JP2013528206A5 - - Google Patents
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- Publication number
- JP2013528206A5 JP2013528206A5 JP2013513760A JP2013513760A JP2013528206A5 JP 2013528206 A5 JP2013528206 A5 JP 2013528206A5 JP 2013513760 A JP2013513760 A JP 2013513760A JP 2013513760 A JP2013513760 A JP 2013513760A JP 2013528206 A5 JP2013528206 A5 JP 2013528206A5
- Authority
- JP
- Japan
- Prior art keywords
- thalidomide
- type
- crystalline
- anhydrous crystalline
- anhydrous
- 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.)
- Pending
Links
- 229960003433 thalidomide Drugs 0.000 claims 82
- 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 claims 76
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 27
- 238000000034 method Methods 0.000 claims 24
- 239000000126 substance Substances 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- ZIMWCUUEMGFXNW-VIFPVBQESA-N 2-[[(1s)-4-amino-1-carboxy-4-oxobutyl]carbamoyl]benzoic acid Chemical compound NC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1C(O)=O ZIMWCUUEMGFXNW-VIFPVBQESA-N 0.000 claims 14
- 239000002904 solvent Substances 0.000 claims 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 12
- GMEPAZUSFGASQZ-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-4-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CC(=O)NC(=O)C1 GMEPAZUSFGASQZ-UHFFFAOYSA-N 0.000 claims 10
- -1 aliphatic ketones Chemical class 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 10
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 8
- 239000007822 coupling agent Substances 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 3
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims 2
- FBAOVPVVMDOHPK-UHFFFAOYSA-N 2-(1h-imidazol-2-ylsulfinyl)-1h-imidazole Chemical compound N=1C=CNC=1S(=O)C1=NC=CN1 FBAOVPVVMDOHPK-UHFFFAOYSA-N 0.000 claims 2
- FEINRNIWVDWBIG-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-1h-imidazole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=NC=CN1 FEINRNIWVDWBIG-UHFFFAOYSA-N 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 claims 2
- 206010015150 Erythema Diseases 0.000 claims 2
- 206010024229 Leprosy Diseases 0.000 claims 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 239000012973 diazabicyclooctane Substances 0.000 claims 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 231100000321 erythema Toxicity 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 2
- XRPITCBWOUOJTH-UHFFFAOYSA-N n,n-diethylpyridin-2-amine Chemical compound CCN(CC)C1=CC=CC=N1 XRPITCBWOUOJTH-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- HLCZHPINLSRYNY-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]sulfonylaniline Chemical compound C1=CC(CN)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 HLCZHPINLSRYNY-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1758MU2010 | 2010-06-09 | ||
| IN1758/MUM/2010 | 2010-06-09 | ||
| PCT/GB2011/051078 WO2011154739A1 (en) | 2010-06-09 | 2011-06-09 | Crystalline forms of thalidomide and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013528206A JP2013528206A (ja) | 2013-07-08 |
| JP2013528206A5 true JP2013528206A5 (enExample) | 2014-07-24 |
Family
ID=44384914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013513760A Pending JP2013528206A (ja) | 2010-06-09 | 2011-06-09 | 結晶形態のサリドマイド及びその調製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20130143923A1 (enExample) |
| EP (1) | EP2580205A1 (enExample) |
| JP (1) | JP2013528206A (enExample) |
| CN (1) | CN103068812A (enExample) |
| AU (1) | AU2011263493B2 (enExample) |
| CA (1) | CA2801835A1 (enExample) |
| NZ (1) | NZ604011A (enExample) |
| WO (1) | WO2011154739A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924432A (zh) * | 2012-11-09 | 2013-02-13 | 常州制药厂有限公司 | 一种高纯度沙利度胺的制备方法 |
| 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 |
| CN105473558B (zh) * | 2013-06-20 | 2019-04-19 | 拜耳作物科学股份公司 | 作为杀螨剂和杀昆虫剂的芳基硫化物衍生物和芳基硫氧化物衍生物 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| MX387318B (es) * | 2014-04-14 | 2025-03-18 | Arvinas Operations Inc | Moduladores de la proteólisis basados en imida y métodos de uso asociados. |
| CN104710411B (zh) * | 2015-03-13 | 2017-04-26 | 安润医药科技（苏州）有限公司 | 阿伐那非的合成方法 |
| CN110498788B (zh) * | 2018-05-16 | 2021-09-17 | 欣凯医药化工中间体（上海）有限公司 | 一种高纯度沙利度胺α晶型的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB768821A (en) | 1954-05-17 | 1957-02-20 | Gruenenthal Chemie | Novel products of the amino-piperidine-2, 6-dione series |
| US5463063A (en) | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
| CN1164586C (zh) | 2002-10-28 | 2004-09-01 | 中国科学院长春应用化学研究所 | 沙利度胺及其衍生物的制备方法 |
| US20050182097A1 (en) * | 2003-12-30 | 2005-08-18 | Zeldis Jerome B. | Methods and compositions using thalidomide for the treatment and management of central nervous system disorders or diseases |
| ITMI20041113A1 (it) | 2004-06-01 | 2004-09-01 | Antibioticos Spa | Processo per la sintesi della talidomide |
| WO2008035378A2 (en) * | 2006-09-20 | 2008-03-27 | Matrix Laboratories Ltd | An improved process for the preparation of thalidomide |
| WO2009083724A1 (en) | 2007-12-27 | 2009-07-09 | Cipla Limited | Processes for the preparation of thalidomide |
| CN102260241A (zh) * | 2010-05-26 | 2011-11-30 | 重庆医药工业研究院有限责任公司 | 一种沙利度胺α晶型的工业化制备方法 |
-
2011
- 2011-06-09 CN CN2011800385583A patent/CN103068812A/zh active Pending
- 2011-06-09 US US13/702,754 patent/US20130143923A1/en not_active Abandoned
- 2011-06-09 AU AU2011263493A patent/AU2011263493B2/en not_active Ceased
- 2011-06-09 NZ NZ604011A patent/NZ604011A/en unknown
- 2011-06-09 JP JP2013513760A patent/JP2013528206A/ja active Pending
- 2011-06-09 WO PCT/GB2011/051078 patent/WO2011154739A1/en not_active Ceased
- 2011-06-09 CA CA2801835A patent/CA2801835A1/en not_active Abandoned
- 2011-06-09 EP EP11726483.8A patent/EP2580205A1/en not_active Withdrawn
-
2015
- 2015-02-12 US US14/621,307 patent/US20150218126A1/en not_active Abandoned
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