ZA200308024B - Inhibitors of integrin alphavbeta6. - Google Patents

Inhibitors of integrin alphavbeta6. Download PDF

Info

Publication number: ZA200308024B
Authority: ZA; South Africa
Prior art keywords: pyridin; ylamino; propionic acid; biphenyl; butanoylamino
Prior art date: 2001-03-16

Application number

ZA200308024A

Other languages

English (en)

Inventor

Oliver Schadt

Wolfgang Staehle

Alfred Jonczyk

Simon Goodman

Original Assignee

Merck Patent Gmbh

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.)

2001-03-16

Filing date

2003-10-15

Publication date

2005-01-17

2003-10-15 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2005-01-17 Publication of ZA200308024B publication Critical patent/ZA200308024B/en

Links

239000003112 inhibitor Substances 0.000 title claims description 9
108010004788 integrin alphavbeta6 Proteins 0.000 title description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 376
235000019260 propionic acid Nutrition 0.000 claims description 188
-1 pyridin-2-ylamino Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 65
108010044426 integrins Proteins 0.000 claims description 50
102000006495 integrins Human genes 0.000 claims description 50
125000006239 protecting group Chemical group 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
206010028980 Neoplasm Diseases 0.000 claims description 19
239000012453 solvate Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
125000003277 amino group Chemical group 0.000 claims description 14
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238000000034 method Methods 0.000 claims description 12
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YKTPPPDELUIVHI-QBHOUYDASA-N 3-[[(2s)-6-amino-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 YKTPPPDELUIVHI-QBHOUYDASA-N 0.000 claims description 2
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MPOIJBCQWRETSO-UXMRNZNESA-N (4s)-5-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-5-oxo-4-[4-(pyridin-2-ylamino)butanoylamino]pentanoic acid Chemical compound N([C@@H](CCC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 MPOIJBCQWRETSO-UXMRNZNESA-N 0.000 claims 1
BPBNVJUUBUTFCD-UHFFFAOYSA-N 3-(3-bromophenyl)-3-[[3-phenylmethoxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C=1C=CC(Br)=CC=1C(CC(=O)O)NC(=O)C(NC(=O)CCCCNC=1N=CC=CC=1)COCC1=CC=CC=C1 BPBNVJUUBUTFCD-UHFFFAOYSA-N 0.000 claims 1
QILMETWBQMEBAZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[[3-phenylmethoxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C=1C=CC(Cl)=CC=1C(CC(=O)O)NC(=O)C(NC(=O)CCCCNC=1N=CC=CC=1)COCC1=CC=CC=C1 QILMETWBQMEBAZ-UHFFFAOYSA-N 0.000 claims 1
SZNCTGONOTXZQF-DDAUYOFQSA-N 3-(4-hydroxy-n-[(2r)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]anilino)-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](C)C(=O)N(C(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(O)=CC=1)C(=O)CCCCNC1=CC=CC=N1 SZNCTGONOTXZQF-DDAUYOFQSA-N 0.000 claims 1
DJBGPUVXNUYDND-CGHJUBPDSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound N([C@H](C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 DJBGPUVXNUYDND-CGHJUBPDSA-N 0.000 claims 1
OUEDEYHFICOQAL-VCHQGTEKSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoic acid Chemical compound N([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 OUEDEYHFICOQAL-VCHQGTEKSA-N 0.000 claims 1
AIODABPXAVUICN-BDCODIICSA-N 3-(4-phenylphenyl)-3-[[(2r)-3-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=CC=C1 AIODABPXAVUICN-BDCODIICSA-N 0.000 claims 1
HWAMMTZNTCKXIB-PUOOBJKZSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[4-(pyridin-2-ylamino)butanoylamino]-3-tritylsulfanylpropanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HWAMMTZNTCKXIB-PUOOBJKZSA-N 0.000 claims 1
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AIODABPXAVUICN-ZSXSBBPPSA-N 3-(4-phenylphenyl)-3-[[(2s)-3-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=CC=C1 AIODABPXAVUICN-ZSXSBBPPSA-N 0.000 claims 1
VINDNIBCWUZHNG-DYJLHVNUSA-N 3-(4-phenylphenyl)-3-[sulfanyl-[(2s)-5,5,5-triphenyl-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)N(S)C(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VINDNIBCWUZHNG-DYJLHVNUSA-N 0.000 claims 1
FZPSMXJOSFPGSK-YPJJGMIRSA-N 3-[[(2r)-3-cyclohexyl-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)C1CCCCC1 FZPSMXJOSFPGSK-YPJJGMIRSA-N 0.000 claims 1
VDDPDNSCNONJFV-OZAIVSQSSA-N 3-[[(2r)-3-hydroxy-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 VDDPDNSCNONJFV-OZAIVSQSSA-N 0.000 claims 1
REJVOUKDMBDPGM-MIHMCVIASA-N 3-[[(2r)-4-hydroxy-2-[4-(pyridin-2-ylamino)butanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 REJVOUKDMBDPGM-MIHMCVIASA-N 0.000 claims 1
KZKUJOPZSWGYCY-IKOFQBKESA-N 3-[[(2r)-4-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 KZKUJOPZSWGYCY-IKOFQBKESA-N 0.000 claims 1
ARAXKGCCMWKXJQ-MIHMCVIASA-N 3-[[(2r)-5-amino-5-oxo-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 ARAXKGCCMWKXJQ-MIHMCVIASA-N 0.000 claims 1
TWBPUTGOWCRJBA-IKOFQBKESA-N 3-[[(2r)-5-amino-5-oxo-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 TWBPUTGOWCRJBA-IKOFQBKESA-N 0.000 claims 1
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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ZA200308024A 2001-03-16 2003-10-15 Inhibitors of integrin alphavbeta6. ZA200308024B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10112771A DE10112771A1 (de)	2001-03-16	2001-03-16	Inhibitoren des Integrins alpha¶v¶beta¶6¶

Publications (1)

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ZA200308024B true ZA200308024B (en)	2005-01-17

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US (1)	US7632951B2 (de)
EP (1)	EP1377540B1 (de)
JP (1)	JP4327461B2 (de)
CN (1)	CN1582271A (de)
AT (1)	ATE416157T1 (de)
AU (1)	AU2002254900B2 (de)
CA (1)	CA2440644C (de)
DE (2)	DE10112771A1 (de)
ES (1)	ES2316556T3 (de)
HU (1)	HUP0303514A2 (de)
MX (1)	MXPA03008215A (de)
WO (1)	WO2002074730A1 (de)
ZA (1)	ZA200308024B (de)

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JP4750701B2 (ja) *	2003-07-07	2011-08-17	メルクパテントゲゼルシャフトミットベシュレンクテルハフツング	マロンアミド誘導体
RU2388472C2 (ru) *	2003-10-01	2010-05-10	Мерк Патент Гмбх	Антагонисты альфаvбета3 и альфаvбета6 интегринов в качестве антифибротических агентов
US20070043078A1 (en) *	2003-10-10	2007-02-22	Kowa Co., Ltd.	Angiogenesis inhibitor
AU2005251745A1 (en) *	2004-06-04	2005-12-22	The Regents Of The University Of California	Compounds having activity in increasing ion transport by mutant-CFTR and uses thereof
US7838252B2 (en) *	2005-02-17	2010-11-23	The Board Of Trustees Of The Leland Stanford Junior University	Methods and compositions for treating a subject having an anthrax toxin mediated condition
WO2009048541A2 (en) *	2007-10-05	2009-04-16	Purdue Research Foundation	Compounds and methods for use in treating neoplasia and cancer
WO2009051910A1 (en) *	2007-10-16	2009-04-23	The Regents Of The University Of California	Compounds having activity in increasing ion transport by mutant-cftr and uses thereof
JP5637855B2 (ja)	2007-11-08	2014-12-10	ザジェネラルホスピタルコーポレイション	蛋白尿症の治療のための方法及び組成物
GB0922014D0 (en)	2009-12-17	2010-02-03	Ge Healthcare Ltd	Novel integrin binders
WO2013016531A2 (en) *	2011-07-26	2013-01-31	Purdue Research Foundation	Compounds and methods for use in treating neoplasia and cancer
GB201305668D0 (en)	2013-03-28	2013-05-15	Glaxosmithkline Ip Dev Ltd	Avs6 Integrin Antagonists
WO2015179823A2 (en) *	2014-05-23	2015-11-26	The California Institute For Biomedical Research	Lung localized inhibitors of alpha(v)beta 6
GB201417094D0 (en)	2014-09-26	2014-11-12	Glaxosmithkline Ip Dev Ltd	Novel compounds
GB201417002D0 (en)	2014-09-26	2014-11-12	Glaxosmithkline Ip Dev Ltd	Novel compound
GB201417018D0 (en)	2014-09-26	2014-11-12	Glaxosmithkline Ip Dev Ltd	Novel compounds
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2001
- 2001-03-16 DE DE10112771A patent/DE10112771A1/de not_active Withdrawn
2002
- 2002-02-21 WO PCT/EP2002/001836 patent/WO2002074730A1/en not_active Ceased
- 2002-02-21 DE DE60230127T patent/DE60230127D1/de not_active Expired - Lifetime
- 2002-02-21 HU HU0303514A patent/HUP0303514A2/hu unknown
- 2002-02-21 AT AT02724175T patent/ATE416157T1/de not_active IP Right Cessation
- 2002-02-21 ES ES02724175T patent/ES2316556T3/es not_active Expired - Lifetime
- 2002-02-21 US US10/471,836 patent/US7632951B2/en not_active Expired - Fee Related
- 2002-02-21 CA CA2440644A patent/CA2440644C/en not_active Expired - Fee Related
- 2002-02-21 CN CNA028067061A patent/CN1582271A/zh active Pending
- 2002-02-21 AU AU2002254900A patent/AU2002254900B2/en not_active Ceased
- 2002-02-21 JP JP2002573739A patent/JP4327461B2/ja not_active Expired - Fee Related
- 2002-02-21 MX MXPA03008215A patent/MXPA03008215A/es unknown
- 2002-02-21 EP EP02724175A patent/EP1377540B1/de not_active Expired - Lifetime
2003
- 2003-10-15 ZA ZA200308024A patent/ZA200308024B/en unknown

Also Published As

Publication number	Publication date
AU2002254900B2 (en)	2008-04-10
MXPA03008215A (es)	2004-01-29
ES2316556T3 (es)	2009-04-16
JP4327461B2 (ja)	2009-09-09
US7632951B2 (en)	2009-12-15
ATE416157T1 (de)	2008-12-15
DE10112771A1 (de)	2002-09-26
HUP0303514A2 (hu)	2004-01-28
EP1377540B1 (de)	2008-12-03
CN1582271A (zh)	2005-02-16
CA2440644C (en)	2011-10-18
CA2440644A1 (en)	2002-09-26
EP1377540A1 (de)	2004-01-07
DE60230127D1 (de)	2009-01-15
JP2004525925A (ja)	2004-08-26
US20040092454A1 (en)	2004-05-13
WO2002074730A1 (en)	2002-09-26

Publication	Publication Date	Title
ZA200308024B (en)	2005-01-17	Inhibitors of integrin alphavbeta6.
AU2002254900A1 (en)	2003-03-27	Inhibitors of integrin AlphavBeta6
US7138417B2 (en)	2006-11-21	Inhibitors of integrin αvβ6
EP1343764B1 (de)	2004-08-25	Harnstoff- und urethanderivate als integrin inhibitoren
US20040142877A1 (en)	2004-07-22	Ligands of the $g(a)v$g(b)6 integrin
ZA200302256B (en)	2004-07-26	Biphenyl derivatives and the use thereof as integrin inhibitors.
US20030187289A1 (en)	2003-10-02	Biphenyl derivatives and the use thereof as integrin inhibitors