CS204954B2 - Method of producing derivatives of 5-aroyl-1,2-dihydro-3h-pyrrole/2,2-a/pyrrole-1-carboxylic acid - Google Patents
Method of producing derivatives of 5-aroyl-1,2-dihydro-3h-pyrrole/2,2-a/pyrrole-1-carboxylic acid Download PDFInfo
- Publication number
- CS204954B2 CS204954B2 CS774646A CS464677A CS204954B2 CS 204954 B2 CS204954 B2 CS 204954B2 CS 774646 A CS774646 A CS 774646A CS 464677 A CS464677 A CS 464677A CS 204954 B2 CS204954 B2 CS 204954B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- pyrrole
- dihydro
- formula
- carboxylate
- carboxylic acid
- Prior art date
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- FDDQRDMHICUGQC-UHFFFAOYSA-N pyrrole-1-carboxylic acid Chemical compound OC(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-N 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 42
- 150000002148 esters Chemical class 0.000 claims description 30
- 231100000252 nontoxic Toxicity 0.000 claims description 28
- 230000003000 nontoxic effect Effects 0.000 claims description 28
- 150000007513 acids Chemical class 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- FDDQRDMHICUGQC-UHFFFAOYSA-M pyrrole-1-carboxylate Chemical compound [O-]C(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-M 0.000 abstract description 107
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000730 antalgic agent Substances 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 239000003527 fibrinolytic agent Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- -1 isodecyl Chemical group 0.000 description 57
- 239000000243 solution Substances 0.000 description 56
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 47
- 239000000203 mixture Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 20
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000003826 tablet Substances 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 17
- BRGYOIOOHWNSMI-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CCCN1 BRGYOIOOHWNSMI-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 13
- 239000008101 lactose Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- URDJRQWTNKGCSD-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-yl-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CCCN1 URDJRQWTNKGCSD-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 235000019759 Maize starch Nutrition 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- 230000035935 pregnancy Effects 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 210000003754 fetus Anatomy 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 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 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- 239000002775 capsule Substances 0.000 description 7
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- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 6
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 6
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 229960002442 glucosamine Drugs 0.000 description 6
- 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 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 5
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
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- KASVZMDBXFWHOT-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)-4-methyl-1-(2-methylsulfonyloxyethyl)pyrrole-3-carboxylate Chemical compound COC(=O)CC1=C(C(=O)OC)C(C)=CN1CCOS(C)(=O)=O KASVZMDBXFWHOT-UHFFFAOYSA-N 0.000 description 1
- HSPOGDNHMZIFDB-UHFFFAOYSA-N methyl 4-butyl-1-(2-hydroxyethyl)-2-(2-methoxy-2-oxoethyl)pyrrole-3-carboxylate Chemical compound CCCCC1=CN(CCO)C(CC(=O)OC)=C1C(=O)OC HSPOGDNHMZIFDB-UHFFFAOYSA-N 0.000 description 1
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- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
- XRBMMOZEBAWKNN-UHFFFAOYSA-M potassium;6-butyl-5-(3-chlorobenzoyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound [K+].CCCCC=1C=C2C(C([O-])=O)CCN2C=1C(=O)C1=CC=CC(Cl)=C1 XRBMMOZEBAWKNN-UHFFFAOYSA-M 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WHEKAHHSTWMPOM-UHFFFAOYSA-N propan-2-yl 5-(4-methylbenzoyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound CC(C)OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=C(C)C=C1 WHEKAHHSTWMPOM-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70490976A | 1976-07-14 | 1976-07-14 | |
| US05/771,286 US4089969A (en) | 1976-07-14 | 1977-02-23 | 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS204954B2 true CS204954B2 (en) | 1981-04-30 |
Family
ID=27107410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774646A CS204954B2 (en) | 1976-07-14 | 1977-07-12 | Method of producing derivatives of 5-aroyl-1,2-dihydro-3h-pyrrole/2,2-a/pyrrole-1-carboxylic acid |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS539788A (en, 2012) |
| AR (1) | AR224997A1 (en, 2012) |
| CA (1) | CA1102809A (en, 2012) |
| CH (3) | CH641458A5 (en, 2012) |
| CS (1) | CS204954B2 (en, 2012) |
| DE (2) | DE2760330C2 (en, 2012) |
| DK (1) | DK151886C (en, 2012) |
| ES (2) | ES460706A1 (en, 2012) |
| FI (1) | FI63406C (en, 2012) |
| FR (2) | FR2358406A1 (en, 2012) |
| GB (1) | GB1554075A (en, 2012) |
| GR (1) | GR61111B (en, 2012) |
| HK (1) | HK15981A (en, 2012) |
| HU (1) | HU174224B (en, 2012) |
| IE (1) | IE45253B1 (en, 2012) |
| IL (2) | IL52493A (en, 2012) |
| IT (1) | IT1117313B (en, 2012) |
| MX (1) | MX163202B (en, 2012) |
| MY (1) | MY8100357A (en, 2012) |
| NL (2) | NL186318C (en, 2012) |
| NO (1) | NO147564C (en, 2012) |
| NZ (1) | NZ184610A (en, 2012) |
| PL (4) | PL124445B1 (en, 2012) |
| PT (1) | PT66780B (en, 2012) |
| SE (1) | SE434643B (en, 2012) |
| SU (1) | SU695558A3 (en, 2012) |
| YU (1) | YU40816B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140698A (en) * | 1977-07-25 | 1979-02-20 | Syntex (Usa) Inc. | 1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles |
| JPS55124633A (en) * | 1979-03-19 | 1980-09-25 | Sohachi Takeuchi | Manufacturing method of tubular vessel |
| US4344943A (en) * | 1980-06-09 | 1982-08-17 | Syntex (U.S.A.) Inc. | 6-Chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof |
| US4353829A (en) * | 1980-11-21 | 1982-10-12 | Syntex (U.S.A.) Inc. | Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters |
| JPS5910589A (ja) * | 1982-06-10 | 1984-01-20 | メルク エンド カムパニー インコーポレーテツド | 抗炎症剤および鎮痛剤として新規な５−（ピロ−ル−２−オイル）−１，２−ジヒドロ−３Ｈ−ピロロ〔１，２−ａ〕ピロ−ル誘導体 |
| US4511724A (en) * | 1982-06-10 | 1985-04-16 | Merck & Co., Inc. | 5-(Pyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo [1,2-a]pyrrole derivatives as anti-inflammatory and analgesic agents |
| US4874871A (en) * | 1987-03-25 | 1989-10-17 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and related compounds |
| JPH0739418B2 (ja) * | 1987-09-10 | 1995-05-01 | 久光製薬株式会社 | 新規な３−アロイル−６，７−ジヒドロ−５Ｈ−ピロロ〔１，２−ｃ〕イミダゾール−７−カルボン酸誘導体 |
| JP2649168B2 (ja) * | 1988-02-25 | 1997-09-03 | 久光製薬株式会社 | 新規な５，６−ジフェニル−１，２−ジヒドロ−３Ｈ−ピロロ［１，２−ａ］ピロール−１−カルボン酸誘導体 |
| IT1250691B (it) * | 1991-07-22 | 1995-04-21 | Giancarlo Santus | Composizioni terapeutiche per somministrazione intranasale comprendenti ketorolac. |
| DK0612521T3 (da) * | 1991-11-11 | 2000-01-17 | Hisamitsu Pharmaceutical Co | Keterolacholdigt varmt omslag |
| DE4300697C1 (de) * | 1993-01-13 | 1994-05-19 | Roemmers Sa | Keterolac-Derivat mit wesentlich geringerer gastrointestinaler Reizung und Ulzeration |
| US5622948A (en) * | 1994-12-01 | 1997-04-22 | Syntex (U.S.A.) Inc. | Pyrrole pyridazine and pyridazinone anti-inflammatory agents |
| JP2008210666A (ja) * | 2007-02-27 | 2008-09-11 | Okamura Corp | 商品陳列棚における照明装置 |
| JP2023553642A (ja) * | 2020-12-16 | 2023-12-25 | ニュー フロンティア ラブズ，エルエルシー | 鎮痛効果を誘導するためのジカルボン酸エステル |
-
1977
- 1977-05-17 JP JP5697777A patent/JPS539788A/ja active Granted
- 1977-07-07 DK DK307577A patent/DK151886C/da active
- 1977-07-07 GR GR53907A patent/GR61111B/el unknown
- 1977-07-07 AR AR268356A patent/AR224997A1/es active
- 1977-07-08 IL IL52493A patent/IL52493A/xx unknown
- 1977-07-08 PT PT66780A patent/PT66780B/pt unknown
- 1977-07-08 NL NLAANVRAGE7707651,A patent/NL186318C/xx not_active IP Right Cessation
- 1977-07-08 CH CH850077A patent/CH641458A5/de not_active IP Right Cessation
- 1977-07-08 IE IE1423/77A patent/IE45253B1/en not_active IP Right Cessation
- 1977-07-11 YU YU1721/77A patent/YU40816B/xx unknown
- 1977-07-11 NZ NZ184610A patent/NZ184610A/xx unknown
- 1977-07-11 FR FR7721356A patent/FR2358406A1/fr active Granted
- 1977-07-11 FI FI772153A patent/FI63406C/fi not_active IP Right Cessation
- 1977-07-11 GB GB28919/77A patent/GB1554075A/en not_active Expired
- 1977-07-12 CA CA282,599A patent/CA1102809A/en not_active Expired
- 1977-07-12 CS CS774646A patent/CS204954B2/cs unknown
- 1977-07-13 SE SE7708141A patent/SE434643B/xx not_active IP Right Cessation
- 1977-07-13 NO NO772494A patent/NO147564C/no unknown
- 1977-07-13 PL PL1977227291A patent/PL124445B1/pl unknown
- 1977-07-13 DE DE2760330A patent/DE2760330C2/de not_active Expired
- 1977-07-13 PL PL1977199603A patent/PL109390B1/pl unknown
- 1977-07-13 ES ES460706A patent/ES460706A1/es not_active Expired
- 1977-07-13 PL PL1977227290A patent/PL124444B1/pl unknown
- 1977-07-13 PL PL1977227289A patent/PL124711B1/pl unknown
- 1977-07-13 DE DE19772731678 patent/DE2731678A1/de active Granted
- 1977-07-13 IT IT68630/77A patent/IT1117313B/it active Protection Beyond IP Right Term
- 1977-07-13 SU SU772501050A patent/SU695558A3/ru active
- 1977-07-14 HU HU77SI1582A patent/HU174224B/hu unknown
- 1977-12-20 FR FR7738508A patent/FR2375234A1/fr active Granted
-
1978
- 1978-05-24 ES ES470214A patent/ES470214A1/es not_active Expired
-
1979
- 1979-11-22 IL IL58779A patent/IL58779A0/xx unknown
-
1981
- 1981-04-23 HK HK159/81A patent/HK15981A/en unknown
- 1981-12-30 MY MY357/81A patent/MY8100357A/xx unknown
-
1984
- 1984-02-22 CH CH86584A patent/CH646972A5/de not_active IP Right Cessation
- 1984-02-22 CH CH86684A patent/CH646973A5/de not_active IP Right Cessation
-
1991
- 1991-07-05 MX MX9100104A patent/MX163202B/es unknown
-
1993
- 1993-03-23 NL NL930021C patent/NL930021I2/nl unknown
Also Published As
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