HRP20041173A2 - Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use - Google Patents

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

Info

Publication number: HRP20041173A2
Authority: HR; Croatia
Prior art keywords: mmol; image; alkyl; aryl; carboxylic acid
Prior art date: 2002-06-14

Application number

HR20041173A

Other languages

English (en)

Croatian (hr)

Inventor

William

Steven Kania Robert

Lou Jihong

Raymond Collins Michael

James Cripps Stephan

He Mingying

Zhou Ru

Louise Palmer Cynthia

Gail Deal Judith

Original Assignee

Pfizer 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.)

2002-06-14

Filing date

2004-12-09

Publication date

2005-06-30

2004-12-09 Application filed by Pfizer Inc. filed Critical Pfizer Inc.

2005-06-30 Publication of HRP20041173A2 publication Critical patent/HRP20041173A2/hr

Links

-1 heteroaryl amide Chemical class 0.000 title claims description 123
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
238000000034 method Methods 0.000 title description 46
239000003814 drug Substances 0.000 title description 10
229940124597 therapeutic agent Drugs 0.000 title description 2
229940125670 thienopyridine Drugs 0.000 title description 2
239000002175 thienopyridine Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 210
238000011282 treatment Methods 0.000 claims description 81
150000003839 salts Chemical class 0.000 claims description 76
125000000623 heterocyclic group Chemical group 0.000 claims description 68
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
229910052757 nitrogen Inorganic materials 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 44
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
239000012453 solvate Substances 0.000 claims description 37
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 35
241000124008 Mammalia Species 0.000 claims description 31
125000001424 substituent group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 27
229910052799 carbon Inorganic materials 0.000 claims description 26
206010028980 Neoplasm Diseases 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 23
201000010099 disease Diseases 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 21
239000000825 pharmaceutical preparation Substances 0.000 claims description 21
201000011510 cancer Diseases 0.000 claims description 19
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 14
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
125000004193 piperazinyl group Chemical group 0.000 claims description 14
230000003463 hyperproliferative effect Effects 0.000 claims description 13
125000002757 morpholinyl group Chemical group 0.000 claims description 13
125000003386 piperidinyl group Chemical group 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 10
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
230000033115 angiogenesis Effects 0.000 claims description 9
125000002393 azetidinyl group Chemical group 0.000 claims description 9
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
125000004069 aziridinyl group Chemical group 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
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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
230000004862 vasculogenesis Effects 0.000 claims description 8
125000005189 alkyl hydroxy group Chemical group 0.000 claims description 7
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
206010012601 diabetes mellitus Diseases 0.000 claims description 7
125000000335 thiazolyl group Chemical group 0.000 claims description 7
208000026310 Breast neoplasm Diseases 0.000 claims description 6
206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
210000001072 colon Anatomy 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
210000000496 pancreas Anatomy 0.000 claims description 6
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
206010033128 Ovarian cancer Diseases 0.000 claims description 5
229940030600 antihypertensive agent Drugs 0.000 claims description 5
239000002220 antihypertensive agent Substances 0.000 claims description 5
208000029742 colonic neoplasm Diseases 0.000 claims description 5
201000011066 hemangioma Diseases 0.000 claims description 5
201000001441 melanoma Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 4
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
208000017442 Retinal disease Diseases 0.000 claims description 4
206010038923 Retinopathy Diseases 0.000 claims description 4
230000032683 aging Effects 0.000 claims description 4
208000037976 chronic inflammation Diseases 0.000 claims description 4
208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
208000020816 lung neoplasm Diseases 0.000 claims description 4
208000002780 macular degeneration Diseases 0.000 claims description 4
208000017520 skin disease Diseases 0.000 claims description 4
230000005747 tumor angiogenesis Effects 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000005936 piperidyl group Chemical group 0.000 claims description 2
230000000366 juvenile effect Effects 0.000 claims 3
201000001514 prostate carcinoma Diseases 0.000 claims 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 294
238000005160 1H NMR spectroscopy Methods 0.000 description 285
239000000463 material Substances 0.000 description 216
239000007787 solid Substances 0.000 description 204
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 199
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 144
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 131
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 124
238000006243 chemical reaction Methods 0.000 description 122
239000000243 solution Substances 0.000 description 117
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 106
239000000203 mixture Substances 0.000 description 102
229910000024 caesium carbonate Inorganic materials 0.000 description 101
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 75
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
239000000651 prodrug Substances 0.000 description 67
229940002612 prodrug Drugs 0.000 description 67
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
239000011541 reaction mixture Substances 0.000 description 63
235000019439 ethyl acetate Nutrition 0.000 description 62
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 60
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 58
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 52
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
239000003795 chemical substances by application Substances 0.000 description 40
210000004027 cell Anatomy 0.000 description 35
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 34
238000012360 testing method Methods 0.000 description 34
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
239000012044 organic layer Substances 0.000 description 31
229910015845 BBr3 Inorganic materials 0.000 description 29
239000003921 oil Substances 0.000 description 29
235000019198 oils Nutrition 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 26
235000019341 magnesium sulphate Nutrition 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
239000010410 layer Substances 0.000 description 25
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 24
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 24
RQNYQQDHUOLGQZ-UHFFFAOYSA-N 6-hydroxy-n,1,2-trimethylindole-3-carboxamide Chemical compound OC1=CC=C2C(C(=O)NC)=C(C)N(C)C2=C1 RQNYQQDHUOLGQZ-UHFFFAOYSA-N 0.000 description 23
239000007832 Na2SO4 Substances 0.000 description 23
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
238000003818 flash chromatography Methods 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
238000002360 preparation method Methods 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 20
230000002159 abnormal effect Effects 0.000 description 20
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 19
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 19
239000003112 inhibitor Substances 0.000 description 19
239000000725 suspension Substances 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 18
239000002585 base Substances 0.000 description 18
239000000460 chlorine Substances 0.000 description 18
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 17
102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 17
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 17
239000002609 medium Substances 0.000 description 17
239000002207 metabolite Substances 0.000 description 17
239000000284 extract Substances 0.000 description 16
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
230000010261 cell growth Effects 0.000 description 15
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 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
239000012267 brine Substances 0.000 description 14
238000001914 filtration Methods 0.000 description 14
230000002401 inhibitory effect Effects 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
230000000694 effects Effects 0.000 description 13
239000002904 solvent Substances 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
239000013543 active substance Substances 0.000 description 11
238000003556 assay Methods 0.000 description 11
238000009833 condensation Methods 0.000 description 11
230000005494 condensation Effects 0.000 description 11
235000003642 hunger Nutrition 0.000 description 11
238000010992 reflux Methods 0.000 description 11
230000037351 starvation Effects 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 10
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
108091000080 Phosphotransferase Proteins 0.000 description 10
102000020233 phosphotransferase Human genes 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
238000000746 purification Methods 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
LNSDBFHIMSCIQB-SSDOTTSWSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-[(3r)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound C1[C@H](O)CCN1C(=O)C1=CC2=NC=CC(Cl)=C2S1 LNSDBFHIMSCIQB-SSDOTTSWSA-N 0.000 description 9
AVZZCZSFTGUOPZ-UHFFFAOYSA-N 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carboxylic acid Chemical compound C=1C=C2C(C(O)=O)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 AVZZCZSFTGUOPZ-UHFFFAOYSA-N 0.000 description 9
108091003079 Bovine Serum Albumin Proteins 0.000 description 9
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108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 9
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108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 9
230000010933 acylation Effects 0.000 description 9
238000005917 acylation reaction Methods 0.000 description 9
150000001412 amines Chemical group 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
GIJGJGRRRASIPR-UHFFFAOYSA-N azetidin-1-yl-(7-chlorothieno[3,2-b]pyridin-2-yl)methanone Chemical compound S1C=2C(Cl)=CC=NC=2C=C1C(=O)N1CCC1 GIJGJGRRRASIPR-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000006184 cosolvent Substances 0.000 description 9
IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 9
238000010828 elution Methods 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
239000012091 fetal bovine serum Substances 0.000 description 9
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 9
239000003981 vehicle Substances 0.000 description 9
MTMHBQNHFZUJPE-UHFFFAOYSA-N (7-chlorothieno[3,2-b]pyridin-2-yl)-trimethylstannane Chemical compound C1=CC(Cl)=C2SC([Sn](C)(C)C)=CC2=N1 MTMHBQNHFZUJPE-UHFFFAOYSA-N 0.000 description 8
OACQHLMJJRQAPO-UHFFFAOYSA-N 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CC(Cl)=C2SC(C(=O)O)=CC2=N1 OACQHLMJJRQAPO-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
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239000007924 injection Substances 0.000 description 8
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MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 8
125000006413 ring segment Chemical group 0.000 description 8
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 8
IXXYDEFBBIUGNN-UHFFFAOYSA-N 2-methyl-6-thieno[3,2-b]pyridin-7-yloxy-1-benzofuran-3-carbonyl chloride Chemical compound C=1C=C2C(C(Cl)=O)=C(C)OC2=CC=1OC1=CC=NC2=C1SC=C2 IXXYDEFBBIUGNN-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
102000001253 Protein Kinase Human genes 0.000 description 7
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XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 7
125000000592 heterocycloalkyl group Chemical group 0.000 description 7
PJOJKBUEADULSE-UHFFFAOYSA-M lithium;7-chlorothieno[3,2-b]pyridine-2-carboxylate Chemical compound [Li+].C1=CC(Cl)=C2SC(C(=O)[O-])=CC2=N1 PJOJKBUEADULSE-UHFFFAOYSA-M 0.000 description 7
230000003211 malignant effect Effects 0.000 description 7
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 7
230000008569 process Effects 0.000 description 7
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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
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Pharmacology & Pharmacy (AREA)
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Medicinal Chemistry (AREA)
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Dermatology (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
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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)

HR20041173A 2002-06-14 2004-12-09 Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use HRP20041173A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US38911002P	2002-06-14	2002-06-14
PCT/IB2003/002393 WO2003106462A1 (fr)	2002-06-14	2003-06-04	Derives d'amide heteroaryle benzocondense de thienopyridines utilisees en tant qu'agents therapeutiques, compositions pharmaceutiques les contenant et procedes d'utilisation associes

Publications (1)

Publication Number	Publication Date
HRP20041173A2 true HRP20041173A2 (en)	2005-06-30

Family

ID=29736588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20041173A HRP20041173A2 (en)	2002-06-14	2004-12-09	Benzofused heteroaryl amide 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 (fr)
EP (1)	EP1515975B1 (fr)
JP (1)	JP2005534669A (fr)
KR (2)	KR100714545B1 (fr)
CN (1)	CN1671714A (fr)
AP (1)	AP2004003184A0 (fr)
AR (1)	AR039673A1 (fr)
AT (1)	ATE373665T1 (fr)
AU (1)	AU2003233134A1 (fr)
BR (1)	BR0311806A (fr)
CA (1)	CA2489466A1 (fr)
CO (1)	CO5631447A2 (fr)
DE (1)	DE60316440T2 (fr)
EA (1)	EA008255B1 (fr)
EC (1)	ECSP045483A (fr)
ES (1)	ES2290460T3 (fr)
GE (1)	GEP20074033B (fr)
GT (1)	GT200300129A (fr)
HN (1)	HN2003000182A (fr)
HR (1)	HRP20041173A2 (fr)
IL (1)	IL165591A0 (fr)
IS (1)	IS7552A (fr)
MA (1)	MA27596A1 (fr)
MX (1)	MXPA04011637A (fr)
NO (1)	NO20045103L (fr)
NZ (1)	NZ537140A (fr)
OA (1)	OA12865A (fr)
PA (1)	PA8575401A1 (fr)
PE (1)	PE20050123A1 (fr)
PL (1)	PL374542A1 (fr)
RS (1)	RS107504A (fr)
TN (1)	TNSN04246A1 (fr)
TW (1)	TW200404070A (fr)
UA (1)	UA77303C2 (fr)
WO (1)	WO2003106462A1 (fr)
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2003
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- 2003-06-04 WO PCT/IB2003/002393 patent/WO2003106462A1/fr active IP Right Grant
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- 2003-06-04 CN CNA038181096A patent/CN1671714A/zh active Pending
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2004
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Publication number	Publication date
BR0311806A (pt)	2005-03-29
MXPA04011637A (es)	2005-03-07
CO5631447A2 (es)	2006-04-28
US7045528B2 (en)	2006-05-16
US20060079548A1 (en)	2006-04-13
DE60316440T2 (de)	2008-01-24
AP2004003184A0 (en)	2004-12-31
EP1515975B1 (fr)	2007-09-19
US6869962B2 (en)	2005-03-22
NZ537140A (en)	2006-10-27
RS107504A (en)	2006-10-27
IS7552A (is)	2004-11-25
CN1671714A (zh)	2005-09-21
OA12865A (en)	2006-09-15
GEP20074033B (en)	2007-02-12
GT200300129A (es)	2004-03-17
EA200500018A1 (ru)	2005-06-30
MA27596A1 (fr)	2005-11-01
HN2003000182A (es)	2004-07-27
EA008255B1 (ru)	2007-04-27
EP1515975A1 (fr)	2005-03-23
AU2003233134A1 (en)	2003-12-31
DE60316440D1 (de)	2007-10-31
KR20050008821A (ko)	2005-01-21
PE20050123A1 (es)	2005-03-22
ES2290460T3 (es)	2008-02-16
TNSN04246A1 (fr)	2007-03-12
WO2003106462A1 (fr)	2003-12-24
ZA200409862B (en)	2006-05-31
ATE373665T1 (de)	2007-10-15
US20040186126A1 (en)	2004-09-23
PA8575401A1 (es)	2004-05-07
PL374542A1 (en)	2005-10-31
TW200404070A (en)	2004-03-16
AR039673A1 (es)	2005-03-09
UA77303C2 (en)	2006-11-15
KR20060110011A (ko)	2006-10-23
IL165591A0 (en)	2006-01-15
KR100671632B1 (ko)	2007-02-28
ECSP045483A (es)	2005-01-28
CA2489466A1 (fr)	2003-12-24
JP2005534669A (ja)	2005-11-17
NO20045103L (no)	2005-02-17
US20040009965A1 (en)	2004-01-15
KR100714545B1 (ko)	2007-05-07

Publication	Publication Date	Title
HRP20041173A2 (en)	2005-06-30	Benzofused heteroaryl amide derivatives of thienopyridines useful as therapeutic agents, pharmaceutical compositions including the same, and methods for their use
NL1026761C2 (nl)	2005-10-18	3,5-gedisubstitueerde indazoolverbindingen, farmaceutische preparaten en werkwijzen voor het medieren of remmen van celproliferatie.
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