CA2986954C - Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one - Google Patents

Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one Download PDF

Info

Publication number
CA2986954C
CA2986954C CA2986954A CA2986954A CA2986954C CA 2986954 C CA2986954 C CA 2986954C CA 2986954 A CA2986954 A CA 2986954A CA 2986954 A CA2986954 A CA 2986954A CA 2986954 C CA2986954 C CA 2986954C
Authority
CA
Canada
Prior art keywords
formula
compound
mixture
process according
prepare
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.)
Active
Application number
CA2986954A
Other languages
English (en)
French (fr)
Other versions
CA2986954A1 (en
Inventor
Rhonan Lee Ford
Premji Meghani
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.)
NOVASSAY SA
Original Assignee
NOVASSAY SA
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 NOVASSAY SA filed Critical NOVASSAY SA
Publication of CA2986954A1 publication Critical patent/CA2986954A1/en
Application granted granted Critical
Publication of CA2986954C publication Critical patent/CA2986954C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/02—Formation or introduction of functional groups containing nitrogen of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B43/00—Formation or introduction of functional groups containing nitrogen
    • C07B43/08—Formation or introduction of functional groups containing nitrogen of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/02—Purification; Separation; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
    • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/627—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing seven carbon atoms
    • 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
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/20—All rings being cycloaliphatic the ring system containing seven carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
CA2986954A 2015-05-27 2016-02-02 Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one Active CA2986954C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562167232P 2015-05-27 2015-05-27
US62/167,232 2015-05-27
PCT/EP2016/052176 WO2016146299A1 (en) 2015-05-27 2016-02-02 Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one

Publications (2)

Publication Number Publication Date
CA2986954A1 CA2986954A1 (en) 2016-09-22
CA2986954C true CA2986954C (en) 2023-06-27

Family

ID=55404679

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2986954A Active CA2986954C (en) 2015-05-27 2016-02-02 Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one

Country Status (11)

Country Link
US (1) US10150723B2 (enExample)
EP (1) EP3303308B1 (enExample)
JP (1) JP6775009B2 (enExample)
KR (1) KR102598202B1 (enExample)
CN (1) CN107667097B (enExample)
AU (1) AU2016232606A1 (enExample)
BR (1) BR112017025135B1 (enExample)
CA (1) CA2986954C (enExample)
RU (1) RU2734475C2 (enExample)
WO (1) WO2016146299A1 (enExample)
ZA (1) ZA201708769B (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114264751B (zh) * 2021-12-28 2024-02-27 江苏威凯尔医药科技有限公司 一种高效液相色谱法分离米洛巴林中间体及其对映异构体的方法
CN115745764B (zh) * 2022-12-08 2024-03-12 重庆华森制药股份有限公司 一种米洛巴林中间体的制备方法
WO2024134671A1 (en) * 2022-12-21 2024-06-27 Bhisaj Pharmaceuticals Pvt Ltd Preparation of 3-ethylbicyclo[3.2.0]hept-3-en-6-one
CN116903468B (zh) * 2023-07-14 2024-01-26 山东新时代药业有限公司 一种米洛巴林中间体的制备方法
CN117886708B (zh) * 2023-12-05 2026-06-30 浙江天宇药业股份有限公司 一种苯磺酸米洛巴林的合成方法
CN117924061B (zh) * 2024-01-17 2026-03-20 北京海步医药科技有限公司 一种3-烷基双环[3.2.0]庚-3-烯-6-酮的拆分方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU147182A1 (ru) * 1961-07-18 1961-11-30 Е.С. Жданович Способ расщеплени синтетического рацемического альфа-окси-бета1-бета-диметил-гамма-бутиролактона
EP0074856A3 (en) * 1981-09-16 1984-02-01 Glaxo Group Limited Resolution of racemic bicycloheptenones
WO2010084798A1 (ja) * 2009-01-21 2010-07-29 第一三共株式会社 3環性化合物
WO2010110361A1 (ja) * 2009-03-26 2010-09-30 第一三共株式会社 二環性γ-アミノ酸誘導体の製造方法
BR112013031360B1 (pt) * 2011-06-08 2022-01-25 Daiichi Sankyo Company, Limited Método para produzir um composto
ES2649968T3 (es) 2011-06-08 2018-01-16 Daiichi Sankyo Company, Limited Procedimiento de producción de un compuesto bicíclico vía transposición de Claisen
HUE040225T2 (hu) * 2011-12-15 2019-02-28 Daiichi Sankyo Co Ltd Eljárás biciklikus vegyület optikai elválasztására aszimmetrikus katalizátort felhasználva
WO2013089189A1 (ja) * 2011-12-16 2013-06-20 第一三共株式会社 ヒドロキシスルホン酸を経由する二環性化合物の光学分割方法
HUE033397T2 (en) * 2012-04-10 2017-12-28 Daiichi Sankyo Co Ltd A method for the optical separation of bicyclic compounds by an enzyme
JP2013245215A (ja) * 2012-05-29 2013-12-09 Daiichi Sankyo Co Ltd 不斉環化反応による光学活性二環性化合物の製造方法
JP6491213B2 (ja) 2013-12-18 2019-03-27 ノヴァッセイ エスエー 疼痛および他の障害の治療のためのガンマ−アミノ酪酸(gaba)類似体

Also Published As

Publication number Publication date
US10150723B2 (en) 2018-12-11
RU2017143338A3 (enExample) 2019-07-17
RU2734475C2 (ru) 2020-10-16
WO2016146299A1 (en) 2016-09-22
BR112017025135A2 (en) 2018-08-07
ZA201708769B (en) 2019-04-24
KR102598202B1 (ko) 2023-11-03
CN107667097B (zh) 2021-02-12
US20180134643A1 (en) 2018-05-17
RU2017143338A (ru) 2019-06-27
JP2018517768A (ja) 2018-07-05
KR20180036919A (ko) 2018-04-10
JP6775009B2 (ja) 2020-10-28
BR112017025135B1 (pt) 2023-01-17
CA2986954A1 (en) 2016-09-22
AU2016232606A1 (en) 2017-12-07
CN107667097A (zh) 2018-02-06
EP3303308A1 (en) 2018-04-11
EP3303308B1 (en) 2019-10-09

Similar Documents

Publication Publication Date Title
EP3303308B1 (en) Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one
KR102444718B1 (ko) 아미노산 유도체의 전구약물
EP2792664B1 (en) Optical resolution method for bicyclic compound using asymmetric catalyst
US9750720B2 (en) γ-aminobutyric acid (GABA) analogues for the treatment of pain and other disorders
JP7314494B2 (ja) アミノ酸誘導体のプロドラッグを含有する医薬
BR112016014193B1 (pt) Composto, composição contendo o mesmo, uso do referido composto, processo para a preparação do referido composto e composto intermediário

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210127

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20250929

R00 Party data change recorded

Free format text: ST27 STATUS EVENT CODE: A-4-4-R10-R00-R119 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: REVOCATION OF AGENT REQUEST

Effective date: 20251009

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20251017

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260112

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260209

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260316

R17 Change to representative recorded

Free format text: ST27 STATUS EVENT CODE: N-6-6-R10-R17-R121 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: REVOCATION OF AGENT REQUIREMENTS DETERMINED COMPLIANT

Effective date: 20260408

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260408