DD202539A5 - Verfahren zur herstellung von 1-(3-hydroxy-4-methoxybenzoyl)-3-hydroxy-2-pyrolidinon - Google Patents
Verfahren zur herstellung von 1-(3-hydroxy-4-methoxybenzoyl)-3-hydroxy-2-pyrolidinon Download PDFInfo
- Publication number
- DD202539A5 DD202539A5 DD82237159A DD23715982A DD202539A5 DD 202539 A5 DD202539 A5 DD 202539A5 DD 82237159 A DD82237159 A DD 82237159A DD 23715982 A DD23715982 A DD 23715982A DD 202539 A5 DD202539 A5 DD 202539A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydroxy
- methoxybenzoyl
- formula
- compound
- pyrrolidinone
- Prior art date
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- -1 3-HYDROXY-4-METHOXYBENZOYL Chemical class 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000006239 protecting group Chemical group 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 14
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VUOZPAGAAMBEGM-QMMMGPOBSA-N (3s)-3-hydroxy-1-(3-hydroxy-4-methoxybenzoyl)pyrrolidin-2-one Chemical compound C1=C(O)C(OC)=CC=C1C(=O)N1C(=O)[C@@H](O)CC1 VUOZPAGAAMBEGM-QMMMGPOBSA-N 0.000 claims description 3
- VUOZPAGAAMBEGM-MRVPVSSYSA-N (3r)-3-hydroxy-1-(3-hydroxy-4-methoxybenzoyl)pyrrolidin-2-one Chemical compound C1=C(O)C(OC)=CC=C1C(=O)N1C(=O)[C@H](O)CC1 VUOZPAGAAMBEGM-MRVPVSSYSA-N 0.000 claims description 2
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- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 239000000543 intermediate Chemical class 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- MVPQFIHPVCQHFQ-UHFFFAOYSA-N pyrrolidin-1-yl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)ON1CCCC1 MVPQFIHPVCQHFQ-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical class O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- AATYKEFFPLPLST-UHFFFAOYSA-N trimethylsilylurea Chemical compound C[Si](C)(C)NC(N)=O AATYKEFFPLPLST-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH77081A CH646149A5 (de) | 1981-02-05 | 1981-02-05 | Pyrrolidin-derivat. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD202539A5 true DD202539A5 (de) | 1983-09-21 |
Family
ID=4194769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82237159A DD202539A5 (de) | 1981-02-05 | 1982-02-03 | Verfahren zur herstellung von 1-(3-hydroxy-4-methoxybenzoyl)-3-hydroxy-2-pyrolidinon |
Country Status (40)
| Country | Link |
|---|---|
| US (1) | US4452807A (es) |
| EP (1) | EP0057846B1 (es) |
| JP (1) | JPS57146753A (es) |
| KR (1) | KR830009023A (es) |
| AR (1) | AR231127A1 (es) |
| AT (2) | ATE13668T1 (es) |
| AU (1) | AU552063B2 (es) |
| BG (1) | BG36932A3 (es) |
| BR (1) | BR8200615A (es) |
| CA (1) | CA1158250A (es) |
| CH (1) | CH646149A5 (es) |
| CS (1) | CS227035B2 (es) |
| DD (1) | DD202539A5 (es) |
| DE (2) | DE3263960D1 (es) |
| DK (1) | DK20682A (es) |
| ES (1) | ES509312A0 (es) |
| FI (1) | FI820192L (es) |
| FR (1) | FR2499075A1 (es) |
| GB (1) | GB2092584B (es) |
| GR (1) | GR76052B (es) |
| HU (1) | HU184988B (es) |
| IE (1) | IE52439B1 (es) |
| IL (1) | IL64896A (es) |
| IS (1) | IS2700A7 (es) |
| IT (1) | IT1153402B (es) |
| LU (1) | LU83923A1 (es) |
| MC (1) | MC1440A1 (es) |
| NL (1) | NL8200337A (es) |
| NO (1) | NO820346L (es) |
| NZ (1) | NZ199624A (es) |
| OA (1) | OA07002A (es) |
| PH (1) | PH18267A (es) |
| PL (1) | PL135221B1 (es) |
| PT (1) | PT74387B (es) |
| RO (1) | RO83099B (es) |
| SE (1) | SE8200647L (es) |
| SU (1) | SU1143315A3 (es) |
| YU (1) | YU23982A (es) |
| ZA (1) | ZA82608B (es) |
| ZW (1) | ZW1982A1 (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2515179A1 (fr) * | 1981-07-24 | 1983-04-29 | Hoffmann La Roche | Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique |
| FR2551751B1 (fr) * | 1983-09-12 | 1986-04-25 | Serobiologiques Lab Sa | Nouveau procede de preparation d'un derive pyroglutamique, nouveaux derives pyroglutamiques, nouveaux intermediaires de synthese de preparation de ceux-ci et utilisation ou application des derives pyroglutamiques comme agents antibacteriens ou antifongiques |
| DE3336024A1 (de) * | 1983-10-04 | 1985-04-18 | Boehringer Ingelheim KG, 6507 Ingelheim | 4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel |
| DE3537075A1 (de) * | 1985-10-18 | 1987-04-23 | Bayer Ag | Verfahren zur herstellung von clausenamid |
| DE3632589A1 (de) * | 1985-10-18 | 1987-04-23 | Bayer Ag | Verfahren zur herstellung von (gamma)-butyrolactamen |
| US4677114A (en) * | 1985-11-22 | 1987-06-30 | Warner-Lambert Company | Pyrrolidone-2 derivatives and pharmaceutical compositions thereof |
| IT1215587B (it) * | 1987-06-26 | 1990-02-14 | Roussel Maestretti Spa | Derivati della 1-benzoil2-oxo 5-alcossi pirrolidina, loro procedimento di preparazione e loro impiego come sostanza medicinale. |
| JPH0720930B2 (ja) * | 1988-07-09 | 1995-03-08 | 明治製菓株式会社 | ピロリジノン化合物及び脳機能障害改善剤 |
| US5049577A (en) * | 1990-01-29 | 1991-09-17 | E. R. Squibb & Sons, Inc. | 2-pyrrolidone substituted dihydroxy alkanoic, alkenoic and alkynoic acids, compositions and HMG-CoA reductase inhibition therewith |
| US5049578A (en) * | 1990-03-09 | 1991-09-17 | E. R. Squibb & Sons, Inc. | 1-aroyl or 1-acyl-2-2pyrrolidinyl-3,5-dihydroxy alkanoic and alkenoic acids, salts, esters and lactones |
| ATE215079T1 (de) * | 1992-07-24 | 2002-04-15 | Univ California | Arzneimittel, die den durch ampa rezeptoren vermittelten synaptischen respons erhöhen |
| US5852008A (en) * | 1995-01-24 | 1998-12-22 | The Regents Of The University Of California | Heteroatom substituted benzoyl derivatives that enhance synaptic response mediated by receptors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES433723A1 (es) * | 1975-01-10 | 1976-11-16 | Lafarquim S A Lab | Procedimiento de obtencion de un derivado de 2-pirrolidi- nona. |
| IT1045043B (it) * | 1975-08-13 | 1980-04-21 | Isf Spa | Derivati pirrolidinici |
| CU21107A3 (es) * | 1978-02-10 | 1988-02-01 | Hoffmann La Roche | Pyrrolidines derivatives |
| CA1115212A (en) * | 1978-02-10 | 1981-12-29 | Emilio Kyburz | Pyrrolidine derivatives |
| IT1131959B (it) * | 1979-08-09 | 1986-06-25 | Hoffmann La Roche | Derivati pirrolidinici |
-
1981
- 1981-02-05 CH CH77081A patent/CH646149A5/de not_active IP Right Cessation
-
1982
- 1982-01-08 CA CA000393829A patent/CA1158250A/en not_active Expired
- 1982-01-14 IT IT19115/82A patent/IT1153402B/it active
- 1982-01-18 DK DK20682A patent/DK20682A/da not_active Application Discontinuation
- 1982-01-20 US US06/340,920 patent/US4452807A/en not_active Expired - Fee Related
- 1982-01-21 FI FI820192A patent/FI820192L/fi not_active Application Discontinuation
- 1982-01-25 DE DE8282100494T patent/DE3263960D1/de not_active Expired
- 1982-01-25 AT AT82100494T patent/ATE13668T1/de not_active IP Right Cessation
- 1982-01-25 DE DE19823202281 patent/DE3202281A1/de not_active Withdrawn
- 1982-01-25 EP EP82100494A patent/EP0057846B1/de not_active Expired
- 1982-01-28 OA OA57598A patent/OA07002A/xx unknown
- 1982-01-29 PH PH26797A patent/PH18267A/en unknown
- 1982-01-29 NL NL8200337A patent/NL8200337A/nl not_active Application Discontinuation
- 1982-01-29 ZW ZW19/82A patent/ZW1982A1/xx unknown
- 1982-01-29 IL IL64896A patent/IL64896A/xx unknown
- 1982-01-29 ZA ZA82608A patent/ZA82608B/xx unknown
- 1982-01-29 CS CS82629A patent/CS227035B2/cs unknown
- 1982-01-30 RO RO106487A patent/RO83099B/ro unknown
- 1982-02-01 NZ NZ199624A patent/NZ199624A/en unknown
- 1982-02-01 HU HU82285A patent/HU184988B/hu unknown
- 1982-02-02 JP JP57014411A patent/JPS57146753A/ja active Granted
- 1982-02-02 AU AU80104/82A patent/AU552063B2/en not_active Ceased
- 1982-02-02 AR AR288323A patent/AR231127A1/es active
- 1982-02-03 GR GR67187A patent/GR76052B/el unknown
- 1982-02-03 DD DD82237159A patent/DD202539A5/de not_active IP Right Cessation
- 1982-02-03 MC MC821572A patent/MC1440A1/xx unknown
- 1982-02-03 SU SU823381951A patent/SU1143315A3/ru active
- 1982-02-03 FR FR8201714A patent/FR2499075A1/fr not_active Withdrawn
- 1982-02-04 ES ES509312A patent/ES509312A0/es active Granted
- 1982-02-04 YU YU00239/82A patent/YU23982A/xx unknown
- 1982-02-04 LU LU83923A patent/LU83923A1/de unknown
- 1982-02-04 AT AT0041882A patent/AT377982B/de not_active IP Right Cessation
- 1982-02-04 BR BR8200615A patent/BR8200615A/pt unknown
- 1982-02-04 IS IS2700A patent/IS2700A7/is unknown
- 1982-02-04 KR KR1019820000475A patent/KR830009023A/ko unknown
- 1982-02-04 GB GB8203264A patent/GB2092584B/en not_active Expired
- 1982-02-04 NO NO820346A patent/NO820346L/no unknown
- 1982-02-04 IE IE249/82A patent/IE52439B1/en unknown
- 1982-02-04 SE SE8200647A patent/SE8200647L/xx not_active Application Discontinuation
- 1982-02-04 PT PT74387A patent/PT74387B/pt unknown
- 1982-02-05 BG BG8255269A patent/BG36932A3/xx unknown
- 1982-02-05 PL PL1982234962A patent/PL135221B1/pl unknown
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Legal Events
| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |