TW201202241A - Chemical compounds - Google Patents

Info

Publication number

TW201202241A

TW201202241A TW100109800A TW100109800A TW201202241A TW 201202241 A TW201202241 A TW 201202241A TW 100109800 A TW100109800 A TW 100109800A TW 100109800 A TW100109800 A TW 100109800A TW 201202241 A TW201202241 A TW 201202241A

Authority

TW

Taiwan

Prior art keywords

amine

dihydro

ethenyl

indol

cancer

Prior art date

2010-03-25

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 156
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• 239000003112 inhibitor Substances 0.000 claims abstract description 75
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• 238000011282 treatment Methods 0.000 claims abstract description 64
• 230000000694 effects Effects 0.000 claims abstract description 41
• 238000000034 method Methods 0.000 claims abstract description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 201000010099 disease Diseases 0.000 claims abstract description 14
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
• 230000037361 pathway Effects 0.000 claims abstract description 12
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
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• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 8
• 206010003119 arrhythmia Diseases 0.000 claims abstract description 8
• 230000006793 arrhythmia Effects 0.000 claims abstract description 8
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• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 6
• 108091008010 PERKs Proteins 0.000 claims abstract description 4
• 102100034174 Eukaryotic translation initiation factor 2-alpha kinase 3 Human genes 0.000 claims abstract 3
• -1 -CONH2 Chemical group 0.000 claims description 327
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 185
• 239000000203 mixture Substances 0.000 claims description 172
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 156
• 125000000217 alkyl group Chemical group 0.000 claims description 146
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 104
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 97
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 70
• 125000001424 substituent group Chemical group 0.000 claims description 63
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 55
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 239000007789 gas Substances 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 43
• 210000004027 cell Anatomy 0.000 claims description 43
• 239000003795 chemical substances by application Substances 0.000 claims description 43
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 33
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• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
• 229960004979 fampridine Drugs 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• 239000011737 fluorine Substances 0.000 claims description 27
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
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• 150000001412 amines Chemical class 0.000 claims description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims description 20
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• 229910052794 bromium Inorganic materials 0.000 claims description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
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• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 17
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 210000003802 sputum Anatomy 0.000 claims description 12
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 11
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• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
• 201000009030 Carcinoma Diseases 0.000 claims description 9
• 238000001914 filtration Methods 0.000 claims description 9
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 9
• 230000019491 signal transduction Effects 0.000 claims description 9
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 9
• LIVYKAHFQBZQRL-UHFFFAOYSA-N thieno[3,2-c]pyridin-4-amine Chemical compound NC1=NC=CC2=C1C=CS2 LIVYKAHFQBZQRL-UHFFFAOYSA-N 0.000 claims description 9
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