CA3208587A1 - Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein - Google Patents

Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Info

Publication number
CA3208587A1
CA3208587A1 CA3208587A CA3208587A CA3208587A1 CA 3208587 A1 CA3208587 A1 CA 3208587A1 CA 3208587 A CA3208587 A CA 3208587A CA 3208587 A CA3208587 A CA 3208587A CA 3208587 A1 CA3208587 A1 CA 3208587A1
Authority
CA
Canada
Prior art keywords
compound
formula
solvent
methods
naoh
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
Application number
CA3208587A
Other languages
English (en)
French (fr)
Inventor
Terrance Joseph Connolly
Hon-Wah Man
Periyandi Nagarajan
Chinnapillai Rajendiran
Jasti Venkateswarlu
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.)
Celgene Corp
Original Assignee
Celgene Corp
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 Celgene Corp filed Critical Celgene Corp
Publication of CA3208587A1 publication Critical patent/CA3208587A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
    • C07C209/58—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from or via amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/86—Separation
    • C07C209/88—Separation of optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
    • C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • 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
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA3208587A 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein Pending CA3208587A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562196363P 2015-07-24 2015-07-24
US62/196,363 2015-07-24
CA2993173A CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA2993173A Division CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Publications (1)

Publication Number Publication Date
CA3208587A1 true CA3208587A1 (en) 2017-02-02

Family

ID=57885143

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3208587A Pending CA3208587A1 (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
CA2993173A Active CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2993173A Active CA2993173C (en) 2015-07-24 2016-07-22 Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein

Country Status (9)

Country Link
US (4) US10252981B2 (enExample)
EP (2) EP3325432B1 (enExample)
JP (2) JP6805232B2 (enExample)
CN (1) CN107922287B (enExample)
AU (2) AU2016297784B2 (enExample)
CA (2) CA3208587A1 (enExample)
ES (2) ES2994877T3 (enExample)
MX (2) MX385379B (enExample)
WO (1) WO2017019487A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3250557B1 (en) 2015-01-29 2024-11-20 Signal Pharmaceuticals, LLC Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
EP3325432B1 (en) 2015-07-24 2020-09-02 Celgene Corporation Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein
CN111848423B (zh) * 2019-04-30 2022-10-14 尚科生物医药（上海）有限公司 3-氧代环丁基氨基甲酸叔丁酯的制备方法

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Also Published As

Publication number Publication date
EP3795553B1 (en) 2024-05-15
WO2017019487A1 (en) 2017-02-02
JP7165178B2 (ja) 2022-11-02
MX2020001720A (es) 2021-08-13
US20180215700A1 (en) 2018-08-02
EP3325432A4 (en) 2019-04-24
MX2018001004A (es) 2018-06-07
EP3325432B1 (en) 2020-09-02
AU2016297784A1 (en) 2018-02-08
JP2018521085A (ja) 2018-08-02
CN107922287B (zh) 2021-04-09
MX385379B (es) 2025-03-18
JP6805232B2 (ja) 2020-12-23
CA2993173C (en) 2023-10-03
CN107922287A (zh) 2018-04-17
AU2016297784B2 (en) 2020-12-24
EP3325432A1 (en) 2018-05-30
US10774033B2 (en) 2020-09-15
US11780801B2 (en) 2023-10-10
US20220234990A1 (en) 2022-07-28
JP2021046426A (ja) 2021-03-25
HK1255553A1 (en) 2019-08-23
US11192847B2 (en) 2021-12-07
US20200369600A1 (en) 2020-11-26
US20190152893A1 (en) 2019-05-23
EP3795553A1 (en) 2021-03-24
AU2021201493B2 (en) 2022-07-14
AU2021201493A1 (en) 2021-03-25
CA2993173A1 (en) 2017-02-02
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