AR044019A1 - Proceso para la preparacion de 2-cianopirrolidinas n-sustituidas - Google Patents
Proceso para la preparacion de 2-cianopirrolidinas n-sustituidasInfo
- Publication number
- AR044019A1 AR044019A1 ARP040101251A ARP040101251A AR044019A1 AR 044019 A1 AR044019 A1 AR 044019A1 AR P040101251 A ARP040101251 A AR P040101251A AR P040101251 A ARP040101251 A AR P040101251A AR 044019 A1 AR044019 A1 AR 044019A1
- Authority
- AR
- Argentina
- Prior art keywords
- reacting
- substituted
- preparation
- resulting compound
- cyanopirrolidins
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- ALSCEGDXFJIYES-UHFFFAOYSA-N pyrrolidine-2-carbonitrile Chemical compound N#CC1CCCN1 ALSCEGDXFJIYES-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La presente se refiere a un procedimiento para la preparación de una 2-cianopirrolidina N-(N´-glicilo sustituida), que comprende por lo menos: a) hacer reaccionar, en presencia de dimetilformamida, un compuesto de la fórmula (1), en donde, independientemente uno del otro, X1 y X3 son halógeno; X2 es halógeno, OH, O-C(=O)-CH2X3, -O-SO2-alquilo (C1-8) o -O-SO2(arilo), con L-prolinamida, seguido por: b) hacer reaccionar el compuesto resultante sin aislamiento con un agente de deshidratación, opcionalmente seguido por: c) hacer reaccionar, en presencia de una base, el compuesto resultante sin aislamiento con una amina apropiada, y d) recuperar el compuesto resultante en forma libre o en forma de sal de adición de ácido.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0308854A GB0308854D0 (en) | 2003-04-16 | 2003-04-16 | Organic compounds |
| GB0311836A GB0311836D0 (en) | 2003-05-22 | 2003-05-22 | Process for the manufacture of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR044019A1 true AR044019A1 (es) | 2005-08-24 |
Family
ID=33301223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040101251A AR044019A1 (es) | 2003-04-16 | 2004-04-14 | Proceso para la preparacion de 2-cianopirrolidinas n-sustituidas |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US7375238B2 (es) |
| EP (1) | EP1620396B1 (es) |
| JP (1) | JP4672647B2 (es) |
| KR (1) | KR101192538B1 (es) |
| AR (1) | AR044019A1 (es) |
| AU (2) | AU2004230245B2 (es) |
| BR (1) | BRPI0409471B8 (es) |
| CA (1) | CA2520128C (es) |
| CL (1) | CL2004000804A1 (es) |
| CO (1) | CO5700735A2 (es) |
| CY (1) | CY1116008T1 (es) |
| DK (1) | DK1620396T3 (es) |
| EC (1) | ECSP056093A (es) |
| ES (1) | ES2531084T3 (es) |
| HR (1) | HRP20150163T1 (es) |
| IL (1) | IL170887A (es) |
| IS (1) | IS2979B (es) |
| MA (1) | MA27765A1 (es) |
| MX (1) | MXPA05011073A (es) |
| MY (1) | MY139476A (es) |
| NO (1) | NO333251B1 (es) |
| NZ (1) | NZ542899A (es) |
| PE (2) | PE20081293A1 (es) |
| PL (1) | PL1620396T3 (es) |
| PT (1) | PT1620396E (es) |
| RU (1) | RU2369598C2 (es) |
| SG (1) | SG160212A1 (es) |
| SI (1) | SI1620396T1 (es) |
| TW (1) | TWI359135B (es) |
| WO (1) | WO2004092127A1 (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR044019A1 (es) | 2003-04-16 | 2005-08-24 | Novartis Ag | Proceso para la preparacion de 2-cianopirrolidinas n-sustituidas |
| JP5122144B2 (ja) | 2004-01-20 | 2013-01-16 | ノバルティス アーゲー | 直接圧縮製剤および方法 |
| GT200600008A (es) | 2005-01-18 | 2006-08-09 | Formulacion de compresion directa y proceso | |
| MX2007011453A (es) | 2005-04-22 | 2008-02-12 | Alantos Pharmaceuticals Holding Inc | Inhibidores de la dipeptidil peptidasa-iv. |
| EP1912938A2 (en) * | 2005-08-04 | 2008-04-23 | Novartis AG | Salts of vildagliptin |
| JP5165584B2 (ja) * | 2006-11-29 | 2013-03-21 | 田辺三菱製薬株式会社 | Ｎ−（ｎ’−置換グリシル）−２−シアノピロリジン誘導体の製法 |
| AR064833A1 (es) * | 2007-01-10 | 2009-04-29 | Medichem Sa | Un procedimiento para la preparacion de vildagliptin |
| CZ2008512A3 (cs) | 2008-08-26 | 2010-03-10 | Zentiva, A. S | Zpusob prípravy vysoce cistého vildagliptinu |
| EA034049B1 (ru) * | 2009-07-31 | 2019-12-23 | КРКА, д.д., НОВО МЕСТО | Гранулят, включающий вилдаглиптин, способ его получения и фармацевтическая композиция |
| HUP0900638A2 (en) * | 2009-10-07 | 2011-05-30 | Egyt Gyogyszervegyeszeti Gyar | Adducts of inorganic salts basea on vildaelitpin applicable for preparation of pharmaceutical compositions |
| IT1400714B1 (it) | 2010-07-06 | 2013-06-28 | Chemelectiva S R L | Processo ed intermedi per la preparazione di un principio attivo. |
| HU231050B1 (hu) | 2010-08-19 | 2020-02-28 | Egis Gyógyszergyár Nyrt. | Eljárás gyógyszerhatóanyag előállítására |
| ITMI20112224A1 (it) | 2011-12-06 | 2013-06-07 | Chemelectiva S R L | Nuovo processo ed intermedi per la sintesi di vildagliptin |
| WO2013179300A2 (en) | 2012-05-04 | 2013-12-05 | Megafine Pharma (P) Ltd. | A process for the preparation of vildagliptin and its intermediate thereof |
| CN103922986B (zh) * | 2013-01-16 | 2017-02-15 | 上海彩迩文生化科技有限公司 | 维大列汀及其类似物、中间体及其制备方法和应用 |
| WO2015145467A1 (en) * | 2014-03-28 | 2015-10-01 | Laurus Labs Private Limited | An improved process for preparing vildagliptin |
| WO2021234430A1 (en) | 2020-05-17 | 2021-11-25 | Lotus International Pte. Ltd. | Modified release dosage form comprising vildagliptin and process for manufacturing the same |
| WO2022003405A1 (en) | 2020-07-03 | 2022-01-06 | Savoi Guilherme | One-pot process to obtain a pyrrolidine-2-carbonitrile intermediate compound and industrial scale telescopic process to prepare (2s)-1-[n-(3-hydroxyadamantan-1-yl)glycyl]-2-pyrrolidinecarbonitrile (vildagliptin) using same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510369A (en) * | 1994-07-22 | 1996-04-23 | Merck & Co., Inc. | Pyrrolidine thrombin inhibitors |
| TW492957B (en) * | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| CO5150173A1 (es) * | 1998-12-10 | 2002-04-29 | Novartis Ag | Compuestos n-(glicilo sustituido)-2-cianopirrolidinas inhibidores de peptidasa de dipeptidilo-iv (dpp-iv) los cuales son efectivos en el tratamiento de condiciones mediadas por la inhibicion de dpp-iv |
| US6380398B2 (en) | 2000-01-04 | 2002-04-30 | Novo Nordisk A/S | Therapeutically active and selective heterocyclic compounds that are inhibitors of the enzyme DPP-IV |
| WO2001055105A1 (en) * | 2000-01-24 | 2001-08-02 | Novo Nordisk A/S | N-substituted 2-cyanopyroles and -pyrrolines which are inhibitors of the enzyme dpp-iv |
| TW583185B (en) * | 2000-06-13 | 2004-04-11 | Novartis Ag | N-(substituted glycyl)-2-cyanopyrrolidines and pharmaceutical composition for inhibiting dipeptidyl peptidase-IV (DPP-IV) or for the prevention or treatment of diseases or conditions associated with elevated levels of DPP-IV comprising the same |
| JP2002265439A (ja) * | 2001-03-08 | 2002-09-18 | Mitsubishi Pharma Corp | シアノピロリジン誘導体およびその医薬用途 |
| AR044019A1 (es) | 2003-04-16 | 2005-08-24 | Novartis Ag | Proceso para la preparacion de 2-cianopirrolidinas n-sustituidas |
-
2004
- 2004-04-14 AR ARP040101251A patent/AR044019A1/es not_active Application Discontinuation
- 2004-04-14 PE PE2007000421A patent/PE20081293A1/es not_active Application Discontinuation
- 2004-04-14 PE PE2004000370A patent/PE20050021A1/es not_active Application Discontinuation
- 2004-04-15 TW TW093110566A patent/TWI359135B/zh not_active IP Right Cessation
- 2004-04-15 SI SI200432220T patent/SI1620396T1/sl unknown
- 2004-04-15 NZ NZ542899A patent/NZ542899A/en not_active IP Right Cessation
- 2004-04-15 US US10/552,835 patent/US7375238B2/en not_active Expired - Fee Related
- 2004-04-15 MY MYPI20041383A patent/MY139476A/en unknown
- 2004-04-15 PT PT04727557T patent/PT1620396E/pt unknown
- 2004-04-15 RU RU2005135331/04A patent/RU2369598C2/ru active
- 2004-04-15 BR BRPI0409471A patent/BRPI0409471B8/pt not_active IP Right Cessation
- 2004-04-15 CA CA2520128A patent/CA2520128C/en not_active Expired - Fee Related
- 2004-04-15 EP EP04727557.3A patent/EP1620396B1/en not_active Expired - Lifetime
- 2004-04-15 WO PCT/EP2004/003980 patent/WO2004092127A1/en not_active Ceased
- 2004-04-15 AU AU2004230245A patent/AU2004230245B2/en not_active Ceased
- 2004-04-15 SG SG200716949-3A patent/SG160212A1/en unknown
- 2004-04-15 CL CL200400804A patent/CL2004000804A1/es unknown
- 2004-04-15 KR KR1020057019568A patent/KR101192538B1/ko not_active Expired - Fee Related
- 2004-04-15 PL PL04727557T patent/PL1620396T3/pl unknown
- 2004-04-15 JP JP2006505132A patent/JP4672647B2/ja not_active Expired - Lifetime
- 2004-04-15 ES ES04727557T patent/ES2531084T3/es not_active Expired - Lifetime
- 2004-04-15 DK DK04727557.3T patent/DK1620396T3/en active
- 2004-04-15 HR HRP20150163TT patent/HRP20150163T1/hr unknown
- 2004-04-15 MX MXPA05011073A patent/MXPA05011073A/es active IP Right Grant
-
2005
- 2005-09-15 IL IL170887A patent/IL170887A/en active IP Right Grant
- 2005-10-12 EC EC2005006093A patent/ECSP056093A/es unknown
- 2005-10-19 MA MA28559A patent/MA27765A1/fr unknown
- 2005-11-03 CO CO05112189A patent/CO5700735A2/es not_active Application Discontinuation
- 2005-11-07 NO NO20055226A patent/NO333251B1/no not_active IP Right Cessation
- 2005-11-10 IS IS8122A patent/IS2979B/is unknown
-
2008
- 2008-05-22 AU AU2008202278A patent/AU2008202278A1/en not_active Abandoned
-
2015
- 2015-02-18 CY CY20151100168T patent/CY1116008T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC | Refusal |