NO162386B - Analogifremgangsmaate for fremstilling av terapeutiske virksomme 5-benzoyl-6-alkylthio-,-6- alkylsulfinyl- og -6-alylsulfonyl-1,2-dihydro-3h-pyrrolo-(1,2-a)-pyrrol-1-carboxylsyrer og salter og lavere alkylestere derav. - Google Patents

Analogifremgangsmaate for fremstilling av terapeutiske virksomme 5-benzoyl-6-alkylthio-,-6- alkylsulfinyl- og -6-alylsulfonyl-1,2-dihydro-3h-pyrrolo-(1,2-a)-pyrrol-1-carboxylsyrer og salter og lavere alkylestere derav. Download PDF

Info

Publication number: NO162386B
Authority: NO; Norway
Prior art keywords: dihydro; pyrrole; pyrrolo; formula; methylthio
Prior art date: 1982-06-08

Application number

NO832053A

Other languages

English (en)

Norwegian (no)

Other versions

NO832053L (no

Inventor

Joseph Martin Muchowski

Robert James Greenhouse

Original Assignee

Syntex 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.)

1982-06-08

Filing date

1983-06-07

Publication date

1989-09-11

1983-06-07 Application filed by Syntex Inc filed Critical Syntex Inc

1983-12-09 Publication of NO832053L publication Critical patent/NO832053L/no

1988-02-09 Priority to NO880573A priority Critical patent/NO162116C/no

1989-09-11 Publication of NO162386B publication Critical patent/NO162386B/no

Links

238000000034 method Methods 0.000 title claims abstract description 42
238000002360 preparation method Methods 0.000 title claims description 20
230000001225 therapeutic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 142
150000003839 salts Chemical class 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 11
231100000252 nontoxic Toxicity 0.000 claims abstract description 11
230000003000 nontoxic effect Effects 0.000 claims abstract description 11
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 4
229920002554 vinyl polymer Polymers 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 25
125000005907 alkyl ester group Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
-1 trifluoromethoxy, nitro, amino Chemical group 0.000 abstract description 28
150000002148 esters Chemical class 0.000 abstract description 15
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239000002260 anti-inflammatory agent Substances 0.000 abstract description 6
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
230000001760 anti-analgesic effect Effects 0.000 abstract description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
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239000001301 oxygen Substances 0.000 abstract description 2
229910052760 oxygen Inorganic materials 0.000 abstract description 2
INKBRQRMBPEPLY-UHFFFAOYSA-N 6-methylsulfonyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical class OC(=O)C1CCN2C=C(S(=O)(=O)C)C=C21 INKBRQRMBPEPLY-UHFFFAOYSA-N 0.000 abstract 1
NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical group NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 abstract 1
241000124008 Mammalia Species 0.000 abstract 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
229940035676 analgesics Drugs 0.000 abstract 1
125000001309 chloro group Chemical group Cl* 0.000 abstract 1
125000001153 fluoro group Chemical group F* 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
239000011593 sulfur Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
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239000000243 solution Substances 0.000 description 63
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239000000047 product Substances 0.000 description 29
238000002844 melting Methods 0.000 description 28
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 14
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238000012360 testing method Methods 0.000 description 14
238000010992 reflux Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
150000004702 methyl esters Chemical class 0.000 description 12
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125000004093 cyano group Chemical group *C#N 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
OJAYJGIPQBPTSY-UHFFFAOYSA-N 5-(4-fluorobenzoyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carbonitrile Chemical compound CSC=1C=C2C(C#N)CCN2C=1C(=O)C1=CC=C(F)C=C1 OJAYJGIPQBPTSY-UHFFFAOYSA-N 0.000 description 10
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239000003795 chemical substances by application Substances 0.000 description 9
WKYQDWGWVKXSJA-UHFFFAOYSA-N methyl 6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=C(SC)C=C2C(C(=O)OC)CCN21 WKYQDWGWVKXSJA-UHFFFAOYSA-N 0.000 description 9
206010061218 Inflammation Diseases 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
230000004054 inflammatory process Effects 0.000 description 8
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 8
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238000003756 stirring Methods 0.000 description 8
WWBBGICOHFLYSR-UHFFFAOYSA-N 5-benzoyl-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid Chemical compound CSC=1C=C2C(C(O)=O)CCN2C=1C(=O)C1=CC=CC=C1 WWBBGICOHFLYSR-UHFFFAOYSA-N 0.000 description 7
FGFPJZQEHWBVNJ-UHFFFAOYSA-N 5-methylsulfinyl-2,3-dihydro-1h-pyrrolizine-1-carbonitrile Chemical compound N#CC1CCN2C(S(=O)C)=CC=C21 FGFPJZQEHWBVNJ-UHFFFAOYSA-N 0.000 description 7
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230000000202 analgesic effect Effects 0.000 description 7
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
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GORMEGFTSUOPJF-UHFFFAOYSA-N methyl 5-benzoyl-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC(SC)=C2C(=O)C1=CC=CC=C1 GORMEGFTSUOPJF-UHFFFAOYSA-N 0.000 description 6
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239000007858 starting material Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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239000004215 Carbon black (E152) Substances 0.000 description 2
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YSCPDQRXQVIEIM-UHFFFAOYSA-N methyl 5-(4-cyclopropylbenzoyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC(SC)=C2C(=O)C(C=C1)=CC=C1C1CC1 YSCPDQRXQVIEIM-UHFFFAOYSA-N 0.000 description 1
XFLPMZNHVQZFSD-UHFFFAOYSA-N methyl 5-(4-ethenylbenzoyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC(SC)=C2C(=O)C1=CC=C(C=C)C=C1 XFLPMZNHVQZFSD-UHFFFAOYSA-N 0.000 description 1
FHVFAIHMLIVWJF-UHFFFAOYSA-N methyl 5-(4-ethoxybenzoyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1C(=O)C1=C(SC)C=C2N1CCC2C(=O)OC FHVFAIHMLIVWJF-UHFFFAOYSA-N 0.000 description 1
UTWZZWNULFAWBH-UHFFFAOYSA-N methyl 5-(4-ethylbenzoyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC(CC)=CC=C1C(=O)C1=C(SC)C=C2N1CCC2C(=O)OC UTWZZWNULFAWBH-UHFFFAOYSA-N 0.000 description 1
SAIRLOTVJGGJCF-UHFFFAOYSA-N methyl 5-(4-methylbenzenecarbothioyl)-6-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC(SC)=C2C(=S)C1=CC=C(C)C=C1 SAIRLOTVJGGJCF-UHFFFAOYSA-N 0.000 description 1
GDZDAOIIOIUWBB-UHFFFAOYSA-N methyl 5-methylsulfanyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound CSC1=CC=C2C(C(=O)OC)CCN21 GDZDAOIIOIUWBB-UHFFFAOYSA-N 0.000 description 1
WNMWZMZCEIFDPK-UHFFFAOYSA-N methyl 6-methylsulfanyl-5-(4-propoxybenzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylate Chemical compound C1=CC(OCCC)=CC=C1C(=O)C1=C(SC)C=C2N1CCC2C(=O)OC WNMWZMZCEIFDPK-UHFFFAOYSA-N 0.000 description 1
QCGOPVNUBDEKJJ-UHFFFAOYSA-N methyl 6-methylsulfanyl-5-(4-propylbenzoyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound C1=CC(CCC)=CC=C1C(=O)C1=C(SC)C=C2N1CCC2C(=O)OC QCGOPVNUBDEKJJ-UHFFFAOYSA-N 0.000 description 1
AWANWLTWGKXFAC-UHFFFAOYSA-N methyl 6-methylsulfanyl-5-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound COC(=O)C1CCN2C1=CC(SC)=C2C(=O)C1=CC=C(C(F)(F)F)C=C1 AWANWLTWGKXFAC-UHFFFAOYSA-N 0.000 description 1
QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical group COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
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 1
125000002347 octyl 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])[H] 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
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 1
229920000768 polyamine Polymers 0.000 description 1
230000003334 potential effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
210000001179 synovial fluid Anatomy 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1

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
- 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]

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (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)
Pain & Pain Management (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrrole Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)
Plural Heterocyclic Compounds (AREA)

NO832053A 1982-06-08 1983-06-07 Analogifremgangsmaate for fremstilling av terapeutiske virksomme 5-benzoyl-6-alkylthio-,-6- alkylsulfinyl- og -6-alylsulfonyl-1,2-dihydro-3h-pyrrolo-(1,2-a)-pyrrol-1-carboxylsyrer og salter og lavere alkylestere derav. NO162386B (no)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO880573A NO162116C (no)	1982-06-08	1988-02-09	Nye der av 1,2-dihydro-3h-pyrrolo-/1,2-a/-pyrrol-1-carbonitril anv f fremst av terap virks 5-benzoyl-6-alkylthio-, -6-alkylsulfinyl- og -6-alk. -1,2-dihyd.-3h -pyrr. -1,2,a-pyrr.-1-carbox. og salter og lavere alk. derav.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/386,174 US4612325A (en)	1982-06-08	1982-06-08	5-Aroyl-6-alkylthio-1,2-dihydro-3H-pyrrolo(1,2-A)pyrrole-1-carboxylic acids and use thereof as analgesics and anti-inflammatories

Publications (2)

Publication Number	Publication Date
NO832053L NO832053L (no)	1983-12-09
NO162386B true NO162386B (no)	1989-09-11

Family

ID=23524483

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO832053A NO162386B (no)	1982-06-08	1983-06-07	Analogifremgangsmaate for fremstilling av terapeutiske virksomme 5-benzoyl-6-alkylthio-,-6- alkylsulfinyl- og -6-alylsulfonyl-1,2-dihydro-3h-pyrrolo-(1,2-a)-pyrrol-1-carboxylsyrer og salter og lavere alkylestere derav.

Country Status (16)

Country	Link
US (1)	US4612325A (fr)
EP (1)	EP0096583B1 (fr)
JP (1)	JPS595190A (fr)
KR (1)	KR880000393B1 (fr)
AT (1)	ATE29497T1 (fr)
AU (1)	AU556295B2 (fr)
CA (1)	CA1200244A (fr)
DE (1)	DE3373474D1 (fr)
DK (1)	DK260483A (fr)
ES (4)	ES523063A0 (fr)
FI (1)	FI77245C (fr)
HU (1)	HU190106B (fr)
IL (1)	IL68909A (fr)
NO (1)	NO162386B (fr)
NZ (1)	NZ204487A (fr)
ZA (1)	ZA834137B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4560699A (en) *	1983-01-17	1985-12-24	Syntex (U.S.A.) Inc.	5-(4-Vinylbenzoyl)-1,2-dihydro-3H-pyrrolo-[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof and use as analgesics and anti-inflammatories
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4097579A (en) *	1977-03-31	1978-06-27	Syntex (U.S.A.) Inc.	5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof
US4232038A (en) *	1979-08-31	1980-11-04	Syntex (U.S.A.) Inc.	5-Alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl-1,2-dihydro-3H-pyrrolo[1,]pyrrole-1-carboxylic acids
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
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

1982
- 1982-06-08 US US06/386,174 patent/US4612325A/en not_active Expired - Fee Related
1983
- 1983-06-07 FI FI832045A patent/FI77245C/fi not_active IP Right Cessation
- 1983-06-07 AU AU15464/83A patent/AU556295B2/en not_active Ceased
- 1983-06-07 HU HU832030A patent/HU190106B/hu not_active IP Right Cessation
- 1983-06-07 IL IL68909A patent/IL68909A/xx unknown
- 1983-06-07 AT AT83303285T patent/ATE29497T1/de not_active IP Right Cessation
- 1983-06-07 KR KR1019830002524A patent/KR880000393B1/ko not_active Expired
- 1983-06-07 ES ES523063A patent/ES523063A0/es active Granted
- 1983-06-07 NZ NZ204487A patent/NZ204487A/xx unknown
- 1983-06-07 DK DK260483A patent/DK260483A/da not_active Application Discontinuation
- 1983-06-07 DE DE8383303285T patent/DE3373474D1/de not_active Expired
- 1983-06-07 ZA ZA834137A patent/ZA834137B/xx unknown
- 1983-06-07 NO NO832053A patent/NO162386B/no unknown
- 1983-06-07 JP JP58102535A patent/JPS595190A/ja active Pending
- 1983-06-07 EP EP83303285A patent/EP0096583B1/fr not_active Expired
- 1983-06-07 CA CA000429837A patent/CA1200244A/fr not_active Expired
1984
- 1984-11-16 ES ES537695A patent/ES537695A0/es active Granted
- 1984-11-16 ES ES537694A patent/ES8600294A1/es not_active Expired
- 1984-11-16 ES ES537696A patent/ES537696A0/es active Granted

Also Published As

Publication number	Publication date
US4612325A (en)	1986-09-16
KR880000393B1 (ko)	1988-03-21
ES8600295A1 (es)	1985-10-16
FI77245B (fi)	1988-10-31
FI832045L (fi)	1983-12-09
IL68909A (en)	1987-02-27
FI832045A0 (fi)	1983-06-07
EP0096583B1 (fr)	1987-09-09
ATE29497T1 (de)	1987-09-15
ES537694A0 (es)	1985-10-16
ES537695A0 (es)	1985-10-16
ES8600296A1 (es)	1985-10-16
CA1200244A (fr)	1986-02-04
FI77245C (fi)	1989-02-10
ES8502999A1 (es)	1985-02-16
JPS595190A (ja)	1984-01-12
DE3373474D1 (en)	1987-10-15
NO832053L (no)	1983-12-09
ZA834137B (en)	1985-01-30
ES8600294A1 (es)	1985-10-16
ES537696A0 (es)	1985-10-16
DK260483D0 (da)	1983-06-07
KR840005144A (ko)	1984-11-03
AU1546483A (en)	1983-12-15
AU556295B2 (en)	1986-10-30
ES523063A0 (es)	1985-02-16
DK260483A (da)	1983-12-09
EP0096583A3 (en)	1985-05-02
NZ204487A (en)	1986-06-11
IL68909A0 (en)	1983-10-31
HU190106B (en)	1986-08-28
EP0096583A2 (fr)	1983-12-21

Publication	Publication Date	Title
US5338756A (en)	1994-08-16	Benzimidazole compounds
US4399136A (en)	1983-08-16	Pyrazolopyridazine antihypertensives
NO340366B1 (no)	2017-04-10	Metode for fremstilling av 3-(2-(1-benzotiofen-5-yl)etoksy)propionsyre eller salter derav
NO874834L (no)	1988-05-24	Fremgangsmaate for fremstilling av terapeutisk aktive tienopyridinoner.
JP3054738B2 (ja)	2000-06-19	チアゾロ［５，４―ｂ］アゼピン誘導体
NO154116B (no)	1986-04-14	Fremgangsm¨te og lamellsepareringsapparat for tilf¯rsel og fordeling av en sammensatt v\|ske til et lamellseparerings apparat.
DK149230B (da)	1986-03-24	Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf
CA1217187A (fr)	1987-01-27	Derives de thiazine
US4560699A (en)	1985-12-24	5-(4-Vinylbenzoyl)-1,2-dihydro-3H-pyrrolo-[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof and use as analgesics and anti-inflammatories
NO162386B (no)	1989-09-11	Analogifremgangsmaate for fremstilling av terapeutiske virksomme 5-benzoyl-6-alkylthio-,-6- alkylsulfinyl- og -6-alylsulfonyl-1,2-dihydro-3h-pyrrolo-(1,2-a)-pyrrol-1-carboxylsyrer og salter og lavere alkylestere derav.
FI76810C (fi)	1988-12-12	Foerfarande foer framstaellning av farmaceutiskt vaerdefulla tiazolo-tieno-azepin- och tiazolo-tieno-pyridinderivat.
SE431643B (sv)	1984-02-20	Terapeutiskt aktiva halogensubstituerade prolinderivat innehallande svavel och forfarande for deras tillverkning
FI81346C (fi)	1990-10-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara -/10-oxi-4h-benso/4,5/cyklohepta/1,2-b/ tiofen-4-yliden/karboxylsyraderivat.
CA1280749C (fr)	1991-02-26	Composes de phenothiazine
NO852663L (no)	1986-01-06	Fremgangsmaate ved fremstilling av 3-aminocarbonylmethoxy-5-fenylpyrazol-forbindelser.
US8536342B2 (en)	2013-09-17	Process for producing thiabenzoazulene-propionic acid derivative
JPS6130676B2 (fr)	1986-07-15
AU704210B2 (en)	1999-04-15	Synthesis of (S)-3-(2-thienylthio) butyric acid and analogs
NO147563B (no)	1983-01-24	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 5-(2-furoyl-, 5-(2-tenoyl)-, 5-(3-furoyl)- og 5-(3-tenoyl)-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrol-1-karboksylsyrederivater
EP0486586B1 (fr)	1994-06-08	Derives d'acide kynurenique, preparation de ses derives et compositions pharmaceutiques contenant ses derives
US3519622A (en)	1970-07-07	Phenothiazine derivatives
NO179948B (no)	1996-10-07	Nye isobutylsubstituerte metansulfonyl-kinolylmetoksyfenyl-cykloalkyleddiksyreamider og anvendelse av disse
SK107394A3 (en)	1995-05-10	Quinoline compounds, method of their preparation and pharmaceutical preparation which containing these compounds
EP0145304B1 (fr)	1988-04-20	Dérivés de la tétrahydro bêta-carboline et procédé pour leur préparation
US5502253A (en)	1996-03-26	Cyclohex-2-enyl acetamides