CA2875132C - Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases - Google Patents

Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases Download PDF

Info

Publication number
CA2875132C
CA2875132C CA2875132A CA2875132A CA2875132C CA 2875132 C CA2875132 C CA 2875132C CA 2875132 A CA2875132 A CA 2875132A CA 2875132 A CA2875132 A CA 2875132A CA 2875132 C CA2875132 C CA 2875132C
Authority
CA
Canada
Prior art keywords
formula
compound
mmol
group
nmr
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
CA2875132A
Other languages
English (en)
French (fr)
Other versions
CA2875132A1 (en
Inventor
Anna Quattropani
Dominique Swinnen
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.)
Ares Trading SA
Original Assignee
Ares Trading 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 Ares Trading SA filed Critical Ares Trading SA
Publication of CA2875132A1 publication Critical patent/CA2875132A1/en
Application granted granted Critical
Publication of CA2875132C publication Critical patent/CA2875132C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/10—Spiro-condensed systems
    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
    • 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
    • A61K31/4245—Oxadiazoles
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/547—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame spiro-condensed or forming part of bridged ring systems
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/10—Spiro-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2875132A 2012-05-31 2013-05-10 Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases Active CA2875132C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP20120170227 EP2669286A1 (en) 2012-05-31 2012-05-31 Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases
EP12170227.8 2012-05-31
US201261655078P 2012-06-04 2012-06-04
US61/655,078 2012-06-04
PCT/EP2013/001389 WO2013178322A1 (en) 2012-05-31 2013-05-10 Spiro tetrahydro - benzothiophen derivatives useful for the treatment neurodegenerative diseases

Publications (2)

Publication Number Publication Date
CA2875132A1 CA2875132A1 (en) 2013-12-05
CA2875132C true CA2875132C (en) 2020-07-28

Family

ID=46210136

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2875132A Active CA2875132C (en) 2012-05-31 2013-05-10 Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases

Country Status (9)

Country Link
US (1) US9233982B2 (enExample)
EP (2) EP2669286A1 (enExample)
JP (1) JP6209210B2 (enExample)
CN (1) CN104364258B (enExample)
AU (1) AU2013269996B2 (enExample)
CA (1) CA2875132C (enExample)
ES (1) ES2581540T3 (enExample)
IL (1) IL235955B (enExample)
WO (1) WO2013178322A1 (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013181202A2 (en) 2012-05-30 2013-12-05 Astellas Pharma Inc. Chromane compounds
US9580396B2 (en) 2012-12-21 2017-02-28 Merck Sharp & Dohme Corp. C6-spiro iminothiadiazine dioxides as BACE inhibitors, compositions, and their use
US9725468B2 (en) 2013-09-13 2017-08-08 Merck Sharp & Dohme Corp. C5-spiro iminothiazine dioxides as BACE inhibitors, compositions, and their use
US10238743B2 (en) 2014-10-03 2019-03-26 Merck Sharp & Dohme Corp. C5-C6-fused tricyclic iminothiadiazine dioxide compounds as BACE inhibitors, compositions, and their use
ES2887087T3 (es) 2015-05-07 2021-12-21 Bristol Myers Squibb Co Sulfonas tricíclicas como moduladores ROR gamma
KR20190057388A (ko) 2016-10-10 2019-05-28 브리스톨-마이어스 스큅 컴퍼니 Ror 감마 조정제로서의 트리시클릭 술폰
BR112019025212A2 (pt) * 2017-06-14 2020-06-16 Nippon Soda Co., Ltd. Composto, formulações para controlar organismos nocivos, para controlar ectoparasitas, para controlar pragas de insetos thysanoptera, e, formulação inseticida ou acaricida

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7763609B2 (en) * 2003-12-15 2010-07-27 Schering Corporation Heterocyclic aspartyl protease inhibitors
CN101489984B (zh) * 2006-07-18 2013-04-03 安斯泰来制药株式会社 氨基茚满衍生物或其盐
WO2008133273A1 (ja) * 2007-04-24 2008-11-06 Shionogi & Co., Ltd. アルツハイマー症治療用医薬組成物
WO2010013794A1 (en) 2008-07-28 2010-02-04 Eisai R&D Management Co., Ltd. Spiroaminodihydrothiazine derivatives
JP5444240B2 (ja) * 2008-07-28 2014-03-19 エーザイ・アール・アンド・ディー・マネジメント株式会社 スピロアミノジヒドロチアジン誘導体
PT2406240E (pt) * 2009-03-13 2016-02-24 Boehringer Ingelheim Int Inibidores de beta-secretase
CN102812005B (zh) * 2010-02-24 2014-12-10 生命医药公司 β-分泌酶抑制剂
US20120065195A1 (en) * 2010-03-31 2012-03-15 Clark Christopher T Compounds for treating neurodegenerative diseases

Also Published As

Publication number Publication date
US20150111882A1 (en) 2015-04-23
US9233982B2 (en) 2016-01-12
WO2013178322A1 (en) 2013-12-05
ES2581540T3 (es) 2016-09-06
AU2013269996B2 (en) 2017-04-13
CN104364258B (zh) 2017-05-24
EP2855486A1 (en) 2015-04-08
IL235955A0 (en) 2015-02-01
JP6209210B2 (ja) 2017-10-04
AU2013269996A1 (en) 2015-01-22
WO2013178322A8 (en) 2014-12-11
CN104364258A (zh) 2015-02-18
EP2669286A1 (en) 2013-12-04
CA2875132A1 (en) 2013-12-05
IL235955B (en) 2018-06-28
JP2015521192A (ja) 2015-07-27
EP2855486B1 (en) 2016-04-06

Similar Documents

Publication Publication Date Title
CA2875132C (en) Spiro tetrahydro-benzothiophen derivatives useful for the treatment of neurodegenerative diseases
JP7299382B2 (ja) Ｔｎｆ活性のモジュレーターとしての縮合五環式イミダゾール誘導体
ES2735750T3 (es) Derivados de imidazol y pirazol condensados como moduladores de la actividad de TNF
CA2930209C (en) Tetrahydroimidazopyridine derivatives as modulators of tnf activity
CA2932008A1 (en) Fused tricyclic benzimidazoles derivatives as modulators of tnf activity
KR20220012244A (ko) Mrgx2의 억제제로서의 3-아미노-4h-벤조[e][1,2,4]티아디아진 1,1-디옥사이드 유도체
WO2019169153A1 (en) Piperidinyl-3-(aryloxy)propanamides and propanoates
US9527853B2 (en) Fused triazole derivatives as gamma secretase modulators
JP2025179155A (ja) Ｓｓｔｒ４アゴニストとしてのｎ－ヘテロアリールアルキル－２－（ヘテロシクリル及びヘテロシクリルメチル）アセトアミド誘導体
US10696690B2 (en) Imidazo-oxadiazole and imidazo-thiadiazole derivatives
JP7734147B2 (ja) Ｓｓｔｒ４アゴニストとしてのｎ－（ヘテロシクリル及びヘテロシクリルアルキル）－３－ベンジルピリジン－２－アミン誘導体

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20180509