OA12865A - Benzofused heteroaryl aminde derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use. - Google Patents

Benzofused heteroaryl aminde derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use. Download PDF

Info

Publication number: OA12865A
Authority: OA; OAPI
Prior art keywords: mmole; alkyl; nmr; aryl; methyl
Prior art date: 2002-06-14

Application number

OA1200400325A

Other languages

English (en)

Inventor

Michael Raymond Collins

Stephan James Cripps

Judith Gail Deal

Mingying He

Robert Steven Kania

Jihong Lou

Cynthia Louise Palmer

William Henry Romines Iii

Ru Zhou

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.)

2002-06-14

Filing date

2003-06-04

Publication date

2006-09-15

2003-06-04 Application filed by Pfizer filed Critical Pfizer

2006-09-15 Publication of OA12865A publication Critical patent/OA12865A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 32
125000001072 heteroaryl group Chemical group 0.000 title claims description 12
238000000034 method Methods 0.000 title abstract description 42
239000003814 drug Substances 0.000 title description 10
229940125670 thienopyridine Drugs 0.000 title description 4
239000002175 thienopyridine Substances 0.000 title description 4
229940124597 therapeutic agent Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 200
150000003839 salts Chemical class 0.000 claims abstract description 35
241000124008 Mammalia Species 0.000 claims abstract description 30
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
238000011282 treatment Methods 0.000 claims description 67
125000000623 heterocyclic group Chemical group 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 59
-1 methylureido group Chemical group 0.000 claims description 54
125000000753 cycloalkyl group Chemical group 0.000 claims description 44
125000003118 aryl group Chemical group 0.000 claims description 41
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
229910052799 carbon Inorganic materials 0.000 claims description 26
206010028980 Neoplasm Diseases 0.000 claims description 23
201000010099 disease Diseases 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 22
201000011510 cancer Diseases 0.000 claims description 15
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 14
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
125000003386 piperidinyl group Chemical group 0.000 claims description 14
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 13
125000004193 piperazinyl group Chemical group 0.000 claims description 13
239000003937 drug carrier Substances 0.000 claims description 12
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 11
230000033115 angiogenesis Effects 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
125000004069 aziridinyl group Chemical group 0.000 claims description 10
125000002757 morpholinyl group Chemical group 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
125000002393 azetidinyl group Chemical group 0.000 claims description 9
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
210000000481 breast Anatomy 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
230000002611 ovarian Effects 0.000 claims description 9
210000002307 prostate Anatomy 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
210000004072 lung Anatomy 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000005189 alkyl hydroxy group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
230000004862 vasculogenesis Effects 0.000 claims description 7
210000001072 colon Anatomy 0.000 claims description 6
206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
208000032612 Glial tumor Diseases 0.000 claims description 5
206010018338 Glioma Diseases 0.000 claims description 5
208000002780 macular degeneration Diseases 0.000 claims description 5
201000001441 melanoma Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
208000007766 Kaposi sarcoma Diseases 0.000 claims description 4
206010038933 Retinopathy of prematurity Diseases 0.000 claims description 4
229940030600 antihypertensive agent Drugs 0.000 claims description 4
239000002220 antihypertensive agent Substances 0.000 claims description 4
208000037976 chronic inflammation Diseases 0.000 claims description 4
208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
201000011066 hemangioma Diseases 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
208000017520 skin disease Diseases 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
206010064930 age-related macular degeneration Diseases 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
230000005747 tumor angiogenesis Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 8
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 2
239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
229940002612 prodrug Drugs 0.000 abstract description 66
239000000651 prodrug Substances 0.000 abstract description 66
239000002207 metabolite Substances 0.000 abstract 2
239000012453 solvate Substances 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 262
239000000463 material Substances 0.000 description 210
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 192
239000007787 solid Substances 0.000 description 188
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
238000006243 chemical reaction Methods 0.000 description 136
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 115
239000000243 solution Substances 0.000 description 112
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 106
229910000024 caesium carbonate Inorganic materials 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
239000000203 mixture Substances 0.000 description 83
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 82
229910001868 water Inorganic materials 0.000 description 80
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 75
235000019439 ethyl acetate Nutrition 0.000 description 68
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 66
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 53
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 51
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 50
239000003795 chemical substances by application Substances 0.000 description 49
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
210000004027 cell Anatomy 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 36
239000011541 reaction mixture Substances 0.000 description 36
229910015845 BBr3 Inorganic materials 0.000 description 32
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
239000003921 oil Substances 0.000 description 32
235000019198 oils Nutrition 0.000 description 32
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
238000012360 testing method Methods 0.000 description 28
239000000460 chlorine Substances 0.000 description 27
239000012044 organic layer Substances 0.000 description 25
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
239000002253 acid Substances 0.000 description 24
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 23
239000007832 Na2SO4 Substances 0.000 description 22
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
239000003112 inhibitor Substances 0.000 description 22
239000010410 layer Substances 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
238000005481 NMR spectroscopy Methods 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 21
235000019341 magnesium sulphate Nutrition 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
150000001412 amines Chemical class 0.000 description 19
238000003818 flash chromatography Methods 0.000 description 18
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 17
239000012267 brine Substances 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 16
239000000725 suspension Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
238000005859 coupling reaction Methods 0.000 description 13
230000000694 effects Effects 0.000 description 13
238000001914 filtration Methods 0.000 description 13
230000002401 inhibitory effect Effects 0.000 description 13
238000010898 silica gel chromatography Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
LJYQFQKUXOCPNI-UHFFFAOYSA-N 7-chloro-2-(1-methylimidazol-2-yl)thieno[3,2-b]pyridine Chemical compound CN1C=CN=C1C1=CC2=NC=CC(Cl)=C2S1 LJYQFQKUXOCPNI-UHFFFAOYSA-N 0.000 description 12
230000002159 abnormal effect Effects 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
230000010261 cell growth Effects 0.000 description 12
230000008878 coupling Effects 0.000 description 12
238000010168 coupling process Methods 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 11
IZNKTHMRXJRKFB-UHFFFAOYSA-N 6-methoxy-1,2-dimethylindole-3-carboxylic acid Chemical compound COC1=CC=C2C(C(O)=O)=C(C)N(C)C2=C1 IZNKTHMRXJRKFB-UHFFFAOYSA-N 0.000 description 11
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
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238000003556 assay Methods 0.000 description 11
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IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 10
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239000000741 silica gel Substances 0.000 description 10
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RXKGVJSYESLRAK-MRVPVSSYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3r)-3-methoxypyrrolidin-1-yl]methanone Chemical compound C1[C@H](OC)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 RXKGVJSYESLRAK-MRVPVSSYSA-N 0.000 description 9
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230000010933 acylation Effects 0.000 description 9
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MVILWLLYYQVYNH-UHFFFAOYSA-N pyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC=N1.NC(=O)C1=CC=CC=N1 MVILWLLYYQVYNH-UHFFFAOYSA-N 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 9
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239000003153 chemical reaction reagent Substances 0.000 description 8
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125000005843 halogen group Chemical group 0.000 description 8
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125000006413 ring segment Chemical group 0.000 description 8
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DRBLTQNCQJXSNU-UHFFFAOYSA-N 1-benzothiophene-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CSC2=C1 DRBLTQNCQJXSNU-UHFFFAOYSA-N 0.000 description 7
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VXGPRUODUDSSME-UHFFFAOYSA-N methyl 6-hydroxy-2-methyl-1-benzothiophene-3-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=C(C)SC2=C1 VXGPRUODUDSSME-UHFFFAOYSA-N 0.000 description 6
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Ophthalmology & Optometry (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Obesity (AREA)
Pulmonology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200400325A 2002-06-14 2003-06-04 Benzofused heteroaryl aminde derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use. OA12865A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US38911002P	2002-06-14	2002-06-14

Publications (1)

Publication Number	Publication Date
OA12865A true OA12865A (en)	2006-09-15

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ID=29736588

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OA1200400325A OA12865A (en)	2002-06-14	2003-06-04	Benzofused heteroaryl aminde derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use.

Country Status (36)

Country	Link
US (3)	US6869962B2 (de)
EP (1)	EP1515975B1 (de)
JP (1)	JP2005534669A (de)
KR (2)	KR100671632B1 (de)
CN (1)	CN1671714A (de)
AP (1)	AP2004003184A0 (de)
AR (1)	AR039673A1 (de)
AT (1)	ATE373665T1 (de)
AU (1)	AU2003233134A1 (de)
BR (1)	BR0311806A (de)
CA (1)	CA2489466A1 (de)
CO (1)	CO5631447A2 (de)
DE (1)	DE60316440T2 (de)
EA (1)	EA008255B1 (de)
EC (1)	ECSP045483A (de)
ES (1)	ES2290460T3 (de)
GE (1)	GEP20074033B (de)
GT (1)	GT200300129A (de)
HN (1)	HN2003000182A (de)
HR (1)	HRP20041173A2 (de)
IL (1)	IL165591A0 (de)
IS (1)	IS7552A (de)
MA (1)	MA27596A1 (de)
MX (1)	MXPA04011637A (de)
NO (1)	NO20045103L (de)
NZ (1)	NZ537140A (de)
OA (1)	OA12865A (de)
PA (1)	PA8575401A1 (de)
PE (1)	PE20050123A1 (de)
PL (1)	PL374542A1 (de)
RS (1)	RS107504A (de)
TN (1)	TNSN04246A1 (de)
TW (1)	TW200404070A (de)
UA (1)	UA77303C2 (de)
WO (1)	WO2003106462A1 (de)
ZA (1)	ZA200409862B (de)

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ATE419239T1 (de) *	2000-10-20	2009-01-15	Eisai R&D Man Co Ltd	Verfahren zur herstellung von 4-phenoxy chinolin derivaten
CA2499329C (en) *	2002-10-03	2009-04-21	F. Hoffmann-La Roche Ag	Indole-3-carboxamides as glucokinase (gk) activators
JPWO2004080462A1 (ja) *	2003-03-10	2006-06-08	エーザイ株式会社	ｃ−Ｋｉｔキナーゼ阻害剤
US7321065B2 (en) *	2003-04-18	2008-01-22	The Regents Of The University Of California	Thyronamine derivatives and analogs and methods of use thereof
CN101337930B (zh) *	2003-11-11	2010-09-08	卫材R&D管理有限公司	脲衍生物的制备方法
WO2005073224A2 (en) *	2004-01-23	2005-08-11	Amgen Inc	Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer
US8772269B2 (en) *	2004-09-13	2014-07-08	Eisai R&D Management Co., Ltd.	Use of sulfonamide-including compounds in combination with angiogenesis inhibitors
WO2006030947A1 (ja)	2004-09-13	2006-03-23	Eisai R & D Management Co., Ltd.	スルホンアミド含有化合物の血管新生阻害物質との併用
JP4834553B2 (ja) *	2004-09-17	2011-12-14	エーザイ・アール・アンド・ディー・マネジメント株式会社	医薬組成物
WO2006043172A1 (en) *	2004-10-19	2006-04-27	Pfizer Inc.	Pharmaceutical compositions and methods for sub-tenon delivery
WO2006117666A2 (en) *	2005-04-29	2006-11-09	Pfizer Inc.	Dosage forms, pharmaceutical compositions and methods for sub-tenon delivery
WO2007015569A1 (ja) *	2005-08-01	2007-02-08	Eisai R & D Management Co., Ltd.	血管新生阻害物質の効果を予測する方法
EP1925676A4 (de)	2005-08-02	2010-11-10	Eisai R&D Man Co Ltd	Testverfahren für die wirkung eines vaskularisierungsinhibitors
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Publication number	Publication date
AR039673A1 (es)	2005-03-09
HN2003000182A (es)	2004-07-27
NZ537140A (en)	2006-10-27
TW200404070A (en)	2004-03-16
US20040009965A1 (en)	2004-01-15
HRP20041173A2 (en)	2005-06-30
KR20060110011A (ko)	2006-10-23
IL165591A0 (en)	2006-01-15
AU2003233134A1 (en)	2003-12-31
DE60316440D1 (de)	2007-10-31
PL374542A1 (en)	2005-10-31
KR100671632B1 (ko)	2007-02-28
US20060079548A1 (en)	2006-04-13
AP2004003184A0 (en)	2004-12-31
UA77303C2 (en)	2006-11-15
CO5631447A2 (es)	2006-04-28
KR100714545B1 (ko)	2007-05-07
KR20050008821A (ko)	2005-01-21
RS107504A (sr)	2006-10-27
EA200500018A1 (ru)	2005-06-30
GEP20074033B (en)	2007-02-12
GT200300129A (es)	2004-03-17
US6869962B2 (en)	2005-03-22
EA008255B1 (ru)	2007-04-27
CN1671714A (zh)	2005-09-21
EP1515975B1 (de)	2007-09-19
ATE373665T1 (de)	2007-10-15
WO2003106462A1 (en)	2003-12-24
DE60316440T2 (de)	2008-01-24
MA27596A1 (fr)	2005-11-01
CA2489466A1 (en)	2003-12-24
IS7552A (is)	2004-11-25
ECSP045483A (es)	2005-01-28
PA8575401A1 (es)	2004-05-07
MXPA04011637A (es)	2005-03-07
PE20050123A1 (es)	2005-03-22
EP1515975A1 (de)	2005-03-23
TNSN04246A1 (fr)	2007-03-12
US20040186126A1 (en)	2004-09-23
ES2290460T3 (es)	2008-02-16
NO20045103L (no)	2005-02-17
ZA200409862B (en)	2006-05-31
JP2005534669A (ja)	2005-11-17
BR0311806A (pt)	2005-03-29
US7045528B2 (en)	2006-05-16

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