HRP20140686T1 - Poboljšani postupak - Google Patents
Poboljšani postupak Download PDFInfo
- Publication number
- HRP20140686T1 HRP20140686T1 HRP20140686AT HRP20140686T HRP20140686T1 HR P20140686 T1 HRP20140686 T1 HR P20140686T1 HR P20140686A T HRP20140686A T HR P20140686AT HR P20140686 T HRP20140686 T HR P20140686T HR P20140686 T1 HRP20140686 T1 HR P20140686T1
- Authority
- HR
- Croatia
- Prior art keywords
- process according
- alcohol
- solvent system
- methanol
- lenalidomide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims 6
- 229960004942 lenalidomide Drugs 0.000 claims 6
- -1 aliphatic alcohols Chemical class 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- JKPJLYIGKKDZDT-UHFFFAOYSA-N 3-(7-nitro-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)N1C1CCC(=O)NC1=O JKPJLYIGKKDZDT-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lighting Device Outwards From Vehicle And Optical Signal (AREA)
- Glass Compositions (AREA)
- Optical Communication System (AREA)
Claims (16)
1. Postupak pripreme lenalidomida, obuhvaća katalitičku redukciju 3-(1-okso-4-nitro-1,3-dihidro-izoindol-2-il)-piperidin-2,6-diona koja obuhvaća:
(i) miješanje 3-(1-okso-4-nitro-1,3-dihidro-izoindol-2-il)-piperidin-2,6-diona u sustavu otapala;
(ii) dovođenje dobivene smjese iz koraka (i) u doticaj s katalizatorom; i
(iii) dovođenje smjese iz koraka (ii) u doticaj s vodikom;
naznačen time što sustav otapala sadrži smjesu polarnih otapala, gdje ta smjesa polarnih otapala obuhvaća alifatske alkohole ravnog ili razgranatog lanca s 1 do 5 atoma ugljika i alifatski nitril s 1 do 3 atoma ugljika.
2. Postupak prema zahtjevu 1, gdje:
(a) alkohol je metanol, etanol ili izopropanol; i/ili
(b) alifatski nitril je acetonitril ili propionitril; i/ili
(c) sustav otapala obuhvaća acetonitril i metanol.
3. Postupak prema bilo kojem od prethodnih zahtjeva, gdje:
(a) redukcija se provodi pri atmosferskom tlaku; i/ili
(b) redukcija se održava između 20-40°C; i/ili
(c) redukcija se ostavlja da traje 1-3,5 sata; i/ili
(d) katalizator je paladij ili ugljen.
4. Postupak prema bilo kojem od prethodnih zahtjeva, dalje obuhvaća pročišćavanje lenalidomide, koje obuhvaća:
(i) miješanje lenalidomida u sustavu otapala;
(ii) priprema soli lenalidomida; i
(iii) dobivanje pročišćenog lenalidomida iz soli pripremljene u koraku (ii).
5. Postupak prema zahtjevu 4, gdje sustav otapala sadrži alkohol ravnog ili razgranatog lanca s 1 do 5 atoma ugljika i alifatski nitril s 1 do 3 atoma ugljika.
6. Postupak prema zahtjevu 5, gdje:
(a) alifatski nitril je acetonitril ili propionitril; i/ili
(b) alkohol je metanol, etanol ili izopropanol.
7. Postupak prema zahtjevu 6, gdje alkohol je metanol.
8. Postupak prema bilo kojem od zahtjeva 4-7, gdje se sol priprema dodavanjem kiseline u koraku (ii), izabrane iz grupe koja obuhvaća octenu, vinsku, oksalnu, jabučnu, fumarnu, klorovodičnu i sumpornu kiselinu.
9. Postupak prema zahtjevu 8, gdje je kiselina klorovodična kiselina.
10. Postupak prema bilo kojem od zahtjeva 4-9, gdje se pročišćeni lenalidomid iz koraka (iii) dobiva dodavanjem baze.
11. Postupak prema zahtjevu 10, gdje je baza sekundarni ili tercijarni alifatski amin.
12. Postupak prema zahtjevu 11, gdje je baza trietilamin.
13. Postupak prema bilo kojem od zahtjeva 10-12, gdje se baza miješa u sustav otapala.
14. Postupak prema zahtjevu 13, gdje sustav otapala sadrži alifatski alkohol ravnog ili razgranatog lanca s 1 do 5 atoma ugljika.
15. Postupak prema zahtjevu 14, gdje alkohol je metanol, etanol ili izopropanol.
16. Postupak prema zahtjevu 15, gdje alkohol je metanol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN383KO2009 | 2009-03-02 | ||
| IN463KO2009 | 2009-03-16 | ||
| PCT/GB2010/050352 WO2010100476A2 (en) | 2009-03-02 | 2010-03-01 | Improved process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140686T1 true HRP20140686T1 (hr) | 2014-09-26 |
Family
ID=54290149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140686AT HRP20140686T1 (hr) | 2009-03-02 | 2014-07-16 | Poboljšani postupak |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8946265B2 (hr) |
| EP (1) | EP2403845B1 (hr) |
| JP (1) | JP5727944B2 (hr) |
| CN (1) | CN102414196A (hr) |
| AU (1) | AU2010220204B2 (hr) |
| CA (1) | CA2753241C (hr) |
| CY (1) | CY1115376T1 (hr) |
| DK (1) | DK2403845T3 (hr) |
| ES (1) | ES2487215T3 (hr) |
| HR (1) | HRP20140686T1 (hr) |
| NZ (1) | NZ595492A (hr) |
| PL (1) | PL2403845T3 (hr) |
| PT (1) | PT2403845E (hr) |
| SI (1) | SI2403845T1 (hr) |
| SM (1) | SMT201400100B (hr) |
| WO (1) | WO2010100476A2 (hr) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA83504C2 (en) | 2003-09-04 | 2008-07-25 | Селджин Корпорейшн | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| TWI475014B (zh) * | 2009-09-17 | 2015-03-01 | Scinopharm Taiwan Ltd | 固體形態的３－（４－胺基－１－側氧基－１，３－二氫－異吲哚－２－基）－哌啶－２，６－二酮及其製造方法 |
| WO2011064574A1 (en) | 2009-11-24 | 2011-06-03 | Generics [Uk] Limited | Hplc method for detecting lenalidomide |
| US8877932B2 (en) | 2010-03-08 | 2014-11-04 | Natco Pharma Limited | Anhydrous lenalidomide form-I |
| KR20130050952A (ko) | 2010-06-16 | 2013-05-16 | 브루스 챈들러 메이 | 인플루엔자, 감기 및 염증의 치료에서 레보세티리진 및 몬테루카스트의 용도 |
| WO2013005229A1 (en) * | 2011-07-05 | 2013-01-10 | Hetero Research Foundation | Process for lenalidomide |
| CA2842316A1 (en) | 2011-07-19 | 2013-01-24 | Amplio Pharma, Llc | Urea cocrystal of 3-(4-amin0-1-0x0-1,3 dihydro-isoindol-2-yl)piperidine-2,6-dione |
| CN102838586A (zh) * | 2012-09-20 | 2012-12-26 | 重庆泰濠制药有限公司 | 一种制备来那度胺的方法 |
| AU2014249456B2 (en) * | 2013-03-13 | 2018-08-09 | IRR, Inc. | Use of levocetirizine and montelukast in the treatment of autoimmune disorders |
| AU2014249531B2 (en) | 2013-03-13 | 2018-11-29 | IRR, Inc. | Use of levocetirizine and montelukast in the treatment of traumatic injury |
| JP2016512262A (ja) | 2013-03-13 | 2016-04-25 | インフラマトリー・レスポンス・リサーチ・インコーポレイテッド | 血管炎の処置におけるレボセチリジン及びモンテルカストの使用 |
| WO2014160686A1 (en) * | 2013-03-26 | 2014-10-02 | Celgene Corporation | Solid forms comprising 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione and a coformer, compositions and methods of use thereof |
| CN103601717A (zh) * | 2013-10-09 | 2014-02-26 | 湖南华腾制药有限公司 | 一种来那度胺的新型制备方法 |
| LV14985B (lv) | 2013-10-14 | 2015-06-20 | Latvijas Organiskās Sintēzes Institūts | Lenalidomīda iegūšanas process |
| WO2014155371A2 (en) * | 2014-04-26 | 2014-10-02 | Shilpa Medicare Limited | Crystalline lenalidomide process |
| WO2016024286A2 (en) * | 2014-08-11 | 2016-02-18 | Avra Laboratories Pvt. Ltd. | An improved process for synthesis of lenalidomide |
| WO2016026785A1 (en) * | 2014-08-19 | 2016-02-25 | Synthon B.V. | Process for making crystalline form a of lenalidomide |
| EP3193875B1 (en) | 2014-09-15 | 2022-02-16 | Inflammatory Response Research, Inc. | Levocetirizine and montelukast in the treatment of inflammation mediated conditions |
| EA036205B1 (ru) * | 2015-12-22 | 2020-10-14 | Синтон Б.В. | Фармацевтическая композиция, содержащая аморфный леналидомид и антиоксидант |
| US10899793B2 (en) | 2016-05-27 | 2021-01-26 | Regents Of The University Of Minnesota | Melanocortin ligands and methods of use thereof |
| US11124541B2 (en) | 2016-10-18 | 2021-09-21 | Regents Of The University Of Minnesota | Chimeric melanocortin ligands and methods of use thereof |
| KR20200092945A (ko) * | 2017-09-27 | 2020-08-04 | 바이오콘 리미티드 | 레날리도마이드의 결정형 |
| WO2019138424A1 (en) * | 2018-01-11 | 2019-07-18 | Natco Pharma Limited | Stable pharmaceutical compositions comprising lenalidomide |
| US11332499B2 (en) | 2018-08-16 | 2022-05-17 | Regents Of The University Of Minnesota | Cyclic peptides and methods of use thereof |
| CN111196800B (zh) * | 2018-11-19 | 2022-10-11 | 欣凯医药化工中间体（上海）有限公司 | 一种制备来那度胺的方法 |
| WO2022144924A1 (en) * | 2021-01-04 | 2022-07-07 | Avra Laboratories Pvt. Ltd. | An improved process for synthesis of lenalidomide |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281230B1 (en) | 1996-07-24 | 2001-08-28 | Celgene Corporation | Isoindolines, method of use, and pharmaceutical compositions |
| US5635517B1 (en) | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| UA83504C2 (en) | 2003-09-04 | 2008-07-25 | Селджин Корпорейшн | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| EP1797068B1 (en) | 2004-09-03 | 2013-10-09 | Celgene Corporation | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines |
| WO2008128225A1 (en) | 2007-04-16 | 2008-10-23 | Momenta Pharmaceuticals, Inc. | Multi-dimensional chromatographic methods for separating n-glycans |
| JP2011506950A (ja) | 2007-12-14 | 2011-03-03 | ジェネリクス・（ユーケー）・リミテッド | クロピドグレルを分析するためのｈｐｌｃ法 |
| EP2262768A4 (en) | 2008-03-11 | 2011-03-23 | Reddys Lab Ltd Dr | PREPARATION OF LENALIDOMIDE |
| AU2009321374A1 (en) | 2008-11-03 | 2010-06-03 | Generics [Uk] Limited | A crystalline form of lenalidomide and a process for its preparation |
| WO2011064574A1 (en) | 2009-11-24 | 2011-06-03 | Generics [Uk] Limited | Hplc method for detecting lenalidomide |
-
2010
- 2010-03-01 ES ES10707950.1T patent/ES2487215T3/es active Active
- 2010-03-01 CA CA2753241A patent/CA2753241C/en active Active
- 2010-03-01 JP JP2011552515A patent/JP5727944B2/ja active Active
- 2010-03-01 DK DK10707950.1T patent/DK2403845T3/da active
- 2010-03-01 US US13/254,249 patent/US8946265B2/en active Active
- 2010-03-01 AU AU2010220204A patent/AU2010220204B2/en active Active
- 2010-03-01 WO PCT/GB2010/050352 patent/WO2010100476A2/en active Application Filing
- 2010-03-01 CN CN2010800195527A patent/CN102414196A/zh active Pending
- 2010-03-01 PL PL10707950T patent/PL2403845T3/pl unknown
- 2010-03-01 PT PT107079501T patent/PT2403845E/pt unknown
- 2010-03-01 NZ NZ595492A patent/NZ595492A/xx unknown
- 2010-03-01 SI SI201030679T patent/SI2403845T1/sl unknown
- 2010-03-01 EP EP10707950.1A patent/EP2403845B1/en active Active
-
2014
- 2014-07-16 HR HRP20140686AT patent/HRP20140686T1/hr unknown
- 2014-07-24 CY CY20141100562T patent/CY1115376T1/el unknown
- 2014-07-28 SM SM201400100T patent/SMT201400100B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012519207A (ja) | 2012-08-23 |
| AU2010220204A1 (en) | 2011-10-20 |
| CY1115376T1 (el) | 2017-01-04 |
| US20120071509A1 (en) | 2012-03-22 |
| CA2753241A1 (en) | 2010-09-10 |
| NZ595492A (en) | 2013-07-26 |
| WO2010100476A2 (en) | 2010-09-10 |
| DK2403845T3 (da) | 2014-08-04 |
| SI2403845T1 (sl) | 2014-09-30 |
| EP2403845B1 (en) | 2014-04-30 |
| AU2010220204B2 (en) | 2015-10-08 |
| PT2403845E (pt) | 2014-08-04 |
| JP5727944B2 (ja) | 2015-06-03 |
| ES2487215T3 (es) | 2014-08-20 |
| WO2010100476A3 (en) | 2011-06-16 |
| EP2403845A2 (en) | 2012-01-11 |
| SMT201400100B (it) | 2014-11-10 |
| CA2753241C (en) | 2015-06-16 |
| CN102414196A (zh) | 2012-04-11 |
| US8946265B2 (en) | 2015-02-03 |
| PL2403845T3 (pl) | 2014-09-30 |
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