IL32089A - P-(pyrryl-1)-phenyl alkanoic acids,their preparation and pharmaceutical compositions containing them - Google Patents
P-(pyrryl-1)-phenyl alkanoic acids,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL32089A IL32089A IL6932089A IL3208969A IL32089A IL 32089 A IL32089 A IL 32089A IL 6932089 A IL6932089 A IL 6932089A IL 3208969 A IL3208969 A IL 3208969A IL 32089 A IL32089 A IL 32089A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- acid
- pharmaceutically acceptable
- pyrryl
- salt
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 64
- 150000007513 acids Chemical class 0.000 title claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 alkali metal salt Chemical class 0.000 claims description 31
- IRJCMFMTKREIQH-UHFFFAOYSA-N 4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1N1C=CC=C1 IRJCMFMTKREIQH-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- WLVZHIDRKXDCQO-UHFFFAOYSA-N 4-(3-chloro-4-pyrrol-1-ylphenyl)butanoic acid Chemical compound ClC=1C=C(C=CC1N1C=CC=C1)CCCC(=O)O WLVZHIDRKXDCQO-UHFFFAOYSA-N 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- YDUDSQOJLRADBS-UHFFFAOYSA-N 4-oxo-4-(4-pyrrol-1-ylphenyl)butanoic acid Chemical compound N1(C=CC=C1)C1=CC=C(C(=O)CCC(=O)O)C=C1 YDUDSQOJLRADBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002633 imido ester group Chemical group 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 61
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000001704 evaporation Methods 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
- 230000008020 evaporation Effects 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 150000007530 organic bases Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 150000007529 inorganic bases Chemical class 0.000 description 9
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- CCHQGGDBHJNLSC-UHFFFAOYSA-N 4-(4-amino-3-chlorophenyl)butanoic acid Chemical compound NC1=CC=C(CCCC(O)=O)C=C1Cl CCHQGGDBHJNLSC-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 5
- 239000001828 Gelatine Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- RBHLFWNKEWLHBP-UHFFFAOYSA-N 4-(4-aminophenyl)butanoic acid Chemical compound NC1=CC=C(CCCC(O)=O)C=C1 RBHLFWNKEWLHBP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000008063 acylals Chemical class 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- XIXXMITZOWKEBB-UHFFFAOYSA-N 1-[4-(2-bromoethyl)phenyl]pyrrole Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)CCBr XIXXMITZOWKEBB-UHFFFAOYSA-N 0.000 description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 3
- WRBOAZUDXNNWNI-UHFFFAOYSA-N 4-(4-aminophenyl)-4-oxobutanoic acid Chemical compound NC1=CC=C(C(=O)CCC(O)=O)C=C1 WRBOAZUDXNNWNI-UHFFFAOYSA-N 0.000 description 3
- PQOBFOICCWHIEM-UHFFFAOYSA-N 4-(4-pyrrol-1-ylphenyl)butanenitrile Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)CCCC#N PQOBFOICCWHIEM-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 235000019759 Maize starch Nutrition 0.000 description 3
- 125000003047 N-acetyl group Chemical group 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- LWUVHONFJXJGSP-UHFFFAOYSA-N ethyl 4-(4-pyrrol-1-ylphenyl)butanoate Chemical compound C(C)OC(CCCC1=CC=C(C=C1)N1C=CC=C1)=O LWUVHONFJXJGSP-UHFFFAOYSA-N 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical class CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- NNTMDTSGHWLWKT-UHFFFAOYSA-N (5-acetyloxyoxolan-2-yl) acetate Chemical compound CC(=O)OC1CCC(OC(C)=O)O1 NNTMDTSGHWLWKT-UHFFFAOYSA-N 0.000 description 2
- PMVLUYJPOCBXNS-UHFFFAOYSA-N 1-(4-aminophenyl)-2-chloroethanone Chemical compound NC1=CC=C(C(=O)CCl)C=C1 PMVLUYJPOCBXNS-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QZXCWMLOWANPMV-UHFFFAOYSA-N 3-(4-pyrrol-1-ylphenyl)propan-1-ol Chemical compound N1(C=CC=C1)C1=CC=C(C=C1)CCCO QZXCWMLOWANPMV-UHFFFAOYSA-N 0.000 description 2
- UTDQPIXNPMGGPK-UHFFFAOYSA-N 4-(2-bromoethyl)aniline;hydrochloride Chemical compound Cl.NC1=CC=C(CCBr)C=C1 UTDQPIXNPMGGPK-UHFFFAOYSA-N 0.000 description 2
- GVHXQQMLYHDQBE-UHFFFAOYSA-N 4-(4-acetamidophenyl)-4-oxobutanoic acid Chemical compound CC(=O)NC1=CC=C(C(=O)CCC(O)=O)C=C1 GVHXQQMLYHDQBE-UHFFFAOYSA-N 0.000 description 2
- PZTXRXFSUPINMW-UHFFFAOYSA-N 4-(4-acetamidophenyl)butanoic acid Chemical compound CC(=O)NC1=CC=C(CCCC(O)=O)C=C1 PZTXRXFSUPINMW-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001741 anti-phlogistic effect Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- KHUZFDXJKAADDB-UHFFFAOYSA-N diethyl 2-[2-(3-chloro-4-pyrrol-1-ylphenyl)ethyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)CCC1=CC(=C(C=C1)N1C=CC=C1)Cl)=O KHUZFDXJKAADDB-UHFFFAOYSA-N 0.000 description 2
- NCKMREVMFZRBJA-UHFFFAOYSA-N diethyl 2-[2-(4-pyrrol-1-ylphenyl)ethyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)CCC1=CC=C(C=C1)N1C=CC=C1)=O NCKMREVMFZRBJA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- DJNMOHZQUVIZMS-UHFFFAOYSA-N ethyl 2-(3-chloro-4-pyrrol-1-ylphenyl)acetate Chemical compound C(C)OC(CC1=CC(=C(C=C1)N1C=CC=C1)Cl)=O DJNMOHZQUVIZMS-UHFFFAOYSA-N 0.000 description 2
- NHGYQADUGSHIGS-UHFFFAOYSA-N ethyl 2-(4-amino-3-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C(Cl)=C1 NHGYQADUGSHIGS-UHFFFAOYSA-N 0.000 description 2
- MMHDZXFAOPMNCS-UHFFFAOYSA-N ethyl 2-[2-(3-chloro-4-pyrrol-1-ylphenyl)ethyl]-3-oxobutanoate Chemical compound C(C)OC(C(C(=O)C)CCC1=CC(=C(C=C1)N1C=CC=C1)Cl)=O MMHDZXFAOPMNCS-UHFFFAOYSA-N 0.000 description 2
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- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 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
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH637968A CH500189A (de) | 1968-04-29 | 1968-04-29 | Verfahren zur Herstellung von neuen, substituierten Phenylalkansäuren |
| CH1732968A CH507234A (de) | 1968-04-29 | 1968-11-20 | Verfahren zur Herstellung von neuen, substituierten Alkansäuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32089A0 IL32089A0 (en) | 1969-06-25 |
| IL32089A true IL32089A (en) | 1972-11-28 |
Family
ID=25699490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL6932089A IL32089A (en) | 1968-04-29 | 1969-04-28 | P-(pyrryl-1)-phenyl alkanoic acids,their preparation and pharmaceutical compositions containing them |
Country Status (19)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183276A (ja) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | 両面接着テ−プ |
| JPS6183275A (ja) * | 1984-10-01 | 1986-04-26 | Kimurashin Kk | 両面接着テ−プの製造方法 |
| FI74723C (fi) * | 1986-10-24 | 1988-03-10 | Yhtyneet Paperitehtaat Oy | Haeftprodukt. |
-
1968
- 1968-04-29 CH CH637968A patent/CH500189A/de not_active IP Right Cessation
- 1968-11-20 CH CH1732968A patent/CH507234A/de not_active IP Right Cessation
-
1969
- 1969-04-22 FI FI691195A patent/FI50971C/fi active
- 1969-04-22 SE SE05684/69A patent/SE338994B/xx unknown
- 1969-04-22 NL NL6906209A patent/NL6906209A/xx unknown
- 1969-04-22 DK DK219769AA patent/DK125132C/da active
- 1969-04-22 US US818393A patent/US3651084A/en not_active Expired - Lifetime
- 1969-04-22 NO NO691670A patent/NO129572B/no unknown
- 1969-04-28 ES ES366545A patent/ES366545A1/es not_active Expired
- 1969-04-28 IL IL6932089A patent/IL32089A/en unknown
- 1969-04-28 AT AT189170A patent/AT290518B/de not_active IP Right Cessation
- 1969-04-28 CS CS7999*A patent/CS161854B2/cs unknown
- 1969-04-28 ES ES366547A patent/ES366547A1/es not_active Expired
- 1969-04-28 AT AT189370A patent/AT290520B/de not_active IP Right Cessation
- 1969-04-28 CS CS3005A patent/CS161851B2/cs unknown
- 1969-04-28 GB GB2152369A patent/GB1264367A/en not_active Expired
- 1969-04-28 DE DE19691921651 patent/DE1921651A1/de active Pending
- 1969-04-28 IE IE577/69A patent/IE33116B1/xx unknown
- 1969-04-28 AT AT189270A patent/AT290519B/de not_active IP Right Cessation
- 1969-04-28 CS CS7998*A patent/CS161853B2/cs unknown
- 1969-04-28 PL PL1969133260A patent/PL69906B1/pl unknown
- 1969-04-28 BG BG013039A patent/BG15547A3/bg unknown
- 1969-04-28 AT AT409069A patent/AT286976B/de active
- 1969-04-28 AT AT189070A patent/AT290517B/de not_active IP Right Cessation
- 1969-04-28 BG BG012132A patent/BG15206A3/bg unknown
- 1969-04-28 ES ES366544A patent/ES366544A1/es not_active Expired
- 1969-04-28 CS CS7997*A patent/CS161852B2/cs unknown
- 1969-04-28 ES ES366546A patent/ES366546A1/es not_active Expired
- 1969-04-29 BE BE732301D patent/BE732301A/xx unknown
- 1969-04-29 FR FR6913602A patent/FR2007555A1/fr not_active Withdrawn
- 1969-09-17 BG BG013040A patent/BG15548A3/bg unknown
- 1969-09-17 BG BG013038A patent/BG15546A3/bg unknown
- 1969-09-17 BG BG013037A patent/BG15752A3/bg unknown
-
1971
- 1971-10-22 JP JP46083856A patent/JPS4827309B1/ja active Pending
- 1971-10-22 JP JP46083858A patent/JPS4813550B1/ja active Pending
Also Published As
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