HU180273B - Process for producing 1,5-disubstituted-2-pyrrolidone derivatives - Google Patents
Process for producing 1,5-disubstituted-2-pyrrolidone derivatives Download PDFInfo
- Publication number
- HU180273B HU180273B HU77PI587A HUPI000587A HU180273B HU 180273 B HU180273 B HU 180273B HU 77PI587 A HU77PI587 A HU 77PI587A HU PI000587 A HUPI000587 A HU PI000587A HU 180273 B HU180273 B HU 180273B
- Authority
- HU
- Hungary
- Prior art keywords
- pyrrolidone
- group
- formula
- reaction
- prepared
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 230000008569 process Effects 0.000 title claims abstract description 19
- -1 1,5-disubstituted-2-pyrrolidone Chemical class 0.000 title claims description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- 230000002829 reductive effect Effects 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 72
- 239000000243 solution Substances 0.000 abstract description 37
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- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 18
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract description 12
- 230000004071 biological effect Effects 0.000 abstract description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 abstract description 11
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- 239000002253 acid Substances 0.000 abstract description 7
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract description 5
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 68
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
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- 238000004821 distillation Methods 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 28
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- 150000004040 pyrrolidinones Chemical class 0.000 description 23
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- 239000003960 organic solvent Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
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- 229910003002 lithium salt Inorganic materials 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 5
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
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- PMVLHRHRTOBBHS-UHFFFAOYSA-N 3-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCC1CCNC1=O PMVLHRHRTOBBHS-UHFFFAOYSA-N 0.000 description 3
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71236276A | 1976-08-06 | 1976-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180273B true HU180273B (en) | 1983-02-28 |
Family
ID=24861795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77PI587A HU180273B (en) | 1976-08-06 | 1977-08-05 | Process for producing 1,5-disubstituted-2-pyrrolidone derivatives |
Country Status (31)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5695569A (en) * | 1979-12-27 | 1981-08-03 | Canon Inc | Forming method for bar lens sphere face |
| US4321201A (en) * | 1980-09-22 | 1982-03-23 | E. I. Du Pont De Nemours And Company | Optically active tert-alkyl 7-(2-oxo-5-carbonyloxypyrrolidinyl) heptanoates |
| IL141120A0 (en) | 2000-01-31 | 2002-02-10 | Pfizer Prod Inc | Use of prostaglandin (pge2) receptor 4 (epa) selective agonists for the treatment of acute and chronic renal failure |
| WO2002024647A1 (fr) * | 2000-09-21 | 2002-03-28 | Ono Pharmaceutical Co., Ltd. | Agonistes du recepteur de l'ep4 comprenant comme principe actif des derives de la 8-azaprostaglandine |
| HUP0400807A2 (hu) * | 2000-11-27 | 2004-07-28 | Pfizer Products Inc. | EP4 receptor szelektív agonisták csontritkulás kezelésében |
| HU230421B1 (hu) * | 2001-07-23 | 2016-05-30 | Ono Pharmaceutical Co., Ltd | Csonttömegveszteséggel kapcsolatos betegségek kezelésére adható, EP4 agonistát tartalmazó gyógyászati készítmények és hatóanyagként alkalmazható vegyületek |
| CA2478653A1 (en) * | 2002-03-18 | 2003-09-25 | Pfizer Products Inc. | Methods of treatment with selective ep4 receptor agonists |
| US6573294B1 (en) * | 2002-05-14 | 2003-06-03 | Allergan, Inc. | 8-azaprostaglandin analogs as agents for lowering intraocular pressure |
| JP4582456B2 (ja) * | 2003-01-21 | 2010-11-17 | 小野薬品工業株式会社 | ８−アザプロスタグランジン誘導体およびその医薬用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386146A (en) * | 1972-05-03 | 1975-03-05 | Ici Ltd | Cyclopentane derivatives |
| JPS511460A (en) * | 1974-06-24 | 1976-01-08 | Tanabe Seiyaku Co | 22 piroridonjudotaino seiho |
| JPS514166A (ja) * | 1974-06-28 | 1976-01-14 | Tanabe Seiyaku Co | 22piroridonjudotaino seiho |
| US3975399A (en) * | 1974-08-06 | 1976-08-17 | E. I. Du Pont De Nemours And Company | 1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones |
| DE2528664A1 (de) * | 1975-06-27 | 1977-01-13 | Hoechst Ag | Pyrrolidone und verfahren zu ihrer herstellung |
-
1977
- 1977-07-27 SE SE7708642A patent/SE423813B/xx unknown
- 1977-07-27 CA CA283,598A patent/CA1077948A/en not_active Expired
- 1977-07-28 IL IL52615A patent/IL52615A/xx unknown
- 1977-07-28 GR GR54058A patent/GR68688B/el unknown
- 1977-08-01 AU AU27515/77A patent/AU508007B2/en not_active Expired
- 1977-08-02 PH PH20060A patent/PH17398A/en unknown
- 1977-08-02 NZ NZ184806A patent/NZ184806A/xx unknown
- 1977-08-04 PT PT66891A patent/PT66891B/pt unknown
- 1977-08-04 ZA ZA00774704A patent/ZA774704B/xx unknown
- 1977-08-04 NL NL7708637A patent/NL7708637A/xx not_active Application Discontinuation
- 1977-08-05 SU SU772511155A patent/SU703016A3/ru active
- 1977-08-05 DD DD77213369A patent/DD143768A5/de unknown
- 1977-08-05 IE IE1641/77A patent/IE45505B1/en unknown
- 1977-08-05 NO NO772752A patent/NO772752L/no unknown
- 1977-08-05 GB GB43588/78A patent/GB1556570A/en not_active Expired
- 1977-08-05 AR AR268699A patent/AR217080A1/es active
- 1977-08-05 CH CH964677A patent/CH624934A5/fr not_active IP Right Cessation
- 1977-08-05 DD DD77200468A patent/DD136135A5/xx unknown
- 1977-08-05 ES ES461388A patent/ES461388A1/es not_active Expired
- 1977-08-05 HU HU77PI587A patent/HU180273B/hu unknown
- 1977-08-05 BE BE1008318A patent/BE857506A/xx not_active IP Right Cessation
- 1977-08-05 GB GB33002/77A patent/GB1556569A/en not_active Expired
- 1977-08-05 FI FI772376A patent/FI70009C/fi not_active IP Right Cessation
- 1977-08-05 YU YU01925/77A patent/YU192577A/xx unknown
- 1977-08-05 DK DK352077A patent/DK352077A/da not_active Application Discontinuation
- 1977-08-05 FR FR7724290A patent/FR2369260A1/fr active Granted
- 1977-08-05 LU LU77936A patent/LU77936A1/xx unknown
- 1977-08-05 DE DE19772735904 patent/DE2735904A1/de not_active Ceased
- 1977-08-05 BG BG037109A patent/BG31073A3/xx unknown
- 1977-08-05 CS CS775202A patent/CS221269B2/cs unknown
- 1977-08-06 JP JP9458977A patent/JPS5321159A/ja active Granted
- 1977-08-08 PL PL77200124A patent/PL200124A1/xx unknown
- 1977-08-08 AT AT0579477A patent/AT362887B/de not_active IP Right Cessation
- 1977-08-08 PL PL1977215666A patent/PL112931B1/pl unknown
-
1978
- 1978-07-01 ES ES471349A patent/ES471349A1/es not_active Expired
- 1978-10-11 SU SU782672200A patent/SU818480A3/ru active
- 1978-10-17 SU SU782674602A patent/SU850000A3/ru active
-
1979
- 1979-09-03 JP JP54112743A patent/JPS585196B2/ja not_active Expired
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