CA2949336C - Process for the synthesis of e1 activating enzyme inhibitors - Google Patents

Process for the synthesis of e1 activating enzyme inhibitors Download PDF

Info

Publication number
CA2949336C
CA2949336C CA2949336A CA2949336A CA2949336C CA 2949336 C CA2949336 C CA 2949336C CA 2949336 A CA2949336 A CA 2949336A CA 2949336 A CA2949336 A CA 2949336A CA 2949336 C CA2949336 C CA 2949336C
Authority
CA
Canada
Prior art keywords
aliphatic
hydrogen
optionally substituted
protecting group
formula
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.)
Expired - Fee Related
Application number
CA2949336A
Other languages
English (en)
French (fr)
Other versions
CA2949336A1 (en
Inventor
Lei Zhu
Ian Armitage
Eric L. Elliott
Marianne Langston
Steven P. Langston
Quentin J. Mccubbin
Hirotake Mizutani
Matthew Stirling
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Millennium Pharmaceuticals Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Millennium Pharmaceuticals Inc filed Critical Millennium Pharmaceuticals Inc
Publication of CA2949336A1 publication Critical patent/CA2949336A1/en
Application granted granted Critical
Publication of CA2949336C publication Critical patent/CA2949336C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/24—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/96—Sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Epoxy Compounds (AREA)
CA2949336A 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors Expired - Fee Related CA2949336C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US96300807P 2007-08-02 2007-08-02
US60/963,008 2007-08-02
US6237808P 2008-01-25 2008-01-25
US61/062,378 2008-01-25
CA2695193A CA2695193C (en) 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2695193A Division CA2695193C (en) 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors

Publications (2)

Publication Number Publication Date
CA2949336A1 CA2949336A1 (en) 2009-04-02
CA2949336C true CA2949336C (en) 2018-11-06

Family

ID=40225413

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2949336A Expired - Fee Related CA2949336C (en) 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors
CA2695193A Expired - Fee Related CA2695193C (en) 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2695193A Expired - Fee Related CA2695193C (en) 2007-08-02 2008-08-01 Process for the synthesis of e1 activating enzyme inhibitors

Country Status (14)

Country Link
US (3) US8933225B2 (enExample)
EP (4) EP2540727B1 (enExample)
JP (3) JP5479336B2 (enExample)
KR (2) KR20100066475A (enExample)
CN (3) CN101868461B (enExample)
AU (1) AU2008305767B2 (enExample)
CA (2) CA2949336C (enExample)
ES (4) ES2655028T3 (enExample)
IL (2) IL203590A (enExample)
MX (1) MX2010001126A (enExample)
RU (2) RU2553476C2 (enExample)
TW (2) TW201434851A (enExample)
WO (1) WO2009042013A1 (enExample)
ZA (1) ZA201000482B (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2949336C (en) 2007-08-02 2018-11-06 Lei Zhu Process for the synthesis of e1 activating enzyme inhibitors
CN102421780A (zh) * 2009-05-14 2012-04-18 米伦纽姆医药公司 氨基磺酸((1s，2s，4r)-4-{4-[(1s)-2，3-二氢-1h-茚-1-基氨基]-7h-吡咯并[2，3-d]嘧啶-7-基}-2-羟基环戊基)甲酯盐酸盐
US20120115892A1 (en) * 2010-11-05 2012-05-10 Millennium Pharmaceuticals, Inc. Administration of nedd8-activating enzyme inhibitor
UA116534C2 (uk) 2012-02-17 2018-04-10 Мілленніум Фармасьютікалз, Інк. Піразолопіримідинілові інгібітори убіквітинактивуючого ферменту
CN104072381B (zh) * 2013-03-26 2017-04-12 安徽贝克联合制药有限公司 光学纯氨基醇盐酸盐的制备方法
EP2996773B1 (en) 2013-05-14 2020-09-16 Millennium Pharmaceuticals, Inc. Administration of nedd8-activating enzyme inhibitor and chemotherapeutic agents
RS59474B1 (sr) 2014-07-01 2019-12-31 Millennium Pharm Inc Heteroarilna jedinjenja koja su korisna kao inhibitori sumo-aktivirajućeg enzima
TW201628621A (zh) 2014-10-29 2016-08-16 千禧製藥公司 泛素活化酶抑制劑及輻射之施用
CN104974051A (zh) * 2015-06-30 2015-10-14 苏州开元民生科技股份有限公司 (1S,4R)-cis-4-氨基-2-环戊烯-1-甲醇盐酸盐的合成方法
CN106854208B (zh) * 2016-11-25 2019-04-09 成都柏睿泰生物科技有限公司 肿瘤抑制剂mln4924的合成方法
JP2020534331A (ja) 2017-09-21 2020-11-26 ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． （（１ｓ，２ｓ，４ｒ）−４−｛４−［（１ｓ）−２，３−ジヒドロ−１ｈ−インデン−１−イルアミノ］−７ｈ−ピロロ［２，３−ｄ］ピリミジン−７−イル｝−２−ヒドロキシシクロペンチル）メチルスルファメートの共結晶形態、その製剤及び使用
KR102018341B1 (ko) * 2018-06-21 2019-09-04 성균관대학교산학협력단 RNF170 및 pUL50을 유효성분으로 포함하는 암 예방 또는 치료용 약학적 조성물
US11198699B2 (en) 2019-04-02 2021-12-14 Aligos Therapeutics, Inc. Compounds targeting PRMT5
EP4160699A4 (en) * 2020-05-26 2023-10-25 Sony Semiconductor Solutions Corporation DISTANCE MEASUREMENT DEVICE
WO2022112951A1 (en) 2020-11-25 2022-06-02 Takeda Pharmaceutical Company Limited Solid state forms of hydrochloride salt of ((1s,2s,4r)-4-{4-[(1s)-2,3-dihydro-1h-inden-1-ylamino]-7h-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl sulfamate

Family Cites Families (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138433A (en) * 1975-06-26 1979-02-06 Hoechst Aktiengesellschaft Process for preparing 1,2-oxa-phospholanes
US4081455A (en) * 1976-06-02 1978-03-28 Pfizer Inc. 6-Amino-2,2-dimethyl-3-cyanopenams
US4803272A (en) * 1987-02-24 1989-02-07 E. I. Du Pont De Nemours And Company S-modified adenosyl-1,8-diamino-3-thiooctane derivatives
US4927830A (en) * 1988-04-08 1990-05-22 The Regents Of The University Of Michigan Acyclic pyrrolo[2,3-D]pyrimidine analogs as antiviral agents
GB9204015D0 (en) 1992-02-25 1992-04-08 Wellcome Found Therapeutic nucleosides
GB9205071D0 (en) 1992-03-09 1992-04-22 Wellcome Found Therapeutic nucleosides
NZ294095A (en) 1994-09-09 1998-08-26 Wellcome Found Antiviral purine nucleoside analogues containing a substituted benzimidazole base attached to a carbocyclic ring
US5912356A (en) 1995-09-11 1999-06-15 Glaxo Wellcome Inc. Antiviral nucleoside analogues containing a substituted benzimidazole base attached to a carbocyclic ring
ZA9811595B (en) 1997-12-17 2000-06-19 Biocryst Pharm Inc Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors.
US6878716B1 (en) 1998-06-02 2005-04-12 Osi Pharmaceuticals, Inc. Compounds specific to adenosine A1 receptor and uses thereof
JP2000290201A (ja) * 1998-07-06 2000-10-17 Toray Ind Inc 光学異性体の分割方法
US6379552B1 (en) 1998-07-06 2002-04-30 Toray Industries, Inc. Method for resolving optical isomers
GB9907082D0 (en) 1999-03-26 1999-05-19 Chirotech Technology Ltd The preparation of carboxylic acid derivatives
CO5261573A1 (es) 1999-11-19 2003-03-31 Novartis Ag Derivados de benzoxa y bezotiazol, compuesto y composicion farmaceutica que los contiene y proceso para la preparacion de la mencionada composicion
WO2001042255A1 (en) 1999-12-10 2001-06-14 Glaxo Group Limited (1R,CIS)-4-(4-AMINO-7H-PYRROLO'2,3-I(D) ! PYRIMIDINE-7-YL)-2-CYCLOPENTENE-1-METHANOL DERIVATIVES AS ANTIVIRAL
EP1250128A2 (en) * 1999-12-16 2002-10-23 Alcon, Inc. Inhibitors of adenosine kinase for the treatment of optic nerve and retinal damage
WO2003053992A2 (en) 2001-12-21 2003-07-03 Schering Aktiengesellschaft Industrially applicable process for the sulfamoylation of alcohols and phenols
WO2003106477A1 (en) 2002-06-01 2003-12-24 Isis Pharmaceuticals, Inc. Oligomeric compounds that include carbocyclic nucleosides and their use in gene modulation
CA2488842A1 (en) 2002-06-17 2003-12-24 Merck & Co., Inc. Carbocyclic nucleoside analogs as rna-antivirals
GB0225986D0 (en) * 2002-11-07 2002-12-11 Astrazeneca Ab Chemical compounds
US7429596B2 (en) * 2003-06-20 2008-09-30 The Regents Of The University Of California 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof
US7338957B2 (en) * 2003-08-28 2008-03-04 Irm Llc Compounds and compositions as protein kinase inhibitors
US20090036448A1 (en) 2004-03-30 2009-02-05 Taisho Pharmecutical Co., Ltd. Pyrimidine derivatives and methods of treatment related to the use thereof
US20080096922A1 (en) 2004-04-06 2008-04-24 Dainippon Sumitomo Pharma Co., Ltd. Novel Sulfonamide derivative
CA2471666C (en) 2004-06-18 2009-10-13 Apotex Pharmachem Inc. An improved process for the preparation of oxcarbazepine and related intermediates
EP1848718B1 (en) 2005-02-04 2012-08-01 Millennium Pharmaceuticals, Inc. Inhibitors of e1 activating enzymes
CN106008512B (zh) * 2006-02-02 2019-03-12 千禧药品公司 E1活化酶抑制剂
NZ574513A (en) * 2006-08-08 2012-02-24 Millennium Pharm Inc Heteroaryl compounds useful as inhibitors of e1 activating enzymes
US8008307B2 (en) 2006-08-08 2011-08-30 Millennium Pharmaceuticals, Inc. Heteroaryl compounds useful as inhibitors of E1 activating enzymes
CA2949336C (en) 2007-08-02 2018-11-06 Lei Zhu Process for the synthesis of e1 activating enzyme inhibitors
CN102421780A (zh) 2009-05-14 2012-04-18 米伦纽姆医药公司 氨基磺酸((1s，2s，4r)-4-{4-[(1s)-2，3-二氢-1h-茚-1-基氨基]-7h-吡咯并[2，3-d]嘧啶-7-基}-2-羟基环戊基)甲酯盐酸盐

Also Published As

Publication number Publication date
CA2695193C (en) 2018-07-17
KR20100066475A (ko) 2010-06-17
CN103483342B (zh) 2016-08-31
TW201434851A (zh) 2014-09-16
EP2540727A1 (en) 2013-01-02
US8933225B2 (en) 2015-01-13
EP2546256A3 (en) 2013-04-17
KR101925902B1 (ko) 2018-12-06
US20090036678A1 (en) 2009-02-05
ZA201000482B (en) 2011-07-27
JP2014015483A (ja) 2014-01-30
US10745404B2 (en) 2020-08-18
CN106243111A (zh) 2016-12-21
WO2009042013A1 (en) 2009-04-02
RU2015108944A (ru) 2015-08-20
KR20150064252A (ko) 2015-06-10
IL251372B (en) 2018-07-31
RU2553476C2 (ru) 2015-06-20
CN101868461B (zh) 2013-09-25
US9802938B2 (en) 2017-10-31
JP2010535217A (ja) 2010-11-18
EP2540726A1 (en) 2013-01-02
US20150353555A9 (en) 2015-12-10
ES2757928T3 (es) 2020-04-30
AU2008305767A1 (en) 2009-04-02
CA2695193A1 (en) 2009-04-02
CN101868461A (zh) 2010-10-20
ES2758027T3 (es) 2020-05-04
TWI426077B (zh) 2014-02-11
JP5479336B2 (ja) 2014-04-23
US20150080573A1 (en) 2015-03-19
IL251372A0 (en) 2017-05-29
CA2949336A1 (en) 2009-04-02
EP2540726B1 (en) 2019-10-09
AU2008305767B2 (en) 2014-07-31
CN103483342A (zh) 2014-01-01
EP2178880B1 (en) 2017-10-04
RU2010107471A (ru) 2011-09-10
JP6148594B2 (ja) 2017-06-14
US20180079755A1 (en) 2018-03-22
MX2010001126A (es) 2010-03-01
EP2546256B1 (en) 2019-10-09
ES2684309T3 (es) 2018-10-02
JP2015025009A (ja) 2015-02-05
EP2540727B1 (en) 2018-07-25
IL203590A (en) 2017-03-30
EP2178880A1 (en) 2010-04-28
EP2546256A2 (en) 2013-01-16
TW200922937A (en) 2009-06-01
CN106243111B (zh) 2019-07-23
ES2655028T3 (es) 2018-02-16

Similar Documents

Publication Publication Date Title
CA2949336C (en) Process for the synthesis of e1 activating enzyme inhibitors
AU2013204601B2 (en) Process for the synthesis of E1 activating enzyme inhibitors
HK1178895A (en) Process for the synthesis of e1 activating enzyme inhibitors
HK1178895B (en) Process for the synthesis of e1 activating enzyme inhibitors
HK1178167A (en) Intermediates for the synthesis of e1 activity activating enzyme inhibitors
HK1178160A (en) Sulfamoylating reagent
HK1178167B (en) Intermediates for the synthesis of e1 activity activating enzyme inhibitors
HK1143592A (en) Process for the synthesis of e1 activating enzyme inhibitors
HK1143592B (en) Process for the synthesis of e1 activating enzyme inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20161125

MKLA Lapsed

Effective date: 20220802