TW200418834A - Indolyl pyrazinone derivatives useful for treating hyper-proliferative disorders - Google Patents

Indolyl pyrazinone derivatives useful for treating hyper-proliferative disorders Download PDF

Info

Publication number: TW200418834A
Authority: TW; Taiwan
Prior art keywords: alkyl; crc3; alkoxy; phenyl; independently selected
Prior art date: 2002-11-12

Application number

TW092131443A

Other languages

English (en)

Chinese (zh)

Inventor

Gaetan H Ladouceur

Brian Bear

Cheng Bi

David R Brittelli

Michael J Burke

Gang Chen

James Cook

Jacques Dumas

Robert Sibley

Michael R Turner

Original Assignee

Bayer Pharmaceuticals Corp

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.)

2002-11-12

Filing date

2003-11-11

Publication date

2004-10-01

2003-11-11 Application filed by Bayer Pharmaceuticals Corp filed Critical Bayer Pharmaceuticals Corp

2004-10-01 Publication of TW200418834A publication Critical patent/TW200418834A/zh

Links

230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 12
YVFNMQLTCRSZOJ-UHFFFAOYSA-N 3-(1h-indol-2-yl)-1h-pyrazin-2-one Chemical class O=C1NC=CN=C1C1=CC2=CC=CC=C2N1 YVFNMQLTCRSZOJ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 126
125000000217 alkyl group Chemical group 0.000 claims description 417
125000003545 alkoxy group Chemical group 0.000 claims description 190
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 150
125000001424 substituent group Chemical group 0.000 claims description 126
-1 alkyl Oxygen Chemical compound 0.000 claims description 124
230000002079 cooperative effect Effects 0.000 claims description 80
229910052736 halogen Inorganic materials 0.000 claims description 60
150000002367 halogens Chemical class 0.000 claims description 60
238000000034 method Methods 0.000 claims description 50
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 48
125000004076 pyridyl group Chemical group 0.000 claims description 43
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 33
XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 29
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 29
150000001412 amines Chemical class 0.000 claims description 27
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
125000000304 alkynyl group Chemical group 0.000 claims description 23
125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 16
201000010099 disease Diseases 0.000 claims description 16
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 16
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
125000002541 furyl group Chemical group 0.000 claims description 13
150000003254 radicals Chemical class 0.000 claims description 13
238000006467 substitution reaction Methods 0.000 claims description 13
150000001335 aliphatic alkanes Chemical group 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 12
238000007639 printing Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
125000001041 indolyl group Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
235000021419 vinegar Nutrition 0.000 claims description 9
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
239000000052 vinegar Substances 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
125000005605 benzo group Chemical group 0.000 claims description 5
238000005516 engineering process Methods 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
206010009944 Colon cancer Diseases 0.000 claims description 4
206010025323 Lymphomas Diseases 0.000 claims description 4
230000033228 biological regulation Effects 0.000 claims description 4
150000007857 hydrazones Chemical class 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
208000032839 leukemia Diseases 0.000 claims description 4
206010006187 Breast cancer Diseases 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
208000000453 Skin Neoplasms Diseases 0.000 claims description 3
238000010586 diagram Methods 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 2
206010060862 Prostate cancer Diseases 0.000 claims description 2
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
125000001317 arsoryl group Chemical group *[As](*)(*)=O 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
201000010536 head and neck cancer Diseases 0.000 claims description 2
208000014829 head and neck neoplasm Diseases 0.000 claims description 2
238000012856 packing Methods 0.000 claims description 2
201000000849 skin cancer Diseases 0.000 claims description 2
235000021286 stilbenes Nutrition 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims 4
125000005630 sialyl group Chemical group 0.000 claims 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
208000029742 colonic neoplasm Diseases 0.000 claims 2
201000005202 lung cancer Diseases 0.000 claims 2
208000020816 lung neoplasm Diseases 0.000 claims 2
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
201000002528 pancreatic cancer Diseases 0.000 claims 2
125000001725 pyrenyl group Chemical group 0.000 claims 2
125000003396 thiol group Chemical group [H]S* 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
241000251468 Actinopterygii Species 0.000 claims 1
101100274575 Caenorhabditis elegans clh-3 gene Proteins 0.000 claims 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 claims 1
150000001345 alkine derivatives Chemical class 0.000 claims 1
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
210000004268 dentin Anatomy 0.000 claims 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001715 oxadiazolyl group Chemical group 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
125000005188 oxoalkyl group Chemical group 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 253
238000002360 preparation method Methods 0.000 description 166
150000002500 ions Chemical class 0.000 description 108
239000000203 mixture Substances 0.000 description 94
239000007787 solid Substances 0.000 description 84
IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 81
238000006243 chemical reaction Methods 0.000 description 73
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 64
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 58
238000005481 NMR spectroscopy Methods 0.000 description 54
239000000047 product Substances 0.000 description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
235000019439 ethyl acetate Nutrition 0.000 description 32
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
239000002253 acid Substances 0.000 description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
239000003795 chemical substances by application Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000725 suspension Substances 0.000 description 18
238000000746 purification Methods 0.000 description 16
235000014113 dietary fatty acids Nutrition 0.000 description 15
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125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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238000004128 high performance liquid chromatography Methods 0.000 description 11
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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239000002585 base Substances 0.000 description 10
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239000002244 precipitate Substances 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
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230000000694 effects Effects 0.000 description 9
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
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BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
229940045145 uridine Drugs 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
208000013139 vaginal neoplasm Diseases 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
229960002066 vinorelbine Drugs 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000341 volatile oil Chemical class 0.000 description 1
210000004916 vomit Anatomy 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

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- 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
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
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- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Immunology (AREA)
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Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Ophthalmology & Optometry (AREA)
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Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

TW092131443A 2002-11-12 2003-11-11 Indolyl pyrazinone derivatives useful for treating hyper-proliferative disorders TW200418834A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US42549002P	2002-11-12	2002-11-12
US46091503P	2003-04-07	2003-04-07
US48420203P	2003-06-30	2003-06-30

Publications (1)

Publication Number	Publication Date
TW200418834A true TW200418834A (en)	2004-10-01

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TW092131443A TW200418834A (en)	2002-11-12	2003-11-11	Indolyl pyrazinone derivatives useful for treating hyper-proliferative disorders

Country Status (17)

Country	Link
EP (1)	EP1565455A1 (es)
JP (1)	JP2006509840A (es)
KR (1)	KR20050072824A (es)
AR (1)	AR043059A1 (es)
AU (1)	AU2003290744A1 (es)
BR (1)	BR0316169A (es)
CA (1)	CA2505819A1 (es)
EC (1)	ECSP055851A (es)
HR (1)	HRP20050496A2 (es)
MA (1)	MA27557A1 (es)
MX (1)	MXPA05004779A (es)
NO (1)	NO20052796D0 (es)
PE (1)	PE20040832A1 (es)
PL (1)	PL376867A1 (es)
TW (1)	TW200418834A (es)
UY (1)	UY28074A1 (es)
WO (1)	WO2004043950A1 (es)

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US20100160322A1 (en)	2008-12-04	2010-06-24	Abbott Laboratories	Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases
US8563735B2 (en)	2008-12-05	2013-10-22	Abbvie Inc.	Bcl-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases
US8586754B2 (en)	2008-12-05	2013-11-19	Abbvie Inc.	BCL-2-selective apoptosis-inducing agents for the treatment of cancer and immune diseases
GB201007286D0 (en)	2010-04-30	2010-06-16	Astex Therapeutics Ltd	New compounds
GB201020179D0 (en)	2010-11-29	2011-01-12	Astex Therapeutics Ltd	New compounds
GB201118654D0 (en)	2011-10-28	2011-12-07	Astex Therapeutics Ltd	New compounds
GB201118675D0 (en)	2011-10-28	2011-12-14	Astex Therapeutics Ltd	New compounds
GB201118656D0 (en)	2011-10-28	2011-12-07	Astex Therapeutics Ltd	New compounds
GB201118652D0 (en)	2011-10-28	2011-12-07	Astex Therapeutics Ltd	New compounds
GB201209613D0 (en)	2012-05-30	2012-07-11	Astex Therapeutics Ltd	New compounds
GB201209609D0 (en)	2012-05-30	2012-07-11	Astex Therapeutics Ltd	New compounds
GB201307577D0 (en)	2013-04-26	2013-06-12	Astex Therapeutics Ltd	New compounds
JO3512B1 (ar)	2014-03-26	2020-07-05	Astex Therapeutics Ltd	مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز
HUE053653T2 (hu)	2014-03-26	2021-07-28	Astex Therapeutics Ltd	FGFR inhibitor és IGF1R inhibitor kombinációi
RU2715236C2 (ru)	2014-03-26	2020-02-26	Астекс Терапьютикс Лтд	Комбинации
EA201692091A1 (ru) *	2014-04-18	2017-04-28	Милленниум Фармасьютикалз, Инк.	Хиноксалиновые соединения и их применение
CN107438598A (zh)	2015-01-20	2017-12-05	米伦纽姆医药公司	喹唑啉和喹啉化合物及其用途
JOP20200201A1 (ar)	2015-02-10	2017-06-16	Astex Therapeutics Ltd	تركيبات صيدلانية تشتمل على n-(3.5- ثنائي ميثوكسي فينيل)-n'-(1-ميثيل إيثيل)-n-[3-(ميثيل-1h-بيرازول-4-يل) كينوكسالين-6-يل]إيثان-1.2-ثنائي الأمين
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2003
- 2003-11-05 AR ARP030104059A patent/AR043059A1/es unknown
- 2003-11-10 MX MXPA05004779A patent/MXPA05004779A/es not_active Application Discontinuation
- 2003-11-10 AU AU2003290744A patent/AU2003290744A1/en not_active Abandoned
- 2003-11-10 WO PCT/US2003/036003 patent/WO2004043950A1/en not_active Ceased
- 2003-11-10 CA CA002505819A patent/CA2505819A1/en not_active Abandoned
- 2003-11-10 KR KR1020057008396A patent/KR20050072824A/ko not_active Withdrawn
- 2003-11-10 PL PL376867A patent/PL376867A1/pl unknown
- 2003-11-10 HR HR20050496A patent/HRP20050496A2/hr not_active Application Discontinuation
- 2003-11-10 BR BR0316169-2A patent/BR0316169A/pt not_active Application Discontinuation
- 2003-11-10 JP JP2005507146A patent/JP2006509840A/ja active Pending
- 2003-11-10 EP EP03783328A patent/EP1565455A1/en not_active Withdrawn
- 2003-11-11 TW TW092131443A patent/TW200418834A/zh unknown
- 2003-11-11 PE PE2003001136A patent/PE20040832A1/es not_active Application Discontinuation
- 2003-11-11 UY UY28074A patent/UY28074A1/es not_active Application Discontinuation
2005
- 2005-06-09 NO NO20052796A patent/NO20052796D0/no not_active Application Discontinuation
- 2005-06-09 MA MA28322A patent/MA27557A1/fr unknown
- 2005-06-10 EC EC2005005851A patent/ECSP055851A/es unknown

Also Published As

Publication number	Publication date
EP1565455A1 (en)	2005-08-24
KR20050072824A (ko)	2005-07-12
MA27557A1 (fr)	2005-10-03
PE20040832A1 (es)	2005-01-27
ECSP055851A (es)	2005-09-20
PL376867A1 (pl)	2006-01-09
JP2006509840A (ja)	2006-03-23
AR043059A1 (es)	2005-07-13
BR0316169A (pt)	2005-09-27
MXPA05004779A (es)	2005-07-22
NO20052796L (no)	2005-06-09
AU2003290744A1 (en)	2004-06-03
WO2004043950A1 (en)	2004-05-27
CA2505819A1 (en)	2004-05-27
NO20052796D0 (no)	2005-06-09
HRP20050496A2 (en)	2006-06-30
UY28074A1 (es)	2004-05-31

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