TW201018681A - Pyrimidine compounds, compositions and methods of use - Google Patents

Info

Publication number

TW201018681A

TW201018681A TW098125944A TW98125944A TW201018681A TW 201018681 A TW201018681 A TW 201018681A TW 098125944 A TW098125944 A TW 098125944A TW 98125944 A TW98125944 A TW 98125944A TW 201018681 A TW201018681 A TW 201018681A

Authority

TW

Taiwan

Prior art keywords

group

phenyl

pyrimidin

alkyl

compound

Prior art date

2008-07-31

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000203 mixture Substances 0.000 title claims description 109
• 238000000034 method Methods 0.000 title description 116
• 150000003230 pyrimidines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 321
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 52
• 201000011510 cancer Diseases 0.000 claims abstract description 44
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 201000010099 disease Diseases 0.000 claims abstract description 24
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 12
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 500
• -1 Ci - 6heteroalkyl Chemical group 0.000 claims description 277
• 125000000217 alkyl group Chemical group 0.000 claims description 131
• 125000001424 substituent group Chemical group 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 50
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
• 125000003118 aryl group Chemical group 0.000 claims description 48
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 43
• 150000002431 hydrogen Chemical class 0.000 claims description 42
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
• 229910052740 iodine Inorganic materials 0.000 claims description 34
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 210000000214 mouth Anatomy 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 25
• 210000004027 cell Anatomy 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
• 239000003814 drug Substances 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 18
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 229910003827 NRaRb Inorganic materials 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 241000124008 Mammalia Species 0.000 claims description 15
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 210000004907 gland Anatomy 0.000 claims description 13
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 13
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
• 150000002923 oximes Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 9
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 9
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 150000002602 lanthanoids Chemical class 0.000 claims description 8
• 229910052701 rubidium Inorganic materials 0.000 claims description 8
• 210000002784 stomach Anatomy 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 7
• 229910052747 lanthanoid Inorganic materials 0.000 claims description 7
• 201000007270 liver cancer Diseases 0.000 claims description 7
• 208000014018 liver neoplasm Diseases 0.000 claims description 7
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 7
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
• 206010039491 Sarcoma Diseases 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 210000003800 pharynx Anatomy 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 229910052703 rhodium Inorganic materials 0.000 claims description 6
• 229910052707 ruthenium Inorganic materials 0.000 claims description 6
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 210000000481 breast Anatomy 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 210000004072 lung Anatomy 0.000 claims description 5
• 208000000649 small cell carcinoma Diseases 0.000 claims description 5
• 206010005003 Bladder cancer Diseases 0.000 claims description 4
• 201000009030 Carcinoma Diseases 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
• 208000009956 adenocarcinoma Diseases 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
• 201000010982 kidney cancer Diseases 0.000 claims description 4
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 4
• 201000001441 melanoma Diseases 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 210000000664 rectum Anatomy 0.000 claims description 4
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 4
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
• 208000003200 Adenoma Diseases 0.000 claims description 3
• 206010001233 Adenoma benign Diseases 0.000 claims description 3
• 206010029260 Neuroblastoma Diseases 0.000 claims description 3
• 206010059394 acanthoma Diseases 0.000 claims description 3
• 210000003445 biliary tract Anatomy 0.000 claims description 3
• 210000000988 bone and bone Anatomy 0.000 claims description 3
• 210000003679 cervix uteri Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 229940127089 cytotoxic agent Drugs 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 210000003238 esophagus Anatomy 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 210000003734 kidney Anatomy 0.000 claims description 3
• 208000003849 large cell carcinoma Diseases 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• 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 description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• 210000000813 small intestine Anatomy 0.000 claims description 3
• 230000002381 testicular Effects 0.000 claims description 3
• 210000002105 tongue Anatomy 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 2
• 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
• 208000021309 Germ cell tumor Diseases 0.000 claims description 2
• 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims description 2
• 210000000133 brain stem Anatomy 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims description 2
• 210000003169 central nervous system Anatomy 0.000 claims description 2
• 239000000470 constituent Substances 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
• 210000002429 large intestine Anatomy 0.000 claims description 2
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
• 229910052762 osmium Inorganic materials 0.000 claims description 2
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
• 210000000496 pancreas Anatomy 0.000 claims description 2
• 201000010198 papillary carcinoma Diseases 0.000 claims description 2
• 239000003016 pheromone Substances 0.000 claims description 2
• 229910052698 phosphorus Inorganic materials 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 claims 2
• 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 claims 2
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
• ICNOQWMTDGMVGW-UHFFFAOYSA-N 3-propan-2-ylmorpholine Chemical compound CC(C)C1COCCN1 ICNOQWMTDGMVGW-UHFFFAOYSA-N 0.000 claims 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
• 229910019567 Re Re Inorganic materials 0.000 claims 1
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
• 229910052802 copper Inorganic materials 0.000 claims 1
• 229910052805 deuterium Inorganic materials 0.000 claims 1
• 230000035622 drinking Effects 0.000 claims 1
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• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
• 229910052738 indium Inorganic materials 0.000 claims 1
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
• 210000000088 lip Anatomy 0.000 claims 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
• 150000003254 radicals Chemical class 0.000 claims 1
• 235000015170 shellfish Nutrition 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
• 125000001425 triazolyl group Chemical group 0.000 claims 1
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 abstract description 38
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• 238000003786 synthesis reaction Methods 0.000 description 126
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 40
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