TW200829594A - Phosphoinositide 3-kinase inhibitor compounds and methods of use - Google Patents

Info

Publication number

TW200829594A

TW200829594A TW096146408A TW96146408A TW200829594A TW 200829594 A TW200829594 A TW 200829594A TW 096146408 A TW096146408 A TW 096146408A TW 96146408 A TW96146408 A TW 96146408A TW 200829594 A TW200829594 A TW 200829594A

Authority

TW

Taiwan

Prior art keywords

pyrimidin

methyl

amine

phenyl

pyrimidine

Prior art date

2006-12-07

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 225
• 238000000034 method Methods 0.000 title claims abstract description 212
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 2
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 39
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 35
• 238000011282 treatment Methods 0.000 claims abstract description 33
• 201000011510 cancer Diseases 0.000 claims abstract description 30
• 239000002207 metabolite Substances 0.000 claims abstract description 24
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 21
• 230000000694 effects Effects 0.000 claims abstract description 18
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 16
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 16
• 150000002632 lipids Chemical class 0.000 claims abstract description 12
• 239000012453 solvate Substances 0.000 claims abstract description 12
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 9
• 238000000338 in vitro Methods 0.000 claims abstract description 7
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 254
• -1 d dilute group Chemical group 0.000 claims description 252
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 183
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 173
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 148
• 239000000203 mixture Substances 0.000 claims description 128
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 112
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 109
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 93
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 61
• 150000001412 amines Chemical class 0.000 claims description 51
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 50
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 50
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 49
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 48
• 239000002253 acid Substances 0.000 claims description 47
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 44
• 210000000214 mouth Anatomy 0.000 claims description 42
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 39
• 239000003814 drug Substances 0.000 claims description 38
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
• 201000010099 disease Diseases 0.000 claims description 33
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 31
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 208000024891 symptom Diseases 0.000 claims description 25
• 239000000126 substance Substances 0.000 claims description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
• 229910052740 iodine Inorganic materials 0.000 claims description 22
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• 229940079593 drug Drugs 0.000 claims description 21
• 150000002576 ketones Chemical class 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 20
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 18
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 17
• 206010036790 Productive cough Diseases 0.000 claims description 16
• 239000011734 sodium Substances 0.000 claims description 16
• 210000003802 sputum Anatomy 0.000 claims description 16
• 208000024794 sputum Diseases 0.000 claims description 16
• 229930192474 thiophene Natural products 0.000 claims description 16
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 150000002923 oximes Chemical class 0.000 claims description 14
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 12
• 239000005711 Benzoic acid Substances 0.000 claims description 12
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 12
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
• 229910052707 ruthenium Inorganic materials 0.000 claims description 12
• 229910021653 sulphate ion Inorganic materials 0.000 claims description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 11
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 235000010233 benzoic acid Nutrition 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 11
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 10
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• 229940127089 cytotoxic agent Drugs 0.000 claims description 10
• 125000003277 amino group Chemical group 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
• 239000002246 antineoplastic agent Substances 0.000 claims description 8
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 8
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
• 229960005181 morphine Drugs 0.000 claims description 8
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229910052708 sodium Inorganic materials 0.000 claims description 8
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
• 125000005605 benzo group Chemical group 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
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