KR101376479B1 - 뮤 오피오이드 수용체 안타고니스트인 8­아자비시클로[3.2.1]옥탄 화합물 - Google Patents

뮤 오피오이드 수용체 안타고니스트인 8­아자비시클로[3.2.1]옥탄 화합물 Download PDF

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KR101376479B1
KR101376479B1 KR1020087024027A KR20087024027A KR101376479B1 KR 101376479 B1 KR101376479 B1 KR 101376479B1 KR 1020087024027 A KR1020087024027 A KR 1020087024027A KR 20087024027 A KR20087024027 A KR 20087024027A KR 101376479 B1 KR101376479 B1 KR 101376479B1
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endo
azabicyclo
oct
ethyl
benzamide
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KR20080100282A (ko
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다니엘 롱
티모시 제이. 쳐치
존 알. 야콥센
란 지앙
다이스케 롤랜드 사이토
이오안나 스터지아데스
다이크 프리실라 반
션 달지엘
레티샤 프레자
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세라밴스 인코포레이티드
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Assigned to 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 reassignment 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 권리의 전부이전등록 Assignors: 세라밴스 인코포레이티드
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/439Heterocyclic 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 the ring forming part of a bridged ring system, e.g. quinuclidine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/468-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/485Morphinan derivatives, e.g. morphine, codeine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10Laxatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents

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  • 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)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
KR1020087024027A 2006-03-01 2007-02-28 뮤 오피오이드 수용체 안타고니스트인 8­아자비시클로[3.2.1]옥탄 화합물 Active KR101376479B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US77796206P 2006-03-01 2006-03-01
US60/777,962 2006-03-01
US84102806P 2006-08-30 2006-08-30
US60/841,028 2006-08-30
PCT/US2007/005388 WO2007103187A2 (en) 2006-03-01 2007-02-28 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists

Publications (2)

Publication Number Publication Date
KR20080100282A KR20080100282A (ko) 2008-11-14
KR101376479B1 true KR101376479B1 (ko) 2014-03-27

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Country Link
US (11) US7622508B2 (https=)
EP (1) EP2001876B1 (https=)
JP (2) JP5086280B2 (https=)
KR (1) KR101376479B1 (https=)
AR (1) AR059690A1 (https=)
AT (1) ATE509928T1 (https=)
AU (1) AU2007224213B2 (https=)
BR (1) BRPI0708490B8 (https=)
CA (1) CA2646409C (https=)
CY (1) CY1111747T1 (https=)
DK (1) DK2001876T3 (https=)
HR (1) HRP20110590T1 (https=)
IL (1) IL193690A (https=)
MA (1) MA30284B1 (https=)
MX (1) MX2008011165A (https=)
MY (1) MY145633A (https=)
NZ (1) NZ570764A (https=)
PE (1) PE20071311A1 (https=)
PL (1) PL2001876T3 (https=)
PT (1) PT2001876E (https=)
RU (1) RU2423362C2 (https=)
SI (1) SI2001876T1 (https=)
TW (1) TWI379832B (https=)
WO (1) WO2007103187A2 (https=)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY145633A (en) 2006-03-01 2012-03-15 Theravance Inc 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
TWI409067B (zh) 2007-02-28 2013-09-21 Theravance Inc 8-氮雜雙環〔3.2.1〕辛烷化合物之結晶型
TWI415850B (zh) * 2007-07-20 2013-11-21 Theravance Inc 製備mu類鴉片受體拮抗劑之中間物的方法
ATE502939T1 (de) * 2007-08-27 2011-04-15 Theravance Inc Disubstituierte alkyl-8-azabicycloä3.2.1üoktan- verbindungen als mu-opioid-rezeptorantagonisten
EP2195313B1 (en) * 2007-08-27 2014-04-02 Theravance, Inc. Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
TWI423801B (zh) * 2007-08-27 2014-01-21 Theravance Inc 作為μ類鴉片受體拮抗劑之8-氮雜雙環〔3.2.1〕辛基-2-羥基苯甲醯胺化合物
ES2390195T3 (es) * 2007-08-27 2012-11-07 Theravance, Inc. Compuestos de amidoalquil-8-azabiciclo(3,2,1)octano, como antagonistas del receptor opioide mu
CA2774021A1 (en) * 2009-09-18 2011-03-24 Adolor Corporation Use of opioid receptor antagonist for gastrointestinal tract disorders
US20120122928A1 (en) 2010-08-11 2012-05-17 Bayer Cropscience Ag Heteroarylpiperidine and -Piperazine Derivatives as Fungicides
US8759527B2 (en) 2010-08-25 2014-06-24 Bayer Cropscience Ag Heteroarylpiperidine and -piperazine derivatives as fungicides
EP2423210A1 (de) 2010-08-25 2012-02-29 Bayer CropScience AG Heteroarylpiperidin- und -piperazinderivate als Fungizide
PE20141002A1 (es) 2010-10-27 2014-08-17 Bayer Ip Gmbh Derivados de heteroarilpiperidina y -piperazina como fungicidas
JP5703009B2 (ja) * 2010-12-16 2015-04-15 住友精化株式会社 スルホン化合物、スルホン化合物の製造方法、および電気化学デバイス用電解液
KR101848116B1 (ko) 2011-02-01 2018-04-11 바이엘 인텔렉쳐 프로퍼티 게엠베하 살진균제로서의 헤테로아릴 피페리딘 및 헤테로아릴 피페라진 유도체
ES2661849T3 (es) 2011-09-15 2018-04-04 Bayer Intellectual Property Gmbh Piperidinpirazoles como fungicidas
DK2921493T3 (da) 2011-12-27 2017-11-27 Bayer Ip Gmbh Heteroarylpiperidin og ¿piperazinderivater
CA2875384A1 (en) 2013-12-20 2015-06-20 AntiOP, Inc. Intranasal naloxone compositions and methods of making and using same
HK1247105A1 (zh) 2015-04-02 2018-09-21 Theravance Biopharma R&D Ip, Llc Mu类鸦片受体拮抗剂与类鸦片药剂的组合剂型
SG11202007422QA (en) 2018-02-05 2020-09-29 Alkermes Inc Compounds for the treatment of pain
KR20230154789A (ko) * 2020-11-06 2023-11-09 액티노젠 메디컬 리미티드 헤테로고리 메탄온 화합물 및 그의 아자-비시클로 중간체의 제조 공정

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004089908A2 (en) * 2003-04-14 2004-10-21 Pfizer Products Inc. 3-azabicyclo[3.2.1]octane derivatives

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1067824B (de) * 1954-10-20 1959-10-29 Sandoz Ag Verfahren zur Herstellung saeureamidartiger Tropanabkoemmlinge
US5159081A (en) 1991-03-29 1992-10-27 Eli Lilly And Company Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists
UA58476C2 (uk) * 1997-10-09 2003-08-15 Санофі-Сентелябо Похідні 8-азабіцикло[3.2.1]октан-3-метанаміну, фармацевтична композиція та лікарський засіб
US6900228B1 (en) 1998-03-10 2005-05-31 Research Triangle Institute Opiate compounds, methods of making and methods of use
GB9810671D0 (en) 1998-05-18 1998-07-15 Pfizer Ltd Anti-pruritic agents
TWI244481B (en) 1998-12-23 2005-12-01 Pfizer 3-azabicyclo[3.1.0]hexane derivatives useful in therapy
GB9912410D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
US6469030B2 (en) 1999-11-29 2002-10-22 Adolor Corporation Methods for the treatment and prevention of ileus
IL151550A0 (en) 2000-03-03 2003-04-10 Ortho Mcneil Pharm Inc 3-(diarylmethylene)-8-azabicyclo [3.2.1] octane derivatives
US20030181447A1 (en) * 2001-02-22 2003-09-25 Boyd Robert E. 3-(Diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives
US20020025948A1 (en) 2000-06-23 2002-02-28 Banks Bernard Joseph 3-azabicyclo[3.1.0]hexane derivatives useful in therapy
EP1443046B1 (en) 2001-10-09 2008-12-17 Kyorin Pharmaceutical Co., Ltd. Novel 4-(2furoyl)aminopiperidines, intermediates in synthesizing the same, process for producing the same and medicinal use of the same
EA006708B1 (ru) 2001-10-22 2006-02-24 Пфайзер Продактс Инк. Производные 3-азабицикло (3.1.0) гексана в качестве антагонистов опиоидного рецептора
US7381721B2 (en) 2003-03-17 2008-06-03 Adolor Corporation Substituted piperidine compounds
US7056930B2 (en) * 2003-04-14 2006-06-06 Pfizer Inc. 2-Azabicyclo[3.3.1]nonane derivatives
US20040204453A1 (en) 2003-04-14 2004-10-14 Pfizer Inc 4-Phenyl-piperidine compounds and their use as modulators of opioid receptors
JP2006523673A (ja) 2003-04-15 2006-10-19 ファイザー・プロダクツ・インク オピオイド受容体活性を有する3−ベンズヒドリリデン−8−アザ−ビシクロ[3.2.1]オクタン誘導体
US6992090B2 (en) 2003-06-16 2006-01-31 Adolor Corporation Substituted piperidine compounds and methods of their use
US7435822B2 (en) 2004-02-03 2008-10-14 Janssen Pharmaceutica N.V. 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1]octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1]octane derivatives
US7087749B2 (en) 2004-03-11 2006-08-08 Adolor Corporation Substituted piperidine compounds and methods of their use
US7538110B2 (en) 2005-10-27 2009-05-26 Adolor Corporation Opioid antagonists
MY145633A (en) 2006-03-01 2012-03-15 Theravance Inc 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
AU2007317788B2 (en) 2006-11-07 2013-05-02 Nektar Therapeutics Dosage forms and co-administration of an opioid agonist and an opioid antagonist
TWI409067B (zh) * 2007-02-28 2013-09-21 Theravance Inc 8-氮雜雙環〔3.2.1〕辛烷化合物之結晶型
TWI415850B (zh) * 2007-07-20 2013-11-21 Theravance Inc 製備mu類鴉片受體拮抗劑之中間物的方法
EP2195313B1 (en) * 2007-08-27 2014-04-02 Theravance, Inc. Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists
TWI423801B (zh) * 2007-08-27 2014-01-21 Theravance Inc 作為μ類鴉片受體拮抗劑之8-氮雜雙環〔3.2.1〕辛基-2-羥基苯甲醯胺化合物
ES2390195T3 (es) 2007-08-27 2012-11-07 Theravance, Inc. Compuestos de amidoalquil-8-azabiciclo(3,2,1)octano, como antagonistas del receptor opioide mu
ATE502939T1 (de) * 2007-08-27 2011-04-15 Theravance Inc Disubstituierte alkyl-8-azabicycloä3.2.1üoktan- verbindungen als mu-opioid-rezeptorantagonisten

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004089908A2 (en) * 2003-04-14 2004-10-21 Pfizer Products Inc. 3-azabicyclo[3.2.1]octane derivatives

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AR059690A1 (es) 2008-04-23
WO2007103187A3 (en) 2007-11-01
US8927573B2 (en) 2015-01-06
EP2001876B1 (en) 2011-05-18
US20070219278A1 (en) 2007-09-20
CA2646409C (en) 2015-11-10
DK2001876T3 (da) 2011-08-29
NZ570764A (en) 2011-08-26
US20190308966A1 (en) 2019-10-10
JP5086280B2 (ja) 2012-11-28
PL2001876T3 (pl) 2011-10-31
BRPI0708490B1 (pt) 2019-07-30
RU2008138875A (ru) 2010-04-10
US8263618B2 (en) 2012-09-11
JP2009528371A (ja) 2009-08-06
US20100035921A1 (en) 2010-02-11
AU2007224213B2 (en) 2012-06-14
US10745394B2 (en) 2020-08-18
US20230183232A1 (en) 2023-06-15
US20150291579A1 (en) 2015-10-15
HRP20110590T1 (hr) 2011-09-30
EP2001876A2 (en) 2008-12-17
IL193690A (en) 2013-02-28
IL193690A0 (en) 2009-08-03
US20160176863A1 (en) 2016-06-23
US7622508B2 (en) 2009-11-24
CA2646409A1 (en) 2007-09-13
ATE509928T1 (de) 2011-06-15
US10081626B2 (en) 2018-09-25
BRPI0708490A2 (pt) 2011-05-31
US10377751B2 (en) 2019-08-13
KR20080100282A (ko) 2008-11-14
PT2001876E (pt) 2011-08-18
HK1125935A1 (en) 2009-08-21
TWI379832B (en) 2012-12-21
TW200800981A (en) 2008-01-01
MY145633A (en) 2012-03-15
US9206172B2 (en) 2015-12-08
US11548887B2 (en) 2023-01-10
US8664242B2 (en) 2014-03-04
US20190119267A1 (en) 2019-04-25
JP2012211193A (ja) 2012-11-01
MA30284B1 (fr) 2009-03-02
WO2007103187A2 (en) 2007-09-13
SI2001876T1 (sl) 2011-09-30
BRPI0708490B8 (pt) 2021-05-25
US20130158060A1 (en) 2013-06-20
RU2423362C2 (ru) 2011-07-10
US20210024515A1 (en) 2021-01-28
US20140288112A1 (en) 2014-09-25
US20170349578A1 (en) 2017-12-07
AU2007224213A1 (en) 2007-09-13
US9663509B2 (en) 2017-05-30
PE20071311A1 (es) 2007-12-29
CY1111747T1 (el) 2015-10-07
MX2008011165A (es) 2008-09-15

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