IE45302L - PYRROLO [1,2-a] PYRROLE DERIVATIVES - Google Patents
PYRROLO [1,2-a] PYRROLE DERIVATIVESInfo
- Publication number
- IE45302L IE45302L IE771422A IE142277A IE45302L IE 45302 L IE45302 L IE 45302L IE 771422 A IE771422 A IE 771422A IE 142277 A IE142277 A IE 142277A IE 45302 L IE45302 L IE 45302L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- image
- pyrrolo
- alkyl
- acid esters
- Prior art date
Links
- HHONATOJHSQDPZ-UHFFFAOYSA-N 3H-pyrrolizine Chemical class C1=CN2CC=CC2=C1 HHONATOJHSQDPZ-UHFFFAOYSA-N 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 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
- 206010061218 Inflammation Diseases 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-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
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical 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)
Abstract
Carboxylic acid esters of the formula <IMAGE> are prepared by condensation of a compound of the formula <IMAGE> with an amide of the formula <IMAGE> In the formulae, X represents oxygen or sulphur, R represents hydrogen or C1-C4-alkyl, R<1> represents hydrogen, methyl, chlorine or bromine and R<2> represents C1-C4-alkyl. Hydrolysis of the carboxylic acid esters results in the corresponding carboxylic acids and their salts. The compounds are novel and exhibit an anti inflammatory, analgesic and antipyretic action. They are suitable in particular for treating inflammations, pain and febrile conditions.
[GB1554076A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70485776A | 1976-07-14 | 1976-07-14 | |
| US05/771,283 US4087539A (en) | 1976-07-14 | 1977-02-23 | 5-(2-Furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- and 5-(3-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE45302L true IE45302L (en) | 1978-01-14 |
| IE45302B1 IE45302B1 (en) | 1982-07-28 |
Family
ID=27107392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1422/77A IE45302B1 (en) | 1976-07-14 | 1977-07-08 | 5-(2-furoyl)-,5-(2-thenoyl)-,5(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS539789A (en) |
| AR (1) | AR218631A1 (en) |
| AU (1) | AU513385B2 (en) |
| CA (1) | CA1100140A (en) |
| CH (2) | CH644861A5 (en) |
| CS (1) | CS208724B2 (en) |
| DE (1) | DE2731662A1 (en) |
| DK (1) | DK152652C (en) |
| ES (2) | ES460705A1 (en) |
| FI (1) | FI63407C (en) |
| FR (1) | FR2361396A1 (en) |
| GB (1) | GB1554076A (en) |
| GR (1) | GR61607B (en) |
| HK (1) | HK17581A (en) |
| IE (1) | IE45302B1 (en) |
| IL (1) | IL52492A (en) |
| IT (1) | IT1117314B (en) |
| MY (1) | MY8100371A (en) |
| NL (1) | NL7707652A (en) |
| NO (1) | NO147563C (en) |
| NZ (1) | NZ184611A (en) |
| PL (1) | PL111408B1 (en) |
| PT (1) | PT66779B (en) |
| SE (1) | SE434644B (en) |
| SU (2) | SU664566A3 (en) |
| YU (2) | YU43156B (en) |
Families Citing this family (7)
| 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 |
| US4140698A (en) * | 1977-07-25 | 1979-02-20 | Syntex (Usa) Inc. | 1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles |
| 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 |
| JPS5910589A (en) * | 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 | Antiinflammatory and analgesic novel 5-(pyrrol-2-oyl)-1,2-dihydro-3h-pyrrolo(1,2-a) pyrrole derivative |
| HU198927B (en) * | 1987-01-14 | 1989-12-28 | Richter Gedeon Vegyeszet | Process for producing 1-/substituted aminomethyl/-octa-hydroindolo-(2,3-a)quinolizine derivatives, pharmaceutically applicable acid addition salts thereof, as well as pharmaceutical compositions comprising same |
| 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 |
-
1977
- 1977-05-17 JP JP5697877A patent/JPS539789A/en active Granted
- 1977-07-07 DK DK307677A patent/DK152652C/en not_active IP Right Cessation
- 1977-07-07 AR AR268357A patent/AR218631A1/en active
- 1977-07-07 GR GR53906A patent/GR61607B/en unknown
- 1977-07-08 PT PT66779A patent/PT66779B/en unknown
- 1977-07-08 CH CH848877A patent/CH644861A5/en not_active IP Right Cessation
- 1977-07-08 IE IE1422/77A patent/IE45302B1/en unknown
- 1977-07-08 IL IL52492A patent/IL52492A/en unknown
- 1977-07-08 NL NL7707652A patent/NL7707652A/en not_active Application Discontinuation
- 1977-07-08 CH CH4005/84A patent/CH651045A5/en not_active IP Right Cessation
- 1977-07-11 NZ NZ184611A patent/NZ184611A/en unknown
- 1977-07-11 GB GB28923/77A patent/GB1554076A/en not_active Expired
- 1977-07-11 FI FI772154A patent/FI63407C/en not_active IP Right Cessation
- 1977-07-12 FR FR7721559A patent/FR2361396A1/en active Granted
- 1977-07-12 CS CS774647A patent/CS208724B2/en unknown
- 1977-07-12 CA CA282,600A patent/CA1100140A/en not_active Expired
- 1977-07-13 IT IT68631/77A patent/IT1117314B/en active
- 1977-07-13 SU SU772504151A patent/SU664566A3/en active
- 1977-07-13 SE SE7708142A patent/SE434644B/en not_active IP Right Cessation
- 1977-07-13 DE DE19772731662 patent/DE2731662A1/en active Granted
- 1977-07-13 AU AU26976/77A patent/AU513385B2/en not_active Expired
- 1977-07-13 ES ES460705A patent/ES460705A1/en not_active Expired
- 1977-07-13 NO NO772493A patent/NO147563C/en unknown
- 1977-07-13 PL PL1977199602A patent/PL111408B1/en unknown
- 1977-12-29 SU SU772558960A patent/SU793400A3/en active
-
1978
- 1978-05-24 ES ES470213A patent/ES470213A1/en not_active Expired
-
1981
- 1981-04-30 HK HK175/81A patent/HK17581A/en unknown
- 1981-12-30 MY MY371/81A patent/MY8100371A/en unknown
-
1983
- 1983-02-28 YU YU475/83A patent/YU43156B/en unknown
- 1983-02-28 YU YU476/83A patent/YU43157B/en unknown
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