HUP0002778A2 - Eljárás szubsztituált perhidroizoindol-származék előállítására - Google Patents
Eljárás szubsztituált perhidroizoindol-származék előállításáraInfo
- Publication number
- HUP0002778A2 HUP0002778A2 HU0002778A HUP0002778A HUP0002778A2 HU P0002778 A2 HUP0002778 A2 HU P0002778A2 HU 0002778 A HU0002778 A HU 0002778A HU P0002778 A HUP0002778 A HU P0002778A HU P0002778 A2 HUP0002778 A2 HU P0002778A2
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- converted
- formula
- salt
- tetrahydrofuran
- Prior art date
Links
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical class C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- 239000000010 aprotic solvent Substances 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000010948 rhodium Substances 0.000 abstract 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 abstract 1
- 102000004877 Insulin Human genes 0.000 abstract 1
- 108090001061 Insulin Proteins 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229940125396 insulin Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 230000003248 secreting effect Effects 0.000 abstract 1
- BFMKBYZEJOQYIM-UCGGBYDDSA-N tert-butyl (2s,4s)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate Chemical compound C([C@@H]1C[C@@H](CN1C(=O)OC(C)(C)C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BFMKBYZEJOQYIM-UCGGBYDDSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Atalálmány tárgya új eljárás az (I) képletű szubsztituáltperhidroizoindolszármazék és gyógyászatilag elfogadható sóielőállítására ipari méretekben. Atalálmány abban áll, hogy dimetil-szukcinátot benzaldehiddel reagáltatnak metanolos közegben, majd akapott disavat aprotikus oldószerben, célszerűen tetrahidrofuránbanvagy diizopropil-éterben, ecetsavanhidrid jelenlétében hevítik, majd akapott anhidridet egy perhidroizoindollal reagáltatják aprotikusoldószerben, célszerűen toluolban, acetonitrilben, etil-acetátban,metil-terc-butil-éterben vagy tetrahidrofuránban, vagy pedigtetrahidrofurán és toluol elegyében, a kapott vegyületet katalitikushidrogénezésnek vetik alá aszimmetrikus hidrogénezőkatalizátorkéntródium/(2S,4S)-N-butoxi-karbonil-4-difenil-foszfino-2-difenil-foszfino-metil-pirrolidin megnevezésű vagy Rh(S,S)BPPM rövidítésseljelölt komplexet használva metanolos vagy metilén-kloridos közegben,az ekkor kapott vegyületet egy aminnal sóvá alakítják, ezután az ígykapott sót bázikus közegben egy ásványi só jelenlétében az (I) képletűvegyület addíciós sójává alakítják, amelyet ezután kívánt esetben amegfelelő szabad savvá konvertálják savas közegben, és kívánt esetbenaz így kapott (I) képletű vegyületet gyógyászatilag elfogadhatóaddíciós sóvá alakítják. Az (I) képletű vegyület inzulinkiválasztóhatással rendelkezik. Ó
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9708431A FR2765578B1 (fr) | 1997-07-03 | 1997-07-03 | Procede de preparation d'un perhydroisoindole substitue |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU0002778D0 HU0002778D0 (en) | 1998-07-01 |
| HUP0002778A2 true HUP0002778A2 (hu) | 2001-01-29 |
| HUP0002778A3 HUP0002778A3 (en) | 2001-12-28 |
Family
ID=9508815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0002778A HUP0002778A3 (en) | 1997-07-03 | 1998-07-01 | Method for preparing a substituted perhydroisoindole |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6133454A (hu) |
| EP (1) | EP0994854B1 (hu) |
| JP (1) | JP4056093B2 (hu) |
| KR (1) | KR100421073B1 (hu) |
| CN (1) | CN1108291C (hu) |
| AT (1) | ATE224368T1 (hu) |
| AU (1) | AU734398B2 (hu) |
| BR (1) | BR9810657A (hu) |
| CA (1) | CA2295992C (hu) |
| DE (1) | DE69808092T2 (hu) |
| DK (1) | DK0994854T3 (hu) |
| EA (1) | EA002151B1 (hu) |
| ES (1) | ES2184304T3 (hu) |
| FR (1) | FR2765578B1 (hu) |
| HK (1) | HK1028610A1 (hu) |
| HU (1) | HUP0002778A3 (hu) |
| NO (1) | NO313095B1 (hu) |
| NZ (1) | NZ501835A (hu) |
| PL (1) | PL190861B1 (hu) |
| PT (1) | PT994854E (hu) |
| WO (1) | WO1999001430A1 (hu) |
| ZA (1) | ZA985882B (hu) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2793411B1 (fr) * | 1999-05-11 | 2001-06-29 | Synthelabo | Utilisation de derives de l'acide succinique pour obtenir un medicament destine au traitement de l'inflammation |
| FR2834892B1 (fr) * | 2002-01-23 | 2004-02-27 | Servier Lab | Composition pharmaceutique orodispersible de mitiglinide |
| US6684422B2 (en) * | 2002-02-27 | 2004-02-03 | Ginger Magnolia | Toy retention blanket and system |
| EP1532979A4 (en) * | 2002-06-28 | 2008-01-16 | Kissei Pharmaceutical | DRUG COMPOSITION FOR REGULATING GLYCEMIA |
| KR100709531B1 (ko) * | 2002-06-28 | 2007-04-23 | 깃세이 야쿠힌 고교 가부시키가이샤 | 당뇨병성 합병증의 예방 또는 진전저지용 의약조성물 |
| KR20050058444A (ko) * | 2002-08-23 | 2005-06-16 | 반유 세이야꾸 가부시끼가이샤 | 인돌로피롤로카르바졸 유도체의 제조법 |
| FR2860231B1 (fr) * | 2003-09-25 | 2005-11-18 | Servier Lab | Nouveau procede de preparation du cis-octahydro-isoindole |
| US7230022B2 (en) * | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| CN1634885B (zh) * | 2004-11-09 | 2011-05-04 | 北京乐力健生物科技有限公司 | 米格列奈晶型及其制备方法 |
| CN1324010C (zh) * | 2005-01-12 | 2007-07-04 | 江苏省药物研究所 | 一种米格列奈的制备方法 |
| JP4918257B2 (ja) * | 2005-12-27 | 2012-04-18 | キッセイ薬品工業株式会社 | 不斉還元方法 |
| WO2009047797A2 (en) * | 2007-10-08 | 2009-04-16 | Ind-Swift Laboratories Limited | Process for the preparation of perhydroisoindole derivative |
| CN102382033B (zh) * | 2010-08-31 | 2013-04-03 | 凯瑞斯德生化(苏州)有限公司 | 一种光学活性米格列奈酯及米格列奈盐的制备方法 |
| EP3492108A1 (en) | 2011-06-10 | 2019-06-05 | Bluebird Bio, Inc. | Gene therapy vectors for adrenoleukodystrophy and adrenomyeloneuropathy |
| KR101327866B1 (ko) * | 2011-10-27 | 2013-11-11 | 주식회사 메디켐코리아 | 미티글리나이드 칼슘염의 개선된 제조방법 |
| ES2546362B1 (es) | 2012-06-22 | 2016-07-07 | Laboratorios Lesvi, S. L. | PROCEDIMIENTO DE OBTENCIÓN DEL ÁCIDO (S) -2 BENCIL 4 - ((3aR, 7aS) -HEXAHIDRO-1H-ISOINDOL-2 (3H) IL) -4-OXOBUTANOICO Y SUS SALES |
| CN103450069B (zh) * | 2013-06-24 | 2015-04-15 | 山西大同大学 | 一种米格列奈钙的制备方法 |
| CN103709092B (zh) * | 2013-11-04 | 2016-07-06 | 河北科技大学 | 米格列奈钙的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU654331B2 (en) * | 1991-03-30 | 1994-11-03 | Kissei Pharmaceutical Co. Ltd. | Succinic acid compounds |
-
1997
- 1997-07-03 FR FR9708431A patent/FR2765578B1/fr not_active Expired - Fee Related
-
1998
- 1998-07-01 AT AT98935072T patent/ATE224368T1/de not_active IP Right Cessation
- 1998-07-01 US US09/446,848 patent/US6133454A/en not_active Expired - Fee Related
- 1998-07-01 PT PT98935072T patent/PT994854E/pt unknown
- 1998-07-01 EA EA200000094A patent/EA002151B1/ru not_active IP Right Cessation
- 1998-07-01 EP EP98935072A patent/EP0994854B1/fr not_active Expired - Lifetime
- 1998-07-01 CN CN98806779A patent/CN1108291C/zh not_active Expired - Fee Related
- 1998-07-01 NZ NZ501835A patent/NZ501835A/xx unknown
- 1998-07-01 CA CA002295992A patent/CA2295992C/fr not_active Expired - Fee Related
- 1998-07-01 DK DK98935072T patent/DK0994854T3/da active
- 1998-07-01 JP JP50653499A patent/JP4056093B2/ja not_active Expired - Fee Related
- 1998-07-01 AU AU84450/98A patent/AU734398B2/en not_active Ceased
- 1998-07-01 HU HU0002778A patent/HUP0002778A3/hu unknown
- 1998-07-01 ES ES98935072T patent/ES2184304T3/es not_active Expired - Lifetime
- 1998-07-01 WO PCT/FR1998/001405 patent/WO1999001430A1/fr active IP Right Grant
- 1998-07-01 BR BR9810657-0A patent/BR9810657A/pt not_active Application Discontinuation
- 1998-07-01 DE DE69808092T patent/DE69808092T2/de not_active Expired - Lifetime
- 1998-07-01 PL PL337728A patent/PL190861B1/pl not_active IP Right Cessation
- 1998-07-02 KR KR10-1998-0026520A patent/KR100421073B1/ko not_active IP Right Cessation
- 1998-07-03 ZA ZA985882A patent/ZA985882B/xx unknown
-
1999
- 1999-12-30 NO NO19996577A patent/NO313095B1/no not_active IP Right Cessation
-
2000
- 2000-12-15 HK HK00108117A patent/HK1028610A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GB9A | Succession in title |
Owner name: KISSEI PHARMACEUTICAL COMPANY LTD, JP Free format text: FORMER OWNER(S): ADIR, FR |
|
| FD9A | Lapse of provisional protection due to non-payment of fees |