HRP20130966T1 - Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-3-ona - Google Patents
Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-3-ona Download PDFInfo
- Publication number
- HRP20130966T1 HRP20130966T1 HRP20130966TT HRP20130966T HRP20130966T1 HR P20130966 T1 HRP20130966 T1 HR P20130966T1 HR P20130966T T HRP20130966T T HR P20130966TT HR P20130966 T HRP20130966 T HR P20130966T HR P20130966 T1 HRP20130966 T1 HR P20130966T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- process according
- image
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 19
- UVSMNLNDYGZFPF-UHFFFAOYSA-N pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- 238000006243 chemical reaction Methods 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- -1 carbonyldiimidazole compound Chemical class 0.000 claims 2
- NUJJHSPYMWDZSJ-UHFFFAOYSA-N ethyl 4-nitro-1,3-dioxoisoindole-2-carboxylate Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C(=O)OCC)C(=O)C2=C1 NUJJHSPYMWDZSJ-UHFFFAOYSA-N 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 claims 1
- BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-GSVOUGTGSA-N D-glutamine Chemical compound OC(=O)[C@H](N)CCC(N)=O ZDXPYRJPNDTMRX-GSVOUGTGSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Claims (17)
1. Postupak dobivanja spoja Formule (I):
[image]
,
ili njegove farmaceutski prihvatljive soli, solvata, polimorfa ili stereoizomera, naznačen time što se sastoji u koraku cikliziranja spoja Formule (II) ili (IIA):
[image]
,
ili njegove soli s ciklizirajućim sredstvom Formule (V):
[image]
,
gdje je R1 H, F, benzil, (C1-C8)alkil, (C2-C8)alkenil ili (C2-C8)alkinil; a svaki od X i Y je neovisno nesupstituirani ili supstituirani imidazolil, benzimidazolil ili benzotriazolil.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je spoj Formule (I) solvat koji je hidrat.
3. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je ciklizirajuće sredstvo spoj karbonildiimidazola, po mogućnosti 1,1′-karbonildiimidazol, poželjnije gdje je omjer između spoja Formule (II) ili (IIA) i 1,1′-karbonildiimidazola od otprilike 1:1 do otprilike 1:1,2.
4. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je ciklizirajuće sredstvo 1,1′-karbonildiimidazol, te što se korak cikliziranja provodi u otapalu, po mogućnosti u acetonitrilu ili N-metilpirolidinonu.
5. Postupak u skladu s patentnim zahtjevom 4, naznačen time što je otapalo acetonitril, a temperatura reakcije je od otprilike 80 °C do otprilike 87 °C, a po mogućnosti je trajanje reakcije od otprilike 1 sat do otprilike 5 sati.
6. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se spoj Formule (II) ili (IIA) dobiva reduciranjem spoja Formule (III) odnosno (IIIA):
[image]
reducensom, gdje je R1 H, F, benzil, (C1-C8)alkil, (C2-C8)alkenil ili (C2-C8)alkinil.
7. Postupak u skladu s patentnim zahtjevom 6, naznačen time što je reducens vodik uz 10% Pd/C;
gdje je vodik izborno pod tlakom od otprilike 2,76 bar (276 kPa) do otprilike 3,45 bar (345 kPa), ili se reakciju provodi u otapalu, po mogućnosti u metanolu.
8. Postupak u skladu s patentnim zahtjevom 6, naznačen time što se spoj Formule (III) ili (IIIA) dobiva reakcijom 3-nitroftalanhidrida sa spojem Formule (IV) odnosno (IVA):
[image]
,
gdje je R1 H, F, benzil, (C1-C8)alkil, (C2-C8)alkenil ili (C2-C8)alkinil.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što se reakciju provodi u otapalu, gdje je po mogućnosti otapalo dimetilformamid, ili je temperatura reakcije od otprilike 80 °C do otprilike 87 °C.
10. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je spoj Formule (I) slobodni amin; gdje postupak izborno dodatno uključuje korak reakcije slobodnog amina s kiselinom, po mogućnosti klorovodičnom kiselinom, u molarnom omjeru od otprilike 1:1, kako bi se dobilo sol s kiselinom.
11. Postupak u skladu s patentnim zahtjevom 6, naznačen time što se spoj Formule (III) dobiva u koracima:
(a) reakcije 3-nitro-N-etoksikarbonilftalimida s esterom glutamina Formule (VIII):
[image]
ili njegovom solju s kiselinom, u prisutnosti prvog katalizatora, kako bi se dobilo spoj Formule (IX) ili njegovu sol, solvat, polimorf ili stereoizomer:
[image]
;
i
(b) reakcije spoja Formule (IX) ili njegove solu, solvata, polimorfa ili stereoizomera s klorovodikom, gdje je R1 H, F, benzil, (C1-C8)alkil, (C2-C8)alkenil ili (C2-C8)alkinil; a R8 je alkil ili aralkil.
12. Postupak u skladu s patentnim zahtjevom 11, naznačen time što dodatno uključuje korak dobivanja 3-nitro-N-etoksikarbonilftalimida reakcijom 3-nitroftalimida s etil-klorformijatom, u prisutnosti drugog katalizatora, gdje je po mogućnosti i prvi katalizator i drugi katalizator trietilamin.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što je R1 H; a R8 je t-butil ili benzil; ili
gdje je spoj Formule (VIII) hidroklorid t-butilnog estera l-glutamina, a spoj Formule (III) je (S)-enantiomer; ili
gdje je spoj Formule (VIII) hidroklorid t-butilnog estera d-glutamina, a spoj Formule (III) je (R)-enantiomer; ili
gdje je spoj Formule (VIII) racemična smjesa hidroklorida t-butilnog estera glutamina, a spoj Formule (III) je racemična smjesa.
14. Postupak u skladu s patentnim zahtjevom 1, 6 ili 8, naznačen time što je R1 H.
15. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je spoj Formule (I) racemična smjesa, (+)-enantiomer ili (–)-enantiomer.
16. Postupak u skladu s patentnim zahtjevom 14, naznačen time što dodatno uključuje korak prekristaliziranja spoja Formule (I) iz smjese otapala koja se sastoji od dimetil-sulfoksida i vode.
17. Postupak u skladu s patentnim zahtjevom 16, naznačen time što je omjer između dimetil-sulfoksida i vode od 1:10 do 10:1, volumno, ili od 1:4 do 1:8, volumno.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US69622405P | 2005-06-30 | 2005-06-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20130966T1 true HRP20130966T1 (hr) | 2013-11-22 |
Family
ID=37305020
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20130102TT HRP20130102T1 (hr) | 2005-06-30 | 2013-02-06 | Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona |
HRP20130966TT HRP20130966T1 (hr) | 2005-06-30 | 2013-10-11 | Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-3-ona |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20130102TT HRP20130102T1 (hr) | 2005-06-30 | 2013-02-06 | Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona |
Country Status (25)
Country | Link |
---|---|
US (5) | US7994327B2 (hr) |
EP (2) | EP1907373B1 (hr) |
JP (2) | JP5366544B2 (hr) |
KR (2) | KR101342241B1 (hr) |
CN (2) | CN102643267B (hr) |
AU (1) | AU2006265019B2 (hr) |
BR (1) | BRPI0612803A2 (hr) |
CA (2) | CA2612612C (hr) |
CR (1) | CR9697A (hr) |
DK (2) | DK1907373T3 (hr) |
EC (1) | ECSP088154A (hr) |
ES (2) | ES2402204T3 (hr) |
HK (2) | HK1121447A1 (hr) |
HR (2) | HRP20130102T1 (hr) |
IL (2) | IL188330A (hr) |
ME (1) | ME01513B (hr) |
MX (1) | MX2007016290A (hr) |
NZ (1) | NZ565309A (hr) |
PE (2) | PE20100151A1 (hr) |
PL (2) | PL2380887T3 (hr) |
PT (2) | PT1907373E (hr) |
RS (2) | RS53030B (hr) |
SI (2) | SI1907373T1 (hr) |
WO (1) | WO2007005972A1 (hr) |
ZA (1) | ZA200800828B (hr) |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ554068A (en) * | 2004-09-03 | 2009-07-31 | Celgene Corp | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindo-lines |
ME01513B (me) | 2005-06-30 | 2014-04-20 | Celgene Corp | Postupak dobijanja spojeva 4-amin0-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona |
US20080064876A1 (en) * | 2006-05-16 | 2008-03-13 | Muller George W | Process for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione |
ZA200901852B (en) * | 2006-09-15 | 2010-06-30 | Celgene Corp | N-methylaminomethyl isoindole compounds and compositions comprising and methods of using the same |
US8288414B2 (en) | 2007-09-12 | 2012-10-16 | Deuteria Pharmaceuticals, Inc. | Deuterium-enriched lenalidomide |
CN101531653B (zh) * | 2008-03-13 | 2014-07-09 | 峡江和美药业有限公司 | 3-(4-氨基-1-氧代-1,3-二氢异吲哚-2-基)哌啶-2,6-二酮及其衍生物的盐或盐的多晶型物及其制备和应用 |
US20110060010A1 (en) * | 2008-03-13 | 2011-03-10 | Tianjin Hemay Bio-Tech Co., Ltd | Salts of 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione and derivatives thereof, or polymorphs of salts, process for preparing same and use thereof |
CN101580501B (zh) * | 2009-06-01 | 2011-03-09 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体 |
CN102060746B (zh) * | 2009-06-01 | 2013-02-13 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮的合成方法及其中间体 |
CN101817813B (zh) * | 2010-01-15 | 2013-04-10 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚酮-2-基)-2,6-哌啶二酮晶体ⅳ及其药用组合物 |
DK2536706T3 (en) | 2010-02-11 | 2017-08-14 | Celgene Corp | ARYLMETHOXYISOINDOLINE DERIVATIVES AND COMPOSITIONS COMPREHENSIVE AND PROCEDURES FOR USING SAME |
US9090585B2 (en) | 2011-03-28 | 2015-07-28 | Deuterx, Llc | 2,6-dioxo-3-deutero-piperdin-3-yl-isoindoline compounds |
US20140221427A1 (en) | 2011-06-22 | 2014-08-07 | Celgene Corporation | Isotopologues of pomalidomide |
WO2013126326A1 (en) * | 2012-02-21 | 2013-08-29 | Celgene Corporation | Solid forms of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione, compositions and methods of use thereof |
EP2877462B1 (en) * | 2012-07-27 | 2019-09-04 | Celgene Corporation | Processes for preparing isoindoline-1,3-dione compounds |
CN104718202B (zh) * | 2012-08-09 | 2018-11-20 | 细胞基因公司 | 用于制备(s)-3-(4-((4-(吗啉基甲基)苄基)氧基)-1-氧代异吲哚啉-2-基)哌啶-2,6-二酮及其可药用形式的方法 |
AU2014205043B2 (en) | 2013-01-14 | 2018-10-04 | Deuterx, Llc | 3-(5-substituted-4-oxoquinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
US9290475B2 (en) | 2013-03-14 | 2016-03-22 | Deuterx, Llc | 3-(substituted-4-oxoquinazolin-3(4H)-yl)-3-deutero-piperidine-2,6-dione derivatives and compositions comprising and methods of using the same |
WO2014170909A2 (en) * | 2013-04-01 | 2014-10-23 | Hetero Research Foundation | Process for pomalidomide |
AU2014248263A1 (en) | 2013-04-02 | 2015-10-15 | Celgene Corporation | Methods and compositions using 4-amino-2-(2,6-dioxo-piperidine-3-yl)-isoindoline-1,3-dione for treatment and management of central nervous system cancers |
CN103232380A (zh) * | 2013-05-08 | 2013-08-07 | 中国药科大学 | 一种泊马度胺关键中间体的制备方法 |
CN103275062B (zh) * | 2013-05-17 | 2016-04-13 | 宁波百思佳医药科技有限公司 | 一种Pomalidomide的纯化方法 |
CN103288797B (zh) * | 2013-05-17 | 2016-03-02 | 宁波百思佳医药科技有限公司 | 一种用亚砜类溶剂纯化Pomalidomide的方法 |
EP2815749A1 (en) | 2013-06-20 | 2014-12-24 | IP Gesellschaft für Management mbH | Solid form of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione having specified X-ray diffraction pattern |
UA117141C2 (uk) | 2013-10-08 | 2018-06-25 | Селджин Корпорейшн | Склади (s)-3-(4-((4-(морфолінометил)бензил)оксі)-1-оксоізоіндолін-2-іл)піперидин-2,6-діону |
CN104557858B (zh) * | 2013-10-29 | 2018-06-01 | 上海医药工业研究院 | 一种泊利度胺的制备方法 |
US20160362391A1 (en) * | 2013-11-25 | 2016-12-15 | Mylan Laboratories Ltd. | Improved Process for the Preparation of Pomalidomide and its Purification |
CN103724323B (zh) * | 2014-01-20 | 2016-08-17 | 上海医药工业研究院 | 泊马度胺的制备方法 |
CN104016967A (zh) * | 2014-04-04 | 2014-09-03 | 南京工业大学 | 一种泊利度胺的合成方法 |
CN105440013B (zh) * | 2014-08-29 | 2018-10-09 | 杭州和泽医药科技有限公司 | 一种泊马度胺的制备方法 |
CN107406231B (zh) | 2015-03-05 | 2019-11-15 | 奥的斯电梯公司 | 电梯轿厢 |
US9809603B1 (en) | 2015-08-18 | 2017-11-07 | Deuterx, Llc | Deuterium-enriched isoindolinonyl-piperidinonyl conjugates and oxoquinazolin-3(4H)-yl-piperidinonyl conjugates and methods of treating medical disorders using same |
ITUB20169994A1 (it) | 2016-01-14 | 2017-07-14 | Phf Sa | Nuove forme cristalline di farmaci immunomodulatori |
HU231259B1 (hu) | 2016-02-04 | 2022-06-28 | Egyt Gyogyszervegyeszeti Gyar | Eljárás pomalidomide elõállítására |
CN106432045B (zh) * | 2016-06-29 | 2018-12-18 | 深圳海王医药科技研究院有限公司 | 一种泊马度胺杂质的合成方法 |
WO2018013689A1 (en) | 2016-07-13 | 2018-01-18 | Celgene Corporation | Solid dispersions and solid forms comprising 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione, method of preparation and use thereof |
WO2018154516A1 (en) * | 2017-02-23 | 2018-08-30 | Sun Pharmaceutical Industries Limited | Process for the preparation of pomalidomide |
US10093647B1 (en) | 2017-05-26 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione dihydrate, compositions and methods of use thereof |
US11439631B2 (en) * | 2017-09-07 | 2022-09-13 | “ChemImmune Therapeutics” Limited Liability Company | Use of a glutarimide derivative to treat diseases related to the aberrant activity of cytokines |
US10093649B1 (en) | 2017-09-22 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione monohydrate, compositions and methods of use thereof |
US10093648B1 (en) | 2017-09-22 | 2018-10-09 | Celgene Corporation | Crystalline 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione hemihydrate, compositions and methods of use thereof |
SI3784663T1 (sl) | 2018-04-23 | 2023-11-30 | Celgene Corporation | Spojine substituiranega 4-aminoizoindolin-1,3-diona in njihova uporaba za zdravljenje limfoma |
CN110343063A (zh) * | 2019-08-09 | 2019-10-18 | 新乡双鹭药业有限公司 | 一种泊马度胺合成中杂质的制备方法 |
CN114605381A (zh) * | 2020-12-03 | 2022-06-10 | 南京海辰药业股份有限公司 | 一种泊马度胺的制备方法 |
Family Cites Families (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB858086A (en) * | 1958-09-16 | 1961-01-04 | American Cyanamid Co | Method for synthesis of amides of imidazoles or benzimidazoles |
US3979416A (en) * | 1973-06-15 | 1976-09-07 | Alelio Gaetano F D | Preparation of aminophthalic anhydrides |
KR0166088B1 (ko) * | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
US6114355A (en) | 1993-03-01 | 2000-09-05 | D'amato; Robert | Methods and compositions for inhibition of angiogenesis |
US5629327A (en) * | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
US5698579A (en) * | 1993-07-02 | 1997-12-16 | Celgene Corporation | Cyclic amides |
US5463063A (en) | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
US5637517A (en) * | 1995-05-26 | 1997-06-10 | Daewoo Electronics Co., Ltd. | Method for forming array of thin film actuated mirrors |
DE19601303A1 (de) * | 1996-01-16 | 1997-07-17 | Boehringer Ingelheim Kg | Neuartige Benzoylguanidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Arzneimitteln |
US6281230B1 (en) * | 1996-07-24 | 2001-08-28 | Celgene Corporation | Isoindolines, method of use, and pharmaceutical compositions |
UA60308C2 (uk) | 1996-07-24 | 2003-10-15 | Селджін Корпорейшн | ЗАМІЩЕНІ 2-(2,6-ДІОКСОПІПЕРИДИН-3-ІЛ)ФТАЛІМІДИ ТА 1-ОКСОІЗОІНДОЛІНИ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЗНИЖЕННЯ РІВНЯ ФПН-α |
US5798368A (en) * | 1996-08-22 | 1998-08-25 | Celgene Corporation | Tetrasubstituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines and method of reducing TNFα levels |
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 |
HU228769B1 (en) | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
KR100539031B1 (ko) * | 1996-08-12 | 2005-12-27 | 셀진 코포레이션 | 면역치료제 및 이를 이용하여 사이토카인 농도를감소시키는 방법 |
US5874448A (en) * | 1997-11-18 | 1999-02-23 | Celgene Corporation | Substituted 2-(2,6 dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing TNFα levels |
US5955476A (en) * | 1997-11-18 | 1999-09-21 | Celgene Corporation | Substituted 2-(2,6-dioxo-3-fluoropiperidin-3-yl)-isoindolines and method of reducing inflammatory cytokine levels |
TR200101502T2 (tr) * | 1998-03-16 | 2002-06-21 | Celgene Corporation | 2-(2,6-dioksopiperidin-3-il) izoindolin türevleri, bunların hazırlanması ve enflamatuar sitokinlerin inhibitörleri olarak kullanımı |
WO2000055134A1 (en) * | 1999-03-18 | 2000-09-21 | Celgene Corporation | Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels |
DE19942700C1 (de) * | 1999-09-07 | 2001-04-05 | Consortium Elektrochem Ind | Verfahren zur Herstellung cyclischer N-Hydroxydicarboximide |
US7182953B2 (en) * | 1999-12-15 | 2007-02-27 | Celgene Corporation | Methods and compositions for the prevention and treatment of atherosclerosis restenosis and related disorders |
JP4622016B2 (ja) * | 1999-12-20 | 2011-02-02 | 東洋インキ製造株式会社 | 顔料分散剤、顔料組成物および顔料分散体 |
US6458810B1 (en) * | 2000-11-14 | 2002-10-01 | George Muller | Pharmaceutically active isoindoline derivatives |
NZ526683A (en) * | 2000-11-30 | 2008-03-28 | Childrens Medical Center | Synthesis of 4-amino-thalidomide and its enantiomers that are suitable for inhibiting angiogenesis |
US7091353B2 (en) * | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
DE60231989D1 (de) * | 2001-08-06 | 2009-05-28 | Childrens Medical Center | Antiangiogenese wirkung von stickstoffsubstituierten thalidomid-analoga |
JP3578752B2 (ja) * | 2001-09-28 | 2004-10-20 | 三井化学株式会社 | 水性インク |
EP1485100B1 (en) | 2002-03-15 | 2010-05-05 | Vertex Pharmaceuticals Incorporated | Azinylaminoazoles as inhibitors of protein kinases |
US6962940B2 (en) * | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
US7968569B2 (en) * | 2002-05-17 | 2011-06-28 | Celgene Corporation | Methods for treatment of multiple myeloma using 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione |
US7189740B2 (en) * | 2002-10-15 | 2007-03-13 | Celgene Corporation | Methods of using 3-(4-amino-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myelodysplastic syndromes |
US20050203142A1 (en) * | 2002-10-24 | 2005-09-15 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for treatment, modification and management of pain |
US20040091455A1 (en) * | 2002-10-31 | 2004-05-13 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for treatment and management of macular degeneration |
US7563810B2 (en) * | 2002-11-06 | 2009-07-21 | Celgene Corporation | Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases |
CH696542A5 (de) | 2003-07-09 | 2007-07-31 | Siegfried Ltd | Verfahren zur Herstellung von substituierten 2,6-Dioxopiperidin-3-yl-Verbindungen. |
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 |
US20050100529A1 (en) * | 2003-11-06 | 2005-05-12 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for the treatment and management of asbestos-related diseases and disorders |
EP2505200A1 (en) * | 2004-03-22 | 2012-10-03 | Celgene Corporation | Methods of using and compositions comprising immunomodulatory compounds for the treatment and management of scleroderma |
ITMI20041113A1 (it) * | 2004-06-01 | 2004-09-01 | Antibioticos Spa | Processo per la sintesi della talidomide |
US7244759B2 (en) * | 2004-07-28 | 2007-07-17 | Celgene Corporation | Isoindoline compounds and methods of making and using the same |
US7405237B2 (en) * | 2004-07-28 | 2008-07-29 | Celgene Corporation | Isoindoline compounds and methods of their use |
NZ554068A (en) | 2004-09-03 | 2009-07-31 | Celgene Corp | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindo-lines |
ME01513B (me) * | 2005-06-30 | 2014-04-20 | Celgene Corp | Postupak dobijanja spojeva 4-amin0-2-(2,6-dioksopiperidin-3-il)izoindolin-1,3-diona |
MX2008002765A (es) | 2005-08-31 | 2008-04-07 | Celgene Corp | Compuestos de isoindol-imida y composiciones que la comprenden y metodos para usar los mismos. |
ZA200901852B (en) | 2006-09-15 | 2010-06-30 | Celgene Corp | N-methylaminomethyl isoindole compounds and compositions comprising and methods of using the same |
US20110021567A1 (en) | 2008-03-11 | 2011-01-27 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
CN101531653B (zh) | 2008-03-13 | 2014-07-09 | 峡江和美药业有限公司 | 3-(4-氨基-1-氧代-1,3-二氢异吲哚-2-基)哌啶-2,6-二酮及其衍生物的盐或盐的多晶型物及其制备和应用 |
-
2006
- 2006-06-29 ME MEP-2013-20A patent/ME01513B/me unknown
- 2006-06-29 DK DK06786385.2T patent/DK1907373T3/da active
- 2006-06-29 MX MX2007016290A patent/MX2007016290A/es active IP Right Grant
- 2006-06-29 ZA ZA200800828A patent/ZA200800828B/xx unknown
- 2006-06-29 PL PL11175056T patent/PL2380887T3/pl unknown
- 2006-06-29 RS RS20130483A patent/RS53030B/en unknown
- 2006-06-29 WO PCT/US2006/026210 patent/WO2007005972A1/en active Application Filing
- 2006-06-29 KR KR1020137003558A patent/KR101342241B1/ko active IP Right Grant
- 2006-06-29 EP EP06786385A patent/EP1907373B1/en active Active
- 2006-06-29 EP EP11175056.8A patent/EP2380887B1/en active Active
- 2006-06-29 CA CA2612612A patent/CA2612612C/en active Active
- 2006-06-29 JP JP2008519728A patent/JP5366544B2/ja active Active
- 2006-06-29 ES ES06786385T patent/ES2402204T3/es active Active
- 2006-06-29 ES ES11175056T patent/ES2430545T3/es active Active
- 2006-06-29 RS RS20130103A patent/RS52704B/en unknown
- 2006-06-29 SI SI200631524T patent/SI1907373T1/sl unknown
- 2006-06-29 AU AU2006265019A patent/AU2006265019B2/en active Active
- 2006-06-29 DK DK11175056.8T patent/DK2380887T3/da active
- 2006-06-29 PT PT67863852T patent/PT1907373E/pt unknown
- 2006-06-29 US US11/479,823 patent/US7994327B2/en active Active
- 2006-06-29 KR KR1020087002421A patent/KR101299321B1/ko active IP Right Grant
- 2006-06-29 CA CA2823088A patent/CA2823088C/en active Active
- 2006-06-29 BR BRPI0612803-3A patent/BRPI0612803A2/pt not_active Application Discontinuation
- 2006-06-29 PL PL06786385T patent/PL1907373T3/pl unknown
- 2006-06-29 NZ NZ565309A patent/NZ565309A/en unknown
- 2006-06-29 CN CN201210105368.5A patent/CN102643267B/zh active Active
- 2006-06-29 SI SI200631669T patent/SI2380887T1/sl unknown
- 2006-06-29 PT PT111750568T patent/PT2380887E/pt unknown
- 2006-06-29 CN CN2006800319453A patent/CN101253163B/zh active Active
- 2006-07-03 PE PE2009001183A patent/PE20100151A1/es not_active Application Discontinuation
- 2006-07-03 PE PE2006000772A patent/PE20070103A1/es not_active Application Discontinuation
-
2007
- 2007-12-23 IL IL188330A patent/IL188330A/en active IP Right Grant
-
2008
- 2008-01-29 CR CR9697A patent/CR9697A/es not_active Application Discontinuation
- 2008-01-30 EC EC2008008154A patent/ECSP088154A/es unknown
-
2009
- 2009-02-13 HK HK09101400.3A patent/HK1121447A1/xx unknown
-
2011
- 2011-05-27 US US13/117,196 patent/US8785644B2/en active Active
- 2011-08-30 IL IL214892A patent/IL214892A/en active IP Right Grant
-
2012
- 2012-09-04 JP JP2012193866A patent/JP5543555B2/ja active Active
- 2012-09-27 HK HK12109557.2A patent/HK1168851A1/zh unknown
-
2013
- 2013-02-06 HR HRP20130102TT patent/HRP20130102T1/hr unknown
- 2013-10-11 HR HRP20130966TT patent/HRP20130966T1/hr unknown
-
2014
- 2014-04-29 US US14/264,415 patent/US9394274B2/en active Active
-
2016
- 2016-06-20 US US15/186,677 patent/US9822093B2/en active Active
-
2017
- 2017-10-19 US US15/787,839 patent/US10266514B2/en active Active
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20130966T1 (hr) | Postupak dobivanja spojeva 4-amino-2-(2,6-dioksopiperidin-3-il)izoindolin-3-ona | |
ES2587738T3 (es) | Derivados de quinoxalina y quinolina como inhibidores de quinasa | |
EP2479172B1 (en) | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines | |
JP2013536826A (ja) | 5−フルオロ−1H−ピラゾロ[3,4−b]ピリジン−3−カルボニトリルを製造する方法 | |
CA2710447A1 (en) | Process for the preparation of 6-substituted-1-(2h)-isoquinolinones | |
EP2590947A1 (en) | Intermediates and process for preparing a thrombin specific inhibitor | |
ES2340861T3 (es) | Procedimientos de sintesis e intermedios para la fabricacion de rizatriptan. | |
ES2270144T3 (es) | Procedimiento para la obtencion de compuestos de zolmitriptan. | |
TWI762527B (zh) | 色氨酸羥化酶-1抑製劑製備方法 | |
JP5017101B2 (ja) | 不斉四置換炭素原子含有化合物の製法 | |
NO322501B1 (no) | Mellomprodukter for fremstilling av kinolonkarboksylsyre-derivater | |
ES2373717T3 (es) | Nuevo procedimiento para preparar metanosulfonato de 4-aminometil-3-alcoxiiminopirrolidina. | |
AU7019700A (en) | Process for production of naphthyridine-3-carboxylic acid derivatives | |
WO2016187028A1 (en) | Heteroaryl compounds, synthesis thereof, and intermediates thereto | |
WO2010049500A2 (en) | A process for the preparation of tadalafil. | |
ES2297415T3 (es) | Compuesto intermedio que se utiliza para la preparacion de pioglitazona. | |
HUT70557A (en) | N,n'-disubstituted amine derivative, pharmaceutical compositions containing them and process for producing the compounds and the compositions | |
US20040180898A1 (en) | Processes for preparing imidazoquinoxalinones, heterocyclic-substituted imidazopyrazinones, imidazoquinoxalines and heterocyclic-substituted imidazopyrazines | |
KR101421032B1 (ko) | (2-메틸-1-(3-메틸벤질)-1H-벤조[d]이미다졸-5일)(피페리딘-5-일)메탄온의 제조방법 | |
Bouchnaka | New Synthesis of 3-Aminohydantoins via Condensation of Hydra-zines with Isocyanates Derived from-Amino Esters | |
ES2418032A2 (es) | Derivados de 2-(1-fenil-4,5,6,7-tetrahidro-1h-indazol-4-il)etilamina útiles como inhibidores de receptores sigma | |
IT202000004075A1 (it) | Processo per la preparazione di panobinostat | |
WO2012085935A2 (en) | Compounds as inhibitors of renin |