EA201490675A1 - Способы и промежуточные соединения для получения макроциклического ингибитора протеазы hcv - Google Patents

Способы и промежуточные соединения для получения макроциклического ингибитора протеазы hcv

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Publication number
EA201490675A1
EA201490675A1 EA201490675A EA201490675A EA201490675A1 EA 201490675 A1 EA201490675 A1 EA 201490675A1 EA 201490675 A EA201490675 A EA 201490675A EA 201490675 A EA201490675 A EA 201490675A EA 201490675 A1 EA201490675 A1 EA 201490675A1
Authority
EA
Eurasian Patent Office
Prior art keywords
salt
obtaining
methods
intermediate compounds
hcv protease
Prior art date
Application number
EA201490675A
Other languages
English (en)
Inventor
Доминик Поль Мишель Депре
Доминик Джон Ормирод
Андраш Хорват
Original Assignee
Янссен Фармасьютикалз, Инк.
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 Янссен Фармасьютикалз, Инк. filed Critical Янссен Фармасьютикалз, Инк.
Publication of EA201490675A1 publication Critical patent/EA201490675A1/ru

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • General Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Раскрывается способ получения цинхонидиновой соли формулы (IV)с помощью водного раствора рацемической 4-гидрокси-1,2-циклопентандикарбоновой кислоты, который подвергают циклизации без удаления воды, путем добавления смешиваемого с водой органического растворителя к водному раствору и опять-таки без удаления воды добавления цинхонидина к раствору в водно-органическом растворителе с получением цинхонидиновой соли лактоновой кислоты. Обеспечивают кристаллизацию цинхонидиновой соли с получением энантиомерно чистой кристаллической цинхонидиновой соли лактоновой кислоты (IV). Энантиомерно чистая соль представляет собой промежуточное соединение в синтезе соединения ингибитора HCV формулы (I).
EA201490675A 2011-09-22 2012-09-21 Способы и промежуточные соединения для получения макроциклического ингибитора протеазы hcv EA201490675A1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP11182375 2011-09-22
PCT/EP2012/068593 WO2013041655A1 (en) 2011-09-22 2012-09-21 Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv

Publications (1)

Publication Number Publication Date
EA201490675A1 true EA201490675A1 (ru) 2014-08-29

Family

ID=46924427

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201490675A EA201490675A1 (ru) 2011-09-22 2012-09-21 Способы и промежуточные соединения для получения макроциклического ингибитора протеазы hcv

Country Status (16)

Country Link
US (1) US9227965B2 (ru)
EP (1) EP2758386A1 (ru)
JP (1) JP6235473B2 (ru)
KR (1) KR20140063726A (ru)
CN (2) CN103906739B (ru)
AR (1) AR087993A1 (ru)
AU (1) AU2012311461B2 (ru)
BR (1) BR112014006984A2 (ru)
CA (1) CA2845720A1 (ru)
CL (1) CL2014000687A1 (ru)
EA (1) EA201490675A1 (ru)
HK (1) HK1199449A1 (ru)
IL (1) IL231024A (ru)
MX (1) MX356686B (ru)
TW (1) TWI565704B (ru)
WO (1) WO2013041655A1 (ru)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MA41812A (fr) 2015-03-27 2018-01-30 Janssen Pharmaceuticals Inc Procédés et intermédiaires pour la préparation d'un inhibiteur de protéase macrocyclique du vhc

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073195A2 (en) 2004-01-30 2005-08-11 Medivir Ab Hcv ns-3 serine protease inhibitors
PE20070211A1 (es) 2005-07-29 2007-05-12 Medivir Ab Compuestos macrociclicos como inhibidores del virus de hepatitis c
CL2008000322A1 (es) 2007-02-01 2008-09-05 Tibotec Pharm Ltd Proceso para la preparacion de un compuesto derivado de 2-tiazol-2-il-quinolina; compuestos intermediarios; y proceso de preparacion de dichos compuestos intermediarios.
US8426360B2 (en) * 2007-11-13 2013-04-23 Enanta Pharmaceuticals, Inc. Carbocyclic oxime hepatitis C virus serine protease inhibitors
CA2745565C (en) * 2008-12-23 2017-03-07 Ortho-Mcneil-Janssen Pharmaceuticals, Inc Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv
CN102741270B (zh) * 2009-09-28 2015-07-22 英特穆恩公司 C型肝炎病毒复制的环肽抑制剂
JP2013522273A (ja) * 2010-03-16 2013-06-13 ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド Ｈｃｖの大環状プロテアーゼ阻害剤の製造のための方法及び中間体

Also Published As

Publication number Publication date
BR112014006984A2 (pt) 2017-04-04
US20140228574A1 (en) 2014-08-14
CN107011339A (zh) 2017-08-04
WO2013041655A1 (en) 2013-03-28
IL231024A0 (en) 2014-03-31
EP2758386A1 (en) 2014-07-30
MX356686B (es) 2018-06-07
TWI565704B (zh) 2017-01-11
CA2845720A1 (en) 2013-03-28
TW201329074A (zh) 2013-07-16
CN103906739B (zh) 2016-12-28
AU2012311461B2 (en) 2017-07-06
IL231024A (en) 2017-09-28
AR087993A1 (es) 2014-04-30
CL2014000687A1 (es) 2014-08-01
MX2014003509A (es) 2014-07-22
US9227965B2 (en) 2016-01-05
JP2014528943A (ja) 2014-10-30
AU2012311461A1 (en) 2014-03-06
JP6235473B2 (ja) 2017-11-22
KR20140063726A (ko) 2014-05-27
CN103906739A (zh) 2014-07-02
HK1199449A1 (en) 2015-07-03

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