HRP20000551A2 - Inhibitors of phospholipase enzymes - Google Patents
Inhibitors of phospholipase enzymes Download PDFInfo
- Publication number
- HRP20000551A2 HRP20000551A2 HR20000551A HRP20000551A HRP20000551A2 HR P20000551 A2 HRP20000551 A2 HR P20000551A2 HR 20000551 A HR20000551 A HR 20000551A HR P20000551 A HRP20000551 A HR P20000551A HR P20000551 A2 HRP20000551 A2 HR P20000551A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- cooh
- indol
- phenyl
- alkoxy
- Prior art date
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- 108010064785 Phospholipases Proteins 0.000 title description 10
- 102000015439 Phospholipases Human genes 0.000 title description 10
- 239000003112 inhibitor Substances 0.000 title description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 280
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 276
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 236
- 150000001875 compounds Chemical class 0.000 claims description 206
- 229910052736 halogen Inorganic materials 0.000 claims description 177
- 150000002367 halogens Chemical class 0.000 claims description 173
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 167
- -1 -O-phenyl Chemical group 0.000 claims description 163
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 141
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 139
- 125000001424 substituent group Chemical group 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 103
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 100
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000000623 heterocyclic group Chemical group 0.000 claims description 77
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 75
- 229910052760 oxygen Inorganic materials 0.000 claims description 75
- 229910052717 sulfur Inorganic materials 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 69
- 125000005842 heteroatom Chemical group 0.000 claims description 62
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 60
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 57
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
- 150000003536 tetrazoles Chemical class 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 38
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 36
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 35
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 34
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 34
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 34
- 125000001544 thienyl group Chemical group 0.000 claims description 29
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 125000005647 linker group Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 22
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 22
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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 21
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 20
- 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
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 17
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 17
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 17
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 230000000996 additive effect Effects 0.000 claims description 8
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 8
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- KWJGZHWBYWXVNE-UHFFFAOYSA-N cyclopentyl n-[3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-propylindol-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC3CCCC3)=CC=C2N(CCC)C=C1CC(C(=C1)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1C KWJGZHWBYWXVNE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=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
- 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
- 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
- DVKDGVPJOILGDS-UHFFFAOYSA-N 2-[1-[[2,4-bis(trifluoromethyl)phenyl]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)=CN1CC1=CC=C(C(F)(F)F)C=C1C(F)(F)F DVKDGVPJOILGDS-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
- 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
- JGSUERAXJBJZRE-UHFFFAOYSA-N 2-[4-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1CC(C1=CC(NC(=O)C2CCCC2)=CC=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JGSUERAXJBJZRE-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
- 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
- BNWHMFLCJJJQNB-UHFFFAOYSA-N 3-[4-[(1-benzhydryl-6-chloroindol-3-yl)methyl]anilino]-3-oxopropanoic acid;sodium Chemical compound [Na].C1=CC(NC(=O)CC(=O)O)=CC=C1CC(C1=CC=C(Cl)C=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BNWHMFLCJJJQNB-UHFFFAOYSA-N 0.000 claims description 2
- YLUUKCKWIYWBAF-UHFFFAOYSA-N 3-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indol-3-yl]methylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NCC=2C3=CC(NC(=O)C4CCCC4)=CC=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 YLUUKCKWIYWBAF-UHFFFAOYSA-N 0.000 claims description 2
- DHXLBYIZWOHOGD-UHFFFAOYSA-N 3-[[1-benzhydryl-5-(cyclopentanecarbonylamino)indole-3-carbonyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C=2C3=CC(NC(=O)C4CCCC4)=CC=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 DHXLBYIZWOHOGD-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
- FRNNGHKTDVMGEM-UHFFFAOYSA-N 3-[[2-(1-benzhydrylindol-3-yl)-2-oxoacetyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C(=O)C=2C3=CC=CC=C3N(C(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 FRNNGHKTDVMGEM-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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- VLYGFQBIUROAIQ-UHFFFAOYSA-N benzyl n-[1-benzhydryl-3-[[2-methoxy-4-(trifluoromethylsulfonylcarbamoyl)phenyl]methyl]indol-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C(F)(F)F)=CC=C1CC(C1=CC(NC(=O)OCC=2C=CC=CC=2)=CC=C11)=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 VLYGFQBIUROAIQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
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- 238000006467 substitution reaction Methods 0.000 claims description 2
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- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- 238000001647 drug administration Methods 0.000 description 1
- 150000002066 eicosanoids Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- DCIFXYFKVKDOLL-UHFFFAOYSA-N ethyl 5-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=1C=C2NC(C(=O)OCC)=CC2=CC=1OCC1=CC=CC=C1 DCIFXYFKVKDOLL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
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- 230000006801 homologous recombination Effects 0.000 description 1
- 238000002744 homologous recombination Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
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- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003617 indole-3-acetic acid Substances 0.000 description 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
- NBKQRVSGHYZUOR-UHFFFAOYSA-N indoline-3-carbaldehyde Natural products C1=CC=C2C(C=O)CNC2=C1 NBKQRVSGHYZUOR-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
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- IAPCVVZLVISVMU-UHFFFAOYSA-N methyl 3-(triphenyl-$l^{5}-phosphanylidene)propanoate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCC(=O)OC)C1=CC=CC=C1 IAPCVVZLVISVMU-UHFFFAOYSA-N 0.000 description 1
- UXSNXOMMJXTFEG-UHFFFAOYSA-N methyl 4-(bromomethyl)-3-methoxybenzoate Chemical compound COC(=O)C1=CC=C(CBr)C(OC)=C1 UXSNXOMMJXTFEG-UHFFFAOYSA-N 0.000 description 1
- SRXOJMOGPYFZKC-UHFFFAOYSA-N methyl 4-chloro-4-oxobutanoate Chemical compound COC(=O)CCC(Cl)=O SRXOJMOGPYFZKC-UHFFFAOYSA-N 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
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- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Substances [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 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
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 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
- TWRVYXVQOJCHIF-UHFFFAOYSA-N tert-butyl-chloro-methylsilane Chemical compound C[SiH](Cl)C(C)(C)C TWRVYXVQOJCHIF-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
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- VHKIEYIESYMHPT-UHFFFAOYSA-N triethyl(methoxycarbonylsulfamoyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)S(=O)(=O)NC(=O)OC VHKIEYIESYMHPT-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- 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
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- 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
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- 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
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- 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
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- 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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- 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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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- 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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- 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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- 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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- 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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- 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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- 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
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- 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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- 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
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US3059298A | 1998-02-25 | 1998-02-25 | |
PCT/US1999/003898 WO1999043654A2 (en) | 1998-02-25 | 1999-02-24 | Inhibitors of phospholipase enzymes |
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HRP20000551A2 true HRP20000551A2 (en) | 2001-04-30 |
Family
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Application Number | Title | Priority Date | Filing Date |
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HR20000551A HRP20000551A2 (en) | 1998-02-25 | 2000-08-24 | Inhibitors of phospholipase enzymes |
Country Status (21)
Country | Link |
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EP (1) | EP1062205A2 (hu) |
JP (1) | JP2002504541A (hu) |
KR (1) | KR20010041344A (hu) |
CN (1) | CN1310706A (hu) |
AU (1) | AU765427B2 (hu) |
BG (1) | BG104779A (hu) |
BR (1) | BR9908275A (hu) |
CA (1) | CA2322162A1 (hu) |
EA (1) | EA003876B1 (hu) |
EE (1) | EE200000488A (hu) |
GE (1) | GEP20032920B (hu) |
HR (1) | HRP20000551A2 (hu) |
HU (1) | HUP0101146A3 (hu) |
ID (1) | ID26250A (hu) |
IL (1) | IL137719A0 (hu) |
NO (1) | NO20004219L (hu) |
NZ (1) | NZ506329A (hu) |
PL (1) | PL343007A1 (hu) |
SK (1) | SK12752000A3 (hu) |
TR (1) | TR200002447T2 (hu) |
WO (1) | WO1999043654A2 (hu) |
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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 |
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-
1999
- 1999-02-24 NZ NZ506329A patent/NZ506329A/xx unknown
- 1999-02-24 ID IDW20001595A patent/ID26250A/id unknown
- 1999-02-24 JP JP2000533412A patent/JP2002504541A/ja not_active Withdrawn
- 1999-02-24 PL PL99343007A patent/PL343007A1/xx unknown
- 1999-02-24 WO PCT/US1999/003898 patent/WO1999043654A2/en not_active Application Discontinuation
- 1999-02-24 AU AU27825/99A patent/AU765427B2/en not_active Ceased
- 1999-02-24 CA CA002322162A patent/CA2322162A1/en not_active Abandoned
- 1999-02-24 EE EEP200000488A patent/EE200000488A/xx unknown
- 1999-02-24 HU HU0101146A patent/HUP0101146A3/hu unknown
- 1999-02-24 GE GEAP19995560A patent/GEP20032920B/en unknown
- 1999-02-24 CN CN99805157A patent/CN1310706A/zh active Pending
- 1999-02-24 EP EP99908378A patent/EP1062205A2/en not_active Withdrawn
- 1999-02-24 EA EA200000871A patent/EA003876B1/ru not_active IP Right Cessation
- 1999-02-24 KR KR1020007009457A patent/KR20010041344A/ko not_active Application Discontinuation
- 1999-02-24 BR BR9908275-6A patent/BR9908275A/pt not_active IP Right Cessation
- 1999-02-24 IL IL13771999A patent/IL137719A0/xx unknown
- 1999-02-24 SK SK1275-2000A patent/SK12752000A3/sk unknown
- 1999-02-24 TR TR2000/02447T patent/TR200002447T2/xx unknown
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2000
- 2000-08-23 NO NO20004219A patent/NO20004219L/no not_active Application Discontinuation
- 2000-08-24 HR HR20000551A patent/HRP20000551A2/hr not_active Application Discontinuation
- 2000-09-19 BG BG104779A patent/BG104779A/xx unknown
Also Published As
Publication number | Publication date |
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WO1999043654A2 (en) | 1999-09-02 |
CN1310706A (zh) | 2001-08-29 |
ID26250A (id) | 2000-12-07 |
AU2782599A (en) | 1999-09-15 |
HUP0101146A2 (hu) | 2001-08-28 |
AU765427B2 (en) | 2003-09-18 |
WO1999043654A3 (en) | 1999-10-28 |
EA003876B1 (ru) | 2003-10-30 |
BR9908275A (pt) | 2000-10-24 |
NO20004219D0 (no) | 2000-08-23 |
EP1062205A2 (en) | 2000-12-27 |
GEP20032920B (en) | 2003-03-25 |
BG104779A (en) | 2001-10-31 |
HUP0101146A3 (en) | 2001-11-28 |
KR20010041344A (ko) | 2001-05-15 |
PL343007A1 (en) | 2001-07-30 |
NZ506329A (en) | 2004-01-30 |
JP2002504541A (ja) | 2002-02-12 |
EE200000488A (et) | 2002-02-15 |
EA200000871A1 (ru) | 2001-04-23 |
CA2322162A1 (en) | 1999-09-02 |
TR200002447T2 (tr) | 2000-11-21 |
IL137719A0 (en) | 2001-10-31 |
NO20004219L (no) | 2000-10-23 |
SK12752000A3 (sk) | 2001-03-12 |
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