NO323378B1 - Pyrrolo(2,3-d)pyrimidinforbindelser, anvendelse derav samt farmasoytisk preparat. - Google Patents

Pyrrolo(2,3-d)pyrimidinforbindelser, anvendelse derav samt farmasoytisk preparat. Download PDF

Info

Publication number: NO323378B1
Authority: NO; Norway
Prior art keywords: methyl; compound according; amino; pharmaceutically acceptable; carbonyl
Prior art date: 1999-12-10

Application number

NO20022738A

Other languages

English (en)

Norwegian (no)

Other versions

NO20022738L (no

NO20022738D0 (no

Inventor

Todd Andrew Blumenkopf

Mark Edward Flanagan

Michael John Munchhof

Original Assignee

Pfizer Prod 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.)

1999-12-10

Filing date

2002-06-07

Publication date

2007-04-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22618882&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO323378(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2002-06-07 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2002-06-07 Publication of NO20022738L publication Critical patent/NO20022738L/no

2002-06-07 Publication of NO20022738D0 publication Critical patent/NO20022738D0/no

2007-04-16 Publication of NO323378B1 publication Critical patent/NO323378B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 14
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 128
150000003839 salts Chemical class 0.000 claims description 44
-1 cyano, amino Chemical group 0.000 claims description 36
108010019421 Janus Kinase 3 Proteins 0.000 claims description 32
102000006500 Janus Kinase 3 Human genes 0.000 claims description 32
238000002360 preparation method Methods 0.000 claims description 24
241000124008 Mammalia Species 0.000 claims description 23
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
239000003795 chemical substances by application Substances 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
230000002265 prevention Effects 0.000 claims description 14
206010039073 rheumatoid arthritis Diseases 0.000 claims description 14
206010052779 Transplant rejections Diseases 0.000 claims description 13
210000000056 organ Anatomy 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
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239000002260 anti-inflammatory agent Substances 0.000 claims description 12
210000000987 immune system Anatomy 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
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206010012601 diabetes mellitus Diseases 0.000 claims description 10
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206010025135 lupus erythematosus Diseases 0.000 claims description 9
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
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KLCACFBGIDQWHE-UHFFFAOYSA-N 1-[3-[(5-chloro-7h-pyrrolo[2,3-d]pyrimidin-4-yl)methylamino]-4-methylpiperidin-1-yl]propan-1-one Chemical compound C1N(C(=O)CC)CCC(C)C1NCC1=NC=NC2=C1C(Cl)=CN2 KLCACFBGIDQWHE-UHFFFAOYSA-N 0.000 claims description 2
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125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
URCTYVNPUZEJJF-UHFFFAOYSA-N n-methyl-n-(4-methyl-1-propylsulfonylpiperidin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1N(S(=O)(=O)CCC)CCC(C)C1N(C)C1=NC=NC2=C1C=CN2 URCTYVNPUZEJJF-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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Classifications

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NO20022738A 1999-12-10 2002-06-07 Pyrrolo(2,3-d)pyrimidinforbindelser, anvendelse derav samt farmasoytisk preparat. NO323378B1 (no)

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Application Number	Priority Date	Filing Date	Title
US17017999P	1999-12-10	1999-12-10
PCT/IB2000/001742 WO2001042246A2 (en)	1999-12-10	2000-11-23	PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS

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NO20022738L NO20022738L (no)	2002-06-07
NO20022738D0 NO20022738D0 (no)	2002-06-07
NO323378B1 true NO323378B1 (no)	2007-04-16

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JP (1)	JP4078074B2 (el)
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Families Citing this family (261)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1087970B1 (en) *	1998-06-19	2004-04-28	Pfizer Products Inc.	PYRROLO 2,3-d]PYRIMIDINE COMPOUNDS
PA8474101A1 (es)	1998-06-19	2000-09-29	Pfizer Prod Inc	Compuestos de pirrolo [2,3-d] pirimidina
JP4078074B2 (ja)	1999-12-10	2008-04-23	ファイザー・プロダクツ・インク	ピロロ［２，３−ｄ］ピリミジン化合物
ITMI992711A1 (it) *	1999-12-27	2001-06-27	Novartis Ag	Composti organici
ES2318605T3 (es) *	2000-06-26	2009-05-01	Pfizer Products Incorporated	Compuestos de pirrolo(2,3-d)pirimidina como agentes inmunosupresores.
US7301023B2 (en) *	2001-05-31	2007-11-27	Pfizer Inc.	Chiral salt resolution
MXPA03011998A (es)	2001-06-23	2005-07-01	Aventis Pharma Inc	Pirrolopirimidinas como inhibidores de protein cinasa.
GB0115393D0 (en) *	2001-06-23	2001-08-15	Aventis Pharma Ltd	Chemical compounds
GB0121033D0 (en) *	2001-08-30	2001-10-24	Novartis Ag	Organic compounds
GT200200234A (es) *	2001-12-06	2003-06-27		Compuestos cristalinos novedosos
TWI329105B (en)	2002-02-01	2010-08-21	Rigel Pharmaceuticals Inc	2,4-pyrimidinediamine compounds and their uses
NZ537752A (en)	2002-07-29	2006-12-22	Rigel Pharmaceuticals Inc	Use of 2,4-pyrimidinediamine compounds in the preparation of medicaments for treating autoimmune diseases
EP1388541A1 (en) *	2002-08-09	2004-02-11	Centre National De La Recherche Scientifique (Cnrs)	Pyrrolopyrazines as kinase inhibitors
BR0316470A (pt) *	2002-11-21	2005-10-11	Pfizer Prod Inc	Derivados de 3-amino-piperadina e métodos de preparação
EP1572213A1 (en)	2002-11-26	2005-09-14	Pfizer Products Inc.	Method of treatment of transplant rejection
US7923467B2 (en)	2003-05-30	2011-04-12	Ranbaxy Laboratories, Inc.	Substituted pyrrole derivatives and their use as HMG-CO inhibitors
CN102358738A (zh)	2003-07-30	2012-02-22	里格尔药品股份有限公司	2,4-嘧啶二胺化合物及其预防和治疗自体免疫疾病的用途
EP1689407A1 (en) *	2003-11-25	2006-08-16	Pfizer Products Inc.	Method of treatment of atherosclerosis
US20050137679A1 (en) *	2003-12-17	2005-06-23	Pfizer Inc	Modified stent useful for delivery of drugs along stent strut
WO2005063251A1 (en) *	2003-12-17	2005-07-14	Pfizer Products Inc.	Modified stent useful for delivery of drugs along stent strut
MXPA06007002A (es) *	2003-12-17	2006-08-31	Pfizer Prod Inc	Compuestos de pirrolo[2,3-d]pirimidina para tratar rechazo de transplantes.
US20050153990A1 (en) *	2003-12-22	2005-07-14	Watkins William J.	Phosphonate substituted kinase inhibitors
US20070281907A1 (en) *	2003-12-22	2007-12-06	Watkins William J	Kinase Inhibitor Phosphonate Conjugates
US20050187389A1 (en) *	2004-01-13	2005-08-25	Ambit Biosciences Corporation	Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases
HUP0400891A2 (en) *	2004-04-29	2006-04-28	Janos Szolcsanyi	7h-pyrrolo[2,3-d]pyrimidine derivatives, their pharmaceutically acceptable salts, pharmaceutical compositions containing them and process for the production of the compounds
AU2005237254B2 (en) *	2004-05-03	2010-02-04	Novartis Ag	Combinations comprising a S1P receptor agonist and a JAK3 kinase inhibitor
MXPA06015237A (es) *	2004-06-29	2007-12-10	Amgen Inc	Pirrolo[2-3-d]pirimidinas que modulan la actividad de ack1 y lck.
KR20070085433A (ko) *	2004-11-24	2007-08-27	노파르티스 아게	Ｊａｋ 저해제들과 ｂｃｒ-ａｂｌ, ｆｌｔ-3, ｆａｋ 또는ｒａｆ 키나제 저해제들 중 하나 이상의 조합물
AR054416A1 (es) *	2004-12-22	2007-06-27	Incyte Corp	Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas.
ATE420883T1 (de)	2005-02-03	2009-01-15	Vertex Pharma	Pyrrolopyrimidine verwendbar als protein kinase inhibitoren
WO2006091450A1 (en) *	2005-02-18	2006-08-31	Lexicon Genetics Incorporated	4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidine compounds
DE602006019088D1 (de)	2005-05-13	2011-02-03	Irm Llc	Verbindungen und zusammensetzungen als proteinkinase-hemmer
EP1904457B1 (en)	2005-06-08	2017-09-06	Rigel Pharmaceuticals, Inc.	Compositions and methods for inhibition of the jak pathway
US20070203161A1 (en)	2006-02-24	2007-08-30	Rigel Pharmaceuticals, Inc.	Compositions and methods for inhibition of the jak pathway
WO2007007919A2 (en)	2005-07-14	2007-01-18	Astellas Pharma Inc.	Heterocyclic janus kinase 3 inhibitors
EP2251341A1 (en)	2005-07-14	2010-11-17	Astellas Pharma Inc.	Heterocyclic Janus kinase 3 inhibitors
US8232394B2 (en)	2005-07-29	2012-07-31	Pfizer Inc.	Pyrrolo[2,3-d]pyrimidine derivatives; their intermediates and synthesis
WO2007038215A1 (en)	2005-09-22	2007-04-05	Incyte Corporation	Tetracyclic inhibitors of janus kinases
US8026377B2 (en)	2005-11-08	2011-09-27	Ranbaxy Laboratories, Limited	Process for (3R, 5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-[(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid hemi calcium salt
DK2474545T3 (en) *	2005-12-13	2017-01-23	Incyte Holdings Corp	Heteroberl-substituted pyrrolo [2,3-b] pyridines and pyrrolo [2,3-b] pyrimidines as Janus kinase inhibitors
US8962643B2 (en)	2006-02-24	2015-02-24	Rigel Pharmaceuticals, Inc.	Compositions and methods for inhibition of the JAK pathway
GB0605691D0 (en) *	2006-03-21	2006-05-03	Novartis Ag	Organic Compounds
WO2007117494A1 (en)	2006-04-05	2007-10-18	Vertex Pharmaceuticals Incorporated	Deazapurines useful as inhibitors of janus kinases
WO2008029237A2 (en) *	2006-09-05	2008-03-13	Pfizer Products Inc.	Combination therapies for rheumatoid arthritis
US20080161320A1 (en) *	2006-09-11	2008-07-03	Xiong Cai	Fused bicyclic pyrimidines as ptk inhibitors containing a zinc binding moiety
WO2008033747A2 (en) *	2006-09-11	2008-03-20	Curis, Inc.	Multi-functional small molecules as anti-proliferative agents
EP1900729A1 (en) *	2006-09-15	2008-03-19	Novartis AG	Benzoxazoles and oxazolopyridines being useful as Janus kinases inhibitors
JP5492565B2 (ja)	2006-12-22	2014-05-14	インサイト・コーポレイション	Ｊａｎｕｓキナーゼ阻害剤としての置換複素環
KR20090106604A (ko)	2007-01-12	2009-10-09	아스텔라스세이야쿠 가부시키가이샤	축합 피리딘 화합물
GEP20125533B (en) *	2007-06-13	2012-05-25	Incyte Corp	Salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentyl propanenitrile
CL2008001709A1 (es)	2007-06-13	2008-11-03	Incyte Corp	Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras.
KR20120115413A (ko)	2007-07-11	2012-10-17	화이자 인코포레이티드	안구 건조증 치료용 약학 조성물 및 방법
WO2009055674A1 (en) *	2007-10-26	2009-04-30	Targegen Inc.	Pyrrolopyrimidine alkynyl compounds and methods of making and using same
CN101910152B (zh)	2007-11-16	2014-08-06	因塞特公司	作为janus激酶抑制剂的4-吡唑基-n-芳基嘧啶-2-胺和4-吡唑基-n-杂芳基嘧啶-2-胺
PE20091485A1 (es)	2008-02-06	2009-10-26	Novartis Ag	DERIVADOS DE PIRROLO-[2,3-d]-PIRIMIDINA COMO INHIBIDORES DE CINASAS
KR101700454B1 (ko)	2008-02-15	2017-01-26	리겔 파마슈티칼스, 인크.	피리미딘-2-아민 화합물 및 ｊａｋ 키나제 억제제로서의 그의 용도
NZ587928A (en)	2008-03-11	2012-08-31	Incyte Corp	Azetidine and cyclobutane derivatives as jak inhibitors
US8138339B2 (en)	2008-04-16	2012-03-20	Portola Pharmaceuticals, Inc.	Inhibitors of protein kinases
EA019973B1 (ru)	2008-04-16	2014-07-30	Портола Фармасьютиклз, Инк.	ИНГИБИТОРЫ Syk ПРОТЕИНКИНАЗ
CN103224497A (zh)	2008-04-22	2013-07-31	波托拉医药品公司	蛋白激酶抑制剂
WO2009132202A2 (en)	2008-04-24	2009-10-29	Incyte Corporation	Macrocyclic compounds and their use as kinase inhibitors
WO2010014930A2 (en) *	2008-08-01	2010-02-04	Biocryst Pharmaceuticals, Inc.	Therapeutic agents
CN102131812B (zh)	2008-08-20	2014-04-09	硕腾有限责任公司	吡咯并[2，3-d]嘧啶化合物
US8385364B2 (en) *	2008-09-24	2013-02-26	Nec Laboratories America, Inc.	Distributed message-passing based resource allocation in wireless systems
KR101686685B1 (ko)	2008-10-31	2016-12-14	제넨테크, 인크.	피라졸로피리미딘 ｊａｋ 억제제 화합물 및 방법
DE102008063597A1 (de)	2008-12-18	2010-07-01	Schaeffler Technologies Gmbh & Co. Kg	Dichtungsanordnung mit Dichtlippenschutz
JOP20190230A1 (ar)	2009-01-15	2017-06-16	Incyte Corp	طرق لاصلاح مثبطات انزيم jak و المركبات الوسيطة المتعلقة به
WO2010085597A1 (en)	2009-01-23	2010-07-29	Incyte Corporation	Macrocyclic compounds and their use as kinase inhibitors
EP2396004A4 (en)	2009-02-11	2012-07-25	Reaction Biology Corp	SELECTIVE KINASE HEMMER
CA2758614A1 (en)	2009-04-14	2010-10-21	Cellzome Limited	Fluoro substituted pyrimidine compounds as jak3 inhibitors
EP3026052A1 (en) *	2009-04-20	2016-06-01	Auspex Pharmaceuticals, Inc.	Preparation of deuterated piperidine inhibitors of janus kinase 3
CN102458581B (zh)	2009-05-22	2016-03-30	因塞特控股公司	作为JANUS激酶抑制剂的吡唑-4-基-吡咯并[2，3-d]嘧啶和吡咯-3-基-吡咯并[2，3-d]嘧啶的N-(杂)芳基-吡咯烷衍生物
UA106078C2 (uk)	2009-05-22	2014-07-25	Інсайт Корпорейшн	3-[4-(7H-ПІРОЛО[2,3-d]ПІРИМІДИН-4-ІЛ)-1H-ПІРАЗОЛ-1-ІЛ]ОКТАН- АБО ГЕПТАННІТРИЛ ЯК JAK-ІНГІБІТОРИ
UA110324C2 (en) *	2009-07-02	2015-12-25	Genentech Inc	Jak inhibitory compounds based on pyrazolo pyrimidine
AR077465A1 (es)	2009-07-08	2011-08-31	Leo Pharma As	Derivados de pirrolopirimidina como inhibidores de receptores jak y protein tirosin quinasas y uso farmaceutico de los mismos
TWI466885B (zh) *	2009-07-31	2015-01-01	Japan Tobacco Inc	含氮螺環化合物及其醫藥用途
US9249145B2 (en)	2009-09-01	2016-02-02	Incyte Holdings Corporation	Heterocyclic derivatives of pyrazol-4-yl-pyrrolo[2,3-d]pyrimidines as janus kinase inhibitors
CA2771675A1 (en)	2009-09-11	2011-03-17	Cellzome Limited	Ortho substituted pyrimidine compounds as jak inhibitors
CA2777114C (en) *	2009-10-09	2018-10-23	Incyte Corporation	Hydroxyl, keto, and glucuronide derivatives of 3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-cyclopentylpropanenitrile
ES2426407T3 (es)	2009-10-15	2013-10-23	Pfizer Inc.	Compuestos de pirrolo[2,3-d]pirimidina
JP5744887B2 (ja)	2009-10-20	2015-07-08	セルゾームリミティッド	Ｊａｋ阻害剤としてのヘテロシクリルピラゾロピリミジン類似体
EP2513114B1 (en)	2009-12-18	2014-04-02	Pfizer Inc.	Pyrrolo[2,3-d]pyrimidine compounds
AR079984A1 (es) *	2010-01-12	2012-03-07	Hoffmann La Roche	Compuestos heterociclicos triciclicos, composiciones y su uso en el tratamiento de enfermedades mediadas por la inhibicion de jak1
AU2011213198B2 (en)	2010-02-05	2014-04-24	Zoetis Llc	Pyrrolo [ 2,3-d] pyrimidine urea compounds as JAK inhibitors
KR102172742B1 (ko)	2010-03-10	2020-11-02	인사이트 홀딩스 코포레이션	Ｊａｋ１ 저해제로서의 피페리딘４일 아제티딘 유도체
KR20130094693A (ko)	2010-04-30	2013-08-26	셀좀 리미티드	Ｊａｋ 저해제로서의 피라졸 화합물
SI2574168T1 (sl)	2010-05-21	2016-07-29	Incyte Holdings Corporation	Topična formulacija zaviralca jak
WO2011149827A1 (en) *	2010-05-24	2011-12-01	Glaxosmithkline Llc	Compounds and methods
CN101851241B (zh) *	2010-07-02	2012-05-23	西安交通大学	一种抗肿瘤化合物及其制备方法和其用途
WO2012022681A2 (en)	2010-08-20	2012-02-23	Cellzome Limited	Heterocyclyl pyrazolopyrimidine analogues as selective jak inhibitors
TW201300360A (zh)	2010-11-01	2013-01-01	Portola Pharm Inc	做為ｊａｋ激酶調節劑之菸鹼醯胺
JP5917544B2 (ja)	2010-11-19	2016-05-18	インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅＨｏｌｄｉｎｇｓＣｏｒｐｏｒａｔｉｏｎ	Ｊａｋ阻害剤としての複素環置換ピロロピリジンおよびピロロピリミジン
SG190839A1 (en)	2010-11-19	2013-07-31	Incyte Corp	Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors
WO2012093169A1 (en)	2011-01-07	2012-07-12	Leo Pharma A/S	Novel sulfamide piperazine derivatives as protein tyrosine kinase inhibitors and pharmaceutical use thereof
WO2012112847A1 (en)	2011-02-18	2012-08-23	Novartis Pharma Ag	mTOR/JAK INHIBITOR COMBINATION THERAPY
BR112013024267A2 (pt)	2011-03-22	2018-06-26	Advinus Therapeutics Ltd	compostos tricíclicos fundidos substituídos, composições e aplicações medicinais dos mesmos.
WO2012135338A1 (en)	2011-03-28	2012-10-04	Ratiopharm Gmbh	Processes for preparing tofacitinib salts
US9050342B2 (en)	2011-03-29	2015-06-09	Pfizer Inc.	Beneficial effects of combination therapy on cholesterol
MX2013009972A (es) *	2011-04-08	2013-09-26	Pfizer	Formas cristalinas y no cristalinas de tofacitinib y composicion farmaceutica que comprende tofacitinib y un potenciador de penetracion.
WO2012143320A1 (en)	2011-04-18	2012-10-26	Cellzome Limited	(7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors
MX344479B (es)	2011-06-20	2016-12-16	Incyte Holdings Corp	Derivados de azetidinil fenil, piridil o pirazinil carboxamida como inhibidores de cinasa janus (jak).
AU2012288892B2 (en)	2011-07-28	2016-04-21	Cellzome Limited	Heterocyclyl pyrimidine analogues as JAK inhibitors
WO2013017479A1 (en)	2011-07-29	2013-02-07	Cellzome Limited	Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors
WO2013017480A1 (en)	2011-07-29	2013-02-07	Cellzome Limited	Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors
WO2013023119A1 (en)	2011-08-10	2013-02-14	Novartis Pharma Ag	JAK P13K/mTOR COMBINATION THERAPY
KR102021159B1 (ko)	2011-08-12	2019-09-11	닛산 가가쿠 가부시키가이샤	트리시클릭 헤테로시클릭 화합물 및 jak 저해제
TW201313721A (zh)	2011-08-18	2013-04-01	Incyte Corp	作為ｊａｋ抑制劑之環己基氮雜環丁烷衍生物
GB2494173A (en)	2011-09-01	2013-03-06	Vectair Systems Ltd	Dispensing apparatus
UA111854C2 (uk)	2011-09-07	2016-06-24	Інсайт Холдінгс Корпорейшн	Способи і проміжні сполуки для отримання інгібіторів jak
US20140323504A1 (en)	2011-09-20	2014-10-30	Cellzome Limited	Pyrazolo[4,3-c]Pyridine Derivatives As Kinase Inhibitors
CN104066431B (zh)	2011-11-23	2017-03-08	波托拉医药品公司	吡嗪激酶抑制剂
CN107898790B (zh)	2011-11-30	2024-06-21	埃默里大学	用于治疗或预防逆转录病毒和其它病毒感染的抗病毒jak抑制剂
US8993756B2 (en) *	2011-12-06	2015-03-31	Merck Sharp & Dohme Corp.	Pyrrolopyrimidines as janus kinase inhibitors
EP2791141B1 (en)	2011-12-15	2017-02-08	ratiopharm GmbH	Tofacitinib mono-tartrate salt
RU2618673C2 (ru)	2011-12-21	2017-05-10	Цзянсу Хэнжуй Медсин Ко., Лтд.	Производные пирролопиримидина, полезные в качестве ингибиторов jak-киназы
EP2794598A1 (en)	2011-12-23	2014-10-29	Cellzome Limited	Pyrimidine-2,4-diamine derivatives as kinase inhibitors
US20130310340A1 (en)	2012-05-16	2013-11-21	Rigel Pharmaceuticals, Inc.	Method of treating muscular degradation
US9193733B2 (en)	2012-05-18	2015-11-24	Incyte Holdings Corporation	Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK inhibitors
US9676756B2 (en)	2012-10-08	2017-06-13	Portola Pharmaceuticals, Inc.	Substituted pyrimidinyl kinase inhibitors
CN102936251A (zh) *	2012-11-05	2013-02-20	上海毕得医药科技有限公司	一种吡咯并[2,3-d]嘧啶衍生物的制备方法
SI2919766T1 (sl)	2012-11-15	2021-11-30	Incyte Holdings Corporation	Farmacevtske oblike ruksolitiniba s podaljšanim sproščanjem
WO2014097150A1 (en)	2012-12-17	2014-06-26	Ranbaxy Laboratories Limited	Process for the preparation of tofacitinib and intermediates thereof
CN103896826B (zh) *	2012-12-26	2016-08-03	上海朴颐化学科技有限公司	氮保护的(3r,4r)-3-甲氨基-4-甲基哌啶的不对称合成方法、相关中间体及原料制备方法
WO2014123167A1 (ja)	2013-02-08	2014-08-14	日産化学工業株式会社	３環性ピロロピリジン化合物及びｊａｋ阻害剤
GEP201606600B (en)	2013-02-22	2017-01-10	Pfizer	Pyrrolo [2, 3 -d]pyrimidine derivatives as inhibitors of janus- related kinases (jak)
BR122021015061B1 (pt)	2013-03-06	2022-10-18	Incyte Holdings Corporation	Processos e intermediários para preparar um inibidor de jak
JP6041823B2 (ja) *	2013-03-16	2016-12-14	ファイザー・インク	トファシチニブの経口持続放出剤形
US20140343034A1 (en) *	2013-04-25	2014-11-20	Japan Tobacco Inc.	Skin barrier function improving agent
US20160122354A1 (en) *	2013-06-05	2016-05-05	Srinivasan Thirumalai Rajan	PROCESS FOR THE PREPARATION OF (3R,4R)-4-METHYL-3-(METHYL-7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL-AMINO)-ß-OXO-1-PIPERIDINEPROPANENITRILE AND ITS SALTS
SG10201801069QA (en)	2013-08-07	2018-03-28	Incyte Corp	Sustained release dosage forms for a jak1 inhibitor
CN103819474A (zh) *	2013-11-04	2014-05-28	湖南华腾制药有限公司	一种托法替尼的制备方法
WO2015078417A1 (zh) *	2013-11-29	2015-06-04	四川好医生药业集团有限公司	吡咯并嘧啶化合物及其在制备降血糖药物中的用途
HUE035264T2 (hu)	2013-12-05	2018-05-02	Pfizer	Pirrolo[2,3-d]pirimidinil-, pirrolo[2,3-b]pirazinil- és pirrolo[2,3-d]-piridinil- akrilamidok
US9951012B2 (en) *	2013-12-09	2018-04-24	Unichem Laboratories Limited	Process for the preparation of (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
CA2881262A1 (en)	2014-02-06	2015-08-06	Prabhudas Bodhuri	Solid forms of tofacitinib salts
EP3110820B1 (en)	2014-02-28	2022-04-06	Nimbus Lakshmi, Inc.	Tyk2 inhibitors and uses thereof
NZ725001A (en)	2014-05-14	2021-08-27	Nissan Chemical Ind Ltd	Tricyclic compound and jak inhibitor
HUE054784T2 (hu)	2014-05-23	2021-09-28	Hoffmann La Roche	5-klór-2-difluor-metoxifenil-pirazolopirimidin vegyületek, amelyek JAK-gátlók
US9498467B2 (en)	2014-05-30	2016-11-22	Incyte Corporation	Treatment of chronic neutrophilic leukemia (CNL) and atypical chronic myeloid leukemia (aCML) by inhibitors of JAK1
ES2750655T3 (es)	2014-08-12	2020-03-26	Pfizer	Derivados de pirrolo[2,3-d]pirimidina útiles para inhibir la Janus cinasa
CN117164657A (zh)	2014-08-12	2023-12-05	莫纳什大学	定向淋巴的前药
KR101710127B1 (ko)	2014-08-29	2017-02-27	한화제약주식회사	야누스인산화효소 억제제로서의 치환된 N-(피롤리딘-3-일)-7H-피롤로[2,3-d]피리미딘-4-아민
WO2016138352A1 (en)	2015-02-27	2016-09-01	Nimbus Lakshmi, Inc.	Tyk2 inhibitors and uses thereof
CN104761556B (zh) *	2015-03-21	2017-06-23	河北国龙制药有限公司	托法替布中间体杂质、托法替布杂质及其合成方法，以及托法替布的质量监控方法
EP3078665A1 (en)	2015-04-10	2016-10-12	OLON S.p.A.	Efficient method for the preparation of tofacitinib citrate
WO2016178110A1 (en)	2015-05-01	2016-11-10	Pfizer Inc.	Pyrrolo[2,3-d]pyrimidinyl, pyrrolo[2,3-b]pyrazinyl, pyrrolo[2,3-b]pyridinyl acrylamides and epoxides thereof
WO2016192563A1 (zh) *	2015-05-29	2016-12-08	南京明德新药研发股份有限公司	Janus激酶抑制剂
WO2017004134A1 (en)	2015-06-29	2017-01-05	Nimbus Iris, Inc.	Irak inhibitors and uses thereof
KR101771219B1 (ko) *	2015-08-21	2017-09-05	양지화학 주식회사	야누스 키나제 1 선택적 억제제 및 그 의약 용도
EP3344624B8 (en)	2015-09-02	2023-11-29	Takeda Pharmaceutical Company Limited	Tyk2 inhibitors and uses thereof
JP7118888B2 (ja)	2015-09-08	2022-08-16	モナッシュユニバーシティ	リンパ指向性プロドラッグ
WO2017044720A1 (en)	2015-09-11	2017-03-16	Navitor Pharmaceuticals, Inc.	Rapamycin analogs and uses thereof
HRP20230331T1 (hr)	2015-10-23	2023-07-07	Navitor Pharmaceuticals, Inc.	Modulatori interakcije sestrin-gator2 i njihova uporaba
WO2017091681A1 (en)	2015-11-24	2017-06-01	Aclaris Therapeutics, Inc.	Selective kinase inhibitors
RS60237B1 (sr)	2015-11-24	2020-06-30	Theravance Biopharma R&D Ip Llc	Prolekovi jak inhibitornih jedinjenja za lečenje gastorintestinalne inflamatorne bolesti
CN106831779B (zh) *	2015-11-28	2019-07-19	南昌弘益药业有限公司	一类jak激酶抑制剂的新化合物
CN105348287A (zh) *	2015-11-30	2016-02-24	宁波立华制药有限公司	一种枸橼酸托法替布的新型合成工艺
US20190083609A1 (en)	2016-01-18	2019-03-21	Helmoltz Zentrum München - Deutsches Forschungszentrum Für Gesundheit And Umwelt (Gmbh)	Tofacitinib as vaccination immune modulator
ES2965264T3 (es)	2016-03-09	2024-04-11	Raze Therapeutics Inc	Inhibidores de la 3-fosfoglicerato deshidrogenasa y sus usos
PL3426244T3 (pl) *	2016-03-09	2023-09-25	Raze Therapeutics, Inc.	Inhibitory dehydrogenazy 3-fosfoglicerynianowej i ich zastosowania
CN107513067A (zh)	2016-06-16	2017-12-26	北京赛林泰医药技术有限公司	含有取代环戊基的吡咯并嘧啶化合物
US10759796B2 (en)	2016-06-21	2020-09-01	X4 Pharmaceuticals, Inc.	CXCR4 inhibitors and uses thereof
AU2017342464B2 (en)	2016-10-14	2021-09-16	Takeda Pharmaceutical Company Limited	TYK2 inhibitors and uses thereof
US10647713B2 (en)	2016-10-21	2020-05-12	Nimbus Lakshmi, Inc.	TYK2 inhibitors and uses thereof
WO2018089499A1 (en)	2016-11-08	2018-05-17	Navitor Pharmaceuticals, Inc.	PHENYL AMINO PIPERIDINE mTORC INHIBITORS AND USES THEREOF
PL3511333T3 (pl) *	2016-11-23	2021-12-06	Wuxi Fortune Pharmaceutical Co., Ltd	Postać krystaliczna i forma soli związku 7h-pirolo[2,3-d]pirymidyny oraz sposób ich wytwarzania
BR112019008812A2 (pt)	2016-11-23	2019-07-16	Jiangsu Hengrui Medicine Co	método de preparação para e intermediário de derivado de pirrolo anel heteroaromático de seis elementos
US11091451B2 (en)	2016-12-05	2021-08-17	Raze Therapeutics, Inc.	SHMT inhibitors and uses thereof
JP2020502238A (ja)	2016-12-23	2020-01-23	バイスクルアールディー・リミテッド	新規連結構造を有するペプチド誘導体
EP3565638B8 (en)	2017-01-06	2024-04-10	BicycleRD Limited	Bicycle conjugate for treating cancer
EP3592755A1 (en)	2017-03-08	2020-01-15	Theravance Biopharma R&D IP, LLC	Glucuronide prodrugs of tofacitinib
TW202321243A (zh)	2017-03-08	2023-06-01	美商林伯士拉克許米公司	Ｔｙｋ２抑制劑之生產方法
EP3375784A1 (en)	2017-03-14	2018-09-19	Artax Biopharma Inc.	Aza-dihydro-acridone derivatives
EP3375778A1 (en)	2017-03-14	2018-09-19	Artax Biopharma Inc.	Aryl-piperidine derivatives
US11339144B2 (en)	2017-04-10	2022-05-24	Navitor Pharmaceuticals, Inc.	Heteroaryl Rheb inhibitors and uses thereof
EP3615550A1 (en)	2017-04-27	2020-03-04	BicycleTx Limited	Bicyclic peptide ligands and uses thereof
AU2018274577A1 (en)	2017-05-22	2019-10-10	F. Hoffmann-La Roche Ag	Therapeutic compounds and compositions, and methods of use thereof
US10233174B2 (en)	2017-05-23	2019-03-19	Theravance Biopharma R&D Ip, Llc	Thiocarbamate prodrugs of tofacitinib
CA3063963A1 (en)	2017-05-23	2018-11-29	Theravance Biopharma R&D Ip, Llc	Glucuronide prodrugs of janus kinase inhibitors
EP3645549A1 (en)	2017-06-26	2020-05-06	BicycleRD Limited	Bicyclic peptide ligands with detectable moieties and uses thereof
US11046698B2 (en)	2017-07-28	2021-06-29	Nimbus Lakshmi, Inc.	TYK2 inhibitors and uses thereof
WO2019025811A1 (en)	2017-08-04	2019-02-07	Bicycletx Limited	SPECIFIC BICYCLIC PEPTIDE LIGANDS OF CD137
EP3668550A1 (en)	2017-08-14	2020-06-24	Bicyclerd Limited	Bicyclic peptide ligand prr-a conjugates and uses thereof
US10759865B2 (en)	2017-08-22	2020-09-01	Eyal Levit	Treatment of diabetes mellitus
US11883497B2 (en)	2017-08-29	2024-01-30	Puretech Lyt, Inc.	Lymphatic system-directing lipid prodrugs
WO2019046491A1 (en)	2017-08-29	2019-03-07	Ariya Therapeutics, Inc.	LIPIDIC PRODRUGS DIRECTING TO THE LYMPHATIC SYSTEM
CA3076613A1 (en)	2017-09-22	2019-03-28	Kymera Therapeutics, Inc.	Protein degraders and uses thereof
EP3684366A4 (en)	2017-09-22	2021-09-08	Kymera Therapeutics, Inc.	CRBN LIGANDS AND USES OF THE LATEST
CN107793418B (zh) *	2017-10-24	2020-08-04	扬子江药业集团有限公司	一种枸橼酸托法替布的工业化生产方法
TW201924683A (zh)	2017-12-08	2019-07-01	美商英塞特公司	用於治療骨髓增生性贅瘤的低劑量組合療法
US11608345B1 (en)	2017-12-19	2023-03-21	Puretech Lyt, Inc.	Lipid prodrugs of rapamycin and its analogs and uses thereof
TWI825046B (zh)	2017-12-19	2023-12-11	英商拜西可泰克斯有限公司	Epha2特用之雙環胜肽配位基
US11304954B2 (en)	2017-12-19	2022-04-19	Puretech Lyt, Inc.	Lipid prodrugs of mycophenolic acid and uses thereof
GB201721265D0 (en)	2017-12-19	2018-01-31	Bicyclerd Ltd	Bicyclic peptide ligands specific for EphA2
IL315310A (en)	2017-12-26	2024-10-01	Kymera Therapeutics Inc	IRAK joints and used in them
EP3737666A4 (en)	2018-01-12	2022-01-05	Kymera Therapeutics, Inc.	PROTEIN DEGRADANTS AND USES THEREOF
US11512080B2 (en)	2018-01-12	2022-11-29	Kymera Therapeutics, Inc.	CRBN ligands and uses thereof
CN117659010A (zh)	2018-01-29	2024-03-08	默克专利股份有限公司	Gcn2抑制剂及其用途
KR20200116481A (ko)	2018-01-29	2020-10-12	메르크 파텐트 게엠베하	Gcn2 억제제 및 이의 용도
TWI797242B (zh)	2018-01-30	2023-04-01	美商英塞特公司	製備ｊａｋ抑制劑之方法及中間物
EA202091742A1 (ru)	2018-02-27	2021-02-19	Артакс Биофарма Инк.	ПРОИЗВОДНЫЕ ХРОМЕНА В КАЧЕСТВЕ ИНГИБИТОРОВ ВЗАИМОДЕЙСТВИЯ TCR-Nck
CA3095487A1 (en)	2018-03-30	2019-10-03	Incyte Corporation	Treatment of hidradenitis suppurativa using jak inhibitors
PT3784666T (pt)	2018-04-24	2022-06-06	Merck Patent Gmbh	Compostos antiproliferação e utilizações dos mesmos
WO2019213562A1 (en)	2018-05-03	2019-11-07	The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	Peptide hydrogels for delivery of immunosuppressive drugs and uses thereof
EP3810096A1 (en)	2018-05-24	2021-04-28	Synthon B.V.	Controlled release tofacitinib compositions
PT3813946T (pt)	2018-06-15	2024-07-10	Janssen Pharmaceutica Nv	Análogos da rapamicina e suas utilizações
US11180531B2 (en)	2018-06-22	2021-11-23	Bicycletx Limited	Bicyclic peptide ligands specific for Nectin-4
GB201810316D0 (en)	2018-06-22	2018-08-08	Bicyclerd Ltd	Peptide ligands for binding to EphA2
WO2020010177A1 (en)	2018-07-06	2020-01-09	Kymera Therapeutics, Inc.	Tricyclic crbn ligands and uses thereof
CN108822112B (zh) *	2018-08-13	2019-12-20	山东罗欣药业集团恒欣药业有限公司	一种托法替尼化合物的制备方法
WO2020081508A1 (en)	2018-10-15	2020-04-23	Nimbus Lakshmi, Inc.	Tyk2 inhibitors and uses thereof
CN112955459A (zh)	2018-10-23	2021-06-11	拜斯科技术开发有限公司	双环肽配体和其用途
US11352350B2 (en)	2018-11-30	2022-06-07	Kymera Therapeutics, Inc.	IRAK degraders and uses thereof
CA3120866A1 (en)	2018-11-30	2020-06-04	Nimbus Lakshmi, Inc.	Tyk2 inhibitors and uses thereof
SG11202106635WA (en)	2018-12-21	2021-07-29	Daiichi Sankyo Co Ltd	Combination of antibody-drug conjugate and kinase inhibitor
KR102131107B1 (ko)	2019-01-15	2020-07-07	주식회사 다산제약	3-아미노-피페리딘 화합물의 신규한 제조 방법
AU2020212001A1 (en)	2019-01-23	2021-07-22	Takeda Pharmaceutical Company Limited	TYK2 inhibitors and uses thereof
EP3938370A4 (en)	2019-03-13	2022-12-21	Intas Pharmaceuticals Ltd.	METHOD FOR THE PREPARATION OF TOFACITINIB AND ITS PHARMACEUTICALLY ACCEPTABLE SALT
EP3946606A1 (en) *	2019-03-27	2022-02-09	Insilico Medicine IP Limited	Bicyclic jak inhibitors and uses thereof
AU2020253990A1 (en)	2019-04-02	2021-10-28	Bicycletx Limited	Bicycle toxin conjugates and uses thereof
US11485750B1 (en)	2019-04-05	2022-11-01	Kymera Therapeutics, Inc.	STAT degraders and uses thereof
JOP20210298A1 (ar)	2019-05-14	2023-01-30	Provention Bio Inc	طرق وتركيبات للوقاية من مرض السكري من النوع الأول
SG11202113154YA (en)	2019-05-31	2021-12-30	Ikena Oncology Inc	Tead inhibitors and uses thereof
JP7261428B2 (ja) *	2019-06-05	2023-04-20	クワンチョウジョーヨーファーマテックカンパニー，リミティド	ピロロピリミジン類化合物及びその使用
TW202118770A (zh)	2019-07-30	2021-05-16	英商拜西可泰克斯有限公司	異質雙環肽複合物
US20220401446A1 (en)	2019-08-29	2022-12-22	Synthon B.V.	Controlled release tofacitinib compositions
EP4028385A4 (en)	2019-09-11	2023-11-08	Vincere Biosciences, Inc.	USP30 INHIBITORS AND USES THEREOF
US20210078996A1 (en)	2019-09-13	2021-03-18	Nimbus Saturn, Inc.	Hpk1 antagonists and uses thereof
BR112022007826A2 (pt)	2019-11-14	2022-07-05	Pfizer	Combinações de 1-(((2s,3s,4s)-3-etil-4-fluoro-5-oxopirrolidin-2-il)metóxi)-7-metóxi-isoquino¬lina-6-carboxamida e formas de dosagem oral
TW202131926A (zh) *	2019-11-22	2021-09-01	美商英塞特公司	包含alk2抑制劑及jak2抑制劑的組合療法
BR112022010754A2 (pt)	2019-12-05	2022-08-23	Anakuria Therapeutics Inc	Análogos de rapamicina e usos dos mesmos
IL293917A (en)	2019-12-17	2022-08-01	Kymera Therapeutics Inc	Iraq joints and their uses
EP4076524A4 (en)	2019-12-17	2023-11-29	Kymera Therapeutics, Inc.	IRAQ DEGRADERS AND USES THEREOF
WO2021133920A1 (en)	2019-12-23	2021-07-01	Kymera Therapeutics, Inc.	Smarca degraders and uses thereof
JP2023514147A (ja)	2020-02-05	2023-04-05	ピュアテック・エル・ワイ・ティ・インコーポレイテッド	神経ステロイドの脂質プロドラッグ
BR112022017727A2 (pt)	2020-03-03	2022-11-16	Pic Therapeutics Inc	Inibidores de eif4e e usos dos mesmos
JP2023518423A (ja)	2020-03-19	2023-05-01	カイメラセラピューティクス，インコーポレイテッド	Ｍｄｍ２分解剤およびそれらの使用
CA3177852A1 (en)	2020-04-04	2021-10-07	Pfizer Inc.	Methods of treating coronavirus disease 2019
US11766438B2 (en)	2020-04-24	2023-09-26	Slayback Pharma Llc	Pharmaceutical compositions of tofacitinib for oral administration
TW202210483A (zh)	2020-06-03	2022-03-16	美商凱麥拉醫療公司	Irak降解劑之結晶型
US11833155B2 (en)	2020-06-03	2023-12-05	Incyte Corporation	Combination therapy for treatment of myeloproliferative neoplasms
US12006366B2 (en)	2020-06-11	2024-06-11	Provention Bio, Inc.	Methods and compositions for preventing type 1 diabetes
KR102673131B1 (ko) *	2020-07-28	2024-06-10	아주대학교산학협력단	신규한 톨-유사 수용체 3/7/9 억제 소분자 화합물
EP3944859A1 (en)	2020-07-30	2022-02-02	Assistance Publique Hôpitaux de Paris	Method for treating immune toxicities induced by immune checkpoint inhibitors
JP2023548087A (ja)	2020-10-30	2023-11-15	ディーネイチャーカンパニーリミテッド	トキンソウ由来の抽出物を含む抗炎症、自己免疫疾患、及び非アルコール性脂肪性肝疾患の予防及び治療用組成物
IL303376A (en)	2020-12-02	2023-08-01	Ikena Oncology Inc	TEAD inhibitors and their uses
AU2022216810A1 (en)	2021-02-02	2023-08-24	Liminal Biosciences Limited	Gpr84 antagonists and uses thereof
CA3207380A1 (en)	2021-02-15	2022-08-18	Haojing RONG	Irak4 degraders and uses thereof
EP4301756A1 (en)	2021-03-05	2024-01-10	Nimbus Saturn, Inc.	Hpk1 antagonists and uses thereof
JP2024513011A (ja)	2021-03-29	2024-03-21	ニンバスサターン，インコーポレイテッド	Ｈｐｋ１アンタゴニスト及びその使用
IL307673A (en)	2021-04-16	2023-12-01	Ikena Oncology Inc	MEK inhibitors and their use
BR112023023223A2 (pt)	2021-05-07	2024-01-30	Kymera Therapeutics Inc	Degradadores de cdk2 e usos dos mesmos
EP4347028A1 (en)	2021-06-04	2024-04-10	Synthon B.V.	Prolonged release tofacitinib compositions
CA3229560A1 (en)	2021-08-25	2023-03-02	Christopher L. Vandeusen	Eif4e inhibitors and uses thereof
US20230134932A1 (en)	2021-08-25	2023-05-04	PIC Therapeutics, Inc.	Eif4e inhibitors and uses thereof
EP4180042A1 (en)	2021-11-15	2023-05-17	Sanovel Ilac Sanayi Ve Ticaret A.S.	A film coated tablet comprising micronized tofacitinib
WO2023114984A1 (en)	2021-12-17	2023-06-22	Ikena Oncology, Inc.	Tead inhibitors and uses thereof
WO2023147594A2 (en)	2022-01-31	2023-08-03	Kymera Therapeutics, Inc.	Irak degraders and uses thereof
WO2023173053A1 (en)	2022-03-10	2023-09-14	Ikena Oncology, Inc.	Mek inhibitors and uses thereof
WO2023173057A1 (en)	2022-03-10	2023-09-14	Ikena Oncology, Inc.	Mek inhibitors and uses thereof
WO2024042218A1 (en)	2022-08-26	2024-02-29	Synthon B.V.	Prolonged release tofacitinib compositions without functional coating

Family Cites Families (63)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3037980A (en) *	1955-08-18	1962-06-05	Burroughs Wellcome Co	Pyrrolopyrimidine vasodilators and method of making them
GB915304A (en)	1958-03-13	1963-01-09	Wellcome Found	Pyrrolo[2,3-d]pyrimidine derivatives
BE640616A (el)	1962-12-19
US3492397A (en)	1967-04-07	1970-01-27	Warner Lambert Pharmaceutical	Sustained release dosage in the pellet form and process thereof
US4060598A (en)	1967-06-28	1977-11-29	Boehringer Mannheim G.M.B.H.	Tablets coated with aqueous resin dispersions
US3538214A (en)	1969-04-22	1970-11-03	Merck & Co Inc	Controlled release medicinal tablets
US4173626A (en)	1978-12-11	1979-11-06	Merck & Co., Inc.	Sustained release indomethacin
JPS59112984A (ja)	1982-12-21	1984-06-29	Shionogi & Co Ltd	１，４−ベンゾジアゼピン誘導体
NL8403224A (nl)	1984-10-24	1986-05-16	Oce Andeno Bv	Dioxafosforinanen, de bereiding ervan en de toepassing voor het splitsen van optisch actieve verbindingen.
US4725599A (en)	1986-09-08	1988-02-16	Pfizer Inc.	Heterocyclic ring fused pyrimidine-4 (3H)-ones as anticoccidial agents
FR2619111B1 (fr)	1987-08-07	1991-01-11	Synthelabo	Derives de (piperidinyl-4)methyl-2 tetrahydro-1,2,3,4 9h-pyrido (3,4-b) indole, leur preparation et leur application en therapeutique
NO169490C (no)	1988-03-24	1992-07-01	Takeda Chemical Industries Ltd	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolopyrimidinderivater
JP2983254B2 (ja)	1989-06-14	1999-11-29	武田薬品工業株式会社	ピロロ〔２，３―ｄ〕ピリミジン誘導体の製造法およびその中間体
NZ239846A (en)	1990-09-27	1994-11-25	Merck & Co Inc	Sulphonamide derivatives and pharmaceutical compositions thereof
US5461156A (en)	1993-03-31	1995-10-24	Eli Lilly And Company	Stereocontrolled synthesis of cis-bicyclic compounds
JPH0710877A (ja)	1993-06-24	1995-01-13	Teijin Ltd	４―ヘテロアリサイクリック―ピロロ［２，３―ｄ］ピリミジン
US6136595A (en)	1993-07-29	2000-10-24	St. Jude Children's Research Hospital	Jak kinases and regulations of cytokine signal transduction
US5389509A (en)	1993-10-04	1995-02-14	Eastman Kodak Company	Ultrathin high chloride tabular grain emulsions
IL112249A (en)	1994-01-25	2001-11-25	Warner Lambert Co	Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds
EP0682027B1 (de)	1994-05-03	1997-10-15	Novartis AG	Pyrrolopyrimidinderivate mit antiproliferativer Wirkung
JPH07330732A (ja)	1994-06-10	1995-12-19	Kyorin Pharmaceut Co Ltd	光学活性な３−アミノ−１−ベンジルピペリジン誘導体
US5559128A (en)	1995-04-18	1996-09-24	Merck & Co., Inc.	3-substituted piperidines promote release of growth hormone
ES2203642T3 (es)	1995-06-07	2004-04-16	Pfizer Inc.	Derivados de pirimidina heterociclicos con anillos condensados.
ES2167586T3 (es)	1995-07-05	2002-05-16	Du Pont	Pirimidinonas fungicidas.
KR100437582B1 (ko)	1995-07-06	2004-12-17	노파르티스 아게	피롤로피리미딘및그들의제조방법
AR004010A1 (es)	1995-10-11	1998-09-30	Glaxo Group Ltd	Compuestos heterociclicos
ES2159760T3 (es)	1995-11-14	2001-10-16	Pharmacia & Upjohn Spa	Derivados de aril purina y piridopirimidina y de heteroaril purina y piridopirimidina.
AU1441497A (en)	1996-01-23	1997-08-20	Novartis Ag	Pyrrolopyrimidines and processes for their preparation
CH690773A5 (de)	1996-02-01	2001-01-15	Novartis Ag	Pyrrolo(2,3-d)pyrimide und ihre Verwendung.
GB9604361D0 (en) *	1996-02-29	1996-05-01	Pharmacia Spa	4-Substituted pyrrolopyrimidine compounds as tyrosine kinase inhibitors
AU1794697A (en)	1996-03-06	1997-09-22	Novartis Ag	7-alkyl-pyrrolo{2,3-d}pyrimidines
WO1997049706A1 (en)	1996-06-25	1997-12-31	Novartis Ag	SUBSTITUTED 7-AMINO-PYRROLO[3,2-d]PYRIMIDINES AND THE USE THEREOF
AP9901435A0 (en)	1996-07-13	1999-03-31	Glaxo Group Ltd	Bicycle heteroaromatic compounds as protein tyrosine kinase inhibitors.
HRP970371A2 (en)	1996-07-13	1998-08-31	Kathryn Jane Smith	Heterocyclic compounds
DE69738468T2 (de)	1996-08-23	2009-01-08	Novartis Ag	Substituierte pyrrolopyrimidine und verfahren zu ihrer herstellung
WO1998023613A1 (en)	1996-11-27	1998-06-04	Pfizer Inc.	Fused bicyclic pyrimidine derivatives
ES2231902T3 (es)	1996-12-02	2005-05-16	MERCK SHARP & DOHME LTD.	Uso de antagonistas del receptor de nk-1 para el tratamiento de transtornos del movimiento.
ES2301194T3 (es)	1997-02-05	2008-06-16	Warner-Lambert Company Llc	Pirido 2,3-d pirimidinas y 4-aminopirimidinas como inhibidores de la proliferacion celular.
WO1998043087A1 (en)	1997-03-24	1998-10-01	Pharmacia & Upjohn Company	Method for identifying inhibitors of jak2/cytokine receptor binding
CA2291734A1 (en)	1997-06-27	1999-01-07	Merck Sharp & Dohme Limited	Substituted 3-(benzylamino)piperidine derivatives and their use as therapeutic agents
AU3378799A (en)	1998-04-02	1999-10-25	Neurogen Corporation	Aminoalkyl substituted pyrrolo(2,3-b)pyridine and pyrrolo(2,3-d)pyrimidine derivatives: modulators of crf1 receptors
HUP0102793A3 (en)	1998-05-28	2002-07-29	Parker Hughes Inst St Paul	Quinazolines for treating brain tumor and medicaments containing them
EP1087970B1 (en)	1998-06-19	2004-04-28	Pfizer Products Inc.	PYRROLO 2,3-d]PYRIMIDINE COMPOUNDS
PA8474101A1 (es)	1998-06-19	2000-09-29	Pfizer Prod Inc	Compuestos de pirrolo [2,3-d] pirimidina
WO2000000202A1 (en)	1998-06-30	2000-01-06	Parker Hughes Institute	Method for inhibiting c-jun expression using jak-3 inhibitors
HUP0103386A3 (en)	1998-08-21	2002-07-29	Parker Hughes Inst St Paul	Use of quinazoline derivatives for producing pharmaceutical compositions having jak 3-inhibitor effect
PL346700A1 (en)	1998-09-18	2002-02-25	Basf Ag	Pyrrolopyrimidines as protein kinase inhibitors
US6080747A (en)	1999-03-05	2000-06-27	Hughes Institute	JAK-3 inhibitors for treating allergic disorders
JP4078074B2 (ja) *	1999-12-10	2008-04-23	ファイザー・プロダクツ・インク	ピロロ［２，３−ｄ］ピリミジン化合物
MXPA02009020A (es)	2000-03-17	2003-02-12	Du Pont Pharm Co	Derivados de beta-aminoacidos ciclicos como inhibidores de las metaloproteasas de matriz y factor de necrosis de tumor alfa.
MY137020A (en)	2000-04-27	2008-12-31	Abbott Lab	Diazabicyclic central nervous system active agents
ES2318605T3 (es)	2000-06-26	2009-05-01	Pfizer Products Incorporated	Compuestos de pirrolo(2,3-d)pirimidina como agentes inmunosupresores.
EP1360180A1 (en)	2001-01-19	2003-11-12	Cytokinetics, Inc.	Phenothiazine kinesin inhibitors
US7301023B2 (en)	2001-05-31	2007-11-27	Pfizer Inc.	Chiral salt resolution
DE10143568C2 (de) *	2001-09-05	2003-07-03	Degussa	Verfahren zur Behandlung von Aminosilanverfärbungen
GT200200234A (es) *	2001-12-06	2003-06-27		Compuestos cristalinos novedosos
KR20040006555A (ko) *	2002-07-12	2004-01-24	삼성전자주식회사	액정 표시 장치
US20050288503A1 (en)	2002-09-06	2005-12-29	Adams Jerry L	Novel compounds
BR0316470A (pt)	2002-11-21	2005-10-11	Pfizer Prod Inc	Derivados de 3-amino-piperadina e métodos de preparação
EP1572213A1 (en)	2002-11-26	2005-09-14	Pfizer Products Inc.	Method of treatment of transplant rejection
MXPA06007002A (es)	2003-12-17	2006-08-31	Pfizer Prod Inc	Compuestos de pirrolo[2,3-d]pirimidina para tratar rechazo de transplantes.
MXPA06015237A (es)	2004-06-29	2007-12-10	Amgen Inc	Pirrolo[2-3-d]pirimidinas que modulan la actividad de ack1 y lck.
TWM358618U (en)	2008-12-26	2009-06-11	Rock Tone Entpr Co Ltd	Combination structure of mop holder and cleaning body

2000
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US7250420B2 (en)	2007-07-31	Method of treatment of transplant rejection
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