CN101641329A - 具有5-ht6受体亲和力的6＇取代的吲哚和吲唑衍生物 - Google Patents

具有5-ht6受体亲和力的6＇取代的吲哚和吲唑衍生物 Download PDF

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Publication number
CN101641329A
CN101641329A CN200880005213A CN200880005213A CN101641329A CN 101641329 A CN101641329 A CN 101641329A CN 200880005213 A CN200880005213 A CN 200880005213A CN 200880005213 A CN200880005213 A CN 200880005213A CN 101641329 A CN101641329 A CN 101641329A
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China
Prior art keywords
alkylsulfonyl
base
piperazine
indoles
indazole
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Pending
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CN200880005213A
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English (en)
Chinese (zh)
Inventor
R·邓恩
T·M·源
W·王
A·郑一姆
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MEMORY PHARM CORP (US)
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MEMORY PHARM CORP (US)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • 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
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    • A61P25/06—Antimigraine agents
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Veterinary Medicine (AREA)
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  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Addiction (AREA)
  • Otolaryngology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
CN200880005213A 2007-02-16 2008-02-19 具有5-ht6受体亲和力的6＇取代的吲哚和吲唑衍生物 Pending CN101641329A (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US89032407P 2007-02-16 2007-02-16
US60/890,324 2007-02-16

Publications (1)

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CN101641329A true CN101641329A (zh) 2010-02-03

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CN200880005213A Pending CN101641329A (zh) 2007-02-16 2008-02-19 具有5-ht6受体亲和力的6＇取代的吲哚和吲唑衍生物

Country Status (10)

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US (1) US20080200471A1 (https=)
EP (1) EP2121603A2 (https=)
JP (1) JP2010519226A (https=)
KR (1) KR20100014413A (https=)
CN (1) CN101641329A (https=)
AU (1) AU2008216032A1 (https=)
BR (1) BRPI0807602A2 (https=)
CA (1) CA2674087A1 (https=)
MX (1) MX2009008324A (https=)
WO (1) WO2008101247A2 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108752342A (zh) * 2018-08-17 2018-11-06 西安瑞联新材料股份有限公司 1-H-吡啶并[1,2-a]-6-氢吡嗪-1,4-二酮的制备方法
CN110183383A (zh) * 2019-06-25 2019-08-30 深圳市格物致欣化学技术有限公司 3-醛基-1h-取代吲唑及其制备方法

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8318725B2 (en) 2008-09-17 2012-11-27 Suven Life Sciences Limited Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands
JO3250B1 (ar) 2009-09-22 2018-09-16 Novartis Ag إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7
FR2955110A1 (fr) 2010-01-08 2011-07-15 Fournier Lab Sa Nouveaux derives de type pyrrolopyridine benzoique
FR2955108B1 (fr) 2010-01-08 2012-03-16 Fournier Lab Sa Utilisation de derives de pyrrolopyridine comme activateurs de nurr-1, pour le traitement de la maladie de parkinson
EP3083588B1 (en) * 2013-12-20 2020-12-09 Sunshine Lake Pharma Co., Ltd. Aromatic heterocyclic compounds and their application in pharmaceuticals
EP3166924B1 (en) * 2014-07-08 2019-02-20 Sunshine Lake Pharma Co., Ltd. Aromatic heterocyclic derivatives and pharmaceutical applications thereof
DK3180001T3 (en) * 2014-08-16 2019-04-01 Suven Life Sciences Ltd ACTIVE METABOLITE OF 1 - [(2-BROMPHENYL) SULPHONYL] -5-METHOXY-3 - [(4-METHYL-1-PIPERAZINYL) METHYL] -1H-INDOL-DIMESYLATE-MONOHYDRATE AND DIMESYLATE-DIHYDRATE SALT

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6100291A (en) * 1998-03-16 2000-08-08 Allelix Biopharmaceuticals Inc. Pyrrolidine-indole compounds having 5-HT6 affinity
US6133287A (en) * 1998-03-24 2000-10-17 Allelix Biopharmaceuticals Inc. Piperidine-indole compounds having 5-HT6 affinity
US6251893B1 (en) * 1998-06-15 2001-06-26 Nps Allelix Corp. Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity
US6191141B1 (en) * 1999-08-12 2001-02-20 Nps Allelix Corp. Azaindoles having serotonin receptor affinity
US6686374B1 (en) * 1999-08-12 2004-02-03 Nps Allelix Corp. Azaindoles having serotonin receptor affinity
WO2001032660A1 (en) * 1999-11-05 2001-05-10 Nps Allelix Corp. Compounds having 5-ht6 receptor antagonist activity
US6897215B1 (en) * 1999-11-05 2005-05-24 Nps Allelix Corp. Compounds having 5-HT6 receptor antagonist activity
US7034029B2 (en) * 2000-11-02 2006-04-25 Wyeth 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands
JP4184077B2 (ja) * 2000-11-02 2008-11-19 ワイス ５−ヒドロキシトリプトアミン−６リガンドとしての１−アリールまたは１−アルキルスルホニル−ヘテロシクリルベンザゾール
WO2002041889A2 (en) * 2000-11-24 2002-05-30 Smithkline Beecham P.L.C. Indolsulfonyl compounds useful in the treatment of cns disorders
WO2002051837A2 (en) * 2000-12-22 2002-07-04 Wyeth Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands
BR0210929A (pt) * 2001-06-07 2004-06-08 Hoffmann La Roche Derivados de indol com afinidade para o receptor 5-ht6
GB0202679D0 (en) * 2002-02-05 2002-03-20 Glaxo Group Ltd Novel compounds
EP1984351A1 (en) * 2006-02-17 2008-10-29 Memory Pharmaceuticals Corporation Compounds having 5-ht6 receptor affinity

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108752342A (zh) * 2018-08-17 2018-11-06 西安瑞联新材料股份有限公司 1-H-吡啶并[1,2-a]-6-氢吡嗪-1,4-二酮的制备方法
CN110183383A (zh) * 2019-06-25 2019-08-30 深圳市格物致欣化学技术有限公司 3-醛基-1h-取代吲唑及其制备方法

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WO2008101247A3 (en) 2008-11-27
BRPI0807602A2 (pt) 2014-07-08
CA2674087A1 (en) 2008-08-21
AU2008216032A1 (en) 2008-08-21
KR20100014413A (ko) 2010-02-10
MX2009008324A (es) 2009-10-20
EP2121603A2 (en) 2009-11-25
JP2010519226A (ja) 2010-06-03
US20080200471A1 (en) 2008-08-21
WO2008101247A2 (en) 2008-08-21

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