AU2012331274B2 - Heterocyclic compounds, medicaments containing said compounds, use thereof and processes for the preparation thereof - Google Patents

Info

Publication number

AU2012331274B2

AU2012331274B2 AU2012331274A AU2012331274A AU2012331274B2 AU 2012331274 B2 AU2012331274 B2 AU 2012331274B2 AU 2012331274 A AU2012331274 A AU 2012331274A AU 2012331274 A AU2012331274 A AU 2012331274A AU 2012331274 B2 AU2012331274 B2 AU 2012331274B2

Authority

AU

Australia

Prior art keywords

alkyl

compound

phenyl

amino

acid

Prior art date

2011-11-02

Legal status (The legal status 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 status listed.)

Ceased

Links

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• 238000000034 method Methods 0.000 title claims description 58
• 239000003814 drug Substances 0.000 title claims description 14
• 238000002360 preparation method Methods 0.000 title description 8
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
• 230000008569 process Effects 0.000 title description 2
• 150000003839 salts Chemical class 0.000 claims abstract description 91
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• 201000010099 disease Diseases 0.000 claims abstract description 24
• 239000001257 hydrogen Substances 0.000 claims description 225
• 229910052739 hydrogen Inorganic materials 0.000 claims description 225
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 183
• 239000002253 acid Substances 0.000 claims description 71
• -1 EGFR-inhibitors Substances 0.000 claims description 42
• 150000002431 hydrogen Chemical group 0.000 claims description 37
• 206010006451 bronchitis Diseases 0.000 claims description 25
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 20
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 18
• 239000013543 active substance Substances 0.000 claims description 16
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• 208000007451 chronic bronchitis Diseases 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
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• 238000004519 manufacturing process Methods 0.000 claims description 2
• MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 claims 1
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• 230000002401 inhibitory effect Effects 0.000 abstract description 2
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• 239000000203 mixture Substances 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
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• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 33
• 239000000243 solution Substances 0.000 description 32
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• 239000002904 solvent Substances 0.000 description 23
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• 230000002829 reductive effect Effects 0.000 description 22
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 21
• 229910052799 carbon Inorganic materials 0.000 description 21
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• 125000003118 aryl group Chemical group 0.000 description 19
• 239000012453 solvate Substances 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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• 125000000623 heterocyclic group Chemical group 0.000 description 14
• 125000001424 substituent group Chemical group 0.000 description 14
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
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• 229920006395 saturated elastomer Polymers 0.000 description 12
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
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• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
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• 229910052717 sulfur Inorganic materials 0.000 description 8
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