TW201206933A - Substituted imidazo [1,2-a] pyrimidines and-pyridines - Google Patents

Info

Publication number

TW201206933A

TW201206933A TW100124649A TW100124649A TW201206933A TW 201206933 A TW201206933 A TW 201206933A TW 100124649 A TW100124649 A TW 100124649A TW 100124649 A TW100124649 A TW 100124649A TW 201206933 A TW201206933 A TW 201206933A

Authority

TW

Taiwan

Prior art keywords

phenyl

imidazo

alkyl

cyclobutylamine

group

Prior art date

2010-07-12

Links

• Espacenet
• Global Dossier
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• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
• 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 332
• 238000000034 method Methods 0.000 claims abstract description 264
• 238000004519 manufacturing process Methods 0.000 claims abstract description 16
• 239000001257 hydrogen Substances 0.000 claims description 239
• 229910052739 hydrogen Inorganic materials 0.000 claims description 239
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 227
• -1 1-3C-alkyl Chemical group 0.000 claims description 190
• 229910052736 halogen Inorganic materials 0.000 claims description 160
• 150000002367 halogens Chemical group 0.000 claims description 154
• 239000000203 mixture Substances 0.000 claims description 142
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 140
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 133
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
• 206010028980 Neoplasm Diseases 0.000 claims description 113
• 150000003839 salts Chemical class 0.000 claims description 110
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 100
• 125000003118 aryl group Chemical group 0.000 claims description 91
• 125000001424 substituent group Chemical group 0.000 claims description 87
• 125000001072 heteroaryl group Chemical group 0.000 claims description 82
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 72
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
• 125000006239 protecting group Chemical group 0.000 claims description 56
• 201000010099 disease Diseases 0.000 claims description 55
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• 150000001204 N-oxides Chemical class 0.000 claims description 46
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 45
• 238000011282 treatment Methods 0.000 claims description 44
• 230000003211 malignant effect Effects 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 32
• 230000009826 neoplastic cell growth Effects 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 28
• 239000002246 antineoplastic agent Substances 0.000 claims description 28
• KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 150000001412 amines Chemical class 0.000 claims description 26
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 24
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 239000004480 active ingredient Substances 0.000 claims description 22
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 21
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
• 239000000796 flavoring agent Substances 0.000 claims description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
• 230000006907 apoptotic process Effects 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 230000015572 biosynthetic process Effects 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 235000021419 vinegar Nutrition 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 230000003463 hyperproliferative effect Effects 0.000 claims description 14
• 239000000052 vinegar Substances 0.000 claims description 14
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 239000002671 adjuvant Substances 0.000 claims description 11
• 239000000126 substance Substances 0.000 claims description 11
• 230000006698 induction Effects 0.000 claims description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 6
• 244000294411 Mirabilis expansa Species 0.000 claims description 6
• 235000015429 Mirabilis expansa Nutrition 0.000 claims description 6
• 235000013536 miso Nutrition 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 150000003573 thiols Chemical group 0.000 claims description 6
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 5
• 150000002923 oximes Chemical class 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 4
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 4
• 230000001613 neoplastic effect Effects 0.000 claims description 4
• 240000007594 Oryza sativa Species 0.000 claims description 3
• 235000007164 Oryza sativa Nutrition 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 235000009566 rice Nutrition 0.000 claims description 3
• CBOPZRDROLVYRN-UHFFFAOYSA-N 1-[4-(7-methoxy-3-phenylimidazo[1,2-a]pyrimidin-2-yl)phenyl]cyclobutan-1-amine Chemical compound N1=C2N=C(OC)C=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 CBOPZRDROLVYRN-UHFFFAOYSA-N 0.000 claims description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
• 210000003296 saliva Anatomy 0.000 claims description 2
• PHBILWMDQNGWID-UHFFFAOYSA-N 1-[4-(1-phenylimidazol-2-yl)phenyl]cyclobutan-1-amine Chemical compound NC1(CCC1)C1=CC=C(C=C1)C1=NC=CN1C1=CC=CC=C1 PHBILWMDQNGWID-UHFFFAOYSA-N 0.000 claims 3
• SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 claims 2
• SEULWJSKCVACTH-UHFFFAOYSA-O 3-phenyl-1h-imidazol-3-ium Chemical compound C1=NC=C[NH+]1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-O 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• PHYLEHPTWGIEHS-UHFFFAOYSA-N C(CCCCCCCCC)OCCNCCCCCCCCCC Chemical compound C(CCCCCCCCC)OCCNCCCCCCCCCC PHYLEHPTWGIEHS-UHFFFAOYSA-N 0.000 claims 1
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004802 cyanophenyl group Chemical group 0.000 claims 1
• 210000000003 hoof Anatomy 0.000 claims 1
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
• QOSAXOJJXBSPPQ-UHFFFAOYSA-N n-decylhydroxylamine Chemical compound CCCCCCCCCCNO QOSAXOJJXBSPPQ-UHFFFAOYSA-N 0.000 claims 1
• OQFQKNFHVKYTDG-UHFFFAOYSA-N n-propan-2-yldecan-1-amine Chemical compound CCCCCCCCCCNC(C)C OQFQKNFHVKYTDG-UHFFFAOYSA-N 0.000 claims 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
• 108091008611 Protein Kinase B Proteins 0.000 abstract description 26
• 230000037361 pathway Effects 0.000 abstract description 21
• 239000003814 drug Substances 0.000 abstract description 15
• 230000008569 process Effects 0.000 abstract description 5
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 274
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
• 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 183
• 239000000543 intermediate Substances 0.000 description 162
• 235000019439 ethyl acetate Nutrition 0.000 description 133
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 130
• 238000005160 1H NMR spectroscopy Methods 0.000 description 81
• 239000000243 solution Substances 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 67
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• 238000006243 chemical reaction Methods 0.000 description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
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• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
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• 230000002829 reductive effect Effects 0.000 description 28
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