ES2487215T3 - Proceso mejorado - Google Patents
Proceso mejorado Download PDFInfo
- Publication number
- ES2487215T3 ES2487215T3 ES10707950.1T ES10707950T ES2487215T3 ES 2487215 T3 ES2487215 T3 ES 2487215T3 ES 10707950 T ES10707950 T ES 10707950T ES 2487215 T3 ES2487215 T3 ES 2487215T3
- Authority
- ES
- Spain
- Prior art keywords
- lenalidomide
- process according
- alcohol
- methanol
- solvent system
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000000034 method Methods 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 57
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims abstract description 79
- 229960004942 lenalidomide Drugs 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- -1 aliphatic nitrile Chemical class 0.000 claims abstract description 21
- 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 abstract description 20
- 239000002798 polar solvent Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000000746 purification Methods 0.000 claims description 14
- 238000006722 reduction reaction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- YCPULGHBTPQLRH-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;hydron;chloride Chemical compound Cl.NC1CCC(=O)NC1=O YCPULGHBTPQLRH-UHFFFAOYSA-N 0.000 description 7
- 208000009144 Pure autonomic failure Diseases 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000013312 porous aromatic framework Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FCGIVHSBEKGQMZ-UHFFFAOYSA-N methyl 2-(bromomethyl)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1CBr FCGIVHSBEKGQMZ-UHFFFAOYSA-N 0.000 description 4
- 238000010606 normalization Methods 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RYWZLJSDFZVVTD-UHFFFAOYSA-N 3-(7-amino-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione;hydrochloride Chemical compound Cl.C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O RYWZLJSDFZVVTD-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
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- 238000001757 thermogravimetry curve Methods 0.000 description 2
- SOHWLKBJOBHROR-MCDZGGTQSA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol;phosphoric acid Chemical compound OP(O)(O)=O.C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O SOHWLKBJOBHROR-MCDZGGTQSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PAMWIQZMLLUFBP-UHFFFAOYSA-N 1-aminopiperidine-2,6-dione Chemical compound NN1C(=O)CCCC1=O PAMWIQZMLLUFBP-UHFFFAOYSA-N 0.000 description 1
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 1
- MYPNWKPZEHVONN-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-5-nitroisoindole-1,3-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)N1C1CCC(=O)NC1=O MYPNWKPZEHVONN-UHFFFAOYSA-N 0.000 description 1
- AUVALWUPUHHNQV-UHFFFAOYSA-N 2-hydroxy-3-propylbenzoic acid Chemical class CCCC1=CC=CC(C(O)=O)=C1O AUVALWUPUHHNQV-UHFFFAOYSA-N 0.000 description 1
- WENKGSGGXGQHSH-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical class C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O WENKGSGGXGQHSH-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Optical Communication System (AREA)
- Lighting Device Outwards From Vehicle And Optical Signal (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| INKO03832009 | 2009-03-02 | ||
| IN383KO2009 | 2009-03-02 | ||
| IN463KO2009 | 2009-03-16 | ||
| INKO04632009 | 2009-03-16 | ||
| PCT/GB2010/050352 WO2010100476A2 (en) | 2009-03-02 | 2010-03-01 | Improved process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2487215T3 true ES2487215T3 (es) | 2014-08-20 |
Family
ID=54290149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10707950.1T Active ES2487215T3 (es) | 2009-03-02 | 2010-03-01 | Proceso mejorado |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8946265B2 (https=) |
| EP (1) | EP2403845B1 (https=) |
| JP (1) | JP5727944B2 (https=) |
| CN (1) | CN102414196A (https=) |
| AU (1) | AU2010220204B2 (https=) |
| CA (1) | CA2753241C (https=) |
| CY (1) | CY1115376T1 (https=) |
| DK (1) | DK2403845T3 (https=) |
| ES (1) | ES2487215T3 (https=) |
| HR (1) | HRP20140686T1 (https=) |
| NZ (1) | NZ595492A (https=) |
| PL (1) | PL2403845T3 (https=) |
| PT (1) | PT2403845E (https=) |
| SI (1) | SI2403845T1 (https=) |
| SM (1) | SMT201400100B (https=) |
| WO (1) | WO2010100476A2 (https=) |
Families Citing this family (27)
| 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 |
| WO2011111053A1 (en) * | 2010-03-08 | 2011-09-15 | 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 |
| US9540341B2 (en) | 2011-07-19 | 2017-01-10 | Amplio Pharma, Llc | Crystalline forms of 3-(4-amino-1-oxo-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 |
| WO2014164285A2 (en) | 2013-03-13 | 2014-10-09 | Inflammatory Response Research, Inc. | Use of levocetirizine and montelukast in the treatment of vasculitis |
| RU2015134423A (ru) | 2013-03-13 | 2017-04-26 | Инфламматори Респонс Ресёрч, Инк. | Применение левоцитиризина и монтелукаста при лечении аутоиммуных расстройств |
| MX382776B (es) | 2013-03-13 | 2025-03-13 | Inflammatory Response Res Inc | Uso de levocetirizina y montelukast en el tratamiento de lesion traumatica. |
| US9808450B2 (en) | 2013-03-26 | 2017-11-07 | 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 |
| EP3183244B1 (en) * | 2014-08-19 | 2019-04-10 | Synthon BV | Process for making crystalline form a of lenalidomide |
| WO2016044095A1 (en) | 2014-09-15 | 2016-03-24 | Inflammatory Response Research, Inc. | Levocetirizine and montelukast in the treatment of inflammation mediated conditions |
| WO2017109041A1 (en) * | 2015-12-22 | 2017-06-29 | Synthon B.V. | Pharmaceutical composition comprising amorphous lenalidomide and an antioxidant |
| 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 |
| EP3687987A4 (en) * | 2017-09-27 | 2021-03-24 | Biocon Limited | CRYSTALLINE FORMS OF LENALIDOMIDE |
| US11452722B2 (en) | 2018-01-11 | 2022-09-27 | 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 |
| WO2021236518A1 (en) | 2020-05-19 | 2021-11-25 | IRR, Inc. | Levocetirizine and montelukast in the treatment of sepsis and symptoms thereof |
| 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 |
| BRPI0514865A (pt) * | 2004-09-03 | 2008-06-24 | Celgene Corp | processo para preparar um composto |
| US8304250B2 (en) | 2007-04-16 | 2012-11-06 | Momenta Pharmaceuticals, Inc. | Multi-dimensional chromatographic methods for separating N-glycans |
| CA2709262A1 (en) | 2007-12-14 | 2009-06-25 | Generics [Uk] Limited | New hplc method |
| CA2717326C (en) | 2008-03-11 | 2018-10-23 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
| WO2010061209A1 (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 CN CN2010800195527A patent/CN102414196A/zh active Pending
- 2010-03-01 PT PT107079501T patent/PT2403845E/pt unknown
- 2010-03-01 NZ NZ595492A patent/NZ595492A/xx not_active IP Right Cessation
- 2010-03-01 CA CA2753241A patent/CA2753241C/en active Active
- 2010-03-01 HR HRP20140686AT patent/HRP20140686T1/hr unknown
- 2010-03-01 EP EP10707950.1A patent/EP2403845B1/en active Active
- 2010-03-01 WO PCT/GB2010/050352 patent/WO2010100476A2/en not_active Ceased
- 2010-03-01 JP JP2011552515A patent/JP5727944B2/ja not_active Expired - Fee Related
- 2010-03-01 SI SI201030679T patent/SI2403845T1/sl unknown
- 2010-03-01 US US13/254,249 patent/US8946265B2/en active Active
- 2010-03-01 DK DK10707950.1T patent/DK2403845T3/da active
- 2010-03-01 AU AU2010220204A patent/AU2010220204B2/en not_active Ceased
- 2010-03-01 ES ES10707950.1T patent/ES2487215T3/es active Active
- 2010-03-01 PL PL10707950T patent/PL2403845T3/pl unknown
-
2014
- 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 |
|---|---|
| CA2753241C (en) | 2015-06-16 |
| AU2010220204B2 (en) | 2015-10-08 |
| SI2403845T1 (sl) | 2014-09-30 |
| DK2403845T3 (da) | 2014-08-04 |
| PL2403845T3 (pl) | 2014-09-30 |
| US8946265B2 (en) | 2015-02-03 |
| CY1115376T1 (el) | 2017-01-04 |
| WO2010100476A2 (en) | 2010-09-10 |
| PT2403845E (pt) | 2014-08-04 |
| SMT201400100B (it) | 2014-11-10 |
| NZ595492A (en) | 2013-07-26 |
| JP5727944B2 (ja) | 2015-06-03 |
| US20120071509A1 (en) | 2012-03-22 |
| JP2012519207A (ja) | 2012-08-23 |
| EP2403845A2 (en) | 2012-01-11 |
| HRP20140686T1 (hr) | 2014-09-26 |
| CN102414196A (zh) | 2012-04-11 |
| WO2010100476A3 (en) | 2011-06-16 |
| AU2010220204A1 (en) | 2011-10-20 |
| EP2403845B1 (en) | 2014-04-30 |
| CA2753241A1 (en) | 2010-09-10 |
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