MX2009009065A - Proceso para sintesis de inhibidores del transportador de glicina 1. - Google Patents

Proceso para sintesis de inhibidores del transportador de glicina 1.

Info

Publication number
MX2009009065A
MX2009009065A MX2009009065A MX2009009065A MX2009009065A MX 2009009065 A MX2009009065 A MX 2009009065A MX 2009009065 A MX2009009065 A MX 2009009065A MX 2009009065 A MX2009009065 A MX 2009009065A MX 2009009065 A MX2009009065 A MX 2009009065A
Authority
MX
Mexico
Prior art keywords
alkyl
compound
formula
halogen
nr4r5
Prior art date
Application number
MX2009009065A
Other languages
English (en)
Inventor
Shaoning Wang
Pius Waldmeier
Christophe Pfleger
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of MX2009009065A publication Critical patent/MX2009009065A/es

Links

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

Landscapes

  • 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)

Abstract

Se describe un proceso para la preparación de un compuesto de la fórmula (I) en donde Het es un grupo heteroarilo de 6 miembros, que contiene uno, dos o tres átomos de nitrógeno; R1 es alquilo de 1 a 6 átomos de carbono, cicloalquilo de 3 a 6 átomos de carbono, NR4R5 o alquilo de 1 a 6 átomos de carbono-sustituido por halógeno; R2 es hidroxi, halógeno, NO2, CN, alquilo de 1 a 6 átomos de carbono, cicloalquilo de 3 a 6 átomos de carbono, alquilo de 1 a 6 átomos de carbono-sustituido por halógeno, alquilo de 1 a 6 átomos de carbono-sustituido por hidroxi, (CH2)o-alcoxi de 1 a 6 átomos de carbono, alcoxi de 1 a 6 átomos de carbono-sustituido por halógeno, NR4R5, C(O)R6 o SO2R7; R3 es alquilo de 1 a 6 átomos de carbono, cicloalquilo de 3 a 6 átomos de carbono o alquilo de 1 a 6 átomos de carbono-sustituido por halógeno; R4 y R5 independientemente entre sí son hidrógeno o alquilo de 1 a 6 átomos de carbono; R6 es hidrógeno, alquilo de 1 a 6 átomos de carbono, alcoxi de 1 a 6 átomos de carbono, o NR4R5; R7 es alquilo de 1 a 6 átomos de carbono, alquilo de 1 a 6 átomos de carbono-sustituido opcionalmente por halógeno, (CH2)o-cicloalquilo de 3 a 6 átomos de carbono, (CH2)o-alcoxi de 3 a 6 átomos de carbono o NR4R5 n es 0, 1, 2 ó 3; o es 0, 1 ó 2; y sales de adición de ácido farmacéuticamente aceptables de las mismas, caracterizado en que comprende las etapas de a) hacer reaccionar un compuesto de la fórmula (21) con un compuesto de la fórmula: R3 OH 8 en un compuesto de la fórmula (11) y b) acoplar el compuesto de la fórmula (11) en presencia de un reactivo de acoplamiento o del halogenuro ácido correspondiente con un compuesto de la fórmula (15) para obtener un compuesto de la fórmula (I).
MX2009009065A 2007-03-05 2008-02-25 Proceso para sintesis de inhibidores del transportador de glicina 1. MX2009009065A (es)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number Publication Date
MX2009009065A true MX2009009065A (es) 2009-08-31

Family

ID=39469606

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2009009065A MX2009009065A (es) 2007-03-05 2008-02-25 Proceso para sintesis de inhibidores del transportador de glicina 1.

Country Status (13)

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

Families Citing this family (5)

* 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
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
JP2001508811A (ja) * 1998-04-20 2001-07-03 藤沢薬品工業株式会社 ｃＧＭＰ−ホスホジエステラーゼ阻害剤としてのアントラニル酸誘導体
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
MXPA06001665A (es) * 2003-08-11 2006-04-28 Hoffmann La Roche Piperazina con grupo fenilo sustituido -or y su uso como inhibidores del transportador de glicina 1 (glyt-1).
DE602005014274D1 (de) * 2004-12-09 2009-06-10 Hoffmann La Roche Phenylpiperazin-methanon-derivate
WO2006072435A1 (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
DE602005022113D1 (de) * 2005-01-07 2010-08-12 Hoffmann La Roche Phenyl)methanon-derivate als glycin-transporter 1 (glyt-1) hemmer zur behandlung von neurologischen und neuropsychiatrischen erkrankungen
JP4219976B2 (ja) * 2005-07-08 2009-02-04 エフ．ホフマン−ラ ロシュ アーゲー １，１，１−トリフルオロアセトンの不斉還元

Also Published As

Publication number Publication date
BRPI0808570B8 (pt) 2021-05-25
KR20090110368A (ko) 2009-10-21
BRPI0808570B1 (pt) 2020-09-15
EP2131843B1 (en) 2011-11-09
US7812161B2 (en) 2010-10-12
JP2010520251A (ja) 2010-06-10
JP4745446B2 (ja) 2011-08-10
AU2008223915B2 (en) 2013-05-02
WO2008107334A2 (en) 2008-09-12
CN101622000B (zh) 2012-07-04
BRPI0808570A2 (pt) 2014-09-02
WO2008107334A3 (en) 2008-10-23
CN101622000A (zh) 2010-01-06
IL200323A (en) 2013-11-28
EP2131843A2 (en) 2009-12-16
ES2375585T3 (es) 2012-03-02
ATE532516T1 (de) 2011-11-15
KR101143073B1 (ko) 2012-05-08
CA2678630C (en) 2015-04-14
US20080221327A1 (en) 2008-09-11
CA2678630A1 (en) 2008-09-12
AU2008223915A1 (en) 2008-09-12
IL200323A0 (en) 2010-04-29

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