JP2020536070A5 - - Google Patents

Info

Publication number

JP2020536070A5

JP2020536070A5 JP2020518078A JP2020518078A JP2020536070A5 JP 2020536070 A5 JP2020536070 A5 JP 2020536070A5 JP 2020518078 A JP2020518078 A JP 2020518078A JP 2020518078 A JP2020518078 A JP 2020518078A JP 2020536070 A5 JP2020536070 A5 JP 2020536070A5

Authority

JP

Japan

Prior art keywords

xrpd pattern

pharmaceutically acceptable

crystal form

methyl

acceptable salt

Prior art date

2018-09-28

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.)

Withdrawn

Links

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• 150000001875 compounds Chemical class 0.000 claims description 41
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 5
• NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical class C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 claims description 3
• FZIPCQLKPTZZIM-UHFFFAOYSA-N 2-oxidanylpropane-1,2,3-tricarboxylic acid Chemical group OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O FZIPCQLKPTZZIM-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
• 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
• 235000006408 oxalic acid Nutrition 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 2
• 229940081974 saccharin Drugs 0.000 claims description 2
• 235000019204 saccharin Nutrition 0.000 claims description 2
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 2
• 239000013078 crystal Substances 0.000 claims 20
• GCZUIPVRHLYYOG-BEFAXECRSA-N (2r,5s)-7-methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one Chemical compound O=C1N(C)CC[C@]11N[C@@H](C=2N=C(C=C(C)N=2)C=2C=CC(=CC=2)C(F)(F)F)CC1 GCZUIPVRHLYYOG-BEFAXECRSA-N 0.000 claims 2
• UZSIJMCGPRLFPE-UHFFFAOYSA-N 1,2-diazaspiro[4.4]nonan-9-one sulfuric acid Chemical compound OS(O)(=O)=O.O=C1CCCC11CCNN1 UZSIJMCGPRLFPE-UHFFFAOYSA-N 0.000 claims 1
• 108010052164 Sodium Channels Proteins 0.000 claims 1
• 102000018674 Sodium Channels Human genes 0.000 claims 1
• 230000001419 dependent effect Effects 0.000 claims 1
• -1 diazaspiro [4.4] nonane-6-one oxalate (oxalate) Chemical compound 0.000 claims 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
• QHDCFDQKXQIXLF-UHFFFAOYSA-N sulfuric acid sulfurous acid Chemical compound OS(O)=O.OS(O)(=O)=O QHDCFDQKXQIXLF-UHFFFAOYSA-N 0.000 claims 1
• 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 description 4
• 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 description 4
• 239000000126 substance Substances 0.000 description 3
• GCZUIPVRHLYYOG-UHFFFAOYSA-N 7-methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one Chemical compound O=C1N(C)CCC11NC(C=2N=C(C=C(C)N=2)C=2C=CC(=CC=2)C(F)(F)F)CC1 GCZUIPVRHLYYOG-UHFFFAOYSA-N 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 238000002560 therapeutic procedure Methods 0.000 description 2
• 239000000654 additive Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 150000003891 oxalate salts Chemical class 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 1