TW593315B - Substituted pyridines and pyridazines with angiogenesis inhibiting activity - Google Patents

Info

Publication number

TW593315B

TW593315B TW089119700A TW89119700A TW593315B TW 593315 B TW593315 B TW 593315B TW 089119700 A TW089119700 A TW 089119700A TW 89119700 A TW89119700 A TW 89119700A TW 593315 B TW593315 B TW 593315B

Authority

TW

Taiwan

Prior art keywords

methyl

amino

oxy

furo

group

Prior art date

1999-09-28

Links

• Espacenet
• Global Dossier
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• 230000033115 angiogenesis Effects 0.000 title claims abstract description 21
• 230000002401 inhibitory effect Effects 0.000 title abstract description 5
• 150000004892 pyridazines Chemical class 0.000 title abstract 2
• 150000003222 pyridines Chemical class 0.000 title abstract 2
• 125000001424 substituent group Chemical group 0.000 claims abstract description 55
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
• 230000002159 abnormal effect Effects 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 241000124008 Mammalia Species 0.000 claims abstract 3
• 125000000217 alkyl group Chemical group 0.000 claims description 137
• 150000001875 compounds Chemical class 0.000 claims description 134
• -1 4-pyridylsulfanyl Chemical group 0.000 claims description 94
• 229910052799 carbon Inorganic materials 0.000 claims description 94
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
• 125000004429 atom Chemical group 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
• 229910001868 water Inorganic materials 0.000 claims description 52
• 230000002079 cooperative effect Effects 0.000 claims description 49
• 238000002360 preparation method Methods 0.000 claims description 44
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 18
• 150000001721 carbon Chemical group 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 230000015572 biosynthetic process Effects 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
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• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical group NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
• 238000009833 condensation Methods 0.000 claims description 6
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• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
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• 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
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• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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• 239000008267 milk Substances 0.000 claims description 2
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• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
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• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• NNJMFJSKMRYHSR-UHFFFAOYSA-M 4-phenylbenzoate Chemical compound C1=CC(C(=O)[O-])=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-M 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
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• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
• 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 claims 1
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• 208000000594 bullous pemphigoid Diseases 0.000 claims 1
• 235000013365 dairy product Nutrition 0.000 claims 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
• GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• 230000003902 lesion Effects 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
• 125000005581 pyrene group Chemical group 0.000 claims 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
• 125000003944 tolyl group Chemical group 0.000 claims 1
• 230000000007 visual effect Effects 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 95
• 125000003118 aryl group Chemical group 0.000 abstract description 17
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 11
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• 125000004076 pyridyl group Chemical group 0.000 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
• 125000003282 alkyl amino group Chemical group 0.000 description 70
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
• 238000006243 chemical reaction Methods 0.000 description 50
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• 125000000623 heterocyclic group Chemical group 0.000 description 35
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