CA1157029A - Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives - Google Patents

Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives

Info

Publication number: CA1157029A
Authority: CA; Canada
Prior art keywords: methyl; loweralkyl; acetate; acetic acid; formula
Prior art date: 1980-04-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000415135A

Other languages

English (en)

Inventor

John R. Carson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceuticals Inc

Original Assignee

McNeilab Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-04-03

Filing date

1982-11-08

Publication date

1983-11-15

1980-04-03 Priority claimed from US06/137,046 external-priority patent/US4255335A/en

1980-04-17 Priority claimed from US06/141,438 external-priority patent/US4294760A/en

1981-03-17 Priority claimed from CA000373216A external-priority patent/CA1155858A/fr

1982-11-08 Application filed by McNeilab Inc filed Critical McNeilab Inc

1982-11-08 Priority to CA000415135A priority Critical patent/CA1157029A/fr

1983-11-15 Application granted granted Critical

1983-11-15 Publication of CA1157029A publication Critical patent/CA1157029A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title abstract description 5
239000002253 acid Substances 0.000 claims abstract description 10
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
238000000034 method Methods 0.000 claims description 19
239000000463 material Substances 0.000 claims description 15
-1 nitro methylthio Chemical group 0.000 claims description 15
ZZHRFRDHPAPENB-UHFFFAOYSA-N 4-methylbenzoyl cyanide Chemical compound CC1=CC=C(C(=O)C#N)C=C1 ZZHRFRDHPAPENB-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 7
UDBBCXDMJVNFLI-UHFFFAOYSA-N 4-chlorobenzoyl cyanide Chemical compound ClC1=CC=C(C(=O)C#N)C=C1 UDBBCXDMJVNFLI-UHFFFAOYSA-N 0.000 claims description 6
125000001475 halogen functional group Chemical group 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
CGYVDYLHQYNGFC-UHFFFAOYSA-N methyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1C CGYVDYLHQYNGFC-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
239000000010 aprotic solvent Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
PISHKRUMARWBKY-UHFFFAOYSA-N ethyl 2-(1,4-dimethylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC(C)=CN1C PISHKRUMARWBKY-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
AGKFMUXEONTGAH-UHFFFAOYSA-N ethyl 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OCC)=CC(C)=C1C(=O)C1=CC=C(Cl)C=C1 AGKFMUXEONTGAH-UHFFFAOYSA-N 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims 4
150000007513 acids Chemical class 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
159000000000 sodium salts Chemical class 0.000 claims 2
RNHKXHKUKJXLAU-UHFFFAOYSA-N 2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1 RNHKXHKUKJXLAU-UHFFFAOYSA-N 0.000 claims 1
QLEXEEKHLIPXHH-UHFFFAOYSA-N 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid;dihydrate Chemical compound O.O.C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C QLEXEEKHLIPXHH-UHFFFAOYSA-N 0.000 claims 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 claims 1
230000001131 transforming effect Effects 0.000 claims 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 17
238000006555 catalytic reaction Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 15
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 14
229910052708 sodium Inorganic materials 0.000 description 14
239000011734 sodium Substances 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
MKVATVUOVMCHJJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetonitrile Chemical compound N#CCC1=CC=CN1 MKVATVUOVMCHJJ-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
IYQHVBPHXDHCOF-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl cyanide Chemical compound FC(F)(F)C1=CC=CC(C(=O)C#N)=C1 IYQHVBPHXDHCOF-UHFFFAOYSA-N 0.000 description 5
UXVLQFKYMQXBGK-UHFFFAOYSA-N 3-propylbenzoyl cyanide Chemical compound CCCC1=CC=CC(C(=O)C#N)=C1 UXVLQFKYMQXBGK-UHFFFAOYSA-N 0.000 description 5
JIMIZSCETMDNEU-UHFFFAOYSA-N 4-methoxybenzoyl cyanide Chemical compound COC1=CC=C(C(=O)C#N)C=C1 JIMIZSCETMDNEU-UHFFFAOYSA-N 0.000 description 5
NQZLRSATRFNIRZ-UHFFFAOYSA-N 4-methylbenzenecarbothioyl cyanide Chemical compound CC1=CC=C(C(=S)C#N)C=C1 NQZLRSATRFNIRZ-UHFFFAOYSA-N 0.000 description 5
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 5
ROSYAUHHRKAPHX-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)acetonitrile Chemical compound CN1C=CC=C1CC#N ROSYAUHHRKAPHX-UHFFFAOYSA-N 0.000 description 4
ISCNNJLEFDUJKH-UHFFFAOYSA-N 4-nitrobenzoyl cyanide Chemical compound [O-][N+](=O)C1=CC=C(C(=O)C#N)C=C1 ISCNNJLEFDUJKH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
AMEDPNSLCLVIQM-UHFFFAOYSA-N methyl 2-[5-(cyano-hydroxy-phenylmethyl)-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=CC=C1 AMEDPNSLCLVIQM-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
IHDSSYQEYNYRBH-UHFFFAOYSA-N 4-bromobenzoyl cyanide Chemical compound BrC1=CC=C(C(=O)C#N)C=C1 IHDSSYQEYNYRBH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
BAMCHNPUPHSVCT-UHFFFAOYSA-N methyl 2-(5-benzoyl-1-methylpyrrol-2-yl)acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(=O)C1=CC=CC=C1 BAMCHNPUPHSVCT-UHFFFAOYSA-N 0.000 description 2
FIGURBGFXLCERZ-UHFFFAOYSA-N methyl 2-[5-[cyano-hydroxy-(4-methylphenyl)methyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=C(C)C=C1 FIGURBGFXLCERZ-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
ZJXLSCXDGPDZOL-UHFFFAOYSA-M sodium;2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetate;dihydrate Chemical compound O.O.[Na+].C1=C(CC([O-])=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZJXLSCXDGPDZOL-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000003643 water by type Substances 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
GVUHUYQEAGMUNJ-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CN1 GVUHUYQEAGMUNJ-UHFFFAOYSA-N 0.000 description 1
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 description 1
FBEUIMIRCUPWKA-UHFFFAOYSA-N 2-[1-methyl-5-(4-nitrobenzoyl)pyrrol-2-yl]acetonitrile Chemical compound CN1C(CC#N)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 FBEUIMIRCUPWKA-UHFFFAOYSA-N 0.000 description 1
RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
NWPBFGWVZQGAHM-UHFFFAOYSA-N 4-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C=C1 NWPBFGWVZQGAHM-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine 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
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical compound ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
QFRZDPNUDCLAAZ-UHFFFAOYSA-N ethyl 2-(1,4-diethylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC(CC)=CN1CC QFRZDPNUDCLAAZ-UHFFFAOYSA-N 0.000 description 1
OORBYQVSQSXKRG-UHFFFAOYSA-N ethyl 2-(1-methylpyrrol-2-yl)acetate Chemical compound CCOC(=O)CC1=CC=CN1C OORBYQVSQSXKRG-UHFFFAOYSA-N 0.000 description 1
QKKVUMXHFUGIGS-UHFFFAOYSA-N ethyl 2-[5-(4-chlorobenzoyl)-1,4-diethylpyrrol-2-yl]acetate Chemical compound CCN1C(CC(=O)OCC)=CC(CC)=C1C(=O)C1=CC=C(Cl)C=C1 QKKVUMXHFUGIGS-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
JIPKLZVKWCJYEX-UHFFFAOYSA-N methyl 2-(1h-pyrrol-2-yl)acetate Chemical compound COC(=O)CC1=CC=CN1 JIPKLZVKWCJYEX-UHFFFAOYSA-N 0.000 description 1
VZLZJBPBUNXUBJ-UHFFFAOYSA-N methyl 2-[1-methyl-5-(3-propylbenzoyl)pyrrol-2-yl]acetate Chemical compound CCCC1=CC=CC(C(=O)C=2N(C(CC(=O)OC)=CC=2)C)=C1 VZLZJBPBUNXUBJ-UHFFFAOYSA-N 0.000 description 1
BFVFPQQDSHPTLS-UHFFFAOYSA-N methyl 2-[5-(4-chlorobenzoyl)-4-ethyl-1-methylpyrrol-2-yl]acetate Chemical compound C1=C(CC(=O)OC)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1CC BFVFPQQDSHPTLS-UHFFFAOYSA-N 0.000 description 1
UBVWRRRECYHABL-UHFFFAOYSA-N methyl 2-[5-[(4-chlorophenyl)-cyano-hydroxymethyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=C(Cl)C=C1 UBVWRRRECYHABL-UHFFFAOYSA-N 0.000 description 1
BMNLGMQWMJUGJO-UHFFFAOYSA-N methyl 2-[5-[cyano-hydroxy-(4-methoxyphenyl)methyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=C(OC)C=C1 BMNLGMQWMJUGJO-UHFFFAOYSA-N 0.000 description 1
CPWCVQMYQWPODX-UHFFFAOYSA-N methyl 2-[5-[cyano-hydroxy-(4-methylsulfanylphenyl)methyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=C(SC)C=C1 CPWCVQMYQWPODX-UHFFFAOYSA-N 0.000 description 1
HNOCQGYFXDBPGQ-UHFFFAOYSA-N methyl 2-[5-[cyano-hydroxy-(4-nitrophenyl)methyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=C([N+]([O-])=O)C=C1 HNOCQGYFXDBPGQ-UHFFFAOYSA-N 0.000 description 1
NDUAKOCINQXIFX-UHFFFAOYSA-N methyl 2-[5-[cyano-hydroxy-[3-(trifluoromethyl)phenyl]methyl]-1-methylpyrrol-2-yl]acetate Chemical compound CN1C(CC(=O)OC)=CC=C1C(O)(C#N)C1=CC=CC(C(F)(F)F)=C1 NDUAKOCINQXIFX-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
XCTJAYWPZSVHJP-UHFFFAOYSA-M sodium;2-[1-methyl-5-[3-(trifluoromethyl)benzoyl]pyrrol-2-yl]acetate;dihydrate Chemical compound O.O.[Na+].CN1C(CC([O-])=O)=CC=C1C(=O)C1=CC=CC(C(F)(F)F)=C1 XCTJAYWPZSVHJP-UHFFFAOYSA-M 0.000 description 1
SGBSJYLYYMQHRC-UHFFFAOYSA-M sodium;2-[5-(4-methoxybenzoyl)-1-methylpyrrol-2-yl]acetate;dihydrate Chemical compound O.O.[Na+].C1=CC(OC)=CC=C1C(=O)C1=CC=C(CC([O-])=O)N1C SGBSJYLYYMQHRC-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
229960002044 tolmetin sodium Drugs 0.000 description 1
QQILXENAYPUNEA-UHFFFAOYSA-M tolmetin sodium dihydrate Chemical compound O.O.[Na+].C1=CC(C)=CC=C1C(=O)C1=CC=C(CC([O-])=O)N1C QQILXENAYPUNEA-UHFFFAOYSA-M 0.000 description 1
229960003516 zomepirac sodium Drugs 0.000 description 1

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Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)

CA000415135A 1980-04-03 1982-11-08 Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives Expired CA1157029A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000415135A CA1157029A (fr)	1980-04-03	1982-11-08	Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US137,046		1980-04-03
US06/137,046 US4255335A (en)	1980-04-03	1980-04-03	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid derivatives
US06/141,438 US4294760A (en)	1980-04-17	1980-04-17	Preparation of 5-(arylcyanohydroxymethyl)-1-loweralkylpyrrole-2-acetic acid derivatives
US141,438		1980-04-17
CA000373216A CA1155858A (fr)	1980-04-03	1981-03-17	Preparation de derives d'acide 5-(arylcyanohydroxymethyl)-1-alkyl inferieur pyrrole-2-acetique, ainsi que de derives d'acide 5-aroyl-1-alkyl inferieur pyrrole-2-acetique
CA000415135A CA1157029A (fr)	1980-04-03	1982-11-08	Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives

Publications (1)

Publication Number	Publication Date
CA1157029A true CA1157029A (fr)	1983-11-15

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CA000415135A Expired CA1157029A (fr)	1980-04-03	1982-11-08	Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives

Country Status (1)

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CA (1)	CA1157029A (fr)

1982
- 1982-11-08 CA CA000415135A patent/CA1157029A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-11-15	MKEX	Expiry

Publication	Publication Date	Title
SU537625A3 (ru)	1976-11-30	Способ получени производных 1,1-диаминоэтилена
Krowicki et al.	1987	Synthesis of novel imidazole-containing DNA minor groove binding oligopeptides related to the antiviral antibiotic netropsin
KR100551501B1 (ko)	2006-02-13	스트론튬 라넬레이트 및 이의 수화물의 산업적 합성 방법
JPH0730031B2 (ja)	1995-04-05	２―ピラゾリン―５―オン類の製造法
US4353829A (en)	1982-10-12	Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters
Tse et al.	1994	Conformationally rigid tricyclic tripods: synthesis and application to preparation of enterobactin analogs
JPS5919536B2 (ja)	1984-05-07	５−アロイル−１−低級アルキルピロ−ル−２−酢酸誘導体の製造法
US5498711A (en)	1996-03-12	Synthesis of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane
CA1235703A (fr)	1988-04-26	Derives de substitution en 6 de 6h-dibenzo/b.d/pyranne; methode de preparation
CA1157029A (fr)	1983-11-15	Preparation de derives d'acide 5- (arylcyanohydroxymethyl)-1-alkyle inferieur-pyrrole-2-acetique et d'acide 5-aroyl-1- alkyle inferieur-pyrrole-2-acetique derives
CA1155858A (fr)	1983-10-25	Preparation de derives d'acide 5-(arylcyanohydroxymethyl)-1-alkyl inferieur pyrrole-2-acetique, ainsi que de derives d'acide 5-aroyl-1-alkyl inferieur pyrrole-2-acetique
CA1065879A (fr)	1979-11-06	PREPARATION DE .beta.-ACYLPYRROLES
US4255335A (en)	1981-03-10	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid derivatives
JPS638368A (ja)	1988-01-14	４−ベンジロキシ−３−ピロリン−２−オン−１−イルアセトアミド、その製造方法および使用方法
Campaigne et al.	1965	Ring Closure of Ylidenemalononitriles. IV. 1, 2a Attempted Cyclizations of Saturated Malononitrile Derivatives
Shimadzu et al.	1986	Studies on furan derivatives. XIV. Nucleophilic substitution of methyl 5‐nitro‐2‐furancarboxylate and 5‐Nitrofuran‐2‐nitrile
Al‐Hajjar et al.	1986	Reaction of acetylenic ketones with hydrazine derivatives. Synthesis of hydroxypyrazoles
Galeazzi et al.	1993	Generation and lithiation of the dimers of 6-(dimethylamino)-1, 4-diazafulvene. A novel synthesis of 2-alkanoylimidazoles
US4017533A (en)	1977-04-12	Diaminomaleonitrile derivatives and processes for preparing the same
Nemeroff et al.	1992	Synthesis and Characterization of Novel Ferrocenyl-Substituted Pyrroles
JPH01316352A (ja)	1989-12-21	３‐シアノ‐４‐アリールピロールの製造法
US4279836A (en)	1981-07-21	Hydroxamic acid derivative and method of preparing metoclopramide using same
Ohnmacht Jr et al.	1983	Synthesis and carbon‐13 NMR study of 2‐benzyl, 2‐methyl, 2‐aryloctahydropyrrolo [3, 4‐c] pyrroles and the 1, 2, 3, 5‐tetrahydropyrrolo [3, 4‐c] pyrrole ring system
Yamazaki et al.	1996	C‐5 functionalization of trisubstituted imidazoles with azodicarbonyl compounds
KR970006248B1 (ko)	1997-04-25	벤조일 -c-(5-메틸 1,3,4- 치아디아졸-2-치오)이미도일 클로라이드 유도체 및 그 제조방법