CA2678630C - Synthesis of glyt-1 inhibitors - Google Patents

Synthesis of glyt-1 inhibitors Download PDF

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Publication number
CA2678630C
CA2678630C CA2678630A CA2678630A CA2678630C CA 2678630 C CA2678630 C CA 2678630C CA 2678630 A CA2678630 A CA 2678630A CA 2678630 A CA2678630 A CA 2678630A CA 2678630 C CA2678630 C CA 2678630C
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CA
Canada
Prior art keywords
formula
compound
alkyl
halogen
alkoxy
Prior art date
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Active
Application number
CA2678630A
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English (en)
French (fr)
Other versions
CA2678630A1 (en
Inventor
Christophe Pfleger
Pius Waldmeier
Shaoning Wang
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2678630A1 publication Critical patent/CA2678630A1/en
Application granted granted Critical
Publication of CA2678630C publication Critical patent/CA2678630C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA2678630A 2007-03-05 2008-02-25 Synthesis of glyt-1 inhibitors Active CA2678630C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07103485 2007-03-05
EP07103485.4 2007-03-05
PCT/EP2008/052244 WO2008107334A2 (en) 2007-03-05 2008-02-25 Process for the synthesis of glyt-1 inhibitors

Publications (2)

Publication Number Publication Date
CA2678630A1 CA2678630A1 (en) 2008-09-12
CA2678630C true CA2678630C (en) 2015-04-14

Family

ID=39469606

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2678630A Active CA2678630C (en) 2007-03-05 2008-02-25 Synthesis of glyt-1 inhibitors

Country Status (13)

Country Link
US (1) US7812161B2 (enExample)
EP (1) EP2131843B1 (enExample)
JP (1) JP4745446B2 (enExample)
KR (1) KR101143073B1 (enExample)
CN (1) CN101622000B (enExample)
AT (1) ATE532516T1 (enExample)
AU (1) AU2008223915B2 (enExample)
BR (1) BRPI0808570B8 (enExample)
CA (1) CA2678630C (enExample)
ES (1) ES2375585T3 (enExample)
IL (1) IL200323A (enExample)
MX (1) MX2009009065A (enExample)
WO (1) WO2008107334A2 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5656474B2 (ja) 2010-06-28 2015-01-21 関東化学株式会社 脂肪族光学活性フルオロアルコールの製造方法
CN104628679B (zh) * 2013-11-08 2018-02-09 江苏恩华药业股份有限公司 Bitopertin的合成方法及其中间体
CN106397312B (zh) * 2015-07-31 2020-03-24 广东东阳光药业有限公司 一种制备glyt-1抑制剂的方法
KR20220125326A (ko) 2020-01-09 2022-09-14 디스크 메디슨, 인크. 적혈구형성 프로토포르피린증, x-연계된 프로토포르피린증, 또는 선천성 적혈구 조혈포르피린증을 글리신 운반 억제제로 치료하는 방법
KR20230088761A (ko) 2020-10-13 2023-06-20 베링거 인겔하임 인터내셔날 게엠베하 재가공하는 방법
WO2024042043A1 (en) 2022-08-24 2024-02-29 Boehringer Ingelheim International Gmbh A scalable process for the preparation of a glyt-1 inhibitor

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992441A (en) * 1972-12-26 1976-11-16 Pfizer Inc. Sulfamylbenzoic acids
US4480102A (en) * 1982-07-23 1984-10-30 The Dow Chemical Company 2,3-Difluoro-5-(trifluoromethyl)pyridine and methods of making and using the same
ES2061953T3 (es) * 1988-11-24 1994-12-16 Akzo Nv Un procedimiento para preparar una composicion farmaceutica.
DE4235155A1 (de) * 1992-10-19 1994-04-21 Basf Ag Verfahren zur Herstellung von Methylsulfonylbenzoesäuren
DE69906059D1 (de) * 1998-04-20 2003-04-24 Fujisawa Pharmaceutical Co Anthranilsäurederivate als inhibitoren der c-gmp-phosphodiesterase
DE10112040A1 (de) 2001-03-14 2002-10-02 Aventis Pharma Gmbh Verbessertes Verfahren zur Herstellung von Sulfonylcarboxamidderivaten
GB0227240D0 (en) * 2002-11-21 2002-12-31 Glaxo Group Ltd Compounds
NZ544820A (en) * 2003-08-11 2009-02-28 Hoffmann La Roche Piperazine with or-substituted phenyl group and their use as GlyT1 inhibitors
PL1828154T3 (pl) * 2004-12-09 2009-10-30 Hoffmann La Roche Pochodne fenylopiperazynometanonu
CA2593453A1 (en) * 2005-01-06 2006-07-13 F. Hoffmann-La Roche Ag Sulfanyl substituted phenyl methanones as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders
ATE472327T1 (de) * 2005-01-07 2010-07-15 Hoffmann La Roche Ä4-(heteroaryl)piperazin-1-ylü-(2,5-substituier e phenyl)methanon-derivate als glycin-transporter 1 (glyt-1) hemmer zur behandlung von neurologischen und neuropsychiatrischen erkrankungen
KR100946461B1 (ko) * 2005-07-08 2010-03-10 에프. 호프만-라 로슈 아게 1,1,1-트라이플루오로아세톤의 비대칭 환원

Also Published As

Publication number Publication date
US20080221327A1 (en) 2008-09-11
CA2678630A1 (en) 2008-09-12
JP2010520251A (ja) 2010-06-10
CN101622000A (zh) 2010-01-06
CN101622000B (zh) 2012-07-04
BRPI0808570B8 (pt) 2021-05-25
EP2131843B1 (en) 2011-11-09
KR20090110368A (ko) 2009-10-21
ES2375585T3 (es) 2012-03-02
US7812161B2 (en) 2010-10-12
IL200323A (en) 2013-11-28
MX2009009065A (es) 2009-08-31
KR101143073B1 (ko) 2012-05-08
EP2131843A2 (en) 2009-12-16
ATE532516T1 (de) 2011-11-15
IL200323A0 (en) 2010-04-29
WO2008107334A3 (en) 2008-10-23
AU2008223915B2 (en) 2013-05-02
BRPI0808570B1 (pt) 2020-09-15
JP4745446B2 (ja) 2011-08-10
AU2008223915A1 (en) 2008-09-12
WO2008107334A2 (en) 2008-09-12
BRPI0808570A2 (pt) 2014-09-02

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