UA71888C2 - Cells adhesion inhibitors, pharmaceutical composiition containing them (variants), and a method for inhibition or suppression of cells adhesion in mammals (variants) - Google Patents

Cells adhesion inhibitors, pharmaceutical composiition containing them (variants), and a method for inhibition or suppression of cells adhesion in mammals (variants) Download PDF

Info

Publication number: UA71888C2
Authority: UA; Ukraine
Prior art keywords: side chain; alkyl; phenylacetyl; compound; cell adhesion
Prior art date: 1995-07-11

Application number

UA98020687A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Biogen 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.)

1995-07-11

Filing date

1996-11-07

Publication date

2005-01-17

1996-11-07 Application filed by Biogen Inc filed Critical Biogen Inc

2005-01-17 Publication of UA71888C2 publication Critical patent/UA71888C2/uk

Links

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150000003573 thiols Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
238000001890 transfection Methods 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000001665 trituration Methods 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

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UA98020687A 1995-07-11 1996-11-07 Cells adhesion inhibitors, pharmaceutical composiition containing them (variants), and a method for inhibition or suppression of cells adhesion in mammals (variants) UA71888C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/498,237 US6248713B1 (en)	1995-07-11	1995-07-11	Cell adhesion inhibitors
PCT/US1996/011570 WO1997003094A1 (fr)	1995-07-11	1996-07-11	Composes inhibiteurs d'adherence cellulaire

Publications (1)

Publication Number	Publication Date
UA71888C2 true UA71888C2 (en)	2005-01-17

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ID=23980177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA98020687A UA71888C2 (en)	1995-07-11	1996-11-07	Cells adhesion inhibitors, pharmaceutical composiition containing them (variants), and a method for inhibition or suppression of cells adhesion in mammals (variants)

Country Status (28)

Country	Link
US (2)	US6248713B1 (fr)
EP (1)	EP0842196B1 (fr)
JP (2)	JPH11511124A (fr)
KR (1)	KR100531586B1 (fr)
CN (1)	CN1195778C (fr)
AU (1)	AU716276B2 (fr)
BG (1)	BG63876B1 (fr)
BR (1)	BR9609782A (fr)
CA (1)	CA2226868A1 (fr)
CZ (1)	CZ299054B6 (fr)
DE (1)	DE69637328T2 (fr)
EA (2)	EA003737B1 (fr)
EE (2)	EE03694B1 (fr)
FI (1)	FI980033A (fr)
HK (1)	HK1010888A1 (fr)
HU (1)	HUP9802202A3 (fr)
IL (1)	IL122783A (fr)
IS (1)	IS4648A (fr)
MX (1)	MX9800348A (fr)
NO (1)	NO980097L (fr)
NZ (1)	NZ312950A (fr)
PL (1)	PL188446B1 (fr)
RO (1)	RO121032B1 (fr)
SK (1)	SK3798A3 (fr)
TR (1)	TR199800028T1 (fr)
TW (1)	TW570927B (fr)
UA (1)	UA71888C2 (fr)
WO (1)	WO1997003094A1 (fr)

Families Citing this family (131)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6248713B1 (en) *	1995-07-11	2001-06-19	Biogen, Inc.	Cell adhesion inhibitors
US6037324A (en) *	1996-01-04	2000-03-14	Leukosite, Inc.	Inhibitors of MAdCAM-1-mediated interactions and methods of use therefor
US6686350B1 (en)	1996-07-25	2004-02-03	Biogen, Inc.	Cell adhesion inhibitors
ATE363658T1 (de)	1996-07-25	2007-06-15	Biogen Idec Inc	Molekülmodell für vla-4-inhibitoren
US6221888B1 (en)	1997-05-29	2001-04-24	Merck & Co., Inc.	Sulfonamides as cell adhesion inhibitors
US6291511B1 (en)	1997-05-29	2001-09-18	Merck & Co., Inc.	Biarylalkanoic acids as cell adhesion inhibitors
US6903075B1 (en)	1997-05-29	2005-06-07	Merck & Co., Inc.	Heterocyclic amide compounds as cell adhesion inhibitors
EP1017382B1 (fr) *	1997-05-29	2006-03-01	Merck & Co., Inc. (a New Jersey corp.)	Acide biarylalcanoique utilise en tant qu'inhibiteur de l'adhesion cellulaire
WO1998054207A1 (fr) *	1997-05-30	1998-12-03	Celltech Therapeutics Limited	Derives anti-inflammatoires de tyrosine
US6559127B1 (en)	1997-07-31	2003-05-06	Athena Neurosciences, Inc.	Compounds which inhibit leukocyte adhesion mediated by VLA-4
US6423688B1 (en)	1997-07-31	2002-07-23	Athena Neurosciences, Inc.	Dipeptide and related compounds which inhibit leukocyte adhesion mediated by VLA-4
US6489300B1 (en)	1997-07-31	2002-12-03	Eugene D. Thorsett	Carbamyloxy compounds which inhibit leukocyte adhesion mediated by VLA-4
US6492421B1 (en)	1997-07-31	2002-12-10	Athena Neurosciences, Inc.	Substituted phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4
US6291453B1 (en)	1997-07-31	2001-09-18	Athena Neurosciences, Inc.	4-amino-phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4
US6939855B2 (en)	1997-07-31	2005-09-06	Elan Pharmaceuticals, Inc.	Anti-inflammatory compositions and method
AR016133A1 (es) *	1997-07-31	2001-06-20	Wyeth Corp	Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria
US6583139B1 (en)	1997-07-31	2003-06-24	Eugene D. Thorsett	Compounds which inhibit leukocyte adhesion mediated by VLA-4
US7030114B1 (en)	1997-07-31	2006-04-18	Elan Pharmaceuticals, Inc.	Compounds which inhibit leukocyte adhesion mediated by VLA-4
US6362341B1 (en)	1997-07-31	2002-03-26	Athena Neurosciences, Inc.	Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4
DE19741235A1 (de)	1997-09-18	1999-03-25	Hoechst Marion Roussel De Gmbh	Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
DE19741873A1 (de) *	1997-09-23	1999-03-25	Hoechst Marion Roussel De Gmbh	Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
US6069163A (en) *	1997-10-21	2000-05-30	Merck & Co., Inc.	Azapeptide acids as cell adhesion inhibitors
AU748041B2 (en) *	1997-10-31	2002-05-30	Aventis Pharma Limited	Substituted anilides
GB9723789D0 (en)	1997-11-12	1998-01-07	Zeneca Ltd	Chemical compounds
AU1415099A (en) *	1997-11-18	1999-06-07	Merck & Co., Inc.	4-substituted-4-piperidine carboxamide derivatives
US6020347A (en) *	1997-11-18	2000-02-01	Merck & Co., Inc.	4-substituted-4-piperidine carboxamide derivatives
DE19751251A1 (de)	1997-11-19	1999-05-20	Hoechst Marion Roussel De Gmbh	Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate
US6191171B1 (en)	1997-11-20	2001-02-20	Merck & Co., Inc.	Para-aminomethylaryl carboxamide derivatives
US6090841A (en) *	1997-11-21	2000-07-18	Merck & Co., Inc.	Substituted pyrrole derivatives as cell adhesion inhibitors
US6645939B1 (en)	1997-11-24	2003-11-11	Merck & Co., Inc.	Substituted β-alanine derivatives as cell adhesion inhibitors
ATE267168T1 (de) *	1997-11-24	2004-06-15	Merck & Co Inc	Beta-alanin-derivate als zell-adhäsions- inhibitoren
US6407065B1 (en)	1998-01-23	2002-06-18	Novartis Ag	VLA-4 antagonists
US6329372B1 (en)	1998-01-27	2001-12-11	Celltech Therapeutics Limited	Phenylalanine derivatives
GB9805655D0 (en)	1998-03-16	1998-05-13	Celltech Therapeutics Ltd	Chemical compounds
US6521626B1 (en)	1998-03-24	2003-02-18	Celltech R&D Limited	Thiocarboxamide derivatives
AU3716499A (en) *	1998-04-21	1999-11-08	Aventis Pharma Limited	Substituted diamines and their use as cell adhesion inhibitors
DE19821483A1 (de)	1998-05-14	1999-11-18	Hoechst Marion Roussel De Gmbh	Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
GB9811159D0 (en)	1998-05-22	1998-07-22	Celltech Therapeutics Ltd	Chemical compounds
EE04639B1 (et)	1998-05-28	2006-06-15	Biogen, Inc.	Raku adhesiooni pärssiv ühend ja seda sisaldav farmatseutiline kompositsioon
GB9811969D0 (en) *	1998-06-03	1998-07-29	Celltech Therapeutics Ltd	Chemical compounds
GB9814414D0 (en)	1998-07-03	1998-09-02	Celltech Therapeutics Ltd	Chemical compounds
WO2000002903A1 (fr) *	1998-07-10	2000-01-20	Cytel Corporation	Peptidomimetique de cs-1, compositions et leurs procedes d'utilisation
GB9916374D0 (en)	1998-07-23	1999-09-15	Zeneca Ltd	Chemical compounds
GB9821061D0 (en)	1998-09-28	1998-11-18	Celltech Therapeutics Ltd	Chemical compounds
GB9821222D0 (en)	1998-09-30	1998-11-25	Celltech Therapeutics Ltd	Chemical compounds
GB9825652D0 (en)	1998-11-23	1999-01-13	Celltech Therapeutics Ltd	Chemical compounds
GB9826174D0 (en)	1998-11-30	1999-01-20	Celltech Therapeutics Ltd	Chemical compounds
GB9828074D0 (en) *	1998-12-18	1999-02-17	Glaxo Group Ltd	Therapeutically useful compounds
WO2000039103A1 (fr) *	1998-12-23	2000-07-06	Aventis Pharma Limited	Dihydro-benzo(1,4)oxazines et tetrahydroquinoxalines
US6407066B1 (en)	1999-01-26	2002-06-18	Elan Pharmaceuticals, Inc.	Pyroglutamic acid derivatives and related compounds which inhibit leukocyte adhesion mediated by VLA-4
DE19922462A1 (de)	1999-05-17	2000-11-23	Aventis Pharma Gmbh	Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate
US6518283B1 (en)	1999-05-28	2003-02-11	Celltech R&D Limited	Squaric acid derivatives
EP1189612A4 (fr) *	1999-06-30	2005-02-16	Daiichi Seiyaku Co	Composes inhibiteurs de vla-4
US6756378B2 (en)	1999-06-30	2004-06-29	Pharmacopeia Drug Discovery, Inc.	VLA-4 inhibitor compounds
EP1741428A3 (fr) *	1999-08-13	2007-05-09	Biogen Idec MA, Inc.	inhibiteurs d'adhésion cellulaire
US6534513B1 (en)	1999-09-29	2003-03-18	Celltech R&D Limited	Phenylalkanoic acid derivatives
EP2332578A1 (fr)	1999-12-16	2011-06-15	Biogen Idec MA Inc.	Procédés de traitement de maladie hémorragique ou ischémique du système nerveux central, utilisant des antagonistes de l'intégrine alpha 4
US6455539B2 (en)	1999-12-23	2002-09-24	Celltech R&D Limited	Squaric acid derivates
JP2003519697A (ja)	1999-12-28	2003-06-24	ファイザー・プロダクツ・インク	炎症性疾患、自己免疫疾患および呼吸器疾患の処置に有用な非ペプチド系のｖｌａ−４依存性細胞結合阻害薬
ATE375330T1 (de)	2000-04-17	2007-10-15	Ucb Pharma Sa	Enamin-derivate als zell-adhäsionsmoleküle
US6545013B2 (en)	2000-05-30	2003-04-08	Celltech R&D Limited	2,7-naphthyridine derivatives
US6403608B1 (en)	2000-05-30	2002-06-11	Celltech R&D, Ltd.	3-Substituted isoquinolin-1-yl derivatives
JP2004502762A (ja)	2000-07-07	2004-01-29	セルテック　アール　アンド　ディ　リミテッド	二環性ヘテロ芳香環を含有するインテグリンアンタゴニストとしてのスクエア酸誘導体
AU2001275724A1 (en)	2000-08-02	2002-02-13	Celltech R&D Limited	3-substituted isoquinolin-1-yl derivatives
AU2002248910A1 (en) *	2000-11-17	2002-05-27	Idenix (Cayman) Limited	Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrmidines
US6875743B1 (en)	2000-11-28	2005-04-05	Biogen, Inc.	Cell adhesion inhibitors
BR0116608A (pt)	2000-12-28	2004-06-29	Daiichi Seiyaku Co	Inibidores vla-4
DE10111877A1 (de)	2001-03-10	2002-09-12	Aventis Pharma Gmbh	Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate
GB2377933A (en)	2001-07-06	2003-01-29	Bayer Ag	Succinic acid derivatives useful as integrin antagonists
DE10137595A1 (de)	2001-08-01	2003-02-13	Aventis Pharma Gmbh	Neue Imidazolidinderivate, ihre Herstellung und ihre Verwendung
EP1419396B1 (fr) *	2001-08-20	2009-05-06	Honeywell International Inc.	Elements flexibles arques pour accelerometre realise au moyen de systemes electromecaniques micro-usines (mems)
AR038136A1 (es)	2002-01-24	2004-12-29	Merck Frosst Canada Inc	Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento
US7247725B2 (en)	2002-10-30	2007-07-24	Merck & Co., Inc.	Gamma-aminoamide modulators of chemokine receptor activity
EP1650205B1 (fr)	2003-07-24	2012-04-25	Daiichi Sankyo Company, Limited	Compose acide cyclohexanecarboxylique
CN1301426C (zh) *	2003-08-19	2007-02-21	友达光电股份有限公司	窄边框设计的液晶显示面板及其制作方法
JPWO2005066124A1 (ja) *	2003-12-26	2007-12-20	第一三共株式会社	ピロリジン誘導体の製造法
WO2005122379A2 (fr) *	2004-05-27	2005-12-22	The Regents Of The University Of California	Ligands d'integrine alpha-4 beta-1 destines a l'imagerie et utilises en therapie
US20060063828A1 (en) *	2004-06-28	2006-03-23	Weingarten M D	1,2-Bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof
US7196112B2 (en)	2004-07-16	2007-03-27	Biogen Idec Ma Inc.	Cell adhesion inhibitors
US7140250B2 (en) *	2005-02-18	2006-11-28	Honeywell International Inc.	MEMS teeter-totter accelerometer having reduced non-linearty
WO2007069635A1 (fr)	2005-12-13	2007-06-21	Daiichi Sankyo Company, Limited	Médicament inhibiteur de vla-4
US20100150915A1 (en)	2007-02-20	2010-06-17	Stewart Edward J	Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist
NZ585888A (en)	2007-12-14	2012-02-24	Pulmagen Therapeutics Asthma Ltd	Indoles and their therapeutic use
CA2721093A1 (fr)	2008-04-11	2009-10-15	Merrimack Pharmaceuticals, Inc.	Lieurs d'albumine de serum humain, et ses conjugues
JP2012502927A (ja)	2008-09-22	2012-02-02	メルクカナダインコーポレイテッド	Ｃｒｔｈ２受容体拮抗薬としてのインドール誘導体
US20100204221A1 (en)	2009-02-09	2010-08-12	Hariprasad Vankayalapati	Pyrrolopyrimidinyl axl kinase inhibitors
EP2398798A1 (fr)	2009-02-17	2011-12-28	CHIESI FARMACEUTICI S.p.A.	Dérivés de triazolopyridine utilisés comme inhibiteurs de la p38 map kinase
GB0902648D0 (en)	2009-02-17	2009-04-01	Argenta Discovery Ltd	Pharmaceutical compounds and compositions
MX2011008869A (es)	2009-02-24	2011-12-16	Merck Sharp & Dohme	Derivados de indol como antagonistas del receptor de la molecula homologa a receptor de quimioatrayente expresada en celulas th2.
CN102822175A (zh) *	2009-12-18	2012-12-12	埃迪尼克斯医药公司	5,5-稠合的亚芳基或亚杂芳基丙型肝炎病毒抑制剂
GB201009731D0 (en)	2010-06-10	2010-07-21	Pulmagen Therapeutics Inflamma	Kinase inhibitors
WO2012031228A2 (fr)	2010-09-02	2012-03-08	The Regents Of The University Of California	Conjugués llp2a-biphosphonate pour traitement de l'ostéoporose
EP2627178B1 (fr)	2010-10-11	2018-05-02	Merck Sharp & Dohme Corp.	Composés de type quinazolinone convenant comme antagonistes de crth2
EP2661428B1 (fr)	2010-12-23	2017-06-07	Merck Sharp & Dohme Corp.	Peptides de liaison à her2 marqués par un composé organosilicium contenant 18f
US8796310B2 (en)	2011-05-04	2014-08-05	Merck Sharp & Dohme Corp.	Amino-pyridine-containing spleen tyrosine kinase (SYK) inhibitors
AR086931A1 (es)	2011-06-17	2014-01-29	Merck Sharp & Dohme	Tetrahidroquinolinas condensadas con cicloalquilo como moduladores de receptores de crth
EP2763975B1 (fr)	2011-10-05	2016-04-06	Merck Sharp & Dohme Corp.	Inhibiteurs de tyrosine kinase de la rate (syk) contenant un 3-pyridyl carboxamide
RU2586333C1 (ru)	2011-12-09	2016-06-10	КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А.	Производные 4-гидрокси-1,2,3,4-тетрагидронафталин-1-ил-мочевины и их применение в лечении, среди прочего, заболеваний дыхательного тракта
CA2858447C (fr)	2011-12-09	2020-10-27	Monique Bodil Van Niel	Derives de tryazolopyridine comme inhibiteurs de kinase
EP2788348B1 (fr)	2011-12-09	2016-10-19	Chiesi Farmaceutici S.p.A.	Inhibiteurs de kinase
CA2914432A1 (fr)	2013-06-06	2014-12-11	Chiesi Farmaceutici S.P.A.	Inhibiteurs de kinase
CN104817625A (zh) *	2014-01-30	2015-08-05	陈光健	寡肽cd03及其制备方法和应用
CN104817622A (zh) *	2014-01-30	2015-08-05	陈光健	寡肽cd04及其制备方法和应用
CN104817613A (zh) *	2014-01-30	2015-08-05	陈光健	寡肽cd06及其制备方法和应用
CN104817615A (zh) *	2014-01-30	2015-08-05	陈光健	寡肽cd05及其制备方法和应用
CN105294830A (zh) *	2014-06-18	2016-02-03	陈光健	一种二肽分子及其制备方法和应用
ES2958531T3 (es)	2015-10-14	2024-02-09	X Therma Inc	Composiciones y métodos para reducir la formación de cristales de hielo
TW201720828A (zh)	2015-11-23	2017-06-16	赫孚孟拉羅股份公司	治療性化合物及組合物以及其使用方法
AR107165A1 (es)	2015-12-23	2018-03-28	Chiesi Farm Spa	Inhibidores de quinasa
AR107164A1 (es)	2015-12-23	2018-03-28	Chiesi Farm Spa	INHIBIDORES DE QUINASA p38
AR107163A1 (es)	2015-12-23	2018-03-28	Chiesi Farm Spa	Inhibidores de quinasa
WO2017191098A1 (fr)	2016-05-05	2017-11-09	F. Hoffmann-La Roche Ag	Dérivés de pyrazole, compositions les comprenant et leur utilisation thérapeutique
JP7050761B2 (ja)	2016-09-06	2022-04-08	エフ．ホフマン－ラロシュアーゲー	８－（アゼチジン－１－イル）－［１，２，４］トリアゾロ［１，５－ａ］ピリジニル化合物、組成物及びその使用方法
ES2884107T3 (es)	2016-11-11	2021-12-10	Zealand Pharma As	Multímeros de péptidos cíclicos con diana en la integrina alfa-4 beta-7
KR20190100337A (ko)	2016-12-29	2019-08-28	에프. 호프만-라 로슈 아게	피라졸로피리미딘 화합물 및 이의 사용 방법
WO2018140510A1 (fr)	2017-01-25	2018-08-02	Biogen Ma Inc.	Composition et méthodes de traitement d'un accident vasculaire cérébral et d'autres troubles du snc
JP2020510061A (ja)	2017-03-14	2020-04-02	エフ．ホフマン−ラロシュアーゲーＦ．Ｈｏｆｆｍａｎｎ−ＬａＲｏｃｈｅＡｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ	ピラゾロクロロフェニル化合物、組成物及びその使用方法
MX2019013362A (es)	2017-05-10	2020-08-17	Zealand Pharma As	PÉPTIDOS CÍCLICOS HOMODÉTICOS CON LA INTEGRINA A4ß7 COMO DIANA.
KR20200010390A (ko)	2017-05-22	2020-01-30	에프. 호프만-라 로슈 아게	치료 화합물 및 조성물, 및 이의 사용 방법
US20180334465A1 (en)	2017-05-22	2018-11-22	Genentech, Inc.	Therapeutic compounds and compositions, and methods of use thereof
US10364245B2 (en)	2017-06-07	2019-07-30	Chiesi Farmaceutici S.P.A.	Kinase inhibitors
CN111587250A (zh)	2018-01-15	2020-08-25	豪夫迈·罗氏有限公司	作为jak抑制剂的吡唑并嘧啶化合物
JP7189369B2 (ja)	2018-10-30	2022-12-13	ギリアードサイエンシーズ，インコーポレイテッド	アルファ４β７インテグリンの阻害のための化合物
JP7214882B2 (ja)	2018-10-30	2023-01-30	ギリアードサイエンシーズ，インコーポレイテッド	アルファ４ベータ７インテグリン阻害剤としてのイミダゾピリジン誘導体
JP7189368B2 (ja)	2018-10-30	2022-12-13	ギリアードサイエンシーズ，インコーポレイテッド	アルファ４ベータ７インテグリンの阻害のための化合物
US11116760B2 (en)	2018-10-30	2021-09-14	Gilead Sciences, Inc.	Quinoline derivatives
JP2022517610A (ja)	2019-01-10	2022-03-09	シーエスピーシーゾンチーファーマシューティカルテクノロジー（シージアチュアン）カンパニー，リミテッド	複素環化合物塩およびその使用
JP2022537964A (ja)	2019-06-18	2022-08-31	エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト	Ｊａｋキナーゼのピラゾロピリミジンスルホン阻害剤およびその使用
WO2020257143A1 (fr)	2019-06-18	2020-12-24	Genentech, Inc.	Inhibiteurs éther-aryl-pyrazolopyrimidine de kinases jak et leurs utilisations
TW202115069A (zh)	2019-06-18	2021-04-16	瑞士商赫孚孟拉羅股份公司	Ｊａｋ激酶之經四唑取代之吡唑并嘧啶抑制劑及其用途
US11578069B2 (en)	2019-08-14	2023-02-14	Gilead Sciences, Inc.	Compounds for inhibition of α4 β7 integrin

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1149971B (it)	1979-06-11	1986-12-10	Syntex Inc	Derivati nonapeptide e decapeptide dell'ormone che rilascia l'ormone luteinizzante
US4725583A (en)	1985-01-23	1988-02-16	Abbott Laboratories	Functionalized peptidylaminoalcohols
US4826815A (en)	1985-05-17	1989-05-02	Abbott Laboratories	Renin inhibiting compounds
DK163689A (da)	1988-04-08	1989-10-30	Sandoz Ag	Peptidderivater
ATE131471T1 (de)	1989-12-22	1995-12-15	Commw Scient Ind Res Org	An fette gebundene aminosäuren, peptide oder deren derivate
CA2043741C (fr)	1990-06-07	2003-04-01	Kiyofumi Ishikawa	Derives de peptides antagonistes d'endotheline
US5192746A (en)	1990-07-09	1993-03-09	Tanabe Seiyaku Co., Ltd.	Cyclic cell adhesion modulation compounds
US5260277A (en)	1990-09-10	1993-11-09	Tanabe Seiyaku Co., Ltd.	Guanidinyl and related cell adhesion modulation compounds
WO1992008464A1 (fr)	1990-11-15	1992-05-29	Tanabe Seiyaku Co. Ltd.	Composes d'uree substitues et composes associes utilises dans la modulation de l'adhesion cellulaire
EP0519748B1 (fr)	1991-06-21	1998-09-02	Merck & Co. Inc.	Dérivés peptidyliques comme inhibiteurs d'enzyme convertissant l'interleukine-1B
WO1993008823A1 (fr)	1991-11-06	1993-05-13	Tanabe Seiyaku Co., Ltd.	Composes de guanidinyle et composes apparentes modulant l'adhesion cellulaire
WO1993009795A1 (fr)	1991-11-22	1993-05-27	Yeda Research And Development Co. Ltd.	Succedanes non peptidiques de la sequence arg-gly-asp, et compositions pharmaceutiques les contenant
AU3420693A (en)	1991-12-24	1993-07-28	Fred Hutchinson Cancer Research Center	Competitive inhibition of high-avidity alpha4-beta1 receptor using tripeptide ldv
DE4212304A1 (de)	1992-04-13	1993-10-14	Cassella Ag	Asparaginsäurederivate, ihre Herstellung und Verwendung
IL102646A (en)	1992-07-26	1996-05-14	Yeda Res & Dev	Non-peptidic surrogates of the ldv sequence and pharmaceutical compositions comprising them
EP0677060A1 (fr)	1993-01-08	1995-10-18	Tanabe Seiyaku Co., Ltd.	Inhibiteurs peptidiques de l'adhesion cellulaire
US5314902A (en) *	1993-01-27	1994-05-24	Monsanto Company	Urea derivatives useful as platelet aggregation inhibitors
DE4309867A1 (de)	1993-03-26	1994-09-29	Cassella Ag	Neue Harnstoffderivate, ihre Herstellung und Verwendung
DE69427907T2 (de)	1993-04-09	2002-04-04	Toyama Chemical Co Ltd	Immunomodulator, zelladhäsionsinhibitor und mittel zur behandlung und vorbeugung von autoimmunerkrankungen
AU693143B2 (en)	1993-12-06	1998-06-25	Cytel Corporation	CS-1 peptidomimetics, compositions and methods of using the same
US5770573A (en) *	1993-12-06	1998-06-23	Cytel Corporation	CS-1 peptidomimetics, compositions and methods of using the same
US5434188A (en)	1994-03-07	1995-07-18	Warner-Lambert Company	1-ether and 1-thioether-naphthalene-2-carboxamides as inhibitors of cell adhesion and as inhibitors of the activation of HIV
US6248713B1 (en) *	1995-07-11	2001-06-19	Biogen, Inc.	Cell adhesion inhibitors
US6239108B1 (en) *	1996-07-11	2001-05-29	Biogen, Inc.	Cell adhesion inhibitors

1995
- 1995-07-11 US US08/498,237 patent/US6248713B1/en not_active Expired - Fee Related
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- 1996-07-11 HU HU9802202A patent/HUP9802202A3/hu unknown
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- 2000-01-13 US US09/482,296 patent/US6596687B1/en not_active Expired - Fee Related
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Publication number	Publication date
DE69637328D1 (de)	2008-01-03
EE200200384A (et)	2002-10-15
RO121032B1 (ro)	2006-11-30
BG102241A (en)	1998-12-30
US6248713B1 (en)	2001-06-19
EA003737B1 (ru)	2003-08-28
EA199800119A1 (ru)	1998-08-27
SK3798A3 (en)	1998-07-08
CA2226868A1 (fr)	1997-01-30
NO980097L (no)	1998-03-11
US6596687B1 (en)	2003-07-22
IL122783A0 (en)	1998-08-16
EE9700362A (et)	1998-06-15
NO980097D0 (no)	1998-01-09
EA001594B1 (ru)	2001-06-25
DE69637328T2 (de)	2008-10-09
TW570927B (en)	2004-01-11
JP2008088171A (ja)	2008-04-17
FI980033A (fi)	1998-03-05
TR199800028T1 (xx)	1998-05-21
MX9800348A (es)	1998-07-31
CZ5298A3 (cs)	1998-04-15
WO1997003094A1 (fr)	1997-01-30
CZ299054B6 (cs)	2008-04-09
EP0842196A1 (fr)	1998-05-20
KR19990028926A (ko)	1999-04-15
HUP9802202A2 (hu)	1999-01-28
IL122783A (en)	2005-08-31
CN1193325A (zh)	1998-09-16
BG63876B1 (bg)	2003-04-30
JPH11511124A (ja)	1999-09-28
EP0842196B1 (fr)	2007-11-21
CN1195778C (zh)	2005-04-06
KR100531586B1 (ko)	2006-10-31
HUP9802202A3 (en)	1999-03-29
PL324491A1 (en)	1998-05-25
AU6489496A (en)	1997-02-10
PL188446B1 (pl)	2005-02-28
EA200100103A1 (ru)	2001-06-25
BR9609782A (pt)	1999-03-09
HK1010888A1 (en)	1999-07-02
AU716276B2 (en)	2000-02-24
FI980033A0 (fi)	1998-01-09
IS4648A (is)	1998-01-08
EE03694B1 (et)	2002-04-15
NZ312950A (en)	2000-01-28

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