CA2834920A1 - Process for the preparation of deuterated compounds containing n-alkyl groups - Google Patents

Process for the preparation of deuterated compounds containing n-alkyl groups Download PDF

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Publication number
CA2834920A1
CA2834920A1 CA2834920A CA2834920A CA2834920A1 CA 2834920 A1 CA2834920 A1 CA 2834920A1 CA 2834920 A CA2834920 A CA 2834920A CA 2834920 A CA2834920 A CA 2834920A CA 2834920 A1 CA2834920 A1 CA 2834920A1
Authority
CA
Canada
Prior art keywords
alkyl
bond
phenyl
process according
alkylene
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.)
Abandoned
Application number
CA2834920A
Other languages
English (en)
French (fr)
Inventor
Jens ATZRODT
Volker Derdau
Wolfgang Holla
Matthias Beller
Lorenz Neubert
Dirk MICHALIK
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.)
Sanofi SA
Original Assignee
Sanofi 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 Sanofi SA filed Critical Sanofi SA
Publication of CA2834920A1 publication Critical patent/CA2834920A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • 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
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2834920A 2011-05-23 2012-05-21 Process for the preparation of deuterated compounds containing n-alkyl groups Abandoned CA2834920A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11305634 2011-05-23
EP11305634.5 2011-05-23
PCT/EP2012/059344 WO2012160015A1 (en) 2011-05-23 2012-05-21 Process for the preparation of deuterated compounds containing n-alkyl groups

Publications (1)

Publication Number Publication Date
CA2834920A1 true CA2834920A1 (en) 2012-11-29

Family

ID=46146876

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2834920A Abandoned CA2834920A1 (en) 2011-05-23 2012-05-21 Process for the preparation of deuterated compounds containing n-alkyl groups

Country Status (10)

Country Link
US (1) US9340489B2 (enExample)
EP (1) EP2714624B1 (enExample)
JP (1) JP5925301B2 (enExample)
KR (1) KR20140030267A (enExample)
CN (1) CN103702961A (enExample)
CA (1) CA2834920A1 (enExample)
IL (1) IL229037A0 (enExample)
RU (1) RU2013156864A (enExample)
SG (1) SG194625A1 (enExample)
WO (1) WO2012160015A1 (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3152200A1 (en) 2014-06-06 2017-04-12 Research Triangle Institute Apelin receptor (apj) agonists and uses thereof
MX377327B (es) * 2014-11-10 2025-03-07 Forge Life Science Llc Metodo y composiciones de anti-hcmv.
US10100059B2 (en) 2015-12-09 2018-10-16 Research Triangle Institute Apelin receptor (APJ) agonists and uses thereof
WO2018053222A1 (en) 2016-09-16 2018-03-22 Research Traingle Institute Tetrahydroisoquinoline kappa opioid antagonists
EP3526209B1 (en) 2016-10-12 2025-04-16 Research Triangle Institute Heterocyclic apelin receptor (apj) agonists and uses thereof
JOP20190072A1 (ar) 2016-10-13 2019-04-07 Glaxosmithkline Ip Dev Ltd مشتقات 1، 3 سيكلوبوتان ثنائي الاستبدال أو آزيتيدين كمثبطات للإنزيم المخلق للبروستاجلاندين d المكون للدم
AU2017382217B2 (en) 2016-12-21 2021-07-08 Research Triangle Institute Diaryl purine derivatives with improved bioavailability
WO2018200882A1 (en) * 2017-04-27 2018-11-01 Deuteria Beverages, Llc Process for the preparation of deuterated ethanol from d2
EA039504B1 (ru) * 2017-04-27 2022-02-03 Дьютерия Бевериджес, Ллс Способ получения дейтерированного этанола из d2o
CA3072362A1 (en) 2017-10-06 2019-04-11 Forma Therapeutics, Inc. Inhibiting ubiquitin specific peptidase 30
CN109748767A (zh) * 2017-11-07 2019-05-14 朱允涛 一种利用微波反应装置制备氘代胺类化合物的方法
SG11202011299PA (en) 2018-05-17 2020-12-30 Forma Therapeutics Inc Fused bicyclic compounds useful as ubiquitin-specific peptidase 30 inhibitors
EP3840745A4 (en) 2018-08-20 2022-06-08 Duke University METHODS AND COMPOSITIONS FOR MEDICINES FOR TREATING OPHTHALMIC DISEASES
MY209034A (en) 2018-10-05 2025-06-17 Forma Therapeutics Inc Fused pyrrolines which act as ubiquitin-specific protease 30 (usp30) inhibitors
TWI767148B (zh) 2018-10-10 2022-06-11 美商弗瑪治療公司 抑制脂肪酸合成酶(fasn)
CN113747870B (zh) * 2018-12-21 2025-08-01 泰兰生物科技有限公司 氟利色林的氘化形式和衍生物
US12441707B2 (en) 2019-12-30 2025-10-14 Tyra Biosciences, Inc. Indazole compounds
PE20240687A1 (es) 2020-12-30 2024-04-10 Tyra Biosciences Inc Compuestos de indazol como inhibidores de cinasas

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4254129A (en) 1979-04-10 1981-03-03 Richardson-Merrell Inc. Piperidine derivatives
US5167948A (en) * 1987-08-07 1992-12-01 Mallinckrodt Medical, Inc. Diagnostic or radiotherapeutic composition comprising a hydrogen containing compound
US5075337A (en) * 1989-07-26 1991-12-24 G. D. Searle & Co. Alpha-deuterated 2-alkylaminoacetamide derivatives having reduced toxicity for treatment of CNS disorders
EP0531410B1 (en) 1990-06-01 1994-11-30 Merrell Dow Pharmaceuticals Inc. (+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(fluorophenyl)ethyl]-4-piperidinemethanol
AU707748B2 (en) * 1994-03-25 1999-07-22 Isotechnika Inc. Enhancement of the efficacy of drugs by deuteration
JP4497815B2 (ja) 2001-02-16 2010-07-07 アベンティス・ファーマスーティカルズ・インコーポレイテツド 新規な複素環式アミド誘導体およびドーパミンｄ３受容体リガンドとしてのその使用
TW200413273A (en) 2002-11-15 2004-08-01 Wako Pure Chem Ind Ltd Heavy hydrogenation method of heterocyclic rings
TW200413274A (en) * 2002-12-27 2004-08-01 Wako Pure Chem Ind Ltd Deuteration or tritiation method
EP1707548A4 (en) 2004-01-23 2007-08-15 Wako Pure Chem Ind Ltd DEUTERIZATION PROCEDURE USING A MIXED CATALYST
US20080261926A1 (en) * 2007-04-02 2008-10-23 Liu Julie F Pharmaceutical Calcimimetics
WO2009005069A1 (ja) * 2007-07-05 2009-01-08 Wako Pure Chemical Industries, Ltd. ルテニウム触媒を用いた重水素化方法
US20100143287A1 (en) * 2008-12-09 2010-06-10 Auspex Pharmaceuticals, Inc. Trifluoromethylphenyl modulators of calcium-sensing receptor

Also Published As

Publication number Publication date
SG194625A1 (en) 2013-12-30
EP2714624A1 (en) 2014-04-09
IL229037A0 (en) 2013-12-31
US9340489B2 (en) 2016-05-17
RU2013156864A (ru) 2015-06-27
EP2714624B1 (en) 2017-12-27
CN103702961A (zh) 2014-04-02
KR20140030267A (ko) 2014-03-11
JP2014524888A (ja) 2014-09-25
WO2012160015A1 (en) 2012-11-29
JP5925301B2 (ja) 2016-05-25
US20140081019A1 (en) 2014-03-20

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Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20160524