KR20140114344A - 키나제 억제제로서의 피리미딘-2,4-디아민 유도체 - Google Patents

키나제 억제제로서의 피리미딘-2,4-디아민 유도체 Download PDF

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Publication number: KR20140114344A
Authority: KR; South Korea
Prior art keywords: methyl; amino; pyrazol; pyrimidin; pyrrolidin
Prior art date: 2011-12-23
Legal status (The legal status 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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

KR1020147016971A

Other languages

English (en)

Korean (ko)

Inventor

앤드류 홉슨

글린 애디슨

나이절 램즈덴

존 해리슨

Original Assignee

셀좀 리미티드

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.)

2011-12-23

Filing date

2012-12-20

Publication date

2014-09-26

2012-12-20 Application filed by 셀좀 리미티드 filed Critical 셀좀 리미티드

2014-09-26 Publication of KR20140114344A publication Critical patent/KR20140114344A/ko

Status Withdrawn legal-status Critical Current

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YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims description 26
229940043355 kinase inhibitor Drugs 0.000 title description 3
239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 125
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201000010099 disease Diseases 0.000 claims abstract description 42
238000011282 treatment Methods 0.000 claims abstract description 29
239000003814 drug Substances 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
230000002757 inflammatory effect Effects 0.000 claims abstract description 15
230000001363 autoimmune Effects 0.000 claims abstract description 14
230000000172 allergic effect Effects 0.000 claims abstract description 13
208000010668 atopic eczema Diseases 0.000 claims abstract description 13
230000001900 immune effect Effects 0.000 claims abstract description 12
230000002265 prevention Effects 0.000 claims abstract description 12
-1 (5-Chloro-2 - ((1 -methyl-1 H- pyrazol-4-yl) amino) pyrimidin- 1-yl) ethanone Chemical compound 0.000 claims description 335
238000000034 method Methods 0.000 claims description 264
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 240
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 200
125000000217 alkyl group Chemical group 0.000 claims description 81
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 67
150000003839 salts Chemical class 0.000 claims description 56
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 55
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 55
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 46
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 34
150000002367 halogens Chemical class 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 31
208000035475 disorder Diseases 0.000 claims description 29
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
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YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 claims description 10
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125000003118 aryl group Chemical group 0.000 claims description 5
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125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
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125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
NGRXFQJESUUKOY-UHFFFAOYSA-N 1-(2-methylsulfonylethyl)pyrrolidine Chemical compound CS(=O)(=O)CCN1CCCC1 NGRXFQJESUUKOY-UHFFFAOYSA-N 0.000 claims description 3
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XWAIHPHTWPDHKD-AAEUAGOBSA-N Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 Chemical compound Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 XWAIHPHTWPDHKD-AAEUAGOBSA-N 0.000 claims description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Immunology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Transplantation (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

KR1020147016971A 2011-12-23 2012-12-20 키나제 억제제로서의 피리미딘-2,4-디아민 유도체 Withdrawn KR20140114344A (ko)

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EP11195662.9		2011-12-23
EP11195662		2011-12-23
PCT/EP2012/076371 WO2013092854A1 (en)	2011-12-23	2012-12-20	Pyrimidine-2,4-diamine derivatives as kinase inhibitors

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US (1)	US20150005281A1 (2)
EP (1)	EP2794598A1 (2)
JP (1)	JP2015500862A (2)
KR (1)	KR20140114344A (2)
CN (1)	CN104169272A (2)
AU (1)	AU2012357038B2 (2)
BR (1)	BR112014015723A8 (2)
CA (1)	CA2860095A1 (2)
RU (1)	RU2014130214A (2)
WO (1)	WO2013092854A1 (2)

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BR112014029310A2 (pt) *	2012-05-24	2018-06-26	Cellzome Ltd	análogos da pirimidina heterocíclica como inibidores da tyk2
TWI582077B (zh)	2013-11-07	2017-05-11	必治妥美雅史谷比公司	作爲ＩＬ－１２、ＩＬ－２３及／或ＩＦＮα反應調節劑之經烷基－醯胺取代之吡啶化合物
WO2015082583A1 (en) *	2013-12-05	2015-06-11	F. Hoffmann-La Roche Ag	Heteroaryl pyridone and aza-pyridone compounds with electrophilic functionality
US9556126B2 (en) *	2013-12-20	2017-01-31	Signal Pharmaceuticals, Llc	Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith
WO2015148867A1 (en)	2014-03-28	2015-10-01	Calitor Sciences, Llc	Substituted heteroaryl compounds and methods of use
WO2016022460A1 (en)	2014-08-03	2016-02-11	H. Lee Moffitt Cancer Center And Research Institute, Inc.	Potent dual brd4-kinase inhibitors as cancer therapeutics
JP2018527362A (ja)	2015-09-11	2018-09-20	サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅＬａｋｅＰｈａｒｍａＣｏ．，Ｌｔｄ．	置換されたヘテロアリール化合物および使用方法
WO2017066428A1 (en) *	2015-10-13	2017-04-20	H. Lee Moffitt Cancer Center & Research Institute, Inc.	Brd4-kinase inhibitors as cancer therapeutics
JP7117029B2 (ja) *	2017-09-21	2022-08-12	北京賽特明強医薬科技有限公司	２－置換ピラゾールアミノ－４－置換アミノ－５－ピリミジンホルムアミド系化合物、組成物およびその使用
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2012
- 2012-12-20 CN CN201280070527.0A patent/CN104169272A/zh active Pending
- 2012-12-20 JP JP2014548012A patent/JP2015500862A/ja not_active Withdrawn
- 2012-12-20 WO PCT/EP2012/076371 patent/WO2013092854A1/en not_active Ceased
- 2012-12-20 CA CA2860095A patent/CA2860095A1/en not_active Abandoned
- 2012-12-20 US US14/367,958 patent/US20150005281A1/en not_active Abandoned
- 2012-12-20 EP EP12806057.1A patent/EP2794598A1/en not_active Withdrawn
- 2012-12-20 RU RU2014130214A patent/RU2014130214A/ru not_active Application Discontinuation
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BR112014015723A2 (pt)	2017-06-13
AU2012357038B2 (en)	2016-05-12
AU2012357038A1 (en)	2014-07-17
BR112014015723A8 (pt)	2017-07-04
JP2015500862A (ja)	2015-01-08
US20150005281A1 (en)	2015-01-01
EP2794598A1 (en)	2014-10-29
CN104169272A (zh)	2014-11-26
WO2013092854A1 (en)	2013-06-27
CA2860095A1 (en)	2013-06-27

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