzoyl]amino]acetic acid Chemical compound COC1=CC(C(=O)NCC(O)=O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZZFHRCKGDQIYCF-UHFFFAOYSA-N 0.000 claims description 2
- VUONEVXDAUPDPA-UHFFFAOYSA-N 3-[1-[3-(3-benzylphenoxy)propyl]indol-3-yl]propanoic acid Chemical compound C12=CC=CC=C2C(CCC(=O)O)=CN1CCCOC(C=1)=CC=CC=1CC1=CC=CC=C1 VUONEVXDAUPDPA-UHFFFAOYSA-N 0.000 claims description 2
- ZHCXKTURUYFQTD-UHFFFAOYSA-N 3-[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]propanoic acid Chemical compound C12=CC=C(NC(=O)C3CCCC3)C=C2C(CCC(=O)O)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZHCXKTURUYFQTD-UHFFFAOYSA-N 0.000 claims description 2
- YAXJOKKNBXDANW-UHFFFAOYSA-N 3-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indole-3-carbonyl]amino]propanoic acid Chemical compound C12=CC=C(NC(=O)C3CCCC3)C=C2C(C(=O)NCCC(=O)O)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YAXJOKKNBXDANW-UHFFFAOYSA-N 0.000 claims description 2
- BPOCKGVPTQODAW-UHFFFAOYSA-N 3-[[2-[1-[(2-benzylsulfonylphenyl)methyl]indol-3-yl]-2-oxoacetyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C(=O)C=2C3=CC=CC=C3N(CC=3C(=CC=CC=3)S(=O)(=O)CC=3C=CC=CC=3)C=2)=C1 BPOCKGVPTQODAW-UHFFFAOYSA-N 0.000 claims description 2
- RMDWGISNCMBXLB-UHFFFAOYSA-N 3-[[2-[1-[(4-benzylphenyl)methyl]-5-phenylmethoxyindol-3-yl]-2-oxoacetyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C(=O)C=2C3=CC(OCC=4C=CC=CC=4)=CC=C3N(CC=3C=CC(CC=4C=CC=CC=4)=CC=3)C=2)=C1 RMDWGISNCMBXLB-UHFFFAOYSA-N 0.000 claims description 2
- URBXOJYDMIXMIE-UHFFFAOYSA-N 3-[[2-[1-[(4-benzylphenyl)methyl]indol-3-yl]-2-oxoacetyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C(=O)C=2C3=CC=CC=C3N(CC=3C=CC(CC=4C=CC=CC=4)=CC=3)C=2)=C1 URBXOJYDMIXMIE-UHFFFAOYSA-N 0.000 claims description 2
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- CSHBFTOJYHWGRS-UHFFFAOYSA-N tert-butyl n-[4-[hydroxy(phenyl)methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(O)C1=CC=CC=C1 CSHBFTOJYHWGRS-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
- 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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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3059298A | 1998-02-25 | 1998-02-25 | |
| PCT/US1999/003898 WO1999043654A2 (en) | 1998-02-25 | 1999-02-24 | Inhibitors of phospholipase enzymes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK12752000A3 true SK12752000A3 (sk) | 2001-03-12 |
Family
ID=21854952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1275-2000A SK12752000A3 (sk) | 1998-02-25 | 1999-02-24 | Inhibítory fosfolipázových enzýmov, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (21)
| Country | Link |
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| EP (1) | EP1062205A2 (et) |
| JP (1) | JP2002504541A (et) |
| KR (1) | KR20010041344A (et) |
| CN (1) | CN1310706A (et) |
| AU (1) | AU765427B2 (et) |
| BG (1) | BG104779A (et) |
| BR (1) | BR9908275A (et) |
| CA (1) | CA2322162A1 (et) |
| EA (1) | EA003876B1 (et) |
| EE (1) | EE200000488A (et) |
| GE (1) | GEP20032920B (et) |
| HR (1) | HRP20000551A2 (et) |
| HU (1) | HUP0101146A3 (et) |
| ID (1) | ID26250A (et) |
| IL (1) | IL137719A0 (et) |
| NO (1) | NO20004219L (et) |
| NZ (1) | NZ506329A (et) |
| PL (1) | PL343007A1 (et) |
| SK (1) | SK12752000A3 (et) |
| TR (1) | TR200002447T2 (et) |
| WO (1) | WO1999043654A2 (et) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE19917504A1 (de) * | 1999-04-17 | 2000-10-19 | Dresden Arzneimittel | Verwendung von Hydroxyindolen, die Inhibitoren der Phosphodiesterase 4 sind, zur Therapie chronisch obstruktiver Lungenerkrankungen |
| AU3656299A (en) * | 1998-05-01 | 1999-11-23 | Eli Lilly And Company | Spla2 inhibitor compounds for treatment of disease |
| TWI269654B (en) * | 1999-09-28 | 2007-01-01 | Baxter Healthcare Sa | N-substituted indole-3-glyoxylamide compounds having anti-tumor action |
| DE19951360A1 (de) * | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| DE19962300A1 (de) * | 1999-12-23 | 2001-06-28 | Asta Medica Ag | Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung |
| DE19963178A1 (de) | 1999-12-27 | 2001-07-05 | Gruenenthal Gmbh | Substituierte Indol-Mannichbasen |
| DE10006139A1 (de) * | 2000-02-11 | 2001-08-16 | Merck Patent Gmbh | Indol-3-yl-Derivate |
| AUPQ876400A0 (en) * | 2000-07-14 | 2000-08-03 | University Of Queensland, The | Compositions and method of using them |
| AU2001277056B2 (en) | 2000-07-25 | 2005-09-29 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
| DE10037310A1 (de) | 2000-07-28 | 2002-02-07 | Asta Medica Ag | Neue Indolderivate und deren Verwendung als Arzneimittel |
| ATE419239T1 (de) | 2000-10-20 | 2009-01-15 | Eisai R&D Man Co Ltd | Verfahren zur herstellung von 4-phenoxy chinolin derivaten |
| CA2465534C (en) | 2000-11-02 | 2009-10-27 | Nigel H. Greig | Agents useful for reducing amyloid precursor protein and treating dementia and methods of use thereof |
| PT1397130E (pt) | 2001-06-20 | 2007-11-13 | Wyeth Corp | Derivados ácidos de indole substituído como inibidores de inibidor 1 do activador de plasminogénio (pai-1) |
| TWI224101B (en) | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
| EP1844771A3 (en) * | 2001-06-20 | 2007-11-07 | Wyeth | Substituted indole acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
| JP2005500345A (ja) | 2001-08-03 | 2005-01-06 | ファルマシア・アンド・アップジョン・カンパニー | 5−ht6受容体親和性を有する5−アリールスルホニルインドール |
| EP1427416A2 (en) | 2001-09-13 | 2004-06-16 | Synta Pharmaceuticals Corporation | 3-glyoxlylamideindoles for treating cancer |
| US6984735B2 (en) | 2001-12-03 | 2006-01-10 | Wyeth | Process for making an aldehyde |
| US7605156B2 (en) | 2001-12-03 | 2009-10-20 | Wyeth | Methods for the use of inhibitors of cytosolic phospholipase A2 |
| US7713964B2 (en) | 2001-12-03 | 2010-05-11 | Wyeth Llc | Methods for treating asthmatic conditions |
| US7101875B2 (en) | 2001-12-03 | 2006-09-05 | Wyeth | Methods for treating arthritic disorders |
| US6797708B2 (en) | 2001-12-03 | 2004-09-28 | Wyeth | Inhibitors of cytosolic phospholipase A2 |
| PL370445A1 (en) * | 2001-12-03 | 2005-05-30 | Wyeth | Inhibitors of cytosolic phospholipase a2 |
| US6635771B2 (en) | 2001-12-03 | 2003-10-21 | Wyeth | N-benzhydryl indole compounds |
| AU2003224257A1 (en) * | 2002-04-09 | 2003-10-27 | Astex Technology Limited | Heterocyclic compounds and their use as modulators of p38 map kinase |
| AUPS282602A0 (en) | 2002-06-07 | 2002-06-27 | Garvan Institute Of Medical Research | Method of inhibiting cell proliferation |
| US7393960B2 (en) | 2002-08-29 | 2008-07-01 | Merck & Co., Inc. | Indoles having anti-diabetic activity |
| CN100457730C (zh) | 2002-08-29 | 2009-02-04 | 默克公司 | 具有抗糖尿病活性的吲哚化合物 |
| CA2509222A1 (en) | 2002-12-10 | 2004-06-24 | Wyeth | Substituted indole oxo-acetyl amino acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (pai-1) |
| EP1569901B1 (en) * | 2002-12-10 | 2008-10-15 | Wyeth | ARYL, ARYLOXY, AND ALKYLOXY SUBSTITUTED i 1H /i -INDOL-3-YL GLYOXYLIC ACID DERIVATIVES AS INHIBITORS OF PLASMINOGEN ACTIVATOR INHIBITOR-1 (PAI-1) |
| UA80453C2 (en) | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
| JP2006514640A (ja) | 2002-12-10 | 2006-05-11 | ワイス | プラスミノゲンアクティベータインヒビターのインヒビターとしての置換3−アルキル及び3−アリールアルキル1h−イル酢酸誘導体 |
| MXPA05006288A (es) | 2002-12-10 | 2005-08-19 | Wyeth Corp | Derivados del acido 3-carbonil-1h-indol-1-ilacetico sustituidos como inhibidores del inhibidor del activador de plasminogeno 1 (pai-1). |
| US7129264B2 (en) * | 2003-04-16 | 2006-10-31 | Bristol-Myers Squibb Company | Biarylmethyl indolines and indoles as antithromboembolic agents |
| US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
| US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
| US7141592B2 (en) | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
| US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
| US7265148B2 (en) | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
| US7442805B2 (en) | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
| US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
| US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
| US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
| US7332521B2 (en) | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
| US7420083B2 (en) | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
| US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
| US7534894B2 (en) | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
| US7417063B2 (en) | 2004-04-13 | 2008-08-26 | Bristol-Myers Squibb Company | Bicyclic heterocycles useful as serine protease inhibitors |
| GB0412769D0 (en) | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| CN101006053A (zh) | 2004-06-18 | 2007-07-25 | 比奥里波克斯公司 | 用于治疗炎症的吲哚 |
| WO2006023866A2 (en) | 2004-08-23 | 2006-03-02 | Wyeth | Thiazolo-naphthyl acids as inhibitors of plasminogen activator inhibitor-1 |
| JP2008510815A (ja) | 2004-08-23 | 2008-04-10 | ワイス | 血栓症および心臓血管疾患の治療にて有用な調節剤であるプラスミノゲン活性化因子阻害剤1型(pai−1)としてのオキサゾロ−ナフチル酸 |
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-
1999
- 1999-02-24 CN CN99805157A patent/CN1310706A/zh active Pending
- 1999-02-24 GE GEAP19995560A patent/GEP20032920B/en unknown
- 1999-02-24 AU AU27825/99A patent/AU765427B2/en not_active Ceased
- 1999-02-24 EE EEP200000488A patent/EE200000488A/et unknown
- 1999-02-24 BR BR9908275-6A patent/BR9908275A/pt not_active IP Right Cessation
- 1999-02-24 HR HR20000551A patent/HRP20000551A2/hr not_active Application Discontinuation
- 1999-02-24 SK SK1275-2000A patent/SK12752000A3/sk unknown
- 1999-02-24 IL IL13771999A patent/IL137719A0/xx unknown
- 1999-02-24 WO PCT/US1999/003898 patent/WO1999043654A2/en not_active Ceased
- 1999-02-24 TR TR2000/02447T patent/TR200002447T2/xx unknown
- 1999-02-24 CA CA002322162A patent/CA2322162A1/en not_active Abandoned
- 1999-02-24 PL PL99343007A patent/PL343007A1/xx unknown
- 1999-02-24 HU HU0101146A patent/HUP0101146A3/hu unknown
- 1999-02-24 EA EA200000871A patent/EA003876B1/ru not_active IP Right Cessation
- 1999-02-24 ID IDW20001595A patent/ID26250A/id unknown
- 1999-02-24 NZ NZ506329A patent/NZ506329A/xx unknown
- 1999-02-24 EP EP99908378A patent/EP1062205A2/en not_active Withdrawn
- 1999-02-24 KR KR1020007009457A patent/KR20010041344A/ko not_active Withdrawn
- 1999-02-24 JP JP2000533412A patent/JP2002504541A/ja not_active Withdrawn
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2000
- 2000-08-23 NO NO20004219A patent/NO20004219L/no not_active Application Discontinuation
- 2000-09-19 BG BG104779A patent/BG104779A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU765427B2 (en) | 2003-09-18 |
| HUP0101146A2 (hu) | 2001-08-28 |
| BG104779A (en) | 2001-10-31 |
| JP2002504541A (ja) | 2002-02-12 |
| WO1999043654A3 (en) | 1999-10-28 |
| HRP20000551A2 (en) | 2001-04-30 |
| TR200002447T2 (tr) | 2000-11-21 |
| NO20004219D0 (no) | 2000-08-23 |
| CA2322162A1 (en) | 1999-09-02 |
| GEP20032920B (en) | 2003-03-25 |
| EA003876B1 (ru) | 2003-10-30 |
| KR20010041344A (ko) | 2001-05-15 |
| EA200000871A1 (ru) | 2001-04-23 |
| HUP0101146A3 (en) | 2001-11-28 |
| AU2782599A (en) | 1999-09-15 |
| BR9908275A (pt) | 2000-10-24 |
| PL343007A1 (en) | 2001-07-30 |
| NO20004219L (no) | 2000-10-23 |
| EP1062205A2 (en) | 2000-12-27 |
| NZ506329A (en) | 2004-01-30 |
| EE200000488A (et) | 2002-02-15 |
| ID26250A (id) | 2000-12-07 |
| IL137719A0 (en) | 2001-10-31 |
| WO1999043654A2 (en) | 1999-09-02 |
| CN1310706A (zh) | 2001-08-29 |
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