JP2018516989A5 - - Google Patents

Info

Publication number

JP2018516989A5

JP2018516989A5 JP2018515192A JP2018515192A JP2018516989A5 JP 2018516989 A5 JP2018516989 A5 JP 2018516989A5 JP 2018515192 A JP2018515192 A JP 2018515192A JP 2018515192 A JP2018515192 A JP 2018515192A JP 2018516989 A5 JP2018516989 A5 JP 2018516989A5

Authority

JP

Japan

Prior art keywords

solvent system

composition according

composition

ratio

appendix

Prior art date

2016-06-03

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

Links

• Espacenet
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• 239000000203 mixture Substances 0.000 claims description 146
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 94
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 81
• 239000002904 solvent Substances 0.000 claims description 65
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 63
• 235000019441 ethanol Nutrition 0.000 claims description 47
• -1 alkylene glycol Chemical compound 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 38
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 230000002401 inhibitory effect Effects 0.000 claims description 29
• 235000019445 benzyl alcohol Nutrition 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 27
• 241000289669 Erinaceus europaeus Species 0.000 claims description 24
• 230000000699 topical effect Effects 0.000 claims description 24
• XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 19
• 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 19
• 241000027355 Ferocactus setispinus Species 0.000 claims description 10
• 150000003138 primary alcohols Chemical class 0.000 claims description 10
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
• 239000000194 fatty acid Substances 0.000 claims description 9
• 229930195729 fatty acid Natural products 0.000 claims description 9
• 150000004665 fatty acids Chemical class 0.000 claims description 9
• 239000012528 membrane Substances 0.000 claims description 9
• 229920005862 polyol Polymers 0.000 claims description 8
• 150000004671 saturated fatty acids Chemical class 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 6
• VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 5
• 229960004130 itraconazole Drugs 0.000 claims description 5
• 210000004207 dermis Anatomy 0.000 claims description 2
• 238000009472 formulation Methods 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• 238000000338 in vitro Methods 0.000 claims description 2
• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 206010004146 Basal cell carcinoma Diseases 0.000 description 20
• 125000002619 bicyclic group Chemical group 0.000 description 11
• 238000000034 method Methods 0.000 description 10
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 239000008280 blood Substances 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
• 230000001225 therapeutic effect Effects 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
• 239000003349 gelling agent Substances 0.000 description 4
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
• VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical group CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 description 2
• TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 2
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
• 235000021360 Myristic acid Nutrition 0.000 description 2
• TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
• 235000021314 Palmitic acid Nutrition 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• 238000007792 addition Methods 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 239000008117 stearic acid Substances 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 208000011580 syndromic disease Diseases 0.000 description 2
• QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• QASFUMOKHFSJGL-LAFRSMQTSA-N Cyclopamine Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H](CC2=C3C)[C@@H]1[C@@H]2CC[C@@]13O[C@@H]2C[C@H](C)CN[C@H]2[C@H]1C QASFUMOKHFSJGL-LAFRSMQTSA-N 0.000 description 1
• HZLFFNCLTRVYJG-WWGOJCOQSA-N Patidegib Chemical group C([C@@]1(CC(C)=C2C3)O[C@@H]4C[C@H](C)CN[C@H]4[C@H]1C)C[C@H]2[C@H]1[C@H]3[C@@]2(C)CC[C@@H](NS(C)(=O)=O)C[C@H]2CC1 HZLFFNCLTRVYJG-WWGOJCOQSA-N 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229930013930 alkaloid Natural products 0.000 description 1
• 150000003797 alkaloid derivatives Chemical class 0.000 description 1
• QASFUMOKHFSJGL-UHFFFAOYSA-N cyclopamine Natural products C1C=C2CC(O)CCC2(C)C(CC2=C3C)C1C2CCC13OC2CC(C)CNC2C1C QASFUMOKHFSJGL-UHFFFAOYSA-N 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• 229950002575 patidegib Drugs 0.000 description 1
• 229960005323 phenoxyethanol Drugs 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• 230000003637 steroidlike Effects 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1