JP2020007308A5 - - Google Patents

Info

Publication number

JP2020007308A5

JP2020007308A5 JP2019124976A JP2019124976A JP2020007308A5 JP 2020007308 A5 JP2020007308 A5 JP 2020007308A5 JP 2019124976 A JP2019124976 A JP 2019124976A JP 2019124976 A JP2019124976 A JP 2019124976A JP 2020007308 A5 JP2020007308 A5 JP 2020007308A5

Authority

JP

Japan

Prior art keywords

compound

salt

pharmaceutical composition

group

propyl

Prior art date

2019-07-04

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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• 150000001875 compounds Chemical class 0.000 claims 30
• 238000000034 method Methods 0.000 claims 13
• -1 salt salt Chemical class 0.000 claims 10
• 239000008194 pharmaceutical composition Substances 0.000 claims 9
• 150000003839 salts Chemical class 0.000 claims 9
• 125000000217 alkyl group Chemical group 0.000 claims 7
• 239000003153 chemical reaction reagent Substances 0.000 claims 6
• 229910052739 hydrogen Inorganic materials 0.000 claims 6
• 239000001257 hydrogen Substances 0.000 claims 6
• KCXFHTAICRTXLI-UHFFFAOYSA-M propane-1-sulfonate Chemical compound CCCS([O-])(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-M 0.000 claims 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
• 201000010099 disease Diseases 0.000 claims 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
• 238000000634 powder X-ray diffraction Methods 0.000 claims 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
• WQILKMOCXWNEBI-UHFFFAOYSA-N 1-propylsulfonyl-1,2,4-triazole Chemical compound CCCS(=O)(=O)N1C=NC=N1 WQILKMOCXWNEBI-UHFFFAOYSA-N 0.000 claims 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 3
• 229910019142 PO4 Inorganic materials 0.000 claims 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
• 201000004681 Psoriasis Diseases 0.000 claims 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
• 239000002253 acid Substances 0.000 claims 3
• 150000008043 acidic salts Chemical class 0.000 claims 3
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
• 239000010452 phosphate Substances 0.000 claims 3
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 3
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
• 201000004384 Alopecia Diseases 0.000 claims 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 2
• 241000124008 Mammalia Species 0.000 claims 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
• 231100000360 alopecia Toxicity 0.000 claims 2
• 239000013078 crystal Substances 0.000 claims 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
• 239000011736 potassium bicarbonate Substances 0.000 claims 2
• 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 2
• 235000015497 potassium bicarbonate Nutrition 0.000 claims 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 2
• 239000012049 topical pharmaceutical composition Substances 0.000 claims 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
• 206010003645 Atopy Diseases 0.000 claims 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
• 206010009900 Colitis ulcerative Diseases 0.000 claims 1
• 208000011231 Crohn disease Diseases 0.000 claims 1
• 206010012438 Dermatitis atopic Diseases 0.000 claims 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
• 239000007983 Tris buffer Substances 0.000 claims 1
• 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
• 206010047642 Vitiligo Diseases 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 claims 1
• 201000008937 atopic dermatitis Diseases 0.000 claims 1
• 239000011575 calcium Substances 0.000 claims 1
• 229910052791 calcium Inorganic materials 0.000 claims 1
• 239000006071 cream Substances 0.000 claims 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• NTBIYBAYFBNTCD-KBPBESRZSA-N dibenzoyl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound O=C([C@@H](O)[C@H](O)C(=O)OC(=O)C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-KBPBESRZSA-N 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 1
• 239000003889 eye drop Substances 0.000 claims 1
• 229940012356 eye drops Drugs 0.000 claims 1
• 239000000499 gel Substances 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
• 208000002741 leukoplakia Diseases 0.000 claims 1
• 229910052744 lithium Inorganic materials 0.000 claims 1
• 239000006210 lotion Substances 0.000 claims 1
• 239000011777 magnesium Substances 0.000 claims 1
• 229910052749 magnesium Inorganic materials 0.000 claims 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
• 150000002690 malonic acid derivatives Chemical class 0.000 claims 1
• 239000002674 ointment Substances 0.000 claims 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• 239000011574 phosphorus Substances 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 239000011591 potassium Substances 0.000 claims 1
• 229910052700 potassium Inorganic materials 0.000 claims 1
• 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
• 235000011181 potassium carbonates Nutrition 0.000 claims 1
• 235000011118 potassium hydroxide Nutrition 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• 125000004076 pyridyl group Chemical group 0.000 claims 1
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
• 239000011734 sodium Substances 0.000 claims 1
• 229910052708 sodium Inorganic materials 0.000 claims 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
• 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
• 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
• 235000017550 sodium carbonate Nutrition 0.000 claims 1
• 235000011121 sodium hydroxide Nutrition 0.000 claims 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
• 229940095064 tartrate Drugs 0.000 claims 1