UA80733C2 - Diazepinoindole derivatives as kinase inhibitors - Google Patents

Diazepinoindole derivatives as kinase inhibitors Download PDF

Info

Publication number: UA80733C2
Authority: UA; Ukraine
Prior art keywords: dihydro; oxo; diazepino; indol; alkyl
Prior art date: 2003-01-09

Application number

UAA200506730A

Other languages

English (en)

Ukrainian (uk)

Inventor

Min Teng

Original Assignee

Pfizer

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.)

2003-01-09

Filing date

2004-05-01

Publication date

2007-10-25

2004-05-01 Application filed by Pfizer filed Critical Pfizer

2007-10-25 Publication of UA80733C2 publication Critical patent/UA80733C2/uk

Links

229940043355 kinase inhibitor Drugs 0.000 title description 3
239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
BSYFXFLGOGQHFU-UHFFFAOYSA-N pyrrolo[2,3-g][1,2]benzodiazepine Chemical class N1=NC=CC=C2C3=NC=CC3=CC=C21 BSYFXFLGOGQHFU-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 394
150000003839 salts Chemical class 0.000 claims abstract description 80
206010028980 Neoplasm Diseases 0.000 claims abstract description 44
102000001253 Protein Kinase Human genes 0.000 claims abstract description 43
108060006633 protein kinase Proteins 0.000 claims abstract description 42
239000002246 antineoplastic agent Substances 0.000 claims abstract description 37
229940034982 antineoplastic agent Drugs 0.000 claims abstract description 36
239000003795 chemical substances by application Substances 0.000 claims abstract description 33
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 30
230000001225 therapeutic effect Effects 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
230000005855 radiation Effects 0.000 claims abstract description 14
230000002401 inhibitory effect Effects 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims description 192
239000000203 mixture Substances 0.000 claims description 119
-1 hydrochloric acid salt Chemical class 0.000 claims description 118
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 95
125000000623 heterocyclic group Chemical group 0.000 claims description 69
125000001424 substituent group Chemical group 0.000 claims description 68
239000002253 acid Substances 0.000 claims description 61
125000001072 heteroaryl group Chemical group 0.000 claims description 57
125000003118 aryl group Chemical group 0.000 claims description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 42
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 41
125000000753 cycloalkyl group Chemical group 0.000 claims description 40
238000011282 treatment Methods 0.000 claims description 34
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 30
241000282414 Homo sapiens Species 0.000 claims description 29
239000012453 solvate Substances 0.000 claims description 28
150000004702 methyl esters Chemical class 0.000 claims description 27
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 24
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 23
238000009472 formulation Methods 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 21
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241000124008 Mammalia Species 0.000 claims description 16
229910052796 boron Inorganic materials 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 13
230000015572 biosynthetic process Effects 0.000 claims description 12
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 12
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
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HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
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MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 4
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 4
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
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WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- 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
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

UAA200506730A 2003-01-09 2004-05-01 Diazepinoindole derivatives as kinase inhibitors UA80733C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US43939603P	2003-01-09	2003-01-09
PCT/IB2004/000026 WO2004063198A1 (fr)	2003-01-09	2004-01-05	Derives de diazepinoindole en tant qu'inhibiteurs de kinase

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US (3)	US6967198B2 (fr)
EP (2)	EP1947102A1 (fr)
JP (1)	JP3990718B2 (fr)
KR (1)	KR100697746B1 (fr)
CN (1)	CN1759118B (fr)
AP (1)	AP2048A (fr)
AT (1)	ATE404564T1 (fr)
AU (1)	AU2004203977B2 (fr)
BR (1)	BRPI0406701A (fr)
CA (1)	CA2512683C (fr)
CR (1)	CR7899A (fr)
CY (1)	CY1108408T1 (fr)
DE (1)	DE602004015724D1 (fr)
DK (1)	DK1585749T3 (fr)
EA (1)	EA009337B1 (fr)
EC (1)	ECSP055911A (fr)
ES (1)	ES2309484T3 (fr)
GE (1)	GEP20084367B (fr)
HR (1)	HRP20050624A2 (fr)
IL (1)	IL169082A (fr)
IS (1)	IS7884A (fr)
MA (1)	MA27703A1 (fr)
MX (1)	MXPA05007352A (fr)
NO (1)	NO20053775L (fr)
NZ (1)	NZ540638A (fr)
OA (1)	OA13017A (fr)
PL (1)	PL378372A1 (fr)
PT (1)	PT1585749E (fr)
RS (1)	RS20050522A (fr)
SI (1)	SI1585749T1 (fr)
TN (1)	TNSN05176A1 (fr)
UA (1)	UA80733C2 (fr)
WO (1)	WO2004063198A1 (fr)
ZA (1)	ZA200504674B (fr)

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AU2003214879B2 (en) *	2002-01-22	2008-02-07	The Regents Of The University Of California	Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof
DK1585749T3 (da) *	2003-01-09	2008-09-22	Pfizer	Diazepinoindol-derivater som kinaseinhibitorer
PL1853721T3 (pl) *	2005-02-18	2010-08-31	Astrazeneca Ab	Sposób określania wrażliwości na inhibitory CHK1
WO2006105262A1 (fr)	2005-03-29	2006-10-05	Icos Corporation	Derives d'uree d'heteroaryle utilises pour inhiber chk1
GB0510390D0 (en) *	2005-05-20	2005-06-29	Novartis Ag	Organic compounds
CN102746336B (zh)	2005-06-29	2015-08-19	施瑞修德制药公司	氨基磷酸酯烷化剂前体药物
JP2009505989A (ja) *	2005-08-15	2009-02-12	ザリージェンツオブザユニバーシティオブカリフォルニア	ＶＥＧＦによって活性化されるＦａｓリガンド
EP1942193A4 (fr)	2005-08-25	2010-10-27	Ube Industries	PROCÉDÉ DE PRODUCTION D ACIDE (S OU R)-a -AMINÉ OPTIQUEMENT ACTIF OU D ESTER D ACIDE (S OU R)-a-AMINÉ OPTIQUEMENT ACTIF
EP1916896A4 (fr) *	2005-08-26	2010-08-11	Univ California	Antiandrogenes non steroidiens
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Publication number	Publication date
CY1108408T1 (el)	2014-02-12
MA27703A1 (fr)	2006-01-02
RS20050522A (sr)	2007-12-31
ES2309484T3 (es)	2008-12-16
US20060004052A1 (en)	2006-01-05
KR20050092397A (ko)	2005-09-21
BRPI0406701A (pt)	2005-12-20
EA009337B1 (ru)	2007-12-28
SI1585749T1 (sl)	2008-10-31
CR7899A (es)	2005-08-05
OA13017A (en)	2006-11-10
WO2004063198A1 (fr)	2004-07-29
US7462713B2 (en)	2008-12-09
NO20053775D0 (no)	2005-08-08
GEP20084367B (en)	2008-05-13
CN1759118A (zh)	2006-04-12
CN1759118B (zh)	2010-12-08
US20050075499A1 (en)	2005-04-07
NO20053775L (no)	2005-09-16
US7132533B2 (en)	2006-11-07
NZ540638A (en)	2007-12-21
ATE404564T1 (de)	2008-08-15
EA200500893A1 (ru)	2006-02-24
IS7884A (is)	2005-06-09
US6967198B2 (en)	2005-11-22
JP3990718B2 (ja)	2007-10-17
AU2004203977A1 (en)	2004-07-29
EP1585749B1 (fr)	2008-08-13
JP2006516274A (ja)	2006-06-29
AU2004203977B2 (en)	2010-06-17
HK1086257A1 (en)	2006-09-15
TNSN05176A1 (fr)	2007-06-11
MXPA05007352A (es)	2006-02-17
IL169082A (en)	2011-02-28
ZA200504674B (en)	2006-07-26
AP2048A (en)	2009-09-24
HRP20050624A2 (en)	2006-02-28
ECSP055911A (es)	2005-11-22
CA2512683A1 (fr)	2004-07-29
US20070135415A1 (en)	2007-06-14
EP1947102A1 (fr)	2008-07-23
DK1585749T3 (da)	2008-09-22
EP1585749A1 (fr)	2005-10-19
DE602004015724D1 (de)	2008-09-25
KR100697746B1 (ko)	2007-03-22
PT1585749E (pt)	2008-10-23
CA2512683C (fr)	2010-03-16
AP2005003353A0 (en)	2005-09-30
PL378372A1 (pl)	2006-04-03

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