CA2602965C - Tricyclic spiro derivatives as crth2 modulators - Google Patents

Tricyclic spiro derivatives as crth2 modulators Download PDF

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Publication number
CA2602965C
CA2602965C CA2602965A CA2602965A CA2602965C CA 2602965 C CA2602965 C CA 2602965C CA 2602965 A CA2602965 A CA 2602965A CA 2602965 A CA2602965 A CA 2602965A CA 2602965 C CA2602965 C CA 2602965C
Authority
CA
Canada
Prior art keywords
chloro
indole
pyrrolidin
acetic acid
trioxospiro
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.)
Expired - Fee Related
Application number
CA2602965A
Other languages
English (en)
French (fr)
Other versions
CA2602965A1 (en
Inventor
Matthias Schwarz
Eric Sebille
Christophe Cleva
Cedric Merlot
Dennis Church
Patrick Page
Jacqueline A. Macritchie
John Frederick Atherall
Stefano Crosignani
Doris Pupowicz
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.)
Merck Serono SA
Original Assignee
Merck Serono 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 Merck Serono SA filed Critical Merck Serono SA
Publication of CA2602965A1 publication Critical patent/CA2602965A1/en
Application granted granted Critical
Publication of CA2602965C publication Critical patent/CA2602965C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Dermatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2602965A 2005-05-24 2006-05-23 Tricyclic spiro derivatives as crth2 modulators Expired - Fee Related CA2602965C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP05104428 2005-05-24
EP05104428.7 2005-05-24
US68863105P 2005-06-08 2005-06-08
PCT/EP2006/062545 WO2006125784A1 (en) 2005-05-24 2006-05-23 Tricyclic spiro derivatives as crth2 modulators
US60/688,631 2006-06-08

Publications (2)

Publication Number Publication Date
CA2602965A1 CA2602965A1 (en) 2006-11-30
CA2602965C true CA2602965C (en) 2013-12-31

Family

ID=35478408

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2602965A Expired - Fee Related CA2602965C (en) 2005-05-24 2006-05-23 Tricyclic spiro derivatives as crth2 modulators

Country Status (20)

Country Link
US (1) US8236963B2 (enExample)
EP (1) EP1891075B1 (enExample)
JP (1) JP5567268B2 (enExample)
KR (1) KR101333861B1 (enExample)
CN (1) CN101300259B (enExample)
AR (1) AR055959A1 (enExample)
AT (1) ATE529429T1 (enExample)
AU (1) AU2006251138C1 (enExample)
BR (1) BRPI0610209A2 (enExample)
CA (1) CA2602965C (enExample)
DK (1) DK1891075T3 (enExample)
ES (1) ES2375614T3 (enExample)
MX (1) MX2007014256A (enExample)
NZ (1) NZ562772A (enExample)
PL (1) PL1891075T3 (enExample)
PT (1) PT1891075E (enExample)
RU (1) RU2478639C2 (enExample)
UA (1) UA90145C2 (enExample)
WO (1) WO2006125784A1 (enExample)
ZA (1) ZA200709819B (enExample)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2316824A1 (en) 2006-08-07 2011-05-04 Actelion Pharmaceuticals Ltd. (3-Amino-1,2,3,4-tetrahydro-9H-carbazoI-9-yl)-acetic acid derivates
US20120115895A1 (en) 2009-07-15 2012-05-10 Merck Serono S.A. Tricyclic indole-derived spiro derivatives as crth2 modulators
CN104876938A (zh) 2009-11-12 2015-09-02 密歇根大学董事会 螺-吲哚酮mdm2拮抗剂
MX2012010820A (es) 2010-03-22 2012-10-10 Actelion Pharmaceuticals Ltd Derivados de 3-(heteroaril-amino)-1, 2, 3, 4-tetrahidro-9h-carbazo l y sus uso como moduladores del receptor de prostaglandina d2.
PE20140408A1 (es) 2010-11-12 2014-04-10 Univ Michigan Derivados espiro-oxindol como antagonistas de mdm2
EP2457900A1 (en) 2010-11-25 2012-05-30 Almirall, S.A. New pyrazole derivatives having CRTh2 antagonistic behaviour
WO2012140612A1 (en) 2011-04-14 2012-10-18 Actelion Pharmaceuticals Ltd 7-(heteroaryl-amino)-6,7,8,9-tetrahydropyrido[1,2-a]indol acetic acid derivatives and their use as prostaglandin d2 receptor modulators
MX346375B (es) 2011-05-11 2017-03-16 Univ Michigan Regents Antagonistas de espiro-oxindol de mdm2.
CN104114169A (zh) 2011-12-16 2014-10-22 阿托佩斯治疗有限公司 用于治疗嗜酸细胞性食管炎的crth2拮抗剂和质子泵抑制剂的组合物
CN103554119B (zh) * 2013-10-15 2015-09-16 华东师范大学 四氢呋喃并苯并二氢吡喃多环化合物的制备方法
CN103554118B (zh) * 2013-10-15 2015-08-19 华东师范大学 四氢呋喃并苯并二氢吡喃多环化合物及其应用
CN103554121B (zh) * 2013-10-16 2015-06-24 华东师范大学 3,3-螺(2-四氢呋喃)氧化吲哚多环状化合物及其应用
CN103554120B (zh) * 2013-10-16 2015-06-24 华东师范大学 3,3-螺(2-四氢呋喃)氧化吲哚多环状化合物的制备方法
PH12016501764B1 (en) 2014-03-17 2024-05-17 Idorsia Pharmaceuticals Ltd Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators
WO2015140701A1 (en) 2014-03-18 2015-09-24 Actelion Pharmaceuticals Ltd Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators
US9745253B2 (en) 2015-03-13 2017-08-29 Forma Therapeutics, Inc. Alpha-cinnamide compounds and compositions as HDAC8 inhibitors
TR201909160T4 (tr) 2015-07-15 2019-07-22 Hoffmann La Roche Metabotropik glutamat reseptörü modülatörleri olarak etinil türevleri.
WO2017046125A1 (en) 2015-09-15 2017-03-23 Actelion Pharmaceuticals Ltd Crystalline forms
RU2631856C1 (ru) * 2016-05-04 2017-09-27 Федеральное государственное бюджетное образовательное учреждение высшего образования "Чувашский государственный университет имени И.Н. Ульянова" Способ получения аммонийных солей 3-амино-8-гидрокси-1,6-диоксо-4-циано-2,7-диазаспиро[4.4]нон-3-ен-2-идов
WO2018015235A1 (en) 2016-07-18 2018-01-25 F. Hoffmann-La Roche Ag Ethynyl derivatives
CN109384787B (zh) * 2017-08-08 2021-04-16 沈阳药科大学 一种一价银催化的氢化吡啶螺二氢吲哚环的合成方法
CN109384794B (zh) * 2017-08-08 2020-06-19 沈阳药科大学 质子酸催化的一类四环吲哚骨架的合成方法
CN109369658B (zh) * 2017-08-08 2020-01-31 沈阳药科大学 一种螺[吡咯烷-3,3`-氧化吲哚]环系的合成方法
KR101857408B1 (ko) 2018-02-28 2018-05-14 경북대학교 산학협력단 탈모 예방 또는 치료용 조성물
EP3902805A4 (en) 2018-12-28 2023-03-01 SPV Therapeutics Inc. CYCLINE-DEPENDENT KINASE INHIBITORS
CN112876488B (zh) * 2021-02-18 2021-12-21 苏州大学 螺环吲哚啉衍生物及其制备方法和应用

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE52879B1 (en) 1981-05-12 1988-03-30 Ici Plc Pharmaceutical spiro-hydantoin derivatives
IE53102B1 (en) 1981-05-12 1988-06-22 Ici Plc Pharmaceutical spiro-succinimide derivatives
US5948807A (en) * 1997-09-03 1999-09-07 Regents Of The University Of Minnesota Spiroindanamines and Spiroindanimides
TR200102817T2 (tr) * 1999-03-12 2002-05-21 Boehringer Ingelheim Pharmaceuticals, Inc. Antiinflamatuar ajanlar olarak faydalı bileşikler
SE0200356D0 (sv) * 2002-02-05 2002-02-05 Astrazeneca Ab Novel use
SE0200411D0 (sv) * 2002-02-05 2002-02-05 Astrazeneca Ab Novel use
GB2388540A (en) 2002-05-17 2003-11-19 Bayer Ag New use of Ramatroban
PL376156A1 (en) 2002-10-04 2005-12-27 Millennium Pharmaceuticals, Inc. Pgd2 receptor antagonists for the treatment of inflammatory diseases
AU2003269327A1 (en) 2002-10-21 2004-05-04 Warner-Lambert Company Llc Tetrahydroquinoline derivatives as crth2 antagonists
DE60303238T2 (de) 2003-04-25 2006-09-14 Actimis Pharmaceuticals, Inc., La Jolla Pyrimidin-Essigsäure Derivate geeignet zur Behandlung von CRTH2-bedingten Krankheiten
SE0301569D0 (sv) 2003-05-27 2003-05-27 Astrazeneca Ab Novel compounds
SE0301650D0 (sv) 2003-06-04 2003-06-04 Astrazeneca Ab Novel compounds
SE0301653D0 (sv) 2003-06-05 2003-06-05 Astrazeneca Ab Novel compounds
US20050038070A1 (en) 2003-07-09 2005-02-17 Amgen Inc. Asthma and allergic inflammation modulators
WO2005102338A1 (en) 2004-04-20 2005-11-03 Pfizer Limited Method of treating neuropathic pain using a crth2 receptor antagonist

Also Published As

Publication number Publication date
AR055959A1 (es) 2007-09-12
MX2007014256A (es) 2008-03-26
CA2602965A1 (en) 2006-11-30
PT1891075E (pt) 2011-11-10
RU2478639C2 (ru) 2013-04-10
UA90145C2 (ru) 2010-04-12
CN101300259A (zh) 2008-11-05
WO2006125784A1 (en) 2006-11-30
DK1891075T3 (da) 2011-12-19
EP1891075A1 (en) 2008-02-27
KR20080031191A (ko) 2008-04-08
CN101300259B (zh) 2013-08-28
KR101333861B1 (ko) 2013-11-28
ZA200709819B (en) 2009-09-30
RU2007147430A (ru) 2009-06-27
EP1891075B1 (en) 2011-10-19
US20090318486A1 (en) 2009-12-24
JP2008542238A (ja) 2008-11-27
US8236963B2 (en) 2012-08-07
ES2375614T3 (es) 2012-03-02
PL1891075T3 (pl) 2011-12-30
AU2006251138A1 (en) 2006-11-30
ATE529429T1 (de) 2011-11-15
AU2006251138C1 (en) 2013-08-29
NZ562772A (en) 2010-01-29
JP5567268B2 (ja) 2014-08-06
AU2006251138B2 (en) 2012-08-09
BRPI0610209A2 (pt) 2010-06-01

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Legal Events

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EEER Examination request
MKLA Lapsed

Effective date: 20170523