JP2008512379A5 - - Google Patents
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- JP2008512379A5 JP2008512379A5 JP2007530398A JP2007530398A JP2008512379A5 JP 2008512379 A5 JP2008512379 A5 JP 2008512379A5 JP 2007530398 A JP2007530398 A JP 2007530398A JP 2007530398 A JP2007530398 A JP 2007530398A JP 2008512379 A5 JP2008512379 A5 JP 2008512379A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- hydrogen
- occurrence
- 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 claims 72
- 150000001875 compounds Chemical class 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 13
- 238000007363 ring formation reaction Methods 0.000 claims 13
- 230000008878 coupling Effects 0.000 claims 11
- 238000010168 coupling process Methods 0.000 claims 11
- 238000005859 coupling reaction Methods 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 10
- 230000002378 acidificating effect Effects 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 239000000047 product Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 125000005605 benzo group Chemical group 0.000 claims 6
- 230000032050 esterification Effects 0.000 claims 6
- 238000005886 esterification reaction Methods 0.000 claims 6
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- -1 glutamine ester Chemical class 0.000 claims 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 4
- 238000010511 deprotection reaction Methods 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- 239000003999 initiator Substances 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- CSBZOZVZNPXUDW-UHFFFAOYSA-N benzyl carbamoyl carbonate Chemical compound NC(=O)OC(=O)OCC1=CC=CC=C1 CSBZOZVZNPXUDW-UHFFFAOYSA-N 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000012084 conversion product Substances 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 0 *CCC(*)(*)N(Cc1c2c(*)c(*)c(*)c1*)C2O Chemical compound *CCC(*)(*)N(Cc1c2c(*)c(*)c(*)c1*)C2O 0.000 description 5
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60740904P | 2004-09-03 | 2004-09-03 | |
| PCT/US2005/031318 WO2006028964A1 (en) | 2004-09-03 | 2005-08-31 | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012162375A Division JP5701824B2 (ja) | 2004-09-03 | 2012-07-23 | 置換２−（２，６−ジオキソピペリジン−３−イル）−１−オキソイソインドリン類の調製方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008512379A JP2008512379A (ja) | 2008-04-24 |
| JP2008512379A5 true JP2008512379A5 (enExample) | 2008-07-10 |
Family
ID=35385616
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007530398A Pending JP2008512379A (ja) | 2004-09-03 | 2005-08-31 | 置換２−（２，６−ジオキソピペリジン−３−イル）−１−オキソイソインドリン類の調製方法 |
| JP2012162375A Expired - Lifetime JP5701824B2 (ja) | 2004-09-03 | 2012-07-23 | 置換２−（２，６−ジオキソピペリジン−３−イル）−１−オキソイソインドリン類の調製方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012162375A Expired - Lifetime JP5701824B2 (ja) | 2004-09-03 | 2012-07-23 | 置換２−（２，６−ジオキソピペリジン−３−イル）−１−オキソイソインドリン類の調製方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7863451B2 (enExample) |
| EP (2) | EP1797068B1 (enExample) |
| JP (2) | JP2008512379A (enExample) |
| KR (1) | KR20070057907A (enExample) |
| CN (1) | CN101080400A (enExample) |
| AR (1) | AR050724A1 (enExample) |
| AU (1) | AU2005282728A1 (enExample) |
| BR (1) | BRPI0514865A (enExample) |
| CA (1) | CA2579291C (enExample) |
| ES (2) | ES2437592T3 (enExample) |
| GT (1) | GT200500242A (enExample) |
| HN (1) | HN2005000508A (enExample) |
| IL (1) | IL181674A0 (enExample) |
| MX (1) | MX2007002521A (enExample) |
| NZ (1) | NZ554068A (enExample) |
| PA (1) | PA8643901A1 (enExample) |
| PE (1) | PE20060648A1 (enExample) |
| SV (1) | SV2007002219A (enExample) |
| TW (1) | TW200621748A (enExample) |
| UY (1) | UY29097A1 (enExample) |
| WO (1) | WO2006028964A1 (enExample) |
| ZA (1) | ZA200702382B (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7629360B2 (en) * | 1999-05-07 | 2009-12-08 | Celgene Corporation | Methods for the treatment of cachexia and graft v. host disease |
| US7323479B2 (en) * | 2002-05-17 | 2008-01-29 | Celgene Corporation | Methods for treatment and management of brain cancer using 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-methylisoindoline |
| 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 |
| DK2380887T3 (da) * | 2005-06-30 | 2013-10-07 | Celgene Corp | Fremgangsmåder til fremstilling af 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindolin-1,3-dion-forbindelser |
| CN101186611B (zh) * | 2006-11-15 | 2011-05-18 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的吡咯啉-2-酮衍生物及其制备和应用 |
| WO2009114601A2 (en) * | 2008-03-11 | 2009-09-17 | Dr. Reddy's Laboratories Ltd. | Preparation of lenalidomide |
| DE102008057285A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidindion in Form einer festen Lösung |
| DE102008057335A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | Amorphes Lenalidomid |
| DE102008057284A1 (de) | 2008-11-14 | 2010-05-20 | Ratiopharm Gmbh | Tabletten enthaltend Lenalidomid und Adhäsionsverstärker |
| WO2010056384A1 (en) * | 2008-11-17 | 2010-05-20 | Dr. Reddy's Laboratories Ltd. | Lenalidomide solvates and processes |
| EP2396312A1 (en) | 2009-02-11 | 2011-12-21 | Celgene Corporation | Isotopologues of lenalidomide |
| CN102414196A (zh) * | 2009-03-02 | 2012-04-11 | 基因里克斯(英国)有限公司 | 改进的方法 |
| 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 |
| MX2012001890A (es) * | 2009-08-12 | 2012-03-26 | Synthon Bv | Sales de lenalidomida. |
| US20120220777A1 (en) * | 2009-09-16 | 2012-08-30 | Ranbaxy Laboratories Limited | Process for the preparation of a crystalline form of lenalidomide |
| 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 |
| WO2011050962A1 (en) | 2009-10-29 | 2011-05-05 | Ratiopharm Gmbh | Acid addition salts of lenalidomide |
| CN102127054B (zh) * | 2009-11-02 | 2013-04-03 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物 |
| CN102060842B (zh) * | 2009-11-02 | 2013-05-08 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物 |
| CN101696205B (zh) | 2009-11-02 | 2011-10-19 | 南京卡文迪许生物工程技术有限公司 | 3-(取代二氢异吲哚-2-基)-2,6-哌啶二酮多晶型物和药用组合物 |
| WO2011069608A1 (en) * | 2009-12-09 | 2011-06-16 | Ratiopharm Gmbh | S-lenalidomide, polymorphic forms thereof and blend comprising s- und r-lenalidomide |
| 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 |
| LT3202460T (lt) | 2010-02-11 | 2019-10-10 | Celgene Corporation | Arilmetoksi izoindolino dariniai ir kompozicijos, apimantys ir jų panaudojimo būdus |
| CN102453021A (zh) * | 2010-10-22 | 2012-05-16 | 重庆医药工业研究院有限责任公司 | 来那度胺的新晶型及其制备方法 |
| WO2012079075A1 (en) | 2010-12-10 | 2012-06-14 | Concert Pharmaceuticals, Inc. | Deuterated phthalimide derivatives |
| WO2013012485A2 (en) * | 2011-07-19 | 2013-01-24 | Amplio Pharma, Llc | Novel crystalline forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |
| EP2877462B1 (en) * | 2012-07-27 | 2019-09-04 | Celgene Corporation | Processes for preparing isoindoline-1,3-dione compounds |
| HK1211577A1 (en) | 2012-08-09 | 2016-05-27 | 细胞基因公司 | Processes for the preparation of (s)-3-4- ((4-(morpholinomethyl) benzyl)oxy)-1-oxoisoindolin-2-yl) piperidine-2,6-dione and pharmaceutically acceptable forms thereof |
| WO2014110322A2 (en) | 2013-01-11 | 2014-07-17 | Concert Pharmaceuticals, Inc. | Substituted dioxopiperidinyl phthalimide derivatives |
| CN103242215A (zh) * | 2013-05-27 | 2013-08-14 | 合肥医工医药有限公司 | 一种来那度胺中间体的制备方法 |
| US10392364B2 (en) | 2014-08-11 | 2019-08-27 | Avra Laboratories Pvt. Ltd. | Process for synthesis of lenalidomide |
| PL3214081T3 (pl) | 2014-10-30 | 2021-04-06 | Kangpu Biopharmaceuticals, Ltd. | Pochodna izoindoliny, półprodukt, sposób wytwarzania, kompozycja farmaceutyczna i ich zastosowanie |
| CN104447689B (zh) * | 2014-12-22 | 2016-07-20 | 上海迈柏医药科技有限公司 | 来那度胺的晶型及其制备方法 |
| TWI793151B (zh) * | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
| CN108191826A (zh) * | 2018-01-08 | 2018-06-22 | 浙江省医学科学院 | 一种来那度胺晶体及其制备方法 |
| MX2020011183A (es) | 2018-04-23 | 2020-11-12 | Celgene Corp | Compuestos de 4-aminoisoindolina-1,3-diona sustituidos y su uso para el tratamiento de linfoma. |
| AR116109A1 (es) | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
| DK3820573T3 (da) | 2018-07-10 | 2023-10-23 | Novartis Ag | 3-(5-hydroxy-1-oxoisoindolin-2-yl)piperidin-2,6-dion-derivativer og anvendelse deraf ved behandling af ikaros family zinc finger 2 (ikzf2)-afhængige sygdomme |
| KR20210056397A (ko) * | 2018-09-07 | 2021-05-18 | 메드샤인 디스커버리 아이엔씨. | 삼환식 치환 피페리딘 디온계 화합물 |
| CA3119343C (en) | 2018-11-13 | 2024-01-16 | Biotheryx, Inc. | Substituted isoindolinones |
| CN109369504B (zh) * | 2018-12-06 | 2020-05-12 | 温州大学 | 含硫3-亚甲基异吲哚啉-1-酮衍生物的制备方法 |
| WO2025118133A1 (zh) * | 2023-12-05 | 2025-06-12 | 浙江普洛家园药业有限公司 | 一种(s)-来那度胺-5-位衍生物及其合成方法和应用 |
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| WO2009111948A1 (zh) | 2008-03-13 | 2009-09-17 | 天津和美生物技术有限公司 | 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 |
-
2005
- 2005-08-31 KR KR1020077007538A patent/KR20070057907A/ko not_active Withdrawn
- 2005-08-31 MX MX2007002521A patent/MX2007002521A/es active IP Right Grant
- 2005-08-31 ES ES05793314.5T patent/ES2437592T3/es not_active Expired - Lifetime
- 2005-08-31 ZA ZA200702382A patent/ZA200702382B/xx unknown
- 2005-08-31 CA CA2579291A patent/CA2579291C/en not_active Expired - Lifetime
- 2005-08-31 JP JP2007530398A patent/JP2008512379A/ja active Pending
- 2005-08-31 BR BRPI0514865-0A patent/BRPI0514865A/pt not_active IP Right Cessation
- 2005-08-31 EP EP05793314.5A patent/EP1797068B1/en not_active Expired - Lifetime
- 2005-08-31 NZ NZ554068A patent/NZ554068A/en not_active IP Right Cessation
- 2005-08-31 EP EP12164781.2A patent/EP2479172B1/en not_active Expired - Lifetime
- 2005-08-31 WO PCT/US2005/031318 patent/WO2006028964A1/en not_active Ceased
- 2005-08-31 AU AU2005282728A patent/AU2005282728A1/en not_active Abandoned
- 2005-08-31 ES ES12164781.2T patent/ES2438725T3/es not_active Expired - Lifetime
- 2005-08-31 CN CNA2005800372200A patent/CN101080400A/zh active Pending
- 2005-09-01 US US11/219,589 patent/US7863451B2/en active Active
- 2005-09-02 PE PE2005001015A patent/PE20060648A1/es not_active Application Discontinuation
- 2005-09-02 PA PA20058643901A patent/PA8643901A1/es unknown
- 2005-09-02 HN HN2005000508A patent/HN2005000508A/es unknown
- 2005-09-02 SV SV2005002219A patent/SV2007002219A/es not_active Application Discontinuation
- 2005-09-02 UY UY29097A patent/UY29097A1/es not_active Application Discontinuation
- 2005-09-02 TW TW094130010A patent/TW200621748A/zh unknown
- 2005-09-02 GT GT200500242A patent/GT200500242A/es unknown
- 2005-09-02 AR ARP050103695A patent/AR050724A1/es unknown
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2007
- 2007-03-01 IL IL181674A patent/IL181674A0/en unknown
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2012
- 2012-07-23 JP JP2012162375A patent/JP5701824B2/ja not_active Expired - Lifetime
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