PE20081293A1 - Procedimiento de preparacion de compuestos 2(s)-cianopirrolidina n-(n'-glicilo sustituida) - Google Patents
Procedimiento de preparacion de compuestos 2(s)-cianopirrolidina n-(n'-glicilo sustituida)Info
- Publication number
- PE20081293A1 PE20081293A1 PE2007000421A PE2007000421A PE20081293A1 PE 20081293 A1 PE20081293 A1 PE 20081293A1 PE 2007000421 A PE2007000421 A PE 2007000421A PE 2007000421 A PE2007000421 A PE 2007000421A PE 20081293 A1 PE20081293 A1 PE 20081293A1
- Authority
- PE
- Peru
- Prior art keywords
- procedure
- halogen
- compound
- cyanopyrrolidine
- glycyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 238000009413 insulation Methods 0.000 abstract 2
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 abstract 1
- -1 PYRIMIDINYL Chemical group 0.000 abstract 1
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical group [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 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)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pyrrole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
SE REFIERE A UN PROCEDIMIENTO PARA LA PREPARACION DE 2-CIANOPIRROLIDINA N-(N´-GLICILO SUSTITUIDA), DE FORMULA I, DONDE R ES R1R1aN(CH2)m, CICLOALQUILO C3-C12, ENTRE OTROS; R1 ES PIRIDINILO O PIRIMIDINILO OPCIONALMENTE SUSTITUIDO CON ALQUILO C1-C4, ALCOXI C1-C4, HALOGENO, ENTRE OTROS; R1a ES H, ALQUILO C1-C8; m ES 2-3. DICHO PROCEDIMIENTO COMPRENDE: (a) HACER REACCIONAR, EN PRESENCIA DE DIMETILFORMAMIDA, UN COMPUESTO DE LA FORMULA (V), DONDE X1 Y X3 SON CADA UNO HALOGENO; X2 ES HALOGENO, OH, O-C(=O)-CH2X3, ENTRE OTROS; CON L-PROLINAMIDA;(b) HACER REACCIONAR EL COMPUESTO RESULTANTE SIN AISLAMIENTO CON UN AGENTE DE DESHIDRATACION TAL COMO CLORURO DE (CLOROMETILEN)DIMETILAMONIO;(c) HACER REACCIONAR, EN PRESENCIA DE UNA BASE, EL COMPUESTO RESULTANTE SIN AISLAMIENTO CON UNA AMINA APROPIADA TAL COMO H2NR; Y (d) RECUPERAR EL COMPUESTO RESULTANTE EN FORMA LIBRE O EN FORMA DE SAL DE ADICION DE ACIDO. UN COMPUESTO OBTENIDO ES PIRROLIDINA ,1-[(3-HIDROXI-1-ADAMANTIL)AMINO]ACETIL-2-CIANO-,(S) , EN FORMA LIBRE CON PUNTO DE FUSION DE 148C
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 |
|---|---|
| PE20081293A1 true PE20081293A1 (es) | 2008-11-04 |
Family
ID=33301223
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2007000421A PE20081293A1 (es) | 2003-04-16 | 2004-04-14 | Procedimiento de preparacion de compuestos 2(s)-cianopirrolidina n-(n'-glicilo sustituida) |
| PE2004000370A PE20050021A1 (es) | 2003-04-16 | 2004-04-14 | Procedimiento para la preparacion de 2-cianopirrolidina n-sustituida |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2004000370A PE20050021A1 (es) | 2003-04-16 | 2004-04-14 | Procedimiento para la preparacion de 2-cianopirrolidina n-sustituida |
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 |
|---|---|---|---|---|
| PE20081293A1 (es) | 2003-04-16 | 2008-11-04 | Novartis Ag | Procedimiento de preparacion de compuestos 2(s)-cianopirrolidina n-(n'-glicilo sustituida) |
| WO2005067976A2 (en) | 2004-01-20 | 2005-07-28 | Novartis Ag | Direct compression formulation and process |
| 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. |
| CN101238099A (zh) * | 2005-08-04 | 2008-08-06 | 诺瓦提斯公司 | 维格列汀的盐 |
| WO2008066083A1 (fr) * | 2006-11-29 | 2008-06-05 | Mitsubishi Tanabe Pharma Corporation | Procédé de production d'un dérivé de n-(n'-glycyle substitué)-2-cyanopyrrolidine |
| EP2118056A2 (en) * | 2007-01-10 | 2009-11-18 | Medichem, S.A. | Process for preparing 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 |
| IN2012MU01383A (es) * | 2012-05-04 | 2014-02-28 | ||
| 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 |
| JP2003520849A (ja) * | 2000-01-24 | 2003-07-08 | ノボ ノルディスク アクティーゼルスカブ | 酵素ｄｐｐ−ｉｖの阻害剤であるｎ−置換２−シアノピロールおよび−ピロリン |
| 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 |
| PE20081293A1 (es) | 2003-04-16 | 2008-11-04 | Novartis Ag | Procedimiento de preparacion de compuestos 2(s)-cianopirrolidina n-(n'-glicilo sustituida) |
-
2004
- 2004-04-14 PE PE2007000421A patent/PE20081293A1/es not_active Application Discontinuation
- 2004-04-14 AR ARP040101251A patent/AR044019A1/es not_active Application Discontinuation
- 2004-04-14 PE PE2004000370A patent/PE20050021A1/es not_active Application Discontinuation
- 2004-04-15 EP EP04727557.3A patent/EP1620396B1/en not_active Expired - Lifetime
- 2004-04-15 BR BRPI0409471A patent/BRPI0409471B8/pt not_active IP Right Cessation
- 2004-04-15 NZ NZ542899A patent/NZ542899A/en not_active IP Right Cessation
- 2004-04-15 SG SG200716949-3A patent/SG160212A1/en unknown
- 2004-04-15 AU AU2004230245A patent/AU2004230245B2/en not_active Ceased
- 2004-04-15 CA CA2520128A patent/CA2520128C/en not_active Expired - Fee Related
- 2004-04-15 MX MXPA05011073A patent/MXPA05011073A/es active IP Right Grant
- 2004-04-15 ES ES04727557T patent/ES2531084T3/es not_active Expired - Lifetime
- 2004-04-15 RU RU2005135331/04A patent/RU2369598C2/ru active
- 2004-04-15 JP JP2006505132A patent/JP4672647B2/ja not_active Expired - Lifetime
- 2004-04-15 DK DK04727557.3T patent/DK1620396T3/en active
- 2004-04-15 PL PL04727557T patent/PL1620396T3/pl unknown
- 2004-04-15 US US10/552,835 patent/US7375238B2/en not_active Expired - Fee Related
- 2004-04-15 HR HRP20150163TT patent/HRP20150163T1/hr unknown
- 2004-04-15 WO PCT/EP2004/003980 patent/WO2004092127A1/en not_active Ceased
- 2004-04-15 PT PT04727557T patent/PT1620396E/pt unknown
- 2004-04-15 KR KR1020057019568A patent/KR101192538B1/ko not_active Expired - Fee Related
- 2004-04-15 SI SI200432220T patent/SI1620396T1/sl unknown
- 2004-04-15 TW TW093110566A patent/TWI359135B/zh not_active IP Right Cessation
- 2004-04-15 MY MYPI20041383A patent/MY139476A/en unknown
- 2004-04-15 CL CL200400804A patent/CL2004000804A1/es unknown
-
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 |