UA79772C2

UA79772C2 - Benzofuran and benzothiophene derivatives useful in the treatment of hyper-proliferative disorders

Benzofuran and benzothiophene derivatives useful in the treatment of hyper-proliferative disorders Download PDF

Info

Publication number: UA79772C2
Authority: UA; Ukraine
Prior art keywords: alkyl; group; amino; benzofuran; substituents
Prior art date: 2002-02-22

Application number

UA20040907632A

Other languages

English (en)

Ukrainian (uk)

Inventor

Chengzhi Zhang

Michael Burke

Zhi Chen

Jacques Dumas

Dongping Fan

Jianmei Fan

Holia Hatoum-Mokdad

Benjamin D Jones

Gaetan Ladouceur

Wendy Lee

Barton Phillips

Original Assignee

Bayer Pharmaceuticals Corp

Priority date

2002-02-22

Filing date

2003-02-21

Publication date

2007-07-25

2003-02-21 Application filed by Bayer Pharmaceuticals Corp filed Critical Bayer Pharmaceuticals Corp

2003-02-21 Priority claimed from PCT/US2003/005396 external-priority patent/WO2003072561A1/en

2007-07-25 Publication of UA79772C2 publication Critical patent/UA79772C2/uk

Links

230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 7
238000011282 treatment Methods 0.000 title abstract description 16
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 15
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title description 25
239000000203 mixture Substances 0.000 claims description 145
150000001875 compounds Chemical class 0.000 claims description 144
238000000034 method Methods 0.000 claims description 136
125000000217 alkyl group Chemical group 0.000 claims description 123
125000001424 substituent group Chemical group 0.000 claims description 71
229910052736 halogen Inorganic materials 0.000 claims description 49
150000002367 halogens Chemical class 0.000 claims description 49
125000000623 heterocyclic group Chemical group 0.000 claims description 39
229920006395 saturated elastomer Polymers 0.000 claims description 30
125000004429 atom Chemical group 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 13
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
229910052727 yttrium Inorganic materials 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000012634 fragment Substances 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
229960005235 piperonyl butoxide Drugs 0.000 claims description 3
125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
125000004122 cyclic group Chemical group 0.000 claims 2
238000012876 topography Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 234
238000002360 preparation method Methods 0.000 description 132
239000011541 reaction mixture Substances 0.000 description 127
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 123
239000000243 solution Substances 0.000 description 94
235000019439 ethyl acetate Nutrition 0.000 description 80
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 74
239000007787 solid Substances 0.000 description 72
239000002904 solvent Substances 0.000 description 72
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 67
238000005160 1H NMR spectroscopy Methods 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
238000004128 high performance liquid chromatography Methods 0.000 description 61
-1 trichloromethoxy, pentafluoroethoxy, fluorobutoxy Chemical group 0.000 description 58
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 55
239000012267 brine Substances 0.000 description 52
230000002829 reductive effect Effects 0.000 description 50
239000000126 substance Substances 0.000 description 50
239000012044 organic layer Substances 0.000 description 47
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
230000015572 biosynthetic process Effects 0.000 description 44
238000006243 chemical reaction Methods 0.000 description 42
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 42
238000003786 synthesis reaction Methods 0.000 description 42
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
239000000047 product Substances 0.000 description 38
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 33
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 31
239000010410 layer Substances 0.000 description 30
239000007864 aqueous solution Substances 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
238000005481 NMR spectroscopy Methods 0.000 description 28
239000012043 crude product Substances 0.000 description 28
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229910052938 sodium sulfate Inorganic materials 0.000 description 26
235000011152 sodium sulphate Nutrition 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000012300 argon atmosphere Substances 0.000 description 23
239000013067 intermediate product Substances 0.000 description 22
238000004809 thin layer chromatography Methods 0.000 description 22
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239000003826 tablet Substances 0.000 description 21
229910052786 argon Inorganic materials 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
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239000010703 silicon Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 19
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 18
238000007429 general method Methods 0.000 description 18
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229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
239000003814 drug Substances 0.000 description 17
YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 16
235000019270 ammonium chloride Nutrition 0.000 description 16
238000001953 recrystallisation Methods 0.000 description 16
239000007858 starting material Substances 0.000 description 16
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
235000014113 dietary fatty acids Nutrition 0.000 description 12
239000000194 fatty acid Substances 0.000 description 12
229930195729 fatty acid Natural products 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
238000000746 purification Methods 0.000 description 12
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 11
239000002253 acid Substances 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 11
239000002585 base Chemical class 0.000 description 11
239000007853 buffer solution Substances 0.000 description 11
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YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
238000013504 emergency use authorization Methods 0.000 description 10
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
238000010992 reflux Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 9
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000012298 atmosphere Substances 0.000 description 9
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ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 9
150000004665 fatty acids Chemical class 0.000 description 9
239000007788 liquid Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
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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
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