JP2015508775A5

JP2015508775A5 -

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Publication number: JP2015508775A5
Authority: JP; Japan
Prior art keywords: halo; aliphatic; compound; pharmaceutically acceptable; acceptable salt
Prior art date: 2013-02-14
Legal status : Granted

Application number

JP2014557765A

Other languages

English (en)

Japanese (ja)

Other versions

JP2015508775A (ja

JP6122877B2 (ja

Filing date

2013-02-14

Publication date

2017-03-16

2013-02-14 Application filed filed Critical

2013-02-14 Priority claimed from PCT/US2013/026113 external-priority patent/WO2013123169A1/en

2015-03-23 Publication of JP2015508775A publication Critical patent/JP2015508775A/ja

2017-03-16 Publication of JP2015508775A5 publication Critical patent/JP2015508775A5/ja

2017-04-26 Application granted granted Critical

2017-04-26 Publication of JP6122877B2 publication Critical patent/JP6122877B2/ja

Status Active legal-status Critical Current

2033-02-14 Anticipated expiration legal-status Critical

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-1 (i) -CN Chemical class 0.000 claims description 440
150000001875 compounds Chemical class 0.000 claims description 293
125000005843 halogen group Chemical group 0.000 claims description 178
125000001931 aliphatic group Chemical group 0.000 claims description 122
150000003839 salts Chemical class 0.000 claims description 106
238000000034 method Methods 0.000 claims description 74
239000000203 mixture Substances 0.000 claims description 66
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
125000000623 heterocyclic group Chemical group 0.000 claims description 51
125000001188 haloalkyl group Chemical group 0.000 claims description 49
125000004452 carbocyclyl group Chemical group 0.000 claims description 47
238000000634 powder X-ray diffraction Methods 0.000 claims description 46
206010028980 Neoplasm Diseases 0.000 claims description 44
125000003118 aryl group Chemical group 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 41
201000011510 cancer Diseases 0.000 claims description 39
125000004438 haloalkoxy group Chemical group 0.000 claims description 39
239000008194 pharmaceutical composition Substances 0.000 claims description 35
125000001309 chloro group Chemical group Cl* 0.000 claims description 34
208000035475 disorder Diseases 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 24
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 22
125000001072 heteroaryl group Chemical group 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 22
150000004682 monohydrates Chemical class 0.000 claims description 22
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 20
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 20
201000010099 disease Diseases 0.000 claims description 18
239000003937 drug carrier Substances 0.000 claims description 18
125000004995 haloalkylthio group Chemical group 0.000 claims description 18
230000005764 inhibitory process Effects 0.000 claims description 18
125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 16
125000004474 heteroalkylene group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 12
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
201000005202 lung cancer Diseases 0.000 claims description 9
208000020816 lung neoplasm Diseases 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
206010006187 Breast cancer Diseases 0.000 claims description 8
208000026310 Breast neoplasm Diseases 0.000 claims description 8
206010009944 Colon cancer Diseases 0.000 claims description 8
206010033128 Ovarian cancer Diseases 0.000 claims description 8
206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
208000029742 colonic neoplasm Diseases 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000002062 proliferating effect Effects 0.000 claims description 7
201000009613 breast lymphoma Diseases 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
208000015181 infectious disease Diseases 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
208000015122 neurodegenerative disease Diseases 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 2
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239000012530 fluid Substances 0.000 claims description 2
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125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
230000000302 ischemic effect Effects 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 239
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 144
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239000000126 substance Substances 0.000 description 99
HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
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OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 52
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
102000044159 Ubiquitin Human genes 0.000 description 34
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125000004432 carbon atom Chemical group C* 0.000 description 33
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 27
235000019253 formic acid Nutrition 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
230000000694 effects Effects 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 23
UFDGEFUTYSMTPD-UHFFFAOYSA-N 1-chloro-4-iodonaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(I)C2=C1 UFDGEFUTYSMTPD-UHFFFAOYSA-N 0.000 description 22
238000001069 Raman spectroscopy Methods 0.000 description 22
210000004027 cell Anatomy 0.000 description 22
239000007787 solid Substances 0.000 description 22
230000015572 biosynthetic process Effects 0.000 description 20
239000000725 suspension Substances 0.000 description 19
238000003786 synthesis reaction Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
125000004093 cyano group Chemical group *C#N 0.000 description 18
239000000523 sample Substances 0.000 description 18
239000003112 inhibitor Substances 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 16
102000004169 proteins and genes Human genes 0.000 description 16
108090000623 proteins and genes Proteins 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000000113 differential scanning calorimetry Methods 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000013058 crude material Substances 0.000 description 13
239000002552 dosage form Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
125000006413 ring segment Chemical group 0.000 description 12
238000002411 thermogravimetry Methods 0.000 description 12
102000004190 Enzymes Human genes 0.000 description 11
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238000004440 column chromatography Methods 0.000 description 11
235000018102 proteins Nutrition 0.000 description 11
239000011734 sodium Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000009472 formulation Methods 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
238000001757 thermogravimetry curve Methods 0.000 description 10
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
150000005829 chemical entities Chemical class 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
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230000004913 activation Effects 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
238000003556 assay Methods 0.000 description 8
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
125000004450 alkenylene group Chemical group 0.000 description 7
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PWSZRRFDVPMZGM-UHFFFAOYSA-N 5-phenyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C=C1C1=CC=CC=C1 PWSZRRFDVPMZGM-UHFFFAOYSA-N 0.000 description 4
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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IWYKAKXWNNUDGA-UHFFFAOYSA-N C1=CC=C2C(C=3C=C4NC=CC(N4N=3)=O)=CC=CC2=C1 Chemical compound C1=CC=C2C(C=3C=C4NC=CC(N4N=3)=O)=CC=CC2=C1 IWYKAKXWNNUDGA-UHFFFAOYSA-N 0.000 description 3
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JP2014557765A 2012-02-17 2013-02-14 ユビキチン活性化酵素のピラゾロピリミジニル阻害剤 Active JP6122877B2 (ja)