NO300210B1 - 1H-indol-3-eddiksyrehydrazid sPLA2 inhibitorer, farmasöytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene for fremstilling av preparater - Google Patents
1H-indol-3-eddiksyrehydrazid sPLA2 inhibitorer, farmasöytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene for fremstilling av preparater Download PDFInfo
- Publication number
- NO300210B1 NO300210B1 NO941360A NO941360A NO300210B1 NO 300210 B1 NO300210 B1 NO 300210B1 NO 941360 A NO941360 A NO 941360A NO 941360 A NO941360 A NO 941360A NO 300210 B1 NO300210 B1 NO 300210B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- indole
- acetic acid
- methoxy
- mmol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 79
- 150000001875 compounds Chemical class 0.000 title claims description 41
- GYHLCXMCGCVVCG-UHFFFAOYSA-N 2-(1h-indol-3-yl)acetohydrazide Chemical compound C1=CC=C2C(CC(=O)NN)=CNC2=C1 GYHLCXMCGCVVCG-UHFFFAOYSA-N 0.000 title claims description 22
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 102000005473 Secretory Phospholipases A2 Human genes 0.000 title description 7
- 108010031873 Secretory Phospholipases A2 Proteins 0.000 title description 7
- 239000003112 inhibitor Substances 0.000 title description 7
- 239000003617 indole-3-acetic acid Substances 0.000 claims description 70
- -1 -OH Chemical group 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 235000021342 arachidonic acid Nutrition 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 229940114079 arachidonic acid Drugs 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 288
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 282
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 249
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 208
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 163
- 238000000034 method Methods 0.000 description 148
- 235000019439 ethyl acetate Nutrition 0.000 description 144
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 130
- 239000000243 solution Substances 0.000 description 106
- 239000000377 silicon dioxide Substances 0.000 description 103
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- 238000004587 chromatography analysis Methods 0.000 description 83
- 238000002425 crystallisation Methods 0.000 description 83
- 230000008025 crystallization Effects 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- 238000002844 melting Methods 0.000 description 51
- 230000008018 melting Effects 0.000 description 51
- 239000003921 oil Substances 0.000 description 51
- 239000002480 mineral oil Substances 0.000 description 47
- 235000010446 mineral oil Nutrition 0.000 description 47
- 229910000104 sodium hydride Inorganic materials 0.000 description 44
- 239000000203 mixture Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 230000002829 reductive effect Effects 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- MDEARKLIJNPQCN-UHFFFAOYSA-N ethyl 2-(5-methoxy-2-methyl-1h-indol-3-yl)acetate Chemical compound C1=C(OC)C=C2C(CC(=O)OCC)=C(C)NC2=C1 MDEARKLIJNPQCN-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000011734 sodium Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000001816 cooling Methods 0.000 description 20
- 238000010828 elution Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 230000004044 response Effects 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 229940073608 benzyl chloride Drugs 0.000 description 8
- 229940040102 levulinic acid Drugs 0.000 description 8
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 8
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 7
- 231100000673 dose–response relationship Toxicity 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 206010040070 Septic Shock Diseases 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000036303 septic shock Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IIISKKWBXAHEHT-UHFFFAOYSA-N benzyl 2-(1-benzyl-5-methoxyindol-3-yl)acetate Chemical compound C1=C(CC(=O)OCC=2C=CC=CC=2)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 IIISKKWBXAHEHT-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- GNAIWTYKMSIQQR-UHFFFAOYSA-N ethyl 2-(5-bromo-2-methyl-1h-indol-3-yl)acetate Chemical compound C1=C(Br)C=C2C(CC(=O)OCC)=C(C)NC2=C1 GNAIWTYKMSIQQR-UHFFFAOYSA-N 0.000 description 5
- NBKDCXIOKALVQU-UHFFFAOYSA-N ethyl 3-(2-ethoxy-2-oxoethyl)-2-methyl-1h-indole-5-carboxylate Chemical compound C1=C(C(=O)OCC)C=C2C(CC(=O)OCC)=C(C)NC2=C1 NBKDCXIOKALVQU-UHFFFAOYSA-N 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 150000002475 indoles Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 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 description 4
- NXLJTHCFJPPFQM-UHFFFAOYSA-N 2-[5-bromo-2-methyl-1-[(3-phenylmethoxyphenyl)methyl]indol-3-yl]acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(Br)=CC=C2N1CC(C=1)=CC=CC=1OCC1=CC=CC=C1 NXLJTHCFJPPFQM-UHFFFAOYSA-N 0.000 description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 102000015439 Phospholipases Human genes 0.000 description 4
- 108010064785 Phospholipases Proteins 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- PXOKVRUWALDBOI-UHFFFAOYSA-N ethyl 1-[(3-chlorophenyl)methyl]-3-(2-ethoxy-2-oxoethyl)-2-methylindole-5-carboxylate Chemical compound C12=CC=C(C(=O)OCC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC(Cl)=C1 PXOKVRUWALDBOI-UHFFFAOYSA-N 0.000 description 4
- ODRUXSVPZYWJJB-UHFFFAOYSA-N ethyl 2-(1-benzyl-2-methyl-4-phenylindol-3-yl)acetate Chemical compound C12=CC=CC(C=3C=CC=CC=3)=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC=C1 ODRUXSVPZYWJJB-UHFFFAOYSA-N 0.000 description 4
- QMAIQHXXPYVSSM-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-[(3-nitrophenyl)methyl]indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC([N+]([O-])=O)=C1 QMAIQHXXPYVSSM-UHFFFAOYSA-N 0.000 description 4
- BTHYGKSWJUOYTO-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-[(4-phenylmethoxyphenyl)methyl]indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC(C=C1)=CC=C1OCC1=CC=CC=C1 BTHYGKSWJUOYTO-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- JYUNCKSXPPDNRM-UHFFFAOYSA-N methyl 2-(5-methoxy-2-methyl-1h-indol-3-yl)acetate Chemical compound C1=C(OC)C=C2C(CC(=O)OC)=C(C)NC2=C1 JYUNCKSXPPDNRM-UHFFFAOYSA-N 0.000 description 4
- YKVJZSZZQKQJMO-UHFFFAOYSA-N n-methoxy-n-methylpropanamide Chemical compound CCC(=O)N(C)OC YKVJZSZZQKQJMO-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- SJGSEDMYDLCWTF-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-3-(2-hydrazinyl-2-oxoethyl)-2-methylindole-5-carboxylic acid Chemical compound CC1=C(CC(=O)NN)C2=CC(C(O)=O)=CC=C2N1CC1=CC=CC(Cl)=C1 SJGSEDMYDLCWTF-UHFFFAOYSA-N 0.000 description 3
- QONRRCZYLSPDKM-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-3-(2-methoxy-2-oxoethyl)-2-methylindole-5-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2C(CC(=O)OC)=C(C)N1CC1=CC=CC(Cl)=C1 QONRRCZYLSPDKM-UHFFFAOYSA-N 0.000 description 3
- XGYROWIDFDKJOY-UHFFFAOYSA-N 1-benzyl-3-(2-hydrazinyl-2-oxoethyl)-2-methylindole-5-carbohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(C(=O)NN)=CC=C2N1CC1=CC=CC=C1 XGYROWIDFDKJOY-UHFFFAOYSA-N 0.000 description 3
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 3
- WUFJPPSZXBUNIN-UHFFFAOYSA-N 2-(1-benzyl-2,5-dimethylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(C)=CC=C2N1CC1=CC=CC=C1 WUFJPPSZXBUNIN-UHFFFAOYSA-N 0.000 description 3
- UKMWYEPIADWDGD-UHFFFAOYSA-N 2-(1-benzyl-2-chloro-5-methoxyindol-3-yl)acetohydrazide Chemical compound ClC1=C(CC(=O)NN)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 UKMWYEPIADWDGD-UHFFFAOYSA-N 0.000 description 3
- GZTZUEWVDCSFGB-UHFFFAOYSA-N 2-(1-benzyl-2-methyl-5-phenylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(C=3C=CC=CC=3)=CC=C2N1CC1=CC=CC=C1 GZTZUEWVDCSFGB-UHFFFAOYSA-N 0.000 description 3
- QNLKBNJUPKXFFP-UHFFFAOYSA-N 2-(1-benzyl-2-methyl-6-phenylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC=C(C=3C=CC=CC=3)C=C2N1CC1=CC=CC=C1 QNLKBNJUPKXFFP-UHFFFAOYSA-N 0.000 description 3
- OIGHBWJNJORSGQ-UHFFFAOYSA-N 2-(1-benzyl-2-methylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC=CC=C2N1CC1=CC=CC=C1 OIGHBWJNJORSGQ-UHFFFAOYSA-N 0.000 description 3
- FUVQLAZKLVTMNN-UHFFFAOYSA-N 2-(1-benzyl-4-bromo-2-methylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=C(Br)C=CC=C2N1CC1=CC=CC=C1 FUVQLAZKLVTMNN-UHFFFAOYSA-N 0.000 description 3
- MZUYSXSMZDAZKG-UHFFFAOYSA-N 2-(1-benzyl-5-bromo-2-methylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(Br)=CC=C2N1CC1=CC=CC=C1 MZUYSXSMZDAZKG-UHFFFAOYSA-N 0.000 description 3
- GTRGZMPVGRXOSM-UHFFFAOYSA-N 2-(1-benzyl-5-cyclopentyloxy-2-ethylindol-3-yl)acetohydrazide Chemical compound C=1C=C2N(CC=3C=CC=CC=3)C(CC)=C(CC(=O)NN)C2=CC=1OC1CCCC1 GTRGZMPVGRXOSM-UHFFFAOYSA-N 0.000 description 3
- UWCQKSFRTIYNMA-UHFFFAOYSA-N 2-(1-benzyl-5-hydroxy-2-methylindol-3-yl)acetohydrazide Chemical compound CC1=C(CC(=O)NN)C2=CC(O)=CC=C2N1CC1=CC=CC=C1 UWCQKSFRTIYNMA-UHFFFAOYSA-N 0.000 description 3
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- IFTNLKSDGBANRV-UHFFFAOYSA-N 2-(1-benzyl-5-phenylmethoxyindol-3-yl)acetohydrazide Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(CC(=O)NN)=CN1CC1=CC=CC=C1 IFTNLKSDGBANRV-UHFFFAOYSA-N 0.000 description 3
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- UATVOCUXCGPWBK-UHFFFAOYSA-N ethyl 2-(1-benzyl-6-bromo-2-methylindol-3-yl)acetate Chemical compound C12=CC(Br)=CC=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC=C1 UATVOCUXCGPWBK-UHFFFAOYSA-N 0.000 description 3
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- SMICMMOLRZOEIL-UHFFFAOYSA-N ethyl 2-[1-[(2-chlorophenyl)methyl]-5-methoxy-2-methylindol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC=C1Cl SMICMMOLRZOEIL-UHFFFAOYSA-N 0.000 description 3
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- SKKLTTAPHPNZKE-UHFFFAOYSA-N ethyl 2-[5-methoxy-1-[(4-methoxyphenyl)methyl]-2-methylindol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=C(OC)C=C1 SKKLTTAPHPNZKE-UHFFFAOYSA-N 0.000 description 3
- KVZCVTCGRHWONN-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(1-phenylethyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1C(C)C1=CC=CC=C1 KVZCVTCGRHWONN-UHFFFAOYSA-N 0.000 description 3
- PZMZCHIFDZXSPQ-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(2-methylpropyl)indol-3-yl]acetate Chemical compound C1=C(OC)C=C2C(CC(=O)OCC)=C(C)N(CC(C)C)C2=C1 PZMZCHIFDZXSPQ-UHFFFAOYSA-N 0.000 description 3
- YHHLGQWPBRDWLW-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(4-phenylbutyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CCCCC1=CC=CC=C1 YHHLGQWPBRDWLW-UHFFFAOYSA-N 0.000 description 3
- YXFMTIVMUHUBOO-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(pyridin-2-ylmethyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CC=N1 YXFMTIVMUHUBOO-UHFFFAOYSA-N 0.000 description 3
- WPNXPLMDXAEOQU-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(pyridin-3-ylmethyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=CN=C1 WPNXPLMDXAEOQU-UHFFFAOYSA-N 0.000 description 3
- PZCXFFYYOLKJDX-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(pyridin-4-ylmethyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=NC=C1 PZCXFFYYOLKJDX-UHFFFAOYSA-N 0.000 description 3
- SNPTXRQULYAFFJ-UHFFFAOYSA-N ethyl 2-[5-methoxy-2-methyl-1-(quinolin-2-ylmethyl)indol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OCC)=C(C)N1CC1=CC=C(C=CC=C2)C2=N1 SNPTXRQULYAFFJ-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D209/22—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 with an aralkyl radical attached to the ring nitrogen atom
-
- 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
- C07D209/24—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 with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- 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
-
- 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
- C07D401/12—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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4860893A | 1993-04-16 | 1993-04-16 |
Publications (3)
Publication Number | Publication Date |
---|---|
NO941360D0 NO941360D0 (no) | 1994-04-15 |
NO941360L NO941360L (no) | 1994-10-17 |
NO300210B1 true NO300210B1 (no) | 1997-04-28 |
Family
ID=21955471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO941360A NO300210B1 (no) | 1993-04-16 | 1994-04-15 | 1H-indol-3-eddiksyrehydrazid sPLA2 inhibitorer, farmasöytiske preparater inneholdende forbindelsene og anvendelse av forbindelsene for fremstilling av preparater |
Country Status (27)
Country | Link |
---|---|
US (1) | US5578634A (fi) |
EP (1) | EP0620214B1 (fi) |
JP (1) | JP3621128B2 (fi) |
KR (1) | KR100330816B1 (fi) |
CN (1) | CN1067986C (fi) |
AT (1) | ATE177081T1 (fi) |
AU (1) | AU669782B2 (fi) |
BR (1) | BR9401484A (fi) |
CA (1) | CA2121321A1 (fi) |
CO (1) | CO4230091A1 (fi) |
CZ (1) | CZ289791B6 (fi) |
DE (1) | DE69416705T2 (fi) |
DK (1) | DK0620214T3 (fi) |
ES (1) | ES2128510T3 (fi) |
FI (1) | FI941766A (fi) |
GR (1) | GR3029689T3 (fi) |
HU (1) | HU220221B (fi) |
IL (1) | IL109309A (fi) |
NO (1) | NO300210B1 (fi) |
NZ (1) | NZ260299A (fi) |
PL (1) | PL179472B1 (fi) |
RU (1) | RU2127725C1 (fi) |
SI (1) | SI0620214T1 (fi) |
TW (1) | TW306914B (fi) |
UA (1) | UA40575C2 (fi) |
YU (1) | YU20094A (fi) |
ZA (1) | ZA942614B (fi) |
Families Citing this family (53)
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BR9501404A (pt) * | 1994-04-01 | 1996-03-05 | Lilly Co Eli | 1H-indol-3 glioxilamida e formulação farmacèutica |
US6214876B1 (en) | 1994-07-21 | 2001-04-10 | Eli Lilly And Company | Indene-1-acetamide sPLA2 inhibitors |
US5641800A (en) * | 1994-07-21 | 1997-06-24 | Eli Lilly And Company | 1H-indole-1-functional sPLA2 inhibitors |
WO1998005637A1 (de) * | 1996-08-01 | 1998-02-12 | Merckle Gmbh | Acylpyrroldicarbonsäuren und acylindoldicarbonsäuren sowie ihre derivate als hemmstoffe der cytosolischen phospholipase a¿2? |
US6630496B1 (en) | 1996-08-26 | 2003-10-07 | Genetics Institute Llc | Inhibitors of phospholipase enzymes |
US6177440B1 (en) | 1996-10-30 | 2001-01-23 | Eli Lilly And Company | Substituted tricyclics |
IL129481A0 (en) * | 1996-10-30 | 2000-02-29 | Lilly Co Eli | Substituted tricyclics |
US6713645B1 (en) * | 1996-10-30 | 2004-03-30 | Eli Lilly And Company | Substituted tricyclics |
EP0987250A4 (en) * | 1997-02-20 | 2000-12-06 | Shionogi & Co | INDOLDICARBONIC ACID DERIVATIVES |
US6828344B1 (en) | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
CN1310706A (zh) * | 1998-02-25 | 2001-08-29 | 遗传研究所有限公司 | 磷脂酶抑制剂 |
US6916841B2 (en) * | 1998-02-25 | 2005-07-12 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
US6500853B1 (en) | 1998-02-28 | 2002-12-31 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
BR9909345A (pt) | 1998-03-31 | 2000-12-12 | Shionogi & Co | Pirrolo [1,2-a] pirazina inibidor de spla2 |
IL129484A0 (en) * | 1998-04-17 | 2000-02-29 | Lilly Co Eli | Substituted tricyclics |
DZ2769A1 (fr) * | 1998-04-17 | 2003-12-01 | Lilly Co Eli | Composés tricycliques substitués. |
KR20010034881A (ko) | 1998-05-21 | 2001-04-25 | 시오노 요시히코 | sPLA2 억제 효과를 갖는 피롤로[1,2-b]피리다진 유도체 |
DE69931496T2 (de) | 1998-08-03 | 2006-11-23 | Eli Lilly And Co., Indianapolis | INDOLVERBINDUNGEN ALS sPLA2 INHIBITOREN |
CA2338727A1 (en) | 1998-08-03 | 2000-02-17 | Edward David Mihelich | Indole spla2 inhibitors |
US6325991B1 (en) | 1998-08-24 | 2001-12-04 | Susan E. Draheim | Methods and compositions for treating periodontal disease with an inhibitor of secretory phospholipase A2 |
AU6004799A (en) | 1998-10-14 | 2000-05-01 | Shionogi & Co., Ltd. | Remedies or preventives for ischemic reflow failure |
ATE247119T1 (de) * | 1998-12-22 | 2003-08-15 | Lilly Co Eli | Substituierte pyrroloindole |
AU2373600A (en) * | 1998-12-22 | 2000-07-12 | Eli Lilly And Company | Novel spla2 inhibitors |
JP4636521B2 (ja) | 1999-07-19 | 2011-02-23 | 塩野義製薬株式会社 | sPLA2阻害作用を有する三環系化合物 |
WO2001012600A1 (en) * | 1999-08-12 | 2001-02-22 | Cor Therapeutics, Inc. | INHIBITORS OF FACTOR Xa |
AU6473600A (en) | 1999-08-23 | 2001-03-19 | Shionogi & Co., Ltd. | Pyrrolotriazine derivatives having spla2-inhibitory activities |
AU7559600A (en) * | 1999-10-15 | 2001-04-23 | Shionogi & Co., Ltd. | V type and/or x type spla2 inhibitors |
AU1304801A (en) | 1999-11-15 | 2001-05-30 | Shionogi & Co., Ltd. | Tricyclic azaindolizine derivatives having an SPLA2- inhibiting effect |
JPWO2002000621A1 (ja) | 2000-06-29 | 2004-04-22 | 塩野義製薬株式会社 | X型sPLA2阻害作用を有する化合物 |
AU2001267825A1 (en) | 2000-06-29 | 2002-01-08 | Shionogi And Co., Ltd. | Remedies for cirrhosis |
ES2294003T3 (es) * | 2000-06-29 | 2008-04-01 | Anthera Pharmaceuticals, Inc. | Remedios contra el cancer. |
WO2002005796A2 (en) * | 2000-07-14 | 2002-01-24 | Eli Lilly And Company | Use of a spla2 inhibitor for the treatment of sepsis |
AU2002233928A1 (en) * | 2000-12-18 | 2002-07-01 | Eli Lilly And Company | Cycloalkylfused (g)-indole compounds as spla2-inhibitors in the treatment of inflammatory diseases |
TWI314457B (fi) * | 2001-03-19 | 2009-09-11 | Shionogi & Co | |
US7205329B2 (en) | 2003-05-30 | 2007-04-17 | Microbia, Inc. | Modulators of CRTH2 activity |
US7348338B2 (en) | 2003-07-17 | 2008-03-25 | Plexxikon, Inc. | PPAR active compounds |
CA2532403A1 (en) | 2003-07-17 | 2005-02-03 | James Arnold | Ppar active compounds |
GB2407318A (en) * | 2003-10-23 | 2005-04-27 | Oxagen Ltd | Substituted Indol-3-yl acetic acid derivatives |
EP1819673A2 (en) | 2004-11-30 | 2007-08-22 | Plexxikon, Inc. | Indole derivatives for use as ppar active compounds |
WO2006102126A2 (en) * | 2005-03-18 | 2006-09-28 | Duke University | Inhibitors of isoprenylcysteine carboxyl methyltransferase |
GT200600228A (es) | 2005-05-27 | 2006-12-26 | Inhibidores de la fosfolipasa a2 citosolica | |
JP2009517341A (ja) * | 2005-11-03 | 2009-04-30 | イリプサ, インコーポレイテッド | C4−アミド置換基を有するインドール化合物およびホスホリパーゼa2インヒビターとしてのその使用 |
EP1960356A2 (en) | 2005-11-03 | 2008-08-27 | Ilypsa, Inc. | Multivalent indole compounds and use thereof as phospholipase-a2 inhibitors |
US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
US8399666B2 (en) | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
US8048880B2 (en) * | 2007-05-03 | 2011-11-01 | Anthera Pharmaceuticals, Inc. | Treatment of cardiovascular disease and dyslipidemia using secretory phospholipase A2 (SPLA2) inhibitors and SPLA2 inhibitor combination therapies |
US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
NZ704807A (en) * | 2012-08-30 | 2016-06-24 | Chong Kun Dang Pharm Corp | N-acylhydrazone derivatives for selective t cell inhibitor and anti-lymphoid malignancy drug |
GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
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US2825734A (en) * | 1955-04-11 | 1958-03-04 | Upjohn Co | Reduction of carbonylic radicals in indolyl-3 compounds |
US2890223A (en) * | 1956-03-22 | 1959-06-09 | Research Corp | 1-benzyl, 2-methyl, 5-methoxy tryptamine |
US3242162A (en) * | 1961-03-13 | 1966-03-22 | Merck & Co Inc | Indolyl aliphatic acids |
US3242163A (en) * | 1961-03-13 | 1966-03-22 | Merck & Co Inc | Indolyl aliphatic acids |
US3242193A (en) * | 1961-03-13 | 1966-03-22 | Merck & Co Inc | Indolyl aliphatic acids |
US3196162A (en) * | 1961-03-13 | 1965-07-20 | Merck & Co Inc | Indolyl aliphatic acids |
US3271416A (en) * | 1961-10-24 | 1966-09-06 | Merck & Co Inc | Indolyl aliphatic acids |
IT1036004B (it) * | 1968-05-21 | 1979-10-30 | Abc Ist Biolog Chem Spa | Acidt 3 indolil adetoidrossamici |
US4012513A (en) * | 1971-11-03 | 1977-03-15 | Imperial Chemical Industries Limited | Indole derivatives for providing analgesic and anti-inflammatory effects |
US4792555A (en) * | 1987-03-20 | 1988-12-20 | American Home Products Corporation | Phospholipase A2 inhibitors |
IL109311A0 (en) * | 1993-04-16 | 1994-07-31 | Lilly Co Eli | 1H-indole-3-acetamide sPla2 inhibitors |
-
1994
- 1994-04-12 IL IL10930994A patent/IL109309A/xx not_active IP Right Cessation
- 1994-04-13 HU HU9401058A patent/HU220221B/hu not_active IP Right Cessation
- 1994-04-13 TW TW083103279A patent/TW306914B/zh active
- 1994-04-13 NZ NZ260299A patent/NZ260299A/en unknown
- 1994-04-14 DK DK94302646T patent/DK0620214T3/da active
- 1994-04-14 SI SI9430246T patent/SI0620214T1/xx unknown
- 1994-04-14 ES ES94302646T patent/ES2128510T3/es not_active Expired - Lifetime
- 1994-04-14 CA CA002121321A patent/CA2121321A1/en not_active Abandoned
- 1994-04-14 DE DE69416705T patent/DE69416705T2/de not_active Expired - Fee Related
- 1994-04-14 BR BR9401484A patent/BR9401484A/pt not_active Application Discontinuation
- 1994-04-14 AT AT94302646T patent/ATE177081T1/de not_active IP Right Cessation
- 1994-04-14 CZ CZ1994894A patent/CZ289791B6/cs not_active IP Right Cessation
- 1994-04-14 CO CO94014980A patent/CO4230091A1/es unknown
- 1994-04-14 EP EP94302646A patent/EP0620214B1/en not_active Expired - Lifetime
- 1994-04-15 CN CN94104433A patent/CN1067986C/zh not_active Expired - Fee Related
- 1994-04-15 JP JP07764694A patent/JP3621128B2/ja not_active Expired - Fee Related
- 1994-04-15 NO NO941360A patent/NO300210B1/no not_active IP Right Cessation
- 1994-04-15 UA UA94005182A patent/UA40575C2/uk unknown
- 1994-04-15 KR KR1019940007934A patent/KR100330816B1/ko not_active IP Right Cessation
- 1994-04-15 ZA ZA942614A patent/ZA942614B/xx unknown
- 1994-04-15 PL PL94303027A patent/PL179472B1/pl unknown
- 1994-04-15 FI FI941766A patent/FI941766A/fi unknown
- 1994-04-15 AU AU59486/94A patent/AU669782B2/en not_active Ceased
- 1994-04-15 YU YU20094A patent/YU20094A/sh unknown
- 1994-04-15 RU RU94012931A patent/RU2127725C1/ru active
-
1995
- 1995-05-12 US US08/440,154 patent/US5578634A/en not_active Expired - Fee Related
-
1999
- 1999-03-12 GR GR990400773T patent/GR3029689T3/el unknown
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