CS208724B2 - Method of making the 5-(2-furoyl)-,5-(2-thonoyl)-,5-(3-furoyl) a 5-(3-thenoyl)-1,2-dihydro-3h-pyrrol/1,2-a/pyrrol-1-karboxyl acid derivatives - Google Patents
Method of making the 5-(2-furoyl)-,5-(2-thonoyl)-,5-(3-furoyl) a 5-(3-thenoyl)-1,2-dihydro-3h-pyrrol/1,2-a/pyrrol-1-karboxyl acid derivatives Download PDFInfo
- Publication number
- CS208724B2 CS208724B2 CS774647A CS464777A CS208724B2 CS 208724 B2 CS208724 B2 CS 208724B2 CS 774647 A CS774647 A CS 774647A CS 464777 A CS464777 A CS 464777A CS 208724 B2 CS208724 B2 CS 208724B2
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- CS
- Czechoslovakia
- Prior art keywords
- pyrrole
- formula
- dihydro
- carboxylic acid
- compounds
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 64
- 238000004519 manufacturing process Methods 0.000 title description 4
- XBDDRFYWURCJTD-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-yl(thiophen-3-yl)methanone Chemical compound C1=CSC=C1C(=O)C1=CCCN1 XBDDRFYWURCJTD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 43
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- 231100000252 nontoxic Toxicity 0.000 claims description 24
- 230000003000 nontoxic effect Effects 0.000 claims description 24
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000005907 alkyl ester group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- 206010061218 Inflammation Diseases 0.000 abstract description 7
- 230000004054 inflammatory process Effects 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
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- 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
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- 239000005864 Sulphur Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
- -1 2-furoyl Chemical group 0.000 description 76
- 239000000243 solution Substances 0.000 description 68
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
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- 239000000203 mixture Substances 0.000 description 42
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
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- 238000006243 chemical reaction Methods 0.000 description 28
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- FDDQRDMHICUGQC-UHFFFAOYSA-M pyrrole-1-carboxylate Chemical compound [O-]C(=O)N1C=CC=C1 FDDQRDMHICUGQC-UHFFFAOYSA-M 0.000 description 19
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- 239000002904 solvent Substances 0.000 description 16
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- QQQAZWNBGHZCJA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrol-5-yl(thiophen-2-yl)methanone Chemical compound C=1C=CSC=1C(=O)C1=CCCN1 QQQAZWNBGHZCJA-UHFFFAOYSA-N 0.000 description 8
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- 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 3
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Classifications
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- 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CS208724B2 true CS208724B2 (en) | 1981-09-15 |
Family
ID=27107392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774647A CS208724B2 (en) | 1976-07-14 | 1977-07-12 | Method of making the 5-(2-furoyl)-,5-(2-thonoyl)-,5-(3-furoyl) a 5-(3-thenoyl)-1,2-dihydro-3h-pyrrol/1,2-a/pyrrol-1-karboxyl acid derivatives |
Country Status (26)
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 (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 |
| 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/ja active Granted
- 1977-07-07 GR GR53906A patent/GR61607B/el unknown
- 1977-07-07 AR AR268357A patent/AR218631A1/es active
- 1977-07-07 DK DK307677A patent/DK152652C/da not_active IP Right Cessation
- 1977-07-08 NL NL7707652A patent/NL7707652A/xx not_active Application Discontinuation
- 1977-07-08 PT PT66779A patent/PT66779B/pt unknown
- 1977-07-08 CH CH4005/84A patent/CH651045A5/de not_active IP Right Cessation
- 1977-07-08 IE IE1422/77A patent/IE45302B1/en unknown
- 1977-07-08 IL IL52492A patent/IL52492A/xx unknown
- 1977-07-08 CH CH848877A patent/CH644861A5/de not_active IP Right Cessation
- 1977-07-11 NZ NZ184611A patent/NZ184611A/xx unknown
- 1977-07-11 GB GB28923/77A patent/GB1554076A/en not_active Expired
- 1977-07-11 FI FI772154A patent/FI63407C/fi not_active IP Right Cessation
- 1977-07-12 CS CS774647A patent/CS208724B2/cs unknown
- 1977-07-12 CA CA282,600A patent/CA1100140A/en not_active Expired
- 1977-07-12 FR FR7721559A patent/FR2361396A1/fr active Granted
- 1977-07-13 SE SE7708142A patent/SE434644B/xx not_active IP Right Cessation
- 1977-07-13 ES ES460705A patent/ES460705A1/es not_active Expired
- 1977-07-13 IT IT68631/77A patent/IT1117314B/it active
- 1977-07-13 AU AU26976/77A patent/AU513385B2/en not_active Expired
- 1977-07-13 NO NO772493A patent/NO147563C/no unknown
- 1977-07-13 PL PL1977199602A patent/PL111408B1/pl unknown
- 1977-07-13 SU SU772504151A patent/SU664566A3/ru active
- 1977-07-13 DE DE19772731662 patent/DE2731662A1/de active Granted
- 1977-12-29 SU SU772558960A patent/SU793400A3/ru active
-
1978
- 1978-05-24 ES ES470213A patent/ES470213A1/es not_active Expired
-
1981
- 1981-04-30 HK HK175/81A patent/HK17581A/xx unknown
- 1981-12-30 MY MY371/81A patent/MY8100371A/xx unknown
-
1983
- 1983-02-28 YU YU475/83A patent/YU43156B/xx unknown
- 1983-02-28 YU YU476/83A patent/YU43157B/xx unknown
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