OA11352A - Substituted 4-amino-thiazol-2-yl compounds as CDKsinhibitors. - Google Patents

Substituted 4-amino-thiazol-2-yl compounds as CDKsinhibitors. Download PDF

Info

Publication number: OA11352A
Authority: OA; OAPI
Prior art keywords: amino; phenyl; fused; calcd; prepared
Prior art date: 1997-10-27

Application number

OA1200000120A

Other languages

English (en)

Inventor

Wesley K M Chong

Shao Song Chu

Rohit K Duvadie

Lin Li

Wei Xiao

Yi Yang

Original Assignee

Agouron Pharma

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.)

1997-10-27

Filing date

2000-04-25

Publication date

2003-12-23

2000-04-25 Application filed by Agouron Pharma filed Critical Agouron Pharma

2003-12-23 Publication of OA11352A publication Critical patent/OA11352A/en

Links

-1 4-amino-thiazol-2-yl compounds Chemical class 0.000 title claims description 53
150000001875 compounds Chemical class 0.000 claims abstract description 245
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 71
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 37
125000002950 monocyclic group Chemical group 0.000 claims abstract description 33
108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims abstract description 29
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
125000003367 polycyclic group Chemical group 0.000 claims abstract description 28
229940002612 prodrug Drugs 0.000 claims abstract description 23
239000000651 prodrug Substances 0.000 claims abstract description 23
125000001424 substituent group Chemical group 0.000 claims abstract description 23
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 21
150000003573 thiols Chemical class 0.000 claims abstract description 19
125000003118 aryl group Chemical group 0.000 claims abstract description 17
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 17
229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
150000002148 esters Chemical class 0.000 claims abstract description 15
150000002576 ketones Chemical class 0.000 claims abstract description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
150000003568 thioethers Chemical class 0.000 claims abstract description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
229940124530 sulfonamide Drugs 0.000 claims abstract description 14
150000003456 sulfonamides Chemical class 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 13
150000002466 imines Chemical class 0.000 claims abstract description 13
125000000394 phosphonato group Chemical group [O-]P([O-])(*)=O 0.000 claims abstract description 13
125000003368 amide group Chemical group 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
102000016736 Cyclin Human genes 0.000 claims description 55
108050006400 Cyclin Proteins 0.000 claims description 55
102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 26
230000022983 regulation of cell cycle Effects 0.000 claims description 23
230000005764 inhibitory process Effects 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000001544 thienyl group Chemical class 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
108091007914 CDKs Proteins 0.000 abstract description 31
108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 abstract description 22
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206010028980 Neoplasm Diseases 0.000 abstract description 19
108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 abstract description 5
102100026804 Cyclin-dependent kinase 6 Human genes 0.000 abstract description 5
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108090000266 Cyclin-dependent kinases Proteins 0.000 abstract description 5
230000002401 inhibitory effect Effects 0.000 abstract description 5
101710106279 Cyclin-dependent kinase 1 Proteins 0.000 abstract description 4
102100032857 Cyclin-dependent kinase 1 Human genes 0.000 abstract description 4
230000001225 therapeutic effect Effects 0.000 abstract description 4
230000036210 malignancy Effects 0.000 abstract description 3
230000000069 prophylactic effect Effects 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
125000006727 (C1-C6) alkenyl group Chemical group 0.000 abstract 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
125000006728 (C1-C6) alkynyl group Chemical group 0.000 abstract 3
150000001299 aldehydes Chemical class 0.000 abstract 2
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract 1
102100036252 Cyclin-dependent kinase 4 Human genes 0.000 abstract 1
239000002207 metabolite Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
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238000002000 high resolution fast-atom bombardment mass spectrometry Methods 0.000 description 78
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239000000725 suspension Substances 0.000 description 16
IMDUFDNFSJWYQT-UHFFFAOYSA-N 4-isothiocyanatobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(N=C=S)C=C1 IMDUFDNFSJWYQT-UHFFFAOYSA-N 0.000 description 15
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UZKLFNHMBFDXEN-UHFFFAOYSA-N 2-bromo-1-(2,6-difluorophenyl)ethanone Chemical compound FC1=CC=CC(F)=C1C(=O)CBr UZKLFNHMBFDXEN-UHFFFAOYSA-N 0.000 description 14
SGXUUCSRVVSMGK-UHFFFAOYSA-N 2-bromo-1-(2-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)CBr SGXUUCSRVVSMGK-UHFFFAOYSA-N 0.000 description 14
239000003112 inhibitor Substances 0.000 description 14
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230000002829 reductive effect Effects 0.000 description 11
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
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MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 8
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239000000706 filtrate Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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OA1200000120A 1997-10-27 2000-04-25 Substituted 4-amino-thiazol-2-yl compounds as CDKsinhibitors. OA11352A (en)

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GB9621757D0 (en)	1996-10-18	1996-12-11	Ciba Geigy Ag	Phenyl-substituted bicyclic heterocyclyl derivatives and their use
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US6569878B1 (en) *	1997-10-27	2003-05-27	Agouron Pharmaceuticals Inc.	Substituted 4-amino-thiazol-2-yl compounds as cyclin-dependent kinase inhibitors
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1998
- 1998-10-27 US US09/179,744 patent/US6569878B1/en not_active Expired - Fee Related
- 1998-10-27 WO PCT/US1998/022809 patent/WO1999021845A2/en not_active Ceased
- 1998-10-27 DE DE69835241T patent/DE69835241T2/de not_active Expired - Fee Related
- 1998-10-27 ES ES98957393T patent/ES2256968T3/es not_active Expired - Lifetime
- 1998-10-27 ID IDW20000740A patent/ID24372A/id unknown
- 1998-10-27 RO ROA200000423A patent/RO119463B1/ro unknown
- 1998-10-27 GE GEAP19985301A patent/GEP20032896B/en unknown
- 1998-10-27 AT AT02001881T patent/ATE332896T1/de not_active IP Right Cessation
- 1998-10-27 TR TR2000/01081T patent/TR200001081T2/xx unknown
- 1998-10-27 AT AT98957393T patent/ATE315553T1/de not_active IP Right Cessation
- 1998-10-27 ES ES02001881T patent/ES2267873T3/es not_active Expired - Lifetime
- 1998-10-27 EP EP98957393A patent/EP1056732B1/en not_active Expired - Lifetime
- 1998-10-27 KR KR1020007004392A patent/KR20010082501A/ko not_active Ceased
- 1998-10-27 YU YU22400A patent/YU22400A/sh unknown
- 1998-10-27 IL IL13557498A patent/IL135574A0/xx unknown
- 1998-10-27 UA UA2000042107A patent/UA66810C2/uk unknown
- 1998-10-27 HU HU0004512A patent/HUP0004512A3/hu unknown
- 1998-10-27 DE DE69833223T patent/DE69833223T2/de not_active Expired - Fee Related
- 1998-10-27 EE EEP200000289A patent/EE200000289A/xx unknown
- 1998-10-27 SI SI9820068A patent/SI20324A/sl unknown
- 1998-10-27 PL PL98342447A patent/PL342447A1/xx not_active Application Discontinuation
- 1998-10-27 EA EA200000464A patent/EA003527B1/ru not_active IP Right Cessation
- 1998-10-27 HR HR20000222A patent/HRP20000222A2/hr not_active Application Discontinuation
- 1998-10-27 AU AU13664/99A patent/AU738792B2/en not_active Ceased
- 1998-10-27 CN CNB988104741A patent/CN1158269C/zh not_active Expired - Fee Related
- 1998-10-27 SK SK521-2000A patent/SK5212000A3/sk unknown
- 1998-10-27 NZ NZ503788A patent/NZ503788A/xx unknown
- 1998-10-27 JP JP2000517957A patent/JP2004500304A/ja active Pending
- 1998-10-27 BR BR9815200-9A patent/BR9815200A/pt not_active Application Discontinuation
- 1998-10-27 AP APAP/P/2000/001795A patent/AP1445A/en active
- 1998-10-27 CA CA002306082A patent/CA2306082A1/en not_active Abandoned
2000
- 2000-04-14 LT LT2000033A patent/LT4855B/lt not_active IP Right Cessation
- 2000-04-14 NO NO20001955A patent/NO20001955L/no not_active Application Discontinuation
- 2000-04-19 IS IS5462A patent/IS5462A/is unknown
- 2000-04-25 OA OA1200000120A patent/OA11352A/en unknown
- 2000-05-03 LV LVP-00-51A patent/LV12592B/en unknown
- 2000-05-26 BG BG104478A patent/BG64195B1/bg unknown
2003
- 2003-03-13 US US10/388,851 patent/US20030220326A1/en not_active Abandoned

Also Published As

Publication number	Publication date
WO1999021845A3 (en)	1999-08-19
DE69835241T2 (de)	2007-05-31
NO20001955D0 (no)	2000-04-14
AU1366499A (en)	1999-05-17
CN1276789A (zh)	2000-12-13
LT2000033A (en)	2001-06-25
HUP0004512A3 (en)	2003-01-28
RO119463B1 (ro)	2004-11-30
NO20001955L (no)	2000-06-16
LT4855B (lt)	2001-11-26
SK5212000A3 (en)	2001-04-09
KR20010082501A (ko)	2001-08-30
NZ503788A (en)	2002-11-26
HRP20000222A2 (en)	2001-02-28
SI20324A (sl)	2001-02-28
WO1999021845A2 (en)	1999-05-06
GEP20032896B (en)	2003-02-25
EA200000464A1 (ru)	2000-12-25
JP2004500304A (ja)	2004-01-08
US20030220326A1 (en)	2003-11-27
EP1056732A2 (en)	2000-12-06
CN1158269C (zh)	2004-07-21
AP1445A (en)	2005-07-10
CA2306082A1 (en)	1999-05-06
ATE315553T1 (de)	2006-02-15
AP2000001795A0 (en)	2000-06-30
DE69833223T2 (de)	2006-09-14
DE69835241D1 (de)	2006-08-24
BG64195B1 (bg)	2004-04-30
BG104478A (en)	2001-02-28
UA66810C2 (uk)	2004-06-15
ES2267873T3 (es)	2007-03-16
PL342447A1 (en)	2001-06-04
IL135574A0 (en)	2001-05-20
DE69833223D1 (de)	2006-04-06
ATE332896T1 (de)	2006-08-15
YU22400A (sh)	2003-08-29
US6569878B1 (en)	2003-05-27
AU738792B2 (en)	2001-09-27
HUP0004512A2 (hu)	2002-03-28
LV12592B (en)	2001-07-20
ES2256968T3 (es)	2006-07-16
EA003527B1 (ru)	2003-06-26
IS5462A (is)	2000-04-19
ID24372A (id)	2000-07-13
EP1056732B1 (en)	2006-01-11
BR9815200A (pt)	2001-10-16
EE200000289A (et)	2001-06-15
TR200001081T2 (tr)	2000-10-23
LV12592A (en)	2000-12-20

Publication	Publication Date	Title
OA11352A (en)	2003-12-23	Substituted 4-amino-thiazol-2-yl compounds as CDKsinhibitors.
AU778071B2 (en)	2004-11-11	Diaminothiazoles and their use for inhibiting protein kinases
NZ522538A (en)	2004-09-24	Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 their use and preparation
CA2452609A1 (en)	2003-01-16	Thiazole benzamide derivatives and pharmaceutical compositions for inhibiting cell proliferation, and methods for their use
US6566363B2 (en)	2003-05-20	Pyrazole-thiazole compounds, pharmaceutical compositions containing them
WO2005075471A2 (en)	2005-08-18	Thiazol-compounds as 11-beta-hydroxysteroid dehydrogenase type 1 inhibitors
US8247412B2 (en)	2012-08-21	Urea derivatives methods for their manufacture and uses thereof
EP1215208A2 (en)	2002-06-19	4-Aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases
NZ517419A (en)	2003-08-29	4-aminothiazole derivatives and their use as inhibitors of cyclin-dependent kinases
MXPA00003812A (en)	2001-05-07	4-aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases
CZ20001285A3 (cs)	2001-01-17	Substituované 4-aminothiazol-2-ylové sloučeniny jako inhibitory cyklin-dependentních kinas