CH518929A - Verfahren zur Herstellung neuer 5-Aroylpyrrolyl-(2)-alkansäurederivate - Google Patents
Verfahren zur Herstellung neuer 5-Aroylpyrrolyl-(2)-alkansäurederivateInfo
- Publication number
- CH518929A CH518929A CH1116368A CH1116368A CH518929A CH 518929 A CH518929 A CH 518929A CH 1116368 A CH1116368 A CH 1116368A CH 1116368 A CH1116368 A CH 1116368A CH 518929 A CH518929 A CH 518929A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylpyrrole
- chlorobenzoyl
- chloride
- acetic acid
- acetonitrile
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 6
- -1 and R2=CN Chemical group 0.000 claims abstract description 63
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 65
- 239000007787 solid Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 35
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- 230000008018 melting Effects 0.000 claims description 30
- 238000002844 melting Methods 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 19
- 238000001953 recrystallisation Methods 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 14
- ROSYAUHHRKAPHX-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)acetonitrile Chemical compound CN1C=CC=C1CC#N ROSYAUHHRKAPHX-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 12
- ZWUBGDPUVGOZMR-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 ZWUBGDPUVGOZMR-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 10
- 230000004048 modification Effects 0.000 claims description 10
- 238000012986 modification Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 230000008020 evaporation Effects 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- UZQLEMLKKBRPQG-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1h-pyrrol-2-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(CC#N)N1 UZQLEMLKKBRPQG-UHFFFAOYSA-N 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012267 brine Substances 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- NXFODIMCJLQNRQ-UHFFFAOYSA-N 2-[1-benzyl-4-(4-chlorobenzoyl)pyrrol-2-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CN(CC=2C=CC=CC=2)C(CC#N)=C1 NXFODIMCJLQNRQ-UHFFFAOYSA-N 0.000 claims description 5
- BKWLJDWIUOFEQK-UHFFFAOYSA-N 2-[5-(2,4-dichlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl BKWLJDWIUOFEQK-UHFFFAOYSA-N 0.000 claims description 5
- GDRPXPPAYAOCIK-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC=C1C(=O)C1=CC=C(Cl)C=C1 GDRPXPPAYAOCIK-UHFFFAOYSA-N 0.000 claims description 5
- GANDSBWEBNXLMG-UHFFFAOYSA-N 3-chloro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1Cl GANDSBWEBNXLMG-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 claims description 5
- GVUURLVADCWORZ-UHFFFAOYSA-N 2-[1-benzyl-5-(4-chlorobenzoyl)pyrrol-2-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(CC#N)N1CC1=CC=CC=C1 GVUURLVADCWORZ-UHFFFAOYSA-N 0.000 claims description 4
- APSWAFZHMYVSMV-UHFFFAOYSA-N 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetonitrile Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC#N)N1C APSWAFZHMYVSMV-UHFFFAOYSA-N 0.000 claims description 4
- LNRUQZRLKRFSGF-UHFFFAOYSA-N 2-[1-methyl-5-(4-nitrobenzoyl)pyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 LNRUQZRLKRFSGF-UHFFFAOYSA-N 0.000 claims description 4
- HDTFMJOVUJMERP-UHFFFAOYSA-N 2-[5-(3-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=CC(Cl)=C1 HDTFMJOVUJMERP-UHFFFAOYSA-N 0.000 claims description 4
- IYHCQYYGQKJKMI-UHFFFAOYSA-N 2-[5-(4-aminobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(N)C=C1 IYHCQYYGQKJKMI-UHFFFAOYSA-N 0.000 claims description 4
- VJYBXSPJIFMJQO-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1h-pyrrol-2-yl]acetic acid Chemical compound N1C(CC(=O)O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 VJYBXSPJIFMJQO-UHFFFAOYSA-N 0.000 claims description 4
- LYGQPHXURYMFJT-UHFFFAOYSA-N 2-[5-(4-cyanobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C#N)C=C1 LYGQPHXURYMFJT-UHFFFAOYSA-N 0.000 claims description 4
- QDZACITZLASKAX-UHFFFAOYSA-N 2-[5-(4-methoxybenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C QDZACITZLASKAX-UHFFFAOYSA-N 0.000 claims description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 4
- SETWKPWDTMJORY-UHFFFAOYSA-N 2-(1-benzylpyrrol-2-yl)acetonitrile Chemical compound N#CCC1=CC=CN1CC1=CC=CC=C1 SETWKPWDTMJORY-UHFFFAOYSA-N 0.000 claims description 3
- WVKPVCGHCFYVKZ-UHFFFAOYSA-N 2-(5-benzoyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=CC=C1 WVKPVCGHCFYVKZ-UHFFFAOYSA-N 0.000 claims description 3
- RVVJEUOAPMNYLC-UHFFFAOYSA-N 2-[1-benzyl-5-(4-chlorobenzoyl)pyrrol-2-yl]acetic acid Chemical compound C=1C=CC=CC=1CN1C(CC(=O)O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RVVJEUOAPMNYLC-UHFFFAOYSA-N 0.000 claims description 3
- DCPQSDRGXGSUKZ-UHFFFAOYSA-N 2-[5-(2,4-dichlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl DCPQSDRGXGSUKZ-UHFFFAOYSA-N 0.000 claims description 3
- SNSQCMKQRKLFLV-UHFFFAOYSA-N 2-[5-(4-bromobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(Br)C=C1 SNSQCMKQRKLFLV-UHFFFAOYSA-N 0.000 claims description 3
- IJORGWGJHZNCNN-UHFFFAOYSA-N 2-[5-(4-fluorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(F)C=C1 IJORGWGJHZNCNN-UHFFFAOYSA-N 0.000 claims description 3
- RGAKSNQOIIYQRM-UHFFFAOYSA-N 3,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1C RGAKSNQOIIYQRM-UHFFFAOYSA-N 0.000 claims description 3
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 claims description 3
- XLWQUESMILVIPR-UHFFFAOYSA-N 4-ethoxybenzoyl chloride Chemical compound CCOC1=CC=C(C(Cl)=O)C=C1 XLWQUESMILVIPR-UHFFFAOYSA-N 0.000 claims description 3
- AVTLLLZVYYPGFX-UHFFFAOYSA-N 4-ethylbenzoyl chloride Chemical compound CCC1=CC=C(C(Cl)=O)C=C1 AVTLLLZVYYPGFX-UHFFFAOYSA-N 0.000 claims description 3
- NWPBFGWVZQGAHM-UHFFFAOYSA-N 4-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C=C1 NWPBFGWVZQGAHM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- MMEYPSTUCSIDCF-UHFFFAOYSA-N benzene;methylcyclohexane Chemical compound C1=CC=CC=C1.CC1CCCCC1 MMEYPSTUCSIDCF-UHFFFAOYSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 3
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- RFQXZWAOEPMHCE-UHFFFAOYSA-N 2,3,5-tribromobenzoyl chloride Chemical compound ClC(=O)C1=CC(Br)=CC(Br)=C1Br RFQXZWAOEPMHCE-UHFFFAOYSA-N 0.000 claims description 2
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 claims description 2
- CHOSHMAFWKKQQF-UHFFFAOYSA-N 3-bromo-4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Br)=C1 CHOSHMAFWKKQQF-UHFFFAOYSA-N 0.000 claims description 2
- SDKUOEOJAXGCLU-UHFFFAOYSA-N 3-chloro-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1Cl SDKUOEOJAXGCLU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 18
- 125000004494 ethyl ester group Chemical group 0.000 claims 4
- WENDCVWGPOVTSZ-UHFFFAOYSA-N 2-(1-ethylpyrrol-2-yl)acetic acid Chemical compound CCN1C=CC=C1CC(O)=O WENDCVWGPOVTSZ-UHFFFAOYSA-N 0.000 claims 1
- OORBYQVSQSXKRG-UHFFFAOYSA-N ethyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CN1C OORBYQVSQSXKRG-UHFFFAOYSA-N 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- CGYVDYLHQYNGFC-UHFFFAOYSA-N methyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1C CGYVDYLHQYNGFC-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 238000001914 filtration Methods 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 206010018691 Granuloma Diseases 0.000 description 6
- 239000012223 aqueous fraction Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- SYYOUHJJSOLSJD-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)acetic acid Chemical class CN1C=CC=C1CC(O)=O SYYOUHJJSOLSJD-UHFFFAOYSA-N 0.000 description 4
- IQMWEUKWCJGKSC-UHFFFAOYSA-N 2-[5-(3-chlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC=C1C(=O)C1=CC=CC(Cl)=C1 IQMWEUKWCJGKSC-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XJXRZWVVELTPCI-UHFFFAOYSA-N 2-[5-(2-chlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC=C1C(=O)C1=CC=CC=C1Cl XJXRZWVVELTPCI-UHFFFAOYSA-N 0.000 description 3
- OFSSFIWENVBKOB-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1-ethylpyrrol-2-yl]acetic acid Chemical compound CCN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OFSSFIWENVBKOB-UHFFFAOYSA-N 0.000 description 3
- JSPRLTOHBSHLGB-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1-ethylpyrrol-2-yl]acetonitrile Chemical compound CCN1C(CC#N)=CC=C1C(=O)C1=CC=C(Cl)C=C1 JSPRLTOHBSHLGB-UHFFFAOYSA-N 0.000 description 3
- KCVJOQCNHSHRDO-UHFFFAOYSA-N ClC1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C Chemical compound ClC1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C KCVJOQCNHSHRDO-UHFFFAOYSA-N 0.000 description 3
- 235000009161 Espostoa lanata Nutrition 0.000 description 3
- 240000001624 Espostoa lanata Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
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- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose 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
- C07D207/33—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 ring carbon atoms
- C07D207/337—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1928470A CH522637A (de) | 1967-07-26 | 1968-07-25 | Verfahren zur Herstellung von 5-Aroyl-pyrrolyl-(2)-alkansäurederivaten |
| CH1937170A CH517092A (de) | 1967-07-26 | 1968-07-25 | Verfahren zur Herstellung neuer 5-Aroylpyrrolyl-(2)-alkansäureamide |
| CH1928370A CH522636A (de) | 1967-07-26 | 1968-07-25 | Verfahren zur Herstellung von neuen Pyrrolderivaten |
| CH1928270A CH529131A (de) | 1967-07-26 | 1968-07-25 | Verfahren zur Herstellung neuer 5-Aroylpyrrolyl-(2)-propionsäureester |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65607467A | 1967-07-26 | 1967-07-26 | |
| US74134868A | 1968-07-01 | 1968-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH518929A true CH518929A (de) | 1972-02-15 |
Family
ID=27097103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1116368A CH518929A (de) | 1967-07-26 | 1968-07-25 | Verfahren zur Herstellung neuer 5-Aroylpyrrolyl-(2)-alkansäurederivate |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT289096B (enrdf_load_stackoverflow) |
| BE (1) | BE718594A (enrdf_load_stackoverflow) |
| CH (1) | CH518929A (enrdf_load_stackoverflow) |
| DK (1) | DK136059B (enrdf_load_stackoverflow) |
| ES (1) | ES356485A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1574570A (enrdf_load_stackoverflow) |
| GB (1) | GB1195628A (enrdf_load_stackoverflow) |
| IL (1) | IL30426A (enrdf_load_stackoverflow) |
| NL (1) | NL162638C (enrdf_load_stackoverflow) |
| SE (1) | SE338993B (enrdf_load_stackoverflow) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2128205B1 (enrdf_load_stackoverflow) * | 1971-03-11 | 1974-05-24 | Roussel Uclaf | |
| FR2068425B1 (enrdf_load_stackoverflow) * | 1969-11-12 | 1973-01-12 | Roussel Uclaf | |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| DE3026402A1 (de) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Die verwendung analgetischer und nicht-hormonaler, entzuendungshemmender mittel bei der behandlung von mikrovaskulaeren erkrankungen |
| US4396626A (en) | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
| US4418074A (en) * | 1981-11-23 | 1983-11-29 | Riker Laboratories, Inc. | 2,6 Di(t-butyl)-4-(2'-pyrrol)-phenol and anti-inflammatory use thereof |
| IT1210673B (it) * | 1982-02-26 | 1989-09-20 | Medosan Ind Biochimi | Antinfiammatoria amidi pirrolacetiche ad attivita' |
| YU251283A (en) * | 1983-01-26 | 1986-04-30 | Mcneilab Inc | Process for obtaining pyrrol-2-acetylamino acid derivatives |
| EP0783488A4 (en) * | 1994-09-27 | 1998-01-07 | Ono Pharmaceutical Co | FIVE-ELEMENT HETEROCYCLIC COMPOUNDS |
| US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
| IT1288123B1 (it) | 1996-09-04 | 1998-09-10 | Nicox Sa | Uso di nitroderivati per l'incontinenza urinaria |
| IT1308633B1 (it) | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
| CA2511582C (en) * | 2003-02-06 | 2012-01-24 | Dompe S.P.A. | 2-aryl-acetic acids, their derivatives and pharmaceutical compositions containing them |
-
1968
- 1968-07-24 ES ES356485A patent/ES356485A1/es not_active Expired
- 1968-07-24 SE SE1007068A patent/SE338993B/xx unknown
- 1968-07-24 GB GB3527768A patent/GB1195628A/en not_active Expired
- 1968-07-25 FR FR1574570D patent/FR1574570A/fr not_active Expired
- 1968-07-25 BE BE718594D patent/BE718594A/xx not_active IP Right Cessation
- 1968-07-25 CH CH1116368A patent/CH518929A/de not_active IP Right Cessation
- 1968-07-25 IL IL3042668A patent/IL30426A/en unknown
- 1968-07-26 DK DK361168A patent/DK136059B/da not_active IP Right Cessation
- 1968-07-26 NL NL6810664A patent/NL162638C/xx not_active IP Right Cessation
- 1968-07-26 AT AT730768A patent/AT289096B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE718594A (enrdf_load_stackoverflow) | 1969-01-27 |
| DE1770984A1 (de) | 1972-04-06 |
| IL30426A (en) | 1972-02-29 |
| NL6810664A (enrdf_load_stackoverflow) | 1969-01-28 |
| NL162638C (nl) | 1980-06-16 |
| AT289096B (de) | 1971-04-13 |
| DE1770984B2 (de) | 1975-05-22 |
| SE338993B (enrdf_load_stackoverflow) | 1971-09-27 |
| NL162638B (nl) | 1980-01-15 |
| DK136059B (da) | 1977-08-08 |
| GB1195628A (en) | 1970-06-17 |
| DK136059C (enrdf_load_stackoverflow) | 1978-01-09 |
| FR1574570A (enrdf_load_stackoverflow) | 1969-07-11 |
| ES356485A1 (es) | 1970-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |