CH624936A5 - - Google Patents
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- Publication number
- CH624936A5 CH624936A5 CH818576A CH818576A CH624936A5 CH 624936 A5 CH624936 A5 CH 624936A5 CH 818576 A CH818576 A CH 818576A CH 818576 A CH818576 A CH 818576A CH 624936 A5 CH624936 A5 CH 624936A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acetic acid
- chloro
- methylpyrrole
- methyl
- bromo
- Prior art date
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- -1 alkyl radical Chemical class 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VDFYOOIXVXQUFQ-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=C(Br)C=C(CC(O)=O)N1C VDFYOOIXVXQUFQ-UHFFFAOYSA-N 0.000 claims description 3
- LJOFMJVCYKMSDH-UHFFFAOYSA-N 2-[4-bromo-5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC(Br)=C1C(=O)C1=CC=C(Cl)C=C1 LJOFMJVCYKMSDH-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- SWJWRHZVLFSWJA-UHFFFAOYSA-N 2-[3-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1CC(O)=O SWJWRHZVLFSWJA-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 8
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- AVZSKMBAQNATFS-UHFFFAOYSA-N 2-(4-chloro-1h-pyrrol-2-yl)acetonitrile Chemical compound ClC1=CNC(CC#N)=C1 AVZSKMBAQNATFS-UHFFFAOYSA-N 0.000 description 5
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- APABABGDMIOGRK-UHFFFAOYSA-N 2-[3-chloro-1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(Cl)=C(CC(O)=O)N1C APABABGDMIOGRK-UHFFFAOYSA-N 0.000 description 4
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- JIPKLZVKWCJYEX-UHFFFAOYSA-N methyl 2-(1h-pyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1 JIPKLZVKWCJYEX-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VLAWMGWMHNAJKK-UHFFFAOYSA-N 2-[4-chloro-5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC(Cl)=C1C(=O)C1=CC=C(Cl)C=C1 VLAWMGWMHNAJKK-UHFFFAOYSA-N 0.000 description 3
- DGOUTGCSMNTDHO-UHFFFAOYSA-N 2-[4-chloro-5-(4-chlorobenzoyl)-1h-pyrrol-2-yl]acetonitrile Chemical compound C1=C(CC#N)NC(C(=O)C=2C=CC(Cl)=CC=2)=C1Cl DGOUTGCSMNTDHO-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 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 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- OZBIETPCMMGBGS-UHFFFAOYSA-N 1,1-dimethyl-2-propylhydrazine Chemical compound CCCNN(C)C OZBIETPCMMGBGS-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MKVATVUOVMCHJJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetonitrile Chemical compound N#CCC1=CC=CN1 MKVATVUOVMCHJJ-UHFFFAOYSA-N 0.000 description 2
- CVQDCIDRYOEKBV-UHFFFAOYSA-N 2-(4-bromo-1h-pyrrol-2-yl)acetonitrile Chemical compound BrC1=CNC(CC#N)=C1 CVQDCIDRYOEKBV-UHFFFAOYSA-N 0.000 description 2
- QFMMHAHOPMPRNG-UHFFFAOYSA-N 2-[3-chloro-1-ethyl-5-(4-methoxybenzoyl)pyrrol-2-yl]acetic acid Chemical compound CCN1C(CC(O)=O)=C(Cl)C=C1C(=O)C1=CC=C(OC)C=C1 QFMMHAHOPMPRNG-UHFFFAOYSA-N 0.000 description 2
- YZKULQWQJBZKBO-UHFFFAOYSA-N 2-[3-chloro-5-(3-chlorobenzoyl)-1-ethylpyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(CC)C(C(=O)C=2C=C(Cl)C=CC=2)=C1 YZKULQWQJBZKBO-UHFFFAOYSA-N 0.000 description 2
- ZUCFTHNEYWRGIA-UHFFFAOYSA-N 2-[3-chloro-5-(3-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(C)C(C(=O)C=2C=C(Cl)C=CC=2)=C1 ZUCFTHNEYWRGIA-UHFFFAOYSA-N 0.000 description 2
- SJFSOVXGRVCMHR-UHFFFAOYSA-N 2-[3-chloro-5-(4-methoxybenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC(Cl)=C(CC(O)=O)N1C SJFSOVXGRVCMHR-UHFFFAOYSA-N 0.000 description 2
- UKSFKCLYQUJFBD-UHFFFAOYSA-N 2-[4-bromo-5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC(Br)=C1C(=O)C1=CC=C(Cl)C=C1 UKSFKCLYQUJFBD-UHFFFAOYSA-N 0.000 description 2
- VDGXAEHNZYQQQN-UHFFFAOYSA-N 2-[4-bromo-5-(4-chlorobenzoyl)-1h-pyrrol-2-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=C(Br)C=C(CC#N)N1 VDGXAEHNZYQQQN-UHFFFAOYSA-N 0.000 description 2
- LMROYLIKYBHFHY-UHFFFAOYSA-N 2-[5-(4-bromobenzoyl)-3-chloro-1-methylpyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Br)=CC=2)=C1 LMROYLIKYBHFHY-UHFFFAOYSA-N 0.000 description 2
- NHLHAYSCZNVCRB-UHFFFAOYSA-N 4-chloro-2-(pyrrolidin-1-ium-1-ylidenemethyl)-1h-pyrrole;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.ClC1=CNC(C=[N+]2CCCC2)=C1 NHLHAYSCZNVCRB-UHFFFAOYSA-N 0.000 description 2
- XAADOFSAMXXKBP-UHFFFAOYSA-N 4-chloro-2-(pyrrolidin-1-ylmethyl)-1h-pyrrole;perchloric acid Chemical compound OCl(=O)(=O)=O.ClC1=CNC(CN2CCCC2)=C1 XAADOFSAMXXKBP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- UFHGJNGPONETPG-UHFFFAOYSA-N ethyl 4-bromo-5-(4-chlorobenzoyl)-2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylate Chemical compound CN1C(CC(=O)OCC)=C(C(=O)OCC)C(Br)=C1C(=O)C1=CC=C(Cl)C=C1 UFHGJNGPONETPG-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- CNHUCBXIKSSPHQ-UHFFFAOYSA-N perchloric acid;pyrrolidine Chemical compound C1CCNC1.OCl(=O)(=O)=O CNHUCBXIKSSPHQ-UHFFFAOYSA-N 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- REGBKMQHVZERFN-UHFFFAOYSA-N 2-(3-ethoxycarbonyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CCOC(=O)C=1C=CN(C)C=1CC(O)=O REGBKMQHVZERFN-UHFFFAOYSA-N 0.000 description 1
- VILPLZMONPLHCL-UHFFFAOYSA-N 2-[3-bromo-1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(Br)=C(CC(O)=O)N1C VILPLZMONPLHCL-UHFFFAOYSA-N 0.000 description 1
- ABSATBPDIKAMEO-UHFFFAOYSA-N 2-[3-chloro-1-ethyl-5-(2,4,6-trimethylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(CC)C(C(=O)C=2C(=CC(C)=CC=2C)C)=C1 ABSATBPDIKAMEO-UHFFFAOYSA-N 0.000 description 1
- BFBFLSYBZFDJIE-UHFFFAOYSA-N 2-[3-chloro-1-methyl-5-(2,4,6-trimethylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC(Cl)=C(CC(O)=O)N1C BFBFLSYBZFDJIE-UHFFFAOYSA-N 0.000 description 1
- GWTQTYBANFHANF-UHFFFAOYSA-N 2-[3-chloro-1-methyl-5-[4-(trifluoromethyl)benzoyl]pyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 GWTQTYBANFHANF-UHFFFAOYSA-N 0.000 description 1
- CAEBEZWWJZMLCD-UHFFFAOYSA-N 2-[3-chloro-5-(3,4-dichlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound ClC1=C(CC(O)=O)N(C)C(C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 CAEBEZWWJZMLCD-UHFFFAOYSA-N 0.000 description 1
- ZHYMZMSXBRRSHU-UHFFFAOYSA-N 2-[4-bromo-1-ethyl-5-(2,4,6-trimethylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound CCN1C(CC(O)=O)=CC(Br)=C1C(=O)C1=C(C)C=C(C)C=C1C ZHYMZMSXBRRSHU-UHFFFAOYSA-N 0.000 description 1
- OVKGACYAVWKCJX-UHFFFAOYSA-N 2-[4-bromo-1-ethyl-5-(4-methoxybenzoyl)pyrrol-2-yl]acetic acid Chemical compound CCN1C(CC(O)=O)=CC(Br)=C1C(=O)C1=CC=C(OC)C=C1 OVKGACYAVWKCJX-UHFFFAOYSA-N 0.000 description 1
- QGYFFNNXGNHJRI-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-(2,4,6-trimethylbenzoyl)pyrrol-2-yl]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=C(Br)C=C(CC(O)=O)N1C QGYFFNNXGNHJRI-UHFFFAOYSA-N 0.000 description 1
- IKFALJXDXASCFV-UHFFFAOYSA-N 2-[4-bromo-1-methyl-5-[4-(trifluoromethyl)benzoyl]pyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC(Br)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1 IKFALJXDXASCFV-UHFFFAOYSA-N 0.000 description 1
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- BRMVJESOAXBNJD-UHFFFAOYSA-N 2-[5-(4-bromobenzoyl)-4-chloro-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC(Cl)=C1C(=O)C1=CC=C(Br)C=C1 BRMVJESOAXBNJD-UHFFFAOYSA-N 0.000 description 1
- BXHNJBZHNPRSAR-UHFFFAOYSA-N 2-[5-(4-bromobenzoyl)-4-chloro-1-methylpyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC(Cl)=C1C(=O)C1=CC=C(Br)C=C1 BXHNJBZHNPRSAR-UHFFFAOYSA-N 0.000 description 1
- BIYAXFRUMMROEQ-UHFFFAOYSA-N 2-[5-(4-bromobenzoyl)-4-chloro-1h-pyrrol-2-yl]acetonitrile Chemical compound C1=C(CC#N)NC(C(=O)C=2C=CC(Br)=CC=2)=C1Cl BIYAXFRUMMROEQ-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XEGCGCLMSCSWNA-UHFFFAOYSA-N 4-bromo-2-(carboxymethyl)-5-(4-chlorobenzoyl)-1-methylpyrrole-3-carboxylic acid Chemical compound CN1C(CC(O)=O)=C(C(O)=O)C(Br)=C1C(=O)C1=CC=C(Cl)C=C1 XEGCGCLMSCSWNA-UHFFFAOYSA-N 0.000 description 1
- HXYMLKYKASLCJO-UHFFFAOYSA-N 4-bromo-5-(4-chlorobenzoyl)-2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylic acid Chemical compound CN1C(CC(=O)OCC)=C(C(O)=O)C(Br)=C1C(=O)C1=CC=C(Cl)C=C1 HXYMLKYKASLCJO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 150000007960 acetonitrile Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WIDHUKOADYLKIO-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylate Chemical compound CCOC(=O)CC1=C(C(=O)OCC)C=CN1C WIDHUKOADYLKIO-UHFFFAOYSA-N 0.000 description 1
- UZSSVYKHFJYIHB-UHFFFAOYSA-N ethyl 2-[4-bromo-1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OCC)=CC(Br)=C1C(=O)C1=CC=C(C)C=C1 UZSSVYKHFJYIHB-UHFFFAOYSA-N 0.000 description 1
- RNASWCMOFWRZHS-UHFFFAOYSA-N ethyl 2-[4-bromo-5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OCC)=CC(Br)=C1C(=O)C1=CC=C(Cl)C=C1 RNASWCMOFWRZHS-UHFFFAOYSA-N 0.000 description 1
- XIUHFUSCEPLUGE-UHFFFAOYSA-N ethyl 5-(4-chlorobenzoyl)-1-methylpyrrole-3-carboxylate Chemical compound CN1C=C(C(=O)OCC)C=C1C(=O)C1=CC=C(Cl)C=C1 XIUHFUSCEPLUGE-UHFFFAOYSA-N 0.000 description 1
- STWNOSLPZQDXKT-UHFFFAOYSA-N ethyl 5-(4-chlorobenzoyl)-2-(2-ethoxy-2-oxoethyl)-1-methylpyrrole-3-carboxylate Chemical compound CN1C(CC(=O)OCC)=C(C(=O)OCC)C=C1C(=O)C1=CC=C(Cl)C=C1 STWNOSLPZQDXKT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- SIXINSDWVSIFEY-UHFFFAOYSA-N methyl 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(=O)C1=CC=C(C)C=C1 SIXINSDWVSIFEY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D207/34—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 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/591,217 US4048191A (en) | 1975-06-27 | 1975-06-27 | Halo-substituted 1-loweralkyl-5-aroylpyrrole-2-acetic acid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624936A5 true CH624936A5 (fr) | 1981-08-31 |
Family
ID=24365579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH818576A CH624936A5 (fr) | 1975-06-27 | 1976-06-25 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4048191A (fr) |
| JP (1) | JPS525761A (fr) |
| AT (1) | AT361462B (fr) |
| AU (1) | AU508884B2 (fr) |
| BE (1) | BE843454A (fr) |
| CA (1) | CA1094084A (fr) |
| CH (1) | CH624936A5 (fr) |
| CS (1) | CS222227B2 (fr) |
| DE (1) | DE2628475A1 (fr) |
| DK (1) | DK274676A (fr) |
| ES (1) | ES449083A1 (fr) |
| FR (1) | FR2316942A1 (fr) |
| GB (1) | GB1540437A (fr) |
| IL (1) | IL49911A (fr) |
| IN (1) | IN144407B (fr) |
| IT (1) | IT1062038B (fr) |
| NL (1) | NL7606999A (fr) |
| PH (1) | PH11645A (fr) |
| PT (1) | PT65280B (fr) |
| RO (1) | RO70264B (fr) |
| SE (1) | SE418083B (fr) |
| YU (1) | YU156276A (fr) |
| ZA (1) | ZA763814B (fr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200645A (en) * | 1977-05-10 | 1980-04-29 | Beecham Group Limited | Pyrrole derivatives |
| US4119639A (en) * | 1977-06-27 | 1978-10-10 | Mcneil Laboratories, Incorporated | Preparation of 5-aroylpyrrole-2-acetic acid derivatives |
| GB1592996A (en) * | 1977-10-10 | 1981-07-15 | Rolland Sa A | Acylated pyrrole carboxylic acids and derivatives thereof |
| US4246175A (en) * | 1979-05-29 | 1981-01-20 | Ethyl Corporation | Synthesis of 5-cyano-1-hydrocarbylpyrrole-2-acetic acid |
| US4213905A (en) * | 1979-06-25 | 1980-07-22 | Mcneilab, Inc. | Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts |
| US4246176A (en) * | 1979-07-05 | 1981-01-20 | Ethyl Corporation | Synthesis of 5-aroyl-1-hydrocarbylpyrrole-2-acetic acid |
| EP0024807B1 (fr) * | 1979-07-28 | 1983-11-02 | Beecham Group Plc | Acides benzocycloheptapyrrole alcanoiques, procédés pour leur préparation et compositions pharmaceutiques les contenant |
| US4363918A (en) * | 1979-09-11 | 1982-12-14 | Janssen Pharmaceutica N.V. | Method of preparing 1-alkyl-3-carboxy-1H pyrrole-2-acetic acids |
| US4333878A (en) * | 1980-04-04 | 1982-06-08 | Ethyl Corporation | Process for producing substituted pyrroles |
| US4388468A (en) * | 1980-04-04 | 1983-06-14 | Ethyl Corporation | Process for producing substituted pyrroles |
| US4374255A (en) * | 1980-04-04 | 1983-02-15 | Ethyl Corporation | Process for producing substituted pyrroles |
| US4565879A (en) * | 1980-04-04 | 1986-01-21 | Ethyl Corporation | Process for producing substituted pyrroles |
| US4565878A (en) * | 1980-04-04 | 1986-01-21 | Ethyl Corporation | Process for producing substituted pyrroles |
| US4299770A (en) * | 1980-05-29 | 1981-11-10 | Mallinckrodt, Inc. | Recovery of substituted pyrrole acetate |
| US4396626A (en) * | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
| US4511576A (en) * | 1981-04-23 | 1985-04-16 | Pfizer Inc. | Antidiabetic pyrrolecarboxylic acids |
| US4374997A (en) * | 1981-06-04 | 1983-02-22 | Merck & Co., Inc. | Process for the preparation of zomepirac and related compounds |
| US4434175A (en) | 1981-08-10 | 1984-02-28 | Merck & Co., Inc. | Nonsteroidal compounds as anti-inflammatory and analgesic agents |
| ES507179A0 (es) * | 1981-11-16 | 1982-08-16 | Pharmedical Sa Lab | Procedimiento de preparacion de derivados del acido 2-pirrol-acetico. |
| IT1153750B (it) * | 1982-09-21 | 1987-01-14 | Montedison Spa | Processo per la preparazione dell'acido 3-carbossi-1-metilpirrol-2-acetico |
| US4533671A (en) * | 1982-10-08 | 1985-08-06 | Merck & Co., Inc. | 5-(2,3-Dihydro-1H-pyrrolizin-5-oyl)-2-alkanoic or carboxylic acids and analogs as anti-inflammatory and analgesic agents |
| US4536512A (en) * | 1982-10-08 | 1985-08-20 | Merck & Co., Inc. | 5-(2,3-Dihydro-1H-pyrrolizin-5-oyl)-2,3-dihydro-1H-pyrrolizine-1-alkanoic or carboxylic acids and use thereof as anti-inflammatory and analgesic agents |
| US4937368A (en) * | 1987-01-14 | 1990-06-26 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-A]pyrrole-1,7-dicarboxylates |
| US4835288A (en) * | 1987-01-14 | 1989-05-30 | Syntex Inc. | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates |
| CA1334975C (fr) * | 1987-11-13 | 1995-03-28 | James H. Holms | Composes inhibiteurs de type lipoxygenase contenant des groupes furane et pyrrole |
| US5622948A (en) * | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655693A (en) * | 1969-06-25 | 1972-04-11 | Merck & Co Inc | Anti-inflammatory salicyclic acid derivatives |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| US3952012A (en) * | 1970-01-26 | 1976-04-20 | Mcneil Laboratories, Incorporated | Aroyl-substituted pyrroles |
| US3721680A (en) * | 1970-06-15 | 1973-03-20 | Mc Neil Labor Inc | 5-aroyl-2-(beta-hydroxyethyl)-1-loweralkylpyrroles |
| US3707478A (en) * | 1970-06-15 | 1972-12-26 | Mcneilab Inc | 5-aroyl-2-(beta-r3-ethyl)-1-loweralkyl-pyrroles |
| BE792042A (fr) * | 1971-11-30 | 1973-05-29 | Ciba Geigy | Procede de preparation de nouvelles alcenylene-amines substituees en 3 |
| US3803169A (en) * | 1972-01-21 | 1974-04-09 | Mc Neil Labor Inc | Cycloalkanoyl-substituted pyrroles |
| US3803171A (en) * | 1972-01-21 | 1974-04-09 | Mc Neil Labor Inc | 5-phenylacetyl-pyrroles |
| US3846447A (en) * | 1972-08-03 | 1974-11-05 | Mcneilab Inc | Preparation of 5-aroyl-pyrroles and intermediates therefor |
| US3998844A (en) * | 1975-06-02 | 1976-12-27 | Mcneil Laboratories, Incorporated | Uncatalyzed aroylation of 1-alkylpyrrole-2-acetic acid derivatives |
-
1975
- 1975-06-27 US US05/591,217 patent/US4048191A/en not_active Expired - Lifetime
-
1976
- 1976-05-24 IN IN897/CAL/76A patent/IN144407B/en unknown
- 1976-05-31 PH PH18494A patent/PH11645A/en unknown
- 1976-06-02 GB GB22759/76A patent/GB1540437A/en not_active Expired
- 1976-06-16 JP JP51069845A patent/JPS525761A/ja active Pending
- 1976-06-18 DK DK274676A patent/DK274676A/da not_active Application Discontinuation
- 1976-06-21 ES ES449083A patent/ES449083A1/es not_active Expired
- 1976-06-23 AU AU15159/76A patent/AU508884B2/en not_active Expired
- 1976-06-23 SE SE7607240A patent/SE418083B/xx unknown
- 1976-06-24 CS CS764179A patent/CS222227B2/cs unknown
- 1976-06-24 CA CA255,611A patent/CA1094084A/fr not_active Expired
- 1976-06-24 RO RO86570A patent/RO70264B/ro unknown
- 1976-06-25 YU YU01562/76A patent/YU156276A/xx unknown
- 1976-06-25 BE BE168356A patent/BE843454A/fr not_active IP Right Cessation
- 1976-06-25 IL IL49911A patent/IL49911A/xx unknown
- 1976-06-25 CH CH818576A patent/CH624936A5/de not_active IP Right Cessation
- 1976-06-25 PT PT65280A patent/PT65280B/pt unknown
- 1976-06-25 DE DE19762628475 patent/DE2628475A1/de not_active Ceased
- 1976-06-25 IT IT50171/76A patent/IT1062038B/it active
- 1976-06-25 FR FR7619467A patent/FR2316942A1/fr active Granted
- 1976-06-25 ZA ZA00763814A patent/ZA763814B/xx unknown
- 1976-06-25 AT AT468276A patent/AT361462B/de not_active IP Right Cessation
- 1976-06-25 NL NL7606999A patent/NL7606999A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU1515976A (en) | 1978-01-05 |
| YU156276A (en) | 1983-01-21 |
| AT361462B (de) | 1981-03-10 |
| IT1062038B (it) | 1983-06-25 |
| DE2628475A1 (de) | 1977-01-13 |
| US4048191A (en) | 1977-09-13 |
| IL49911A (en) | 1979-09-30 |
| JPS525761A (en) | 1977-01-17 |
| ES449083A1 (es) | 1977-11-16 |
| SE7607240L (sv) | 1976-12-28 |
| NL7606999A (nl) | 1976-12-29 |
| PT65280A (en) | 1976-07-01 |
| CA1094084A (fr) | 1981-01-20 |
| CS222227B2 (en) | 1983-05-27 |
| SE418083B (sv) | 1981-05-04 |
| RO70264B (ro) | 1983-04-30 |
| BE843454A (fr) | 1976-12-27 |
| DK274676A (da) | 1976-12-28 |
| ATA468276A (de) | 1980-08-15 |
| ZA763814B (en) | 1978-02-22 |
| AU508884B2 (en) | 1980-04-03 |
| RO70264A (fr) | 1983-04-29 |
| IL49911A0 (en) | 1976-08-31 |
| FR2316942B1 (fr) | 1978-12-22 |
| PH11645A (en) | 1978-05-08 |
| FR2316942A1 (fr) | 1977-02-04 |
| GB1540437A (en) | 1979-02-14 |
| PT65280B (en) | 1978-05-08 |
| IN144407B (fr) | 1978-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |