JP2016515096A5 - - Google Patents

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Publication number

JP2016515096A5

JP2016515096A5 JP2015559497A JP2015559497A JP2016515096A5 JP 2016515096 A5 JP2016515096 A5 JP 2016515096A5 JP 2015559497 A JP2015559497 A JP 2015559497A JP 2015559497 A JP2015559497 A JP 2015559497A JP 2016515096 A5 JP2016515096 A5 JP 2016515096A5

Authority

JP

Japan

Prior art keywords

alkyl

stereoisomer

solvate

pharmaceutically acceptable

acceptable salt

Prior art date

2014-02-27

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.)

Granted

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• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 150000001875 compounds Chemical class 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 5
• 239000000203 mixture Substances 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 238000009472 formulation Methods 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• TZKBVRDEOITLRB-UHFFFAOYSA-N 4-methyl-n-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-3-[2-(1h-pyrazolo[3,4-b]pyridin-5-yl)ethynyl]benzamide Chemical compound C1CN(C)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(C#CC=2C=C3C=NNC3=NC=2)=C1 TZKBVRDEOITLRB-UHFFFAOYSA-N 0.000 description 2
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
• BZNLFJMZVGEPDC-CYBMUJFWSA-N [(2r)-2-[[3-[(4-fluoro-3-methylphenyl)carbamoyl]phenyl]sulfonylamino]propyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](C)NS(=O)(=O)C1=CC=CC(C(=O)NC=2C=C(C)C(F)=CC=2)=C1 BZNLFJMZVGEPDC-CYBMUJFWSA-N 0.000 description 2
• 235000019439 ethyl acetate Nutrition 0.000 description 2
• 238000010898 silica gel chromatography Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1