SK6042003A3 - 3-Arylindole derivatives and their use as CB2 receptor agonists - Google Patents

3-Arylindole derivatives and their use as CB2 receptor agonists Download PDF

Info

Publication number: SK6042003A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; group; atom; nhso
Prior art date: 2000-11-22

Application number

SK604-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Francis Barth

Christian Congy

Carole Guillaumont

Murielle Rinaldi

Fabienne Vasse

Claude Vernhet

Original Assignee

Sanofi Synthelabo

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.)

2000-11-22

Filing date

2001-11-21

Publication date

2003-12-02

2001-11-21 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

2003-12-02 Publication of SK6042003A3 publication Critical patent/SK6042003A3/sk

Links

102000009135 CB2 Cannabinoid Receptor Human genes 0.000 title abstract description 4
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 title abstract description 4
239000000018 receptor agonist Substances 0.000 title 1
229940044601 receptor agonist Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 203
238000002360 preparation method Methods 0.000 claims abstract description 45
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
-1 nitro, hydroxyl Chemical group 0.000 claims description 92
238000000034 method Methods 0.000 claims description 78
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000005843 halogen group Chemical group 0.000 claims description 27
125000001309 chloro group Chemical group Cl* 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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SK604-2003A 2000-11-22 2001-11-21 3-Arylindole derivatives and their use as CB2 receptor agonists SK6042003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0015158A FR2816938B1 (fr)	2000-11-22	2000-11-22	Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant
PCT/FR2001/003665 WO2002042269A1 (fr)	2000-11-22	2001-11-21	Derives de 3-aroylindole et leur utilisation en tant qu'agonistes des recepteurs cb2

Publications (1)

Publication Number	Publication Date
SK6042003A3 true SK6042003A3 (en)	2003-12-02

Family

ID=8856819

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK604-2003A SK6042003A3 (en)	2000-11-22	2001-11-21	3-Arylindole derivatives and their use as CB2 receptor agonists

Country Status (32)

Country	Link
US (1)	US6995184B2 (de)
EP (1)	EP1339679B1 (de)
JP (1)	JP4264258B2 (de)
KR (1)	KR20030048161A (de)
CN (1)	CN1234688C (de)
AR (1)	AR033594A1 (de)
AT (1)	ATE301638T1 (de)
AU (1)	AU2002222001A1 (de)
BG (1)	BG107827A (de)
BR (1)	BR0115580A (de)
CA (1)	CA2427444A1 (de)
CZ (1)	CZ20031392A3 (de)
DE (1)	DE60112607T2 (de)
DK (1)	DK1339679T3 (de)
DZ (1)	DZ3443A1 (de)
EA (1)	EA005854B1 (de)
EE (1)	EE200300244A (de)
ES (1)	ES2247201T3 (de)
FR (1)	FR2816938B1 (de)
HR (1)	HRP20030417A2 (de)
HU (1)	HUP0400561A2 (de)
IL (1)	IL155634A0 (de)
IS (1)	IS6802A (de)
MA (1)	MA26959A1 (de)
MX (1)	MXPA03004549A (de)
NO (1)	NO20031952L (de)
NZ (1)	NZ525609A (de)
PL (1)	PL362276A1 (de)
SK (1)	SK6042003A3 (de)
TW (1)	TWI224592B (de)
WO (1)	WO2002042269A1 (de)
ZA (1)	ZA200303728B (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200407110A (en) *	2001-11-23	2004-05-16	Astrazeneca Ab	New use for the treatment of gastroesophageal reflux disease
EP1487436A4 (de)	2002-03-08	2009-06-03	Signal Pharm Inc	Kombinationstherapie zur behandlung, prävention oder versorgung von proliferativen erkrankungen und krebs
JP2006517194A (ja)	2002-06-06	2006-07-20	イッサムリサーチディベロップメントカンパニーオブザヘブリューユニバーシティオブエルサレム	骨成長を調節するための方法、組成物および製造物
AU2003257145B2 (en)	2002-08-02	2008-11-13	Merck Sharp & Dohme Corp.	Substituted furo (2,3-b) pyridine derivatives
FR2843964B1 (fr) *	2002-08-29	2004-10-01	Sanofi Synthelabo	Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique
FR2847899B1 (fr) *	2002-11-29	2006-04-28	Sanofi Synthelabo	Derives d'indole-3-carboxamide, leur preparation et leur application en therapeutique
FR2854633B1 (fr) *	2003-05-07	2005-06-24	Sanofi Synthelabo	Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique
FR2856684B1 (fr) *	2003-06-26	2008-04-11	Sanofi Synthelabo	Derives de diphenylpyridine, leur preparation et leur application en therapeutique
FR2865205B1 (fr) *	2004-01-16	2006-02-24	Sanofi Synthelabo	Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique
EP1758566A2 (de) *	2004-06-22	2007-03-07	Pharmos Limited	Verwendung von agonisten des cb-2-rezeptors zur behandlung von chorea huntington
CN101014605A (zh)	2004-07-12	2007-08-08	卡地拉健康护理有限公司	用作大麻素受体调节物的三环吡唑衍生物
US20060025448A1 (en)	2004-07-22	2006-02-02	Cadila Healthcare Limited	Hair growth stimulators
CA2587210A1 (en) *	2004-11-22	2006-06-01	Threshold Pharmaceuticals, Inc.	Tubulin binding anti cancer agents and prodrugs thereof
US7560481B2 (en)	2004-12-21	2009-07-14	Abbott Laboratories	Indoles are cannabinoid receptor ligands
FR2893615B1 (fr) *	2005-11-18	2008-03-07	Sanofi Aventis Sa	Derives de 3-acylindole, leur preparation et leur application en therapeutique
RU2306906C1 (ru) *	2006-04-21	2007-09-27	Федеральное государственное учреждение "Межотраслевой научно-технический комплекс "Микрохирургия глаза" имени академика С.Н. Федорова Федерального агентства по здравоохранению и социальному развитию"	Способ повышения зрительных функций при сублюксации хрусталика в случаях нарушения обмена в системе соединительной ткани
WO2007140439A2 (en)	2006-05-31	2007-12-06	Abbott Laboratories	Compounds as cannabinoid receptor ligands and uses thereof
US8841334B2 (en)	2006-05-31	2014-09-23	Abbvie Inc.	Compounds as cannabinoid receptor ligands and uses thereof
GB0702862D0 (en) *	2007-02-14	2007-03-28	Univ Aberdeen	Therapeutic compounds
EP2142522A1 (de)	2007-03-28	2010-01-13	Abbott Laboratories	1,3-thiazol-2(3h)-ylidene verbindungen als cannabinoid rezeptor liganden
US7872033B2 (en)	2007-04-17	2011-01-18	Abbott Laboratories	Compounds as cannabinoid receptor ligands
FR2915199B1 (fr) *	2007-04-18	2010-01-22	Sanofi Aventis	Derives de triazolopyridine-carboxamides et triazolopyrimidine-carboxamides, leur preparation et leur application en therapeutique.
MX2009012374A (es) *	2007-05-18	2009-12-01	Abbott Lab	Compuestos novedosos como ligandos del receptor de canabinoides.
US9193713B2 (en)	2007-10-12	2015-11-24	Abbvie Inc.	Compounds as cannabinoid receptor ligands
FR2933697B1 (fr) *	2008-07-11	2010-08-13	Sanofi Aventis	Derives de 1-benzyl-cinnolin-4-(1h)-one substitues, leur preparation et leur application en therapeutique
US8846730B2 (en)	2008-09-08	2014-09-30	Abbvie Inc.	Compounds as cannabinoid receptor ligands
US8859596B2 (en)	2008-09-16	2014-10-14	Abbvie Inc.	Compounds as cannabinoid receptor ligands
PA8854001A1 (es)	2008-12-16	2010-07-27	Abbott Lab	Compuestos novedosos como ligandos de receptores de canabinoides
FR2941696B1 (fr)	2009-02-05	2011-04-15	Sanofi Aventis	Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique
FR2945533B1 (fr)	2009-05-12	2011-05-27	Sanofi Aventis	Derives de cyclopenta°c!pyrrolyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique
EP2456428A1 (de)	2009-07-23	2012-05-30	INSERM - Institut National de la Santé et de la Recherche Médicale	Selektive cb2-rezeptoragonisten zur prävention oder behandlung von alkoholbedingten lebererkrankungen
FR2950055A1 (fr)	2009-09-17	2011-03-18	Sanofi Aventis	Derives de 3-amino-cinnolin-4(1h)-one substitues, leur preparation et leur application en therapeutique
US20130178453A1 (en) *	2010-02-09	2013-07-11	Ironwood Pharmaceuticals, Inc.	Cannabinoid Agonists
FR2983859B1 (fr)	2011-12-12	2014-01-17	Sanofi Sa	Derives de 1,3,5-triazine-2-amine, leur preparation et leur application en diagnostique et en therapeutique
AP2016009270A0 (en) *	2013-11-28	2016-06-30	Commw Scient Ind Res Org	Method of detecting plasmodium infection
CN108794379A (zh) *	2017-04-26	2018-11-13	华东师范大学	1h-吲哚-2-甲酰胺衍生物及其制备方法和应用
WO2022128050A1 (en)	2020-12-14	2022-06-23	Symrise Ag	Medicament for fighting inflammation and pain

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5532237A (en) *	1995-02-15	1996-07-02	Merck Frosst Canada, Inc.	Indole derivatives with affinity for the cannabinoid receptor
FR2735774B1 (fr) *	1995-06-21	1997-09-12	Sanofi Sa	Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant
AU1095101A (en) *	1999-10-18	2001-04-30	University Of Connecticut, The	Cannabimimetic indole derivatives

2000
- 2000-11-22 FR FR0015158A patent/FR2816938B1/fr not_active Expired - Fee Related
2001
- 2001-11-21 AU AU2002222001A patent/AU2002222001A1/en not_active Abandoned
- 2001-11-21 EA EA200300453A patent/EA005854B1/ru not_active IP Right Cessation
- 2001-11-21 EE EEP200300244A patent/EE200300244A/xx unknown
- 2001-11-21 AT AT01997476T patent/ATE301638T1/de not_active IP Right Cessation
- 2001-11-21 CZ CZ20031392A patent/CZ20031392A3/cs unknown
- 2001-11-21 CN CNB018211755A patent/CN1234688C/zh not_active Expired - Fee Related
- 2001-11-21 US US10/416,617 patent/US6995184B2/en not_active Expired - Fee Related
- 2001-11-21 JP JP2002544405A patent/JP4264258B2/ja not_active Expired - Fee Related
- 2001-11-21 HR HR20030417A patent/HRP20030417A2/hr not_active Application Discontinuation
- 2001-11-21 DK DK01997476T patent/DK1339679T3/da active
- 2001-11-21 DE DE60112607T patent/DE60112607T2/de not_active Expired - Lifetime
- 2001-11-21 MX MXPA03004549A patent/MXPA03004549A/es active IP Right Grant
- 2001-11-21 DZ DZ013443A patent/DZ3443A1/fr active
- 2001-11-21 NZ NZ525609A patent/NZ525609A/en unknown
- 2001-11-21 PL PL01362276A patent/PL362276A1/xx not_active Application Discontinuation
- 2001-11-21 KR KR10-2003-7006862A patent/KR20030048161A/ko not_active Withdrawn
- 2001-11-21 BR BR0115580-6A patent/BR0115580A/pt not_active IP Right Cessation
- 2001-11-21 IL IL15563401A patent/IL155634A0/xx unknown
- 2001-11-21 HU HU0400561A patent/HUP0400561A2/hu unknown
- 2001-11-21 CA CA002427444A patent/CA2427444A1/fr not_active Abandoned
- 2001-11-21 ES ES01997476T patent/ES2247201T3/es not_active Expired - Lifetime
- 2001-11-21 AR ARP010105425A patent/AR033594A1/es not_active Application Discontinuation
- 2001-11-21 WO PCT/FR2001/003665 patent/WO2002042269A1/fr not_active Ceased
- 2001-11-21 EP EP01997476A patent/EP1339679B1/de not_active Expired - Lifetime
- 2001-11-21 SK SK604-2003A patent/SK6042003A3/sk unknown
- 2001-11-22 TW TW090128947A patent/TWI224592B/zh active
2003
- 2003-04-29 NO NO20031952A patent/NO20031952L/no unknown
- 2003-04-30 IS IS6802A patent/IS6802A/is unknown
- 2003-05-13 MA MA27157A patent/MA26959A1/fr unknown
- 2003-05-14 ZA ZA200303728A patent/ZA200303728B/en unknown
- 2003-05-19 BG BG107827A patent/BG107827A/bg unknown

Also Published As

Publication number	Publication date
ES2247201T3 (es)	2006-03-01
PL362276A1 (en)	2004-10-18
DK1339679T3 (da)	2005-12-12
NZ525609A (en)	2004-11-26
EP1339679A1 (de)	2003-09-03
MA26959A1 (fr)	2004-12-20
BG107827A (bg)	2004-01-30
NO20031952L (no)	2003-07-22
EA200300453A1 (ru)	2003-10-30
US6995184B2 (en)	2006-02-07
FR2816938A1 (fr)	2002-05-24
ZA200303728B (en)	2004-05-14
EA005854B1 (ru)	2005-06-30
FR2816938B1 (fr)	2003-01-03
DZ3443A1 (fr)	2002-05-30
EP1339679B1 (de)	2005-08-10
NO20031952D0 (no)	2003-04-29
US20040034090A1 (en)	2004-02-19
AU2002222001A1 (en)	2002-06-03
CN1483023A (zh)	2004-03-17
AR033594A1 (es)	2003-12-26
KR20030048161A (ko)	2003-06-18
CZ20031392A3 (cs)	2003-09-17
CN1234688C (zh)	2006-01-04
EE200300244A (et)	2003-10-15
MXPA03004549A (es)	2004-03-26
JP2004514668A (ja)	2004-05-20
JP4264258B2 (ja)	2009-05-13
DE60112607D1 (de)	2005-09-15
HRP20030417A2 (en)	2003-08-31
DE60112607T2 (de)	2006-06-14
TWI224592B (en)	2004-12-01
ATE301638T1 (de)	2005-08-15
BR0115580A (pt)	2003-09-09
CA2427444A1 (fr)	2002-05-30
WO2002042269A1 (fr)	2002-05-30
IL155634A0 (en)	2003-11-23
IS6802A (is)	2003-04-30
HUP0400561A2 (hu)	2004-07-28

Publication	Publication Date	Title
SK6042003A3 (en)	2003-12-02	3-Arylindole derivatives and their use as CB2 receptor agonists
RU2200736C2 (ru)	2003-03-20	Применение соединений-агонистов человеческого рецептора cb2 для получения лекарственных иммуномодуляторов, новые соединения-агонисты рецептора cb2 и фармацевтические композиции на их основе
Yee et al.	1990	A novel series of selective leukotriene antagonists: exploration and optimization of the acidic region in 1, 6-disubstituted indoles and indazoles
CZ307144B6 (cs)	2018-02-07	Indolylmaleinimidová sloučenina, způsob její přípravy, její použití jako léčivo a farmaceutická kompozice obsahující tuto sloučeninu
JPH07165708A (ja)	1995-06-27	二環式ヘテロ環含有スルホンアミドおよびスルホン酸エステル誘導体
WO2001017963A2 (en)	2001-03-15	Aminoalkoxy carbazoles and their use as 5-ht ligands
IE60013B1 (en)	1994-05-18	Heterocyclic carboxamides
JPH05163240A (ja)	1993-06-29	置換ジアミノフタルイミドおよび同族体
EP1507758B1 (de)	2005-11-02	Indolderivate und deren verwendung als liganden der receptoren cb2
CZ20022603A3 (cs)	2002-10-16	4-fenyl-1-piperazinylové deriváty
US4898863A (en)	1990-02-06	Heterocyclic carboxamides
JP2003519683A (ja)	2003-06-24	Ｍｃｐ−１受容体アンタゴニストとしてのインドール誘導体
US20080275102A1 (en)	2008-11-06	3-acylindole derivatives, preparation and therapeutic use thereof
JP2001525398A (ja)	2001-12-11	選択的β３アドレナリン作動性アゴニスト