IE43142B1 - Phenylacetic acid derivatives - Google Patents
Phenylacetic acid derivativesInfo
- Publication number
- IE43142B1 IE43142B1 IE1410/76A IE141076A IE43142B1 IE 43142 B1 IE43142 B1 IE 43142B1 IE 1410/76 A IE1410/76 A IE 1410/76A IE 141076 A IE141076 A IE 141076A IE 43142 B1 IE43142 B1 IE 43142B1
- Authority
- IE
- Ireland
- Prior art keywords
- ethyl
- acid
- phenylacetic acid
- chloro
- phenylacetate
- Prior art date
Links
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title claims abstract description 34
- -1 heterocyclyl radical Chemical class 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 229960003424 phenylacetic acid Drugs 0.000 claims description 26
- 239000003279 phenylacetic acid Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229940049953 phenylacetate Drugs 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000005672 Willgerodt-Kindler rearrangement reaction Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- JPPXVKFDEFETOG-UHFFFAOYSA-N 2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 JPPXVKFDEFETOG-UHFFFAOYSA-N 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- JNFOMZKKUJUXSJ-UHFFFAOYSA-N 2-[4-(2-benzamidoethyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNC(=O)C1=CC=CC=C1 JNFOMZKKUJUXSJ-UHFFFAOYSA-N 0.000 claims description 2
- UNRCSUZPRRSORQ-UHFFFAOYSA-N 2-[4-[2-[(2-butoxy-5-chlorobenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound CCCCOC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 UNRCSUZPRRSORQ-UHFFFAOYSA-N 0.000 claims description 2
- VQLQVTALMSVCFW-UHFFFAOYSA-N 2-[4-[2-[(2-methoxybenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=CC=CC=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 VQLQVTALMSVCFW-UHFFFAOYSA-N 0.000 claims description 2
- FRMJLJWSQBLVAM-UHFFFAOYSA-N 2-[4-[2-[(2-methoxypyridine-3-carbonyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=NC=CC=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 FRMJLJWSQBLVAM-UHFFFAOYSA-N 0.000 claims description 2
- JLKFMKWXBCGFFA-UHFFFAOYSA-N 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 JLKFMKWXBCGFFA-UHFFFAOYSA-N 0.000 claims description 2
- AFPQXPNHBFSEHB-UHFFFAOYSA-N 2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]-2-methylpropanoic acid Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(C)(C)C(O)=O)C=C1 AFPQXPNHBFSEHB-UHFFFAOYSA-N 0.000 claims description 2
- CAYVJVZQBQRNKU-UHFFFAOYSA-N 2-[4-[2-[(6-chloro-3,4-dihydro-2h-chromene-8-carbonyl)amino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNC(=O)C1=CC(Cl)=CC2=C1OCCC2 CAYVJVZQBQRNKU-UHFFFAOYSA-N 0.000 claims description 2
- MPWCHLVMIVVPLP-UHFFFAOYSA-N 2-[4-[2-[[3-(trifluoromethyl)benzoyl]amino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNC(=O)C1=CC=CC(C(F)(F)F)=C1 MPWCHLVMIVVPLP-UHFFFAOYSA-N 0.000 claims description 2
- QUIZFZOGRQCKAA-UHFFFAOYSA-N 2-[4-[[(5-chloro-2-ethoxybenzoyl)amino]methyl]phenyl]acetic acid Chemical compound CCOC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(CC(O)=O)C=C1 QUIZFZOGRQCKAA-UHFFFAOYSA-N 0.000 claims description 2
- RHOPUUFLVKWWFP-UHFFFAOYSA-N 2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=C1 RHOPUUFLVKWWFP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- YCCBASNMIZPISJ-UHFFFAOYSA-N ethyl 2-[4-[2-(quinoline-8-carbonylamino)ethyl]phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC2=CC=CN=C12 YCCBASNMIZPISJ-UHFFFAOYSA-N 0.000 claims description 2
- OUWRLTOOKIFIGG-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-bromo-2-methoxybenzoyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Br)=CC=C1OC OUWRLTOOKIFIGG-UHFFFAOYSA-N 0.000 claims description 2
- INODVWJXZGVPKE-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-bromo-2-methoxypyridine-3-carbonyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Br)=CN=C1OC INODVWJXZGVPKE-UHFFFAOYSA-N 0.000 claims description 2
- WNCVDXIENAUIJI-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-chloro-2-methoxypyridine-3-carbonyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CN=C1OC WNCVDXIENAUIJI-UHFFFAOYSA-N 0.000 claims description 2
- WALOVXUYSYIUOU-UHFFFAOYSA-N ethyl 2-[4-[2-[(6-chloro-3,4-dihydro-2h-chromene-8-carbonyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC2=C1OCCC2 WALOVXUYSYIUOU-UHFFFAOYSA-N 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 8
- HNTMUVWFPGRQRD-UHFFFAOYSA-N 2-[4-[2-[(2-methoxy-5-methylbenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=CC=C(C)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 HNTMUVWFPGRQRD-UHFFFAOYSA-N 0.000 claims 1
- ZWVDZTLAIKVFGU-UHFFFAOYSA-N 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 ZWVDZTLAIKVFGU-UHFFFAOYSA-N 0.000 claims 1
- JHCNMGVCXMSIPK-UHFFFAOYSA-N 2-[4-[2-[(5-bromo-2-methoxybenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=CC=C(Br)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 JHCNMGVCXMSIPK-UHFFFAOYSA-N 0.000 claims 1
- AUJFCJHCPBHEGP-UHFFFAOYSA-N 2-[4-[2-[(5-chloro-2-ethoxybenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound CCOC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 AUJFCJHCPBHEGP-UHFFFAOYSA-N 0.000 claims 1
- LXIFVNGQXRWWCC-UHFFFAOYSA-N 2-[4-[2-[(5-chloro-2-methoxypyridine-3-carbonyl)amino]ethyl]phenyl]acetic acid Chemical compound COC1=NC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC(O)=O)C=C1 LXIFVNGQXRWWCC-UHFFFAOYSA-N 0.000 claims 1
- QBJAZYDVYKPKEQ-UHFFFAOYSA-N 2-[4-[[(2-butoxy-5-chlorobenzoyl)amino]methyl]phenyl]acetic acid Chemical compound CCCCOC1=CC=C(Cl)C=C1C(=O)NCC1=CC=C(CC(O)=O)C=C1 QBJAZYDVYKPKEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- CLKAOTQJXKJTNE-UHFFFAOYSA-N ethyl 2-[4-[2-[(2-butoxy-5-chlorobenzoyl)amino]ethyl]phenyl]acetate Chemical compound CCCCOC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC(=O)OCC)C=C1 CLKAOTQJXKJTNE-UHFFFAOYSA-N 0.000 claims 1
- IOKHPFJFEMUHRM-UHFFFAOYSA-N ethyl 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]-2-methylpropanoate Chemical compound C1=CC(C(C)(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IOKHPFJFEMUHRM-UHFFFAOYSA-N 0.000 claims 1
- NHSVVNWSVZGCEJ-UHFFFAOYSA-N ethyl 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 NHSVVNWSVZGCEJ-UHFFFAOYSA-N 0.000 claims 1
- VTIWZNUJGLFGLR-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]-2-methylpropanoate Chemical compound C1=CC(C(C)(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC VTIWZNUJGLFGLR-UHFFFAOYSA-N 0.000 claims 1
- XNOKOORQXXOCCA-UHFFFAOYSA-N ethyl 2-[4-[2-[[2-methoxy-5-(trifluoromethyl)benzoyl]amino]ethyl]phenyl]butanoate Chemical compound C1=CC(C(CC)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(C(F)(F)F)=CC=C1OC XNOKOORQXXOCCA-UHFFFAOYSA-N 0.000 claims 1
- QMFQASUYHKZNGI-UHFFFAOYSA-N ethyl 2-[4-[2-[[5-chloro-2-(2-methoxyethoxy)benzoyl]amino]ethyl]phenyl]propanoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OCCOC QMFQASUYHKZNGI-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 3
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- 239000000243 solution Substances 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- LATLQSMOBLIWQV-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenyl]acetate;hydrochloride Chemical compound Cl.CCOC(=O)CC1=CC=C(CCN)C=C1 LATLQSMOBLIWQV-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- JVLUMHRASWENRU-UHFFFAOYSA-N 5-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC=C(Cl)C=C1C(Cl)=O JVLUMHRASWENRU-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- KLBIUKJOZFWCLW-UHFFFAOYSA-N thallium(iii) nitrate Chemical compound [Tl+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KLBIUKJOZFWCLW-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- CYQGECQHJKNBOG-UHFFFAOYSA-N 2-[4-(2-aminoethyl)phenyl]butanoic acid;hydrochloride Chemical compound Cl.CCC(C(O)=O)C1=CC=C(CCN)C=C1 CYQGECQHJKNBOG-UHFFFAOYSA-N 0.000 description 3
- PJDXJVFXKIXEGW-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]acetic acid;hydrochloride Chemical compound Cl.NCC1=CC=C(CC(O)=O)C=C1 PJDXJVFXKIXEGW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- ABPWRDTYSVAUHK-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenyl]-2-methylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)(C)C1=CC=C(CCN)C=C1 ABPWRDTYSVAUHK-UHFFFAOYSA-N 0.000 description 3
- XKCZVOWGVYXSAQ-UHFFFAOYSA-N ethyl 2-[4-(2-aminoethyl)phenyl]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)C(C)C1=CC=C(CCN)C=C1 XKCZVOWGVYXSAQ-UHFFFAOYSA-N 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KKUXHNTUGSIDBR-UHFFFAOYSA-N 2-[4-[2-[(5-chloro-2-phenoxybenzoyl)amino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC1=CC=CC=C1 KKUXHNTUGSIDBR-UHFFFAOYSA-N 0.000 description 2
- SKBXLNZBGAILBW-UHFFFAOYSA-N 2-butoxy-5-chlorobenzoyl chloride Chemical compound CCCCOC1=CC=C(Cl)C=C1C(Cl)=O SKBXLNZBGAILBW-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- BXINAIGLJUMHPW-UHFFFAOYSA-N 5-chloro-2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(Cl)C=C1C(Cl)=O BXINAIGLJUMHPW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- GYSWXCMBCODCTA-UHFFFAOYSA-N ethyl 2-[4-[2-[(2-butoxybenzoyl)amino]propyl]phenyl]acetate Chemical compound CCCCOC1=CC=CC=C1C(=O)NC(C)CC1=CC=C(CC(=O)OCC)C=C1 GYSWXCMBCODCTA-UHFFFAOYSA-N 0.000 description 1
- LRGHRHOWQJLKQM-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-chloro-1h-indole-2-carbonyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC2=CC(Cl)=CC=C2N1 LRGHRHOWQJLKQM-UHFFFAOYSA-N 0.000 description 1
- JPPMYKBEQJPMDC-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-chloro-2-ethoxybenzoyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OCC JPPMYKBEQJPMDC-UHFFFAOYSA-N 0.000 description 1
- RZKQQQYYPGLOKD-UHFFFAOYSA-N ethyl 2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC=C1OC RZKQQQYYPGLOKD-UHFFFAOYSA-N 0.000 description 1
- GWCXBAZUZYBAEK-UHFFFAOYSA-N ethyl 2-[4-[2-[(6-chloroquinoline-8-carbonyl)amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC(Cl)=CC2=CC=CN=C12 GWCXBAZUZYBAEK-UHFFFAOYSA-N 0.000 description 1
- MGXHDLIDFBQPFF-UHFFFAOYSA-N ethyl 2-[4-[2-[[3-(trifluoromethyl)benzoyl]amino]ethyl]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1CCNC(=O)C1=CC=CC(C(F)(F)F)=C1 MGXHDLIDFBQPFF-UHFFFAOYSA-N 0.000 description 1
- UTUVIKZNQWNGIM-UHFFFAOYSA-N ethyl 2-phenylpropanoate Chemical compound CCOC(=O)C(C)C1=CC=CC=C1 UTUVIKZNQWNGIM-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- GFXKTZQLBMPONQ-UHFFFAOYSA-N n-[1-(4-acetylphenyl)propan-2-yl]acetamide Chemical compound CC(=O)NC(C)CC1=CC=C(C(C)=O)C=C1 GFXKTZQLBMPONQ-UHFFFAOYSA-N 0.000 description 1
- MWPMMSVYHPAOIO-UHFFFAOYSA-N n-[2-(4-acetylphenyl)ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=C(C(C)=O)C=C1 MWPMMSVYHPAOIO-UHFFFAOYSA-N 0.000 description 1
- MZBYRVBVNGSJGY-UHFFFAOYSA-N n-[2-(4-acetylphenyl)ethyl]benzamide Chemical compound C1=CC(C(=O)C)=CC=C1CCNC(=O)C1=CC=CC=C1 MZBYRVBVNGSJGY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- FYWSTUCDSVYLPV-UHFFFAOYSA-N nitrooxythallium Chemical compound [Tl+].[O-][N+]([O-])=O FYWSTUCDSVYLPV-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- JLZCPFISUMNHDT-UHFFFAOYSA-N quinoline-8-carbonyl chloride Chemical compound C1=CN=C2C(C(=O)Cl)=CC=CC2=C1 JLZCPFISUMNHDT-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- OTECRMIOFOCDKE-UHFFFAOYSA-M sodium;2-[4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]phenyl]acetate Chemical compound [Na+].COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(CC([O-])=O)C=C1 OTECRMIOFOCDKE-UHFFFAOYSA-M 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752532420 DE2532420A1 (de) | 1975-07-19 | 1975-07-19 | Phenylessigsaeure-derivate und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43142L IE43142L (en) | 1977-01-19 |
| IE43142B1 true IE43142B1 (en) | 1980-12-31 |
Family
ID=5951971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1410/76A IE43142B1 (en) | 1975-07-19 | 1976-06-29 | Phenylacetic acid derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4207341A (enExample) |
| JP (1) | JPS5212144A (enExample) |
| AT (1) | AT343637B (enExample) |
| BE (1) | BE843685A (enExample) |
| CA (1) | CA1076126A (enExample) |
| DE (1) | DE2532420A1 (enExample) |
| DK (1) | DK297076A (enExample) |
| FR (1) | FR2318627A1 (enExample) |
| GB (1) | GB1511095A (enExample) |
| HU (1) | HU172453B (enExample) |
| IE (1) | IE43142B1 (enExample) |
| LU (1) | LU75270A1 (enExample) |
| NL (1) | NL7607159A (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77316A1 (enExample) * | 1977-05-11 | 1979-01-19 | ||
| LU79008A1 (de) * | 1978-02-03 | 1979-09-06 | Byk Gulden Lomberg Chem Fab | W-(n-alkyl-n-benzoyl-amino)-phenylalkansaeuren,ihre verwendung und herstellung sowie sie enthaltende arzneimittel |
| US4281018A (en) * | 1978-04-12 | 1981-07-28 | American Cyanamid Company | Novel 4-[(carboxyl- and sulfamyl-substituted alkyl)-amino]benzoic acids and analogs |
| DE2948056A1 (de) * | 1979-11-29 | 1981-06-04 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JPS575853A (en) * | 1980-06-13 | 1982-01-12 | Nisshin Steel Co Ltd | Continuous hot-dip coating apparatus |
| JPS56145261A (en) * | 1980-04-10 | 1981-11-11 | Kaken Pharmaceut Co Ltd | Novel oxyacetic acid derivative, its preparation, and lowering agent of lipid in blood comprising it as active ingredient |
| JPS5763603A (en) * | 1980-10-02 | 1982-04-17 | Sumitomo Electric Ind Ltd | Manufacture of cylinder liner |
| US5274000A (en) * | 1982-10-19 | 1993-12-28 | Kotobuki Seiyaku Company Limited | Benzofuran and benzothiophene derivatives, anti-hyperuricemia agents |
| IT1177966B (it) * | 1984-08-14 | 1987-09-03 | Medosan Ind Biochimi | Derivati amidici dell'acido 2-(p-aminobenzil)butirrico e relativi e-steri provvisti di attivita' ipolipidemizzante |
| IT1199652B (it) * | 1985-01-28 | 1988-12-30 | Boehringer Biochemia Srl | Composti ad attivita'antiiperlipidemica,loro preparazione e composizioni farmaceutiche che li contengono |
| US4587096A (en) * | 1985-05-23 | 1986-05-06 | Inco Alloys International, Inc. | Canless method for hot working gas atomized powders |
| US4689182A (en) * | 1985-12-20 | 1987-08-25 | Warner-Lambert Company | Benzoic acid and benzoic acid ester derivatives having anti-inflammatory and analgesic activity |
| JPH01208813A (ja) * | 1988-02-17 | 1989-08-22 | Matsushita Electric Ind Co Ltd | 希土類磁石の製造方法 |
| JPH0660323B2 (ja) * | 1988-06-16 | 1994-08-10 | 山陽特殊製鋼株式会社 | 粉末材料の加圧焼結方法 |
| US5227511A (en) * | 1988-12-23 | 1993-07-13 | Hodogaya Chemical Co., Ltd. | Benzamide derivatives and plant growth regulants containing them |
| US5166401A (en) * | 1991-06-25 | 1992-11-24 | Pfizer Inc | Intermediates for 5-fluoro-6-chlorooxindole |
| US5210212A (en) * | 1991-06-25 | 1993-05-11 | Pfizer Inc | Process for 5-fluoro-6-chlorooxindole |
| US6916489B2 (en) | 1992-06-15 | 2005-07-12 | Emisphere Technologies, Inc. | Active agent transport systems |
| TW279845B (enExample) * | 1992-12-01 | 1996-07-01 | Ciba Geigy Ag | |
| US20010003001A1 (en) | 1993-04-22 | 2001-06-07 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6001347A (en) | 1995-03-31 | 1999-12-14 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| IL126318A (en) | 1996-03-29 | 2004-09-27 | Emisphere Tech Inc | Compounds and compositions for delivering active agents and some novel carrier compounds |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| WO2000059863A1 (en) | 1999-04-05 | 2000-10-12 | Emisphere Technologies, Inc. | Disodium salts, monohydrates, and ethanol solvates |
| ES2298168T3 (es) * | 1999-12-16 | 2008-05-16 | Emisphere Technologies, Inc. | Compuestos y composiciones para suministrar agentes activos. |
| JP2005209106A (ja) * | 2004-01-26 | 2005-08-04 | Nec Corp | 携帯通信端末、受信メール管理方法、プログラムおよび記録媒体 |
| JP4848969B2 (ja) * | 2007-02-06 | 2011-12-28 | 凸版印刷株式会社 | 紙製包装容器 |
| US9714238B2 (en) | 2010-07-02 | 2017-07-25 | Allergan, Inc. | Therapeutic agents for ocular hypertension |
| WO2012003145A2 (en) | 2010-07-02 | 2012-01-05 | Allergan, Inc. | Therapeutic agents for ocular hypertension |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629450A (en) * | 1970-01-16 | 1971-12-21 | Ciba Geigy Corp | O-(substituted benzamido) phenylacetic acids as anti-inflammatory agents |
| DE2230383C3 (de) * | 1971-10-01 | 1981-12-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Phenoxyalkylcarbonsäurederivate und Verfahren zur Herstellung derselben |
| DE2320387A1 (de) * | 1973-04-21 | 1974-10-31 | Boehringer Mannheim Gmbh | Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben |
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
| DK148576A (da) * | 1975-04-18 | 1976-10-19 | Boehringer Mannheim Gmbh | Fenylalkankarbonsyrederivater og fremgangsmade til deres fremstilling |
-
1975
- 1975-07-19 DE DE19752532420 patent/DE2532420A1/de not_active Withdrawn
-
1976
- 1976-06-29 IE IE1410/76A patent/IE43142B1/en unknown
- 1976-06-30 LU LU75270A patent/LU75270A1/xx unknown
- 1976-06-30 NL NL7607159A patent/NL7607159A/xx not_active Application Discontinuation
- 1976-06-30 HU HU76BO00001621A patent/HU172453B/hu unknown
- 1976-06-30 JP JP51077696A patent/JPS5212144A/ja active Pending
- 1976-07-01 BE BE168556A patent/BE843685A/xx unknown
- 1976-07-01 GB GB27420/76A patent/GB1511095A/en not_active Expired
- 1976-07-01 US US05/701,717 patent/US4207341A/en not_active Expired - Lifetime
- 1976-07-01 AT AT482676A patent/AT343637B/de not_active IP Right Cessation
- 1976-07-01 DK DK297076A patent/DK297076A/da unknown
- 1976-07-02 FR FR7620230A patent/FR2318627A1/fr active Granted
- 1976-07-19 CA CA257,234A patent/CA1076126A/en not_active Expired
-
1979
- 1979-12-10 US US06/101,978 patent/US4278680A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4207341A (en) | 1980-06-10 |
| US4278680A (en) | 1981-07-14 |
| FR2318627A1 (fr) | 1977-02-18 |
| CA1076126A (en) | 1980-04-22 |
| DE2532420A1 (de) | 1977-02-03 |
| HU172453B (hu) | 1978-09-28 |
| FR2318627B1 (enExample) | 1978-11-17 |
| IE43142L (en) | 1977-01-19 |
| DK297076A (da) | 1977-01-20 |
| NL7607159A (nl) | 1977-01-21 |
| ATA482676A (de) | 1977-10-15 |
| BE843685A (fr) | 1977-01-03 |
| LU75270A1 (enExample) | 1977-02-23 |
| AT343637B (de) | 1978-06-12 |
| GB1511095A (en) | 1978-05-17 |
| JPS5212144A (en) | 1977-01-29 |
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