ZA200606479B - Indazole-carboxamide compounds as 5-HT4 receptor agonists - Google Patents

Indazole-carboxamide compounds as 5-HT4 receptor agonists Download PDF

Info

Publication number: ZA200606479B
Authority: ZA; South Africa
Prior art keywords: indazole; carboxylic acid; azabicyclo; amide; isopropyl
Prior art date: 2004-02-18

Application number

ZA200606479A

Other languages

English (en)

Inventor

Marquess Daniel

Paul R Fatheree

Adam A Goldblum

Turner S Derek

Choi Seok-Ki

Gendron Roland

Daniel D Long

Liu Jyanwei

Original Assignee

Theravance Inc

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.)

2004-02-18

Filing date

2006-08-03

Publication date

2008-01-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34886184&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200606479(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-08-03 Application filed by Theravance Inc filed Critical Theravance Inc

2008-01-30 Publication of ZA200606479B publication Critical patent/ZA200606479B/en

Links

108091005482 5-HT4 receptors Proteins 0.000 title claims description 6
239000000018 receptor agonist Substances 0.000 title description 10
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FHUPHXAYPNYFIU-UHFFFAOYSA-N 1-propan-2-ylindazole-3-carboxylic acid Chemical compound C1=CC=C2N(C(C)C)N=C(C(O)=O)C2=C1 FHUPHXAYPNYFIU-UHFFFAOYSA-N 0.000 claims description 65
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 58
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- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
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- 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
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- A—HUMAN NECESSITIES
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- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- C07D451/02—Heterocyclic 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
- C07D451/04—Heterocyclic 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 with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
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- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
- G01N2333/705—Assays involving receptors, cell surface antigens or cell surface determinants
- G01N2333/70571—Assays involving receptors, cell surface antigens or cell surface determinants for neuromediators, e.g. serotonin receptor, dopamine receptor

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ZA200606479A 2004-02-18 2006-08-03 Indazole-carboxamide compounds as 5-HT4 receptor agonists ZA200606479B (en)

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EP (1)	EP1718643A1 (zh)
JP (1)	JP2007523175A (zh)
KR (1)	KR20060132727A (zh)
CN (1)	CN1922175A (zh)
AR (1)	AR047681A1 (zh)
AU (1)	AU2005214368A1 (zh)
BR (1)	BRPI0507791A (zh)
CA (1)	CA2553696A1 (zh)
IL (1)	IL177059A0 (zh)
MA (1)	MA28435B1 (zh)
NO (1)	NO20064156L (zh)
RU (1)	RU2006133320A (zh)
TW (1)	TW200533348A (zh)
WO (1)	WO2005080389A1 (zh)
ZA (1)	ZA200606479B (zh)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200533348A (en) *	2004-02-18	2005-10-16	Theravance Inc	Indazole-carboxamide compounds as 5-ht4 receptor agonists
US7728006B2 (en) *	2004-04-07	2010-06-01	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
US8309575B2 (en)	2004-04-07	2012-11-13	Theravance, Inc.	Quinolinone-carboxamide compounds as 5-HT4 receptor agonists
TWI351282B (en)	2004-04-07	2011-11-01	Theravance Inc	Quinolinone-carboxamide compounds as 5-ht4 recepto
ES2327142T3 (es) *	2004-11-05	2009-10-26	Theravance, Inc.	Compuestos de quinolinona-carboxamida.
DE602005016446D1 (de) *	2004-11-05	2009-10-15	Theravance Inc	5-HT4-Rezeptoragonistenverbindungen
KR20070091665A (ko) *	2004-12-22	2007-09-11	세라밴스 인코포레이티드	인다졸－카르복사미드 화합물
TW200640921A (en) *	2005-02-17	2006-12-01	Theravance Inc	Crystalline form of an indazole-carboxamide compound
US7446114B2 (en) *	2005-03-02	2008-11-04	Theravance, Inc.	Quinolinone compounds as 5-HT4 receptor agonists
WO2006133104A2 (en) *	2005-06-07	2006-12-14	Theravance, Inc.	Benzoimidazolone-carboxamide compounds as 5-ht4 receptor agonists
WO2007102883A2 (en) *	2005-10-25	2007-09-13	Smithkline Beecham Corporation	Chemical compounds
MY143574A (en) *	2005-11-22	2011-05-31	Theravance Inc	Carbamate compounds as 5-ht4 receptor agonists
GB0525068D0 (en)	2005-12-08	2006-01-18	Novartis Ag	Organic compounds
ATE509021T1 (de)	2006-02-16	2011-05-15	Theravance Inc	Verfahren zur herstellung von zwischenverbindungen zu 5-ht4-rezeptoragonist- verbindungen
KR100812499B1 (ko) *	2006-10-16	2008-03-11	이도훈	항경련제
WO2008101728A1 (de) *	2007-02-23	2008-08-28	K.H.S. Pharma Holding Gmbh	Verfahren zur herstellung von azoniaspironortropinestern und von nortropan-3-on verbindungen
MX2010008818A (es) *	2008-02-13	2010-09-07	Eisai R&D Man Co Ltd	Derivado de bicicloamina.
US8349852B2 (en)	2009-01-13	2013-01-08	Novartis Ag	Quinazolinone derivatives useful as vanilloid antagonists
WO2011092293A2 (en)	2010-02-01	2011-08-04	Novartis Ag	Cyclohexyl amide derivatives as crf receptor antagonists
WO2011092290A1 (en)	2010-02-01	2011-08-04	Novartis Ag	Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists
US8835444B2 (en)	2010-02-02	2014-09-16	Novartis Ag	Cyclohexyl amide derivatives as CRF receptor antagonists
CA2789663C (en) *	2010-02-12	2018-10-02	Raqualia Pharma Inc.	5-ht4 receptor agonists for the treatment of dementia
US8546416B2 (en)	2011-05-27	2013-10-01	Novartis Ag	3-spirocyclic piperidine derivatives as ghrelin receptor agonists
KR20140041519A (ko) *	2011-06-07	2014-04-04	다이닛본 스미토모 세이야꾸 가부시끼가이샤	인다졸-유도체 및 피롤로피리딘-유도체 및 그의 약제학적 용도
SG11201405810UA (en)	2012-05-03	2014-11-27	Novartis Ag	L-malate salt of 2, 7 - diaza - spiro [4.5 ] dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists
JP2014133739A (ja) *	2012-12-12	2014-07-24	Dainippon Sumitomo Pharma Co Ltd	インダゾール誘導体またはピロロピリジン誘導体からなる医薬
NZ728918A (en) *	2014-08-16	2018-05-25	Suven Life Sciences Ltd	Process for large scale production of 1-isopropyl-3-{ 5-[1-(3-methoxypropyl)piperidin-4-yl]-[1,3,4]oxadiazol-2-yl} -1h-indazole oxalate
CN112805282A (zh) *	2019-09-12	2021-05-14	广东东阳光药业有限公司	吲唑-甲酰胺衍生物及其用途

Family Cites Families (61)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4321378A (en) *	1979-01-16	1982-03-23	Delalande S.A.	8-(5-Pyrimidinecarboxamide)nor-tropane derivatives
US4937247A (en) *	1985-04-27	1990-06-26	Beecham Group P.L.C.	1-acyl indazoles
GB8527052D0 (en) *	1985-11-02	1985-12-04	Beecham Group Plc	Compounds
HU202108B (en) *	1986-07-30	1991-02-28	Sandoz Ag	Process for producing pharmaceutical compositions containing serotonine antqgonistic derivatives of indol-carboxylic acid or imidazolyl-methyl-carbazol
DE3777805D1 (de) *	1986-11-21	1992-04-30	Glaxo Group Ltd	Arzneimittel zur behandlung oder vorbeugung des entzugssyndromes.
GB8701022D0 (en) *	1987-01-19	1987-02-18	Beecham Group Plc	Treatment
US5223511A (en) *	1987-09-23	1993-06-29	Boehringer Ingelheim Italia S.P.A.	Benzimidazoline-2-oxo-1-carboxylic acid compounds useful as 5-HT receptor antagonists
IT1231413B (it)	1987-09-23	1991-12-04	Angeli Inst Spa	Derivati dell'acido benzimidazolin-2-osso-1-carbossilico utili come antagonisti dei recettori 5-ht
IT1226389B (it) *	1988-07-12	1991-01-15	Angeli Inst Spa	Nuovi derivati ammidinici e guanidinici
NZ230068A (en) *	1988-07-29	1991-07-26	Dainippon Pharmaceutical Co	Indazole-3-carboxylic acid esters and amides of diaza compounds having 6,7, or 8 ring members: preparatory processes and pharmaceutical compositions
EP0410509A1 (en) *	1989-07-25	1991-01-30	Duphar International Research B.V	New substituted 1H-indazole-3-carboxamides
JPH045289A (ja)	1990-04-24	1992-01-09	Hokuriku Seiyaku Co Ltd	アミド化合物
JP3122671B2 (ja) *	1990-05-23	2001-01-09	協和醗酵工業株式会社	複素環式化合物
HU211081B (en) *	1990-12-18	1995-10-30	Sandoz Ag	Process for producing indole derivatives as serotonin antagonists and pharmaceutical compositions containing the same
DE69113284T2 (de) *	1990-12-28	1996-02-22	Kyowa Hakko Kogyo Co., Ltd., Tokio/Tokyo	Chinolinderivat.
EP0600955A1 (en)	1991-08-20	1994-06-15	Smithkline Beecham Plc	5-ht4 receptor antagonists
AU2491092A (en) *	1991-09-12	1993-04-05	Smithkline Beecham Plc	Azabicyclic compounds as 5-ht4 receptor antagonists
MX9305947A (es) *	1992-09-29	1994-06-30	Smithkline Beecham Plc	Compuestos antagonistas del receptor 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que las contienen.
AU5161593A (en) *	1992-11-20	1994-06-22	Taisho Pharmaceutical Co., Ltd.	Heterocyclic compound
TW251287B (zh)	1993-04-30	1995-07-11	Nissei Co Ltd
GB9310582D0 (en) *	1993-05-22	1993-07-07	Smithkline Beecham Plc	Pharmaceuticals
WO1995023147A1 (fr) *	1994-02-28	1995-08-31	Taisho Pharmaceutical Co., Ltd.	Compose heterocyclique
US5864039A (en) *	1994-03-30	1999-01-26	Yoshitomi Pharmaceutical Industries, Ltd.	Benzoic acid compounds and use thereof as medicaments
GB9406857D0 (en) *	1994-04-07	1994-06-01	Sandoz Ltd	Improvements in or relating to organic compounds
JP3829879B2 (ja) *	1994-05-18	2006-10-04	大正製薬株式会社	キノリンカルボン酸誘導体
US5684003A (en) *	1994-10-20	1997-11-04	Nisshin Flour Milling Co., Ltd.	5-HT4 receptor agonists
JP3829880B2 (ja)	1994-12-27	2006-10-04	大正製薬株式会社	化学中間体
IT1275903B1 (it) *	1995-03-14	1997-10-24	Boehringer Ingelheim Italia	Esteri e ammidi della 1,4-piperidina disostituita
US5654320A (en) *	1995-03-16	1997-08-05	Eli Lilly And Company	Indazolecarboxamides
CA2222532A1 (en) *	1995-05-31	1996-12-05	Nisshin Flour Milling Co., Ltd.	Indazole derivatives having monocyclic amine
ES2109190B1 (es)	1996-03-22	1998-07-01	Univ Madrid Complutense	Nuevos derivados de bencimidazol con afinidad por los receptores serotoninergicos 5-ht /5-ht
IT1291569B1 (it) *	1997-04-15	1999-01-11	Angelini Ricerche Spa	Indazolammidi come agenti serotoninergici
TW402591B (en) *	1997-07-11	2000-08-21	Janssen Pharmaceutica Nv	Monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives
US5914405A (en) *	1997-10-07	1999-06-22	Eli Lilly And Company	Process for preparing 3-substituted indazoles
US6069152A (en) *	1997-10-07	2000-05-30	Eli Lilly And Company	5-HT4 agonists and antagonists
FR2769915B1 (fr)	1997-10-21	2000-10-13	Synthelabo	Derives d'indazole tricycliques, leur preparation et leur application en therapeutique
IT1298271B1 (it)	1998-02-18	1999-12-20	Boehringer Ingelheim Italia	Esteri ed ammidi dell'acido 2-oxo-2,3-diidro-benzimidazol-1- carbossilico
SK15852000A3 (sk) *	1998-04-28	2001-06-11	Dainippon Pharmaceutical Co., Ltd.	Derivát 1-[(1-substituovaného-4-piperidinyl)metyl]-4-piperidínu, spôsob jeho prípravy, farmaceutický prípravok obsahujúci tento derivát a medziprodukt tohto derivátu
JP3366323B2 (ja) *	1998-09-10	2003-01-14	エフ．ホフマン−ラロシュアーゲー	５−ｈｔ４受容体アンタゴニストとしてのジヒドロベンゾジオキシンカルボキサミド及びケトン誘導体
TW570920B (en) *	1998-12-22	2004-01-11	Janssen Pharmaceutica Nv	4-(aminomethyl)-piperidine benzamides for treating gastrointestinal disorders
PE20001420A1 (es)	1998-12-23	2000-12-18	Pfizer	Moduladores de ccr5
FR2792318B1 (fr)	1999-04-16	2001-06-15	Synthelabo	Derives d'indazole, leur preparation et leur application en therapeutique
AU5259100A (en) *	1999-04-28	2000-11-10	Respiratorius Ab	Medicament
ES2154605B1 (es)	1999-09-14	2001-11-16	Univ Madrid Complutense	Nuevos derivados mixtos de bencimidazol-arilpiperazina con afinidad por los receptores serotoninergicos 5-ht1a y 5-ht3
IT1313625B1 (it) *	1999-09-22	2002-09-09	Boehringer Ingelheim Italia	Derivati benzimidazolonici aventi affinita' mista per i recettori diserotonina e dopamina.
IT1313660B1 (it)	1999-10-01	2002-09-09	Dompe Spa	Procedimento stereoselettivo per la preparazione di endo-3-amminoazabicicloalcani.
WO2002036113A1 (en)	2000-11-01	2002-05-10	Respiratorius Ab	Composition comprising: serotonin receptor antagonists (5ht-2, 5ht-3) and agonist (5ht-4)
US6624162B2 (en) *	2001-10-22	2003-09-23	Pfizer Inc.	Imidazopyridine compounds as 5-HT4 receptor modulators
MXPA03000145A (es) *	2002-01-07	2003-07-15	Pfizer	Compuestos de oxo u oxi-piridina como moduladores de receptores 5-ht4.
PL372968A1 (en)	2002-04-08	2005-08-08	Pfizer Inc.	Tropane derivatives as ccr5 modulators
US6696468B2 (en) *	2002-05-16	2004-02-24	Dainippon Pharmaceutical Co., Ltd.	(s)-4-amino-5-chloro-2-methoxy-n-[1-[1-(2-tetrahydrofuryl-carbonyl)-4-piperidinylmethyl]-4-piperidinyl]benzamide, process for the preparation thereof, pharmaceutical composition containing the same, and intermediate therefor
WO2004026868A1 (en) *	2002-09-20	2004-04-01	Pfizer Japan Inc.	N-substituted piperidinyl-imidazopyridine compounds as 5-ht4 receptor modulators
DOP2003000703A (es) *	2002-09-20	2004-03-31	Pfizer	Compuestos de imidazopiradina como agonistas del receptor 5-ht4
WO2004094418A1 (en) *	2003-04-21	2004-11-04	Pfizer Inc.	Imidazopyridine compounds having 5-ht4 receptor agonistic activity and 5-ht3 receptor antagonistic activity
US7652040B2 (en)	2003-06-19	2010-01-26	Janssen Pharmaceutica N.V.	Aminosulfonyl substituted 4-(aminomethyl)-piperidine benzamides as 5HT4-antagonists
JO2478B1 (en)	2003-06-19	2009-01-20	جانسين فارماسوتيكا ان. في.	(Aminomethyl) -biperidine benzamides as 5 HT4 antagonists
PT1664036E (pt) *	2003-09-03	2012-02-16	Pfizer	Compostos de benzimidazolona que possuem actividade agonística do receptor 5-ht4
WO2005049608A1 (en)	2003-11-24	2005-06-02	Pfizer Japan, Inc.	Quinolonecarboxylic acid compounds having 5-ht4 receptor agonistic activity
ATE388146T1 (de)	2004-01-29	2008-03-15	Pfizer	1-isopropyl-2-oxo-1,2-dihydropyridin-3- carbonsäureamidderivate mit agonistischer wirkung am 5-ht4-rezeptor
TW200533348A (en) *	2004-02-18	2005-10-16	Theravance Inc	Indazole-carboxamide compounds as 5-ht4 receptor agonists
DE602005016446D1 (de) *	2004-11-05	2009-10-15	Theravance Inc	5-HT4-Rezeptoragonistenverbindungen

2005
- 2005-02-15 TW TW094104343A patent/TW200533348A/zh unknown
- 2005-02-17 US US11/060,195 patent/US7351704B2/en active Active
- 2005-02-17 JP JP2006554207A patent/JP2007523175A/ja active Pending
- 2005-02-17 BR BRPI0507791-5A patent/BRPI0507791A/pt not_active IP Right Cessation
- 2005-02-17 CN CNA200580005307XA patent/CN1922175A/zh active Pending
- 2005-02-17 EP EP05723216A patent/EP1718643A1/en not_active Withdrawn
- 2005-02-17 AU AU2005214368A patent/AU2005214368A1/en not_active Abandoned
- 2005-02-17 KR KR1020067019088A patent/KR20060132727A/ko not_active Application Discontinuation
- 2005-02-17 CA CA002553696A patent/CA2553696A1/en not_active Abandoned
- 2005-02-17 WO PCT/US2005/005070 patent/WO2005080389A1/en active Application Filing
- 2005-02-17 AR ARP050100560A patent/AR047681A1/es unknown
- 2005-02-17 RU RU2006133320/04A patent/RU2006133320A/ru not_active Application Discontinuation
2006
- 2006-07-25 IL IL177059A patent/IL177059A0/en unknown
- 2006-08-03 ZA ZA200606479A patent/ZA200606479B/en unknown
- 2006-08-18 MA MA29276A patent/MA28435B1/fr unknown
- 2006-09-14 NO NO20064156A patent/NO20064156L/no not_active Application Discontinuation
2008
- 2008-02-04 US US12/012,579 patent/US7674908B2/en not_active Expired - Lifetime
2010
- 2010-01-19 US US12/689,763 patent/US8044045B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20100261716A1 (en)	2010-10-14
MA28435B1 (fr)	2007-02-01
KR20060132727A (ko)	2006-12-21
US20080146807A1 (en)	2008-06-19
US20050197335A1 (en)	2005-09-08
AR047681A1 (es)	2006-02-01
RU2006133320A (ru)	2008-03-27
BRPI0507791A (pt)	2007-07-17
AU2005214368A1 (en)	2005-09-01
CA2553696A1 (en)	2005-09-01
US8044045B2 (en)	2011-10-25
WO2005080389A1 (en)	2005-09-01
US7674908B2 (en)	2010-03-09
CN1922175A (zh)	2007-02-28
NO20064156L (no)	2006-11-10
US7351704B2 (en)	2008-04-01
EP1718643A1 (en)	2006-11-08
IL177059A0 (en)	2006-12-10
JP2007523175A (ja)	2007-08-16
TW200533348A (en)	2005-10-16

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