JPH0410466B2 - - Google Patents
Info
- Publication number
- JPH0410466B2 JPH0410466B2 JP11944383A JP11944383A JPH0410466B2 JP H0410466 B2 JPH0410466 B2 JP H0410466B2 JP 11944383 A JP11944383 A JP 11944383A JP 11944383 A JP11944383 A JP 11944383A JP H0410466 B2 JPH0410466 B2 JP H0410466B2
- Authority
- JP
- Japan
- Prior art keywords
- alpha
- phenyl
- acetoxyacetamide
- diphenyl
- phenethyl
- Prior art date
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 40
- 230000001139 anti-pruritic effect Effects 0.000 claims description 38
- -1 N-phenyl phenyl-alpha-acetoxyacetamide Chemical compound 0.000 claims description 36
- ZZUSRGQPKDOYIZ-UHFFFAOYSA-N [2-(ethylamino)-2-oxo-1-phenylethyl] acetate Chemical compound CCNC(=O)C(OC(C)=O)C1=CC=CC=C1 ZZUSRGQPKDOYIZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- MAGPZHKLEZXLNU-UHFFFAOYSA-N phenyl-alpha-hydroxyacetamide Natural products NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 claims description 23
- FCZWNTWSYOQRRZ-UHFFFAOYSA-N (2-amino-2-oxo-1-phenylethyl) acetate Chemical compound CC(=O)OC(C(N)=O)C1=CC=CC=C1 FCZWNTWSYOQRRZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 230000000699 topical effect Effects 0.000 claims description 19
- NVBOEGNMVKLHOS-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(2-phenylethylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)NCCC1=CC=CC=C1 NVBOEGNMVKLHOS-UHFFFAOYSA-N 0.000 claims description 17
- 208000017520 skin disease Diseases 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000003908 antipruritic agent Substances 0.000 claims description 11
- REQXYFLFNBBIRX-UHFFFAOYSA-N 2-hydroxy-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(O)(C(=O)N)C1=CC=CC=C1 REQXYFLFNBBIRX-UHFFFAOYSA-N 0.000 claims description 9
- VJWNKDKKWLHRLK-UHFFFAOYSA-N [2-oxo-1,1-diphenyl-2-(2-phenylethylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C)C(=O)NCCC1=CC=CC=C1 VJWNKDKKWLHRLK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- HZUAABDZTNOQFU-UHFFFAOYSA-N [2-(benzylamino)-2-oxo-1-phenylethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)NCC1=CC=CC=C1 HZUAABDZTNOQFU-UHFFFAOYSA-N 0.000 claims description 8
- RUHMPUREMYQLEN-UHFFFAOYSA-N [2-(ethylamino)-2-oxo-1,1-diphenylethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(C)=O)(C(=O)NCC)C1=CC=CC=C1 RUHMPUREMYQLEN-UHFFFAOYSA-N 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 239000003246 corticosteroid Substances 0.000 claims description 7
- DMLYTGPBYWHKHU-UHFFFAOYSA-N (2-amino-2-oxoethyl) acetate Chemical compound CC(=O)OCC(N)=O DMLYTGPBYWHKHU-UHFFFAOYSA-N 0.000 claims description 6
- XKMYXUPLRAEBQX-UHFFFAOYSA-N [2-(diethylamino)-2-oxo-1-phenylethyl] acetate Chemical compound CCN(CC)C(=O)C(OC(C)=O)C1=CC=CC=C1 XKMYXUPLRAEBQX-UHFFFAOYSA-N 0.000 claims description 6
- AWSWCDNSSJHDOQ-UHFFFAOYSA-N [2-[2-(3,4-dimethoxyphenyl)ethylamino]-2-oxo-1-phenylethyl] acetate Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)C(OC(C)=O)C1=CC=CC=C1 AWSWCDNSSJHDOQ-UHFFFAOYSA-N 0.000 claims description 6
- UVYYQGYAUDCKBU-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(propan-2-ylamino)ethyl] acetate Chemical compound CC(C)NC(=O)C(OC(C)=O)C1=CC=CC=C1 UVYYQGYAUDCKBU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- INQYKMBFJLYPMV-UHFFFAOYSA-N [2-(methylamino)-2-oxo-1-phenylethyl] acetate Chemical compound CNC(=O)C(OC(C)=O)C1=CC=CC=C1 INQYKMBFJLYPMV-UHFFFAOYSA-N 0.000 claims description 5
- BOVCFKRFRLLZFA-UHFFFAOYSA-N [2-(tert-butylamino)-2-oxo-1-phenylethyl] acetate Chemical compound CC(C)(C)NC(=O)C(OC(=O)C)C1=CC=CC=C1 BOVCFKRFRLLZFA-UHFFFAOYSA-N 0.000 claims description 5
- 229960004022 clotrimazole Drugs 0.000 claims description 5
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 5
- 229960001334 corticosteroids Drugs 0.000 claims description 5
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 claims description 5
- JFZQEAPJMNLYFL-UHFFFAOYSA-N 2-hydroxy-2-phenyl-n-(2-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(O)C(=O)NCCC1=CC=CC=C1 JFZQEAPJMNLYFL-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- RVTCAQIJTUFJEI-UHFFFAOYSA-N [2-(diethylamino)-2-oxo-1,1-diphenylethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(C)=O)(C(=O)N(CC)CC)C1=CC=CC=C1 RVTCAQIJTUFJEI-UHFFFAOYSA-N 0.000 claims description 4
- ZHLDUJIMTKMXCR-UHFFFAOYSA-N [2-(ethylamino)-2-oxo-1,1-diphenylethyl] 2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)NCC)OC(=O)CC1=CC=CC=C1 ZHLDUJIMTKMXCR-UHFFFAOYSA-N 0.000 claims description 4
- FZKQUFNTADDIJC-UHFFFAOYSA-N [2-oxo-1,1-diphenyl-2-(2-phenylethylamino)ethyl] propanoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)CC)C(=O)NCCC1=CC=CC=C1 FZKQUFNTADDIJC-UHFFFAOYSA-N 0.000 claims description 4
- GPKCQGDCBJQLGA-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(2-phenylethylamino)ethyl] propanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CC)C(=O)NCCC1=CC=CC=C1 GPKCQGDCBJQLGA-UHFFFAOYSA-N 0.000 claims description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 4
- HSXFVHLMNNGPBN-UHFFFAOYSA-N n-ethyl-2-hydroxy-2-phenylacetamide Chemical compound CCNC(=O)C(O)C1=CC=CC=C1 HSXFVHLMNNGPBN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 229940088710 antibiotic agent Drugs 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229960002509 miconazole Drugs 0.000 claims description 3
- PBBKIPKCSOHKOQ-UHFFFAOYSA-N n-benzyl-2-hydroxy-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(O)C(=O)NCC1=CC=CC=C1 PBBKIPKCSOHKOQ-UHFFFAOYSA-N 0.000 claims description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- UVDGPZWLWWCWRU-UHFFFAOYSA-N 2-hydroxy-2,2-diphenyl-n-(2-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(=O)NCCC1=CC=CC=C1 UVDGPZWLWWCWRU-UHFFFAOYSA-N 0.000 claims description 2
- NDQYBAWWYUCLSW-UHFFFAOYSA-N 2-hydroxy-2-phenyl-n-(2-piperazin-1-ylethyl)acetamide Chemical compound C=1C=CC=CC=1C(O)C(=O)NCCN1CCNCC1 NDQYBAWWYUCLSW-UHFFFAOYSA-N 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 claims description 2
- 108010026389 Gramicidin Proteins 0.000 claims description 2
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 claims description 2
- 229940124091 Keratolytic Drugs 0.000 claims description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 2
- 229930182555 Penicillin Natural products 0.000 claims description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 2
- HBEDSKVEEHMKNP-UHFFFAOYSA-N [2-(benzylamino)-2-oxo-1,1-diphenylethyl] acetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C)C(=O)NCC1=CC=CC=C1 HBEDSKVEEHMKNP-UHFFFAOYSA-N 0.000 claims description 2
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 230000000840 anti-viral effect Effects 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 229940125715 antihistaminic agent Drugs 0.000 claims description 2
- 239000000739 antihistaminic agent Substances 0.000 claims description 2
- 229960002903 benzyl benzoate Drugs 0.000 claims description 2
- DNTGGZPQPQTDQF-XBXARRHUSA-N crotamiton Chemical compound C/C=C/C(=O)N(CC)C1=CC=CC=C1C DNTGGZPQPQTDQF-XBXARRHUSA-N 0.000 claims description 2
- 229960003338 crotamiton Drugs 0.000 claims description 2
- 229940000033 dermatological agent Drugs 0.000 claims description 2
- 239000003241 dermatological agent Substances 0.000 claims description 2
- 229960002311 dithranol Drugs 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229960004905 gramicidin Drugs 0.000 claims description 2
- ZWCXYZRRTRDGQE-SORVKSEFSA-N gramicidina Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-SORVKSEFSA-N 0.000 claims description 2
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 2
- 229960002867 griseofulvin Drugs 0.000 claims description 2
- 230000001530 keratinolytic effect Effects 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- KNZREWROVBTKTG-UHFFFAOYSA-N n,n-diethyl-2-hydroxy-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(O)(C(=O)N(CC)CC)C1=CC=CC=C1 KNZREWROVBTKTG-UHFFFAOYSA-N 0.000 claims description 2
- DFZIEDJPYOAOQK-UHFFFAOYSA-N n-benzyl-2-hydroxy-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(=O)NCC1=CC=CC=C1 DFZIEDJPYOAOQK-UHFFFAOYSA-N 0.000 claims description 2
- 229960000988 nystatin Drugs 0.000 claims description 2
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229940049954 penicillin Drugs 0.000 claims description 2
- 229960003742 phenol Drugs 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- VIDTVPHHDGRGAF-UHFFFAOYSA-N selenium sulfide Chemical compound [Se]=S VIDTVPHHDGRGAF-UHFFFAOYSA-N 0.000 claims description 2
- 229960005265 selenium sulfide Drugs 0.000 claims description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 2
- 229940001474 sodium thiosulfate Drugs 0.000 claims description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 2
- 229940043810 zinc pyrithione Drugs 0.000 claims description 2
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- IBGVVRIAUVUTCO-UHFFFAOYSA-N [acetyl(ethyl)amino] 2,2-diphenylacetate Chemical compound C(C)(=O)N(CC)OC(C(C1=CC=CC=C1)C1=CC=CC=C1)=O IBGVVRIAUVUTCO-UHFFFAOYSA-N 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 2
- 229930183010 Amphotericin Natural products 0.000 claims 1
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 claims 1
- 229940009444 amphotericin Drugs 0.000 claims 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 230000002682 anti-psoriatic effect Effects 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 98
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 208000003251 Pruritus Diseases 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 34
- 238000003786 synthesis reaction Methods 0.000 description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 238000003756 stirring Methods 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- 238000004809 thin layer chromatography Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 230000001225 therapeutic effect Effects 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 238000004566 IR spectroscopy Methods 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 230000007803 itching Effects 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 201000004624 Dermatitis Diseases 0.000 description 9
- 230000021736 acetylation Effects 0.000 description 9
- 238000006640 acetylation reaction Methods 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- 230000001823 pruritic effect Effects 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- 208000001126 Keratosis Diseases 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000008311 hydrophilic ointment Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 206010020649 Hyperkeratosis Diseases 0.000 description 7
- 208000010668 atopic eczema Diseases 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 7
- 238000007910 systemic administration Methods 0.000 description 7
- SFCRMFXXDWMQDU-UHFFFAOYSA-N (2-amino-2-oxo-1,1-diphenylethyl) acetate Chemical compound C=1C=CC=CC=1C(C(N)=O)(OC(=O)C)C1=CC=CC=C1 SFCRMFXXDWMQDU-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
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- KIBBLMZOFIFGAB-UHFFFAOYSA-N [2-oxo-1,1-diphenyl-2-(4-phenylbutylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C)C(=O)NCCCCC1=CC=CC=C1 KIBBLMZOFIFGAB-UHFFFAOYSA-N 0.000 description 1
- CCZVCSVMZWJEFA-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(2-phenylethylamino)ethyl] 2-(2-acetylphenyl)-2-hydroxyacetate Chemical compound CC(=O)C1=CC=CC=C1C(O)C(=O)OC(C=1C=CC=CC=1)C(=O)NCCC1=CC=CC=C1 CCZVCSVMZWJEFA-UHFFFAOYSA-N 0.000 description 1
- GPMFAENUNJSDAN-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(2-phenylethylamino)ethyl] 2-phenylacetate Chemical compound C=1C=CC=CC=1CCNC(=O)C(C=1C=CC=CC=1)OC(=O)CC1=CC=CC=C1 GPMFAENUNJSDAN-UHFFFAOYSA-N 0.000 description 1
- JGDSBHVIOJXNHH-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(3-phenylpropylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)NCCCC1=CC=CC=C1 JGDSBHVIOJXNHH-UHFFFAOYSA-N 0.000 description 1
- RHOBRDGCACDGDR-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(4-phenylbutylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)NCCCCC1=CC=CC=C1 RHOBRDGCACDGDR-UHFFFAOYSA-N 0.000 description 1
- 230000037374 absorbed through the skin Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
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- 239000000654 additive Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
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- 230000002141 anti-parasite Effects 0.000 description 1
- 230000000656 anti-yeast Effects 0.000 description 1
- 239000002488 antieczema agent Substances 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 229940030999 antipsoriatics Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
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- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 229960002537 betamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- BMCQMVFGOVHVNG-TUFAYURCSA-N cortisol 17-butyrate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CO)(OC(=O)CCC)[C@@]1(C)C[C@@H]2O BMCQMVFGOVHVNG-TUFAYURCSA-N 0.000 description 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229960001524 hydrocortisone butyrate Drugs 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 201000004607 keratosis follicularis Diseases 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- MEQKVIFABYGVLG-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)C(O)C1=CC=CC=C1 MEQKVIFABYGVLG-UHFFFAOYSA-N 0.000 description 1
- SITVMODNFWATKJ-UHFFFAOYSA-N n-ethyl-2-hydroxy-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(O)(C(=O)NCC)C1=CC=CC=C1 SITVMODNFWATKJ-UHFFFAOYSA-N 0.000 description 1
- BPBMYZSXEMWTHM-UHFFFAOYSA-N n-tert-butyl-2-hydroxy-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(O)(C(=O)NC(C)(C)C)C1=CC=CC=C1 BPBMYZSXEMWTHM-UHFFFAOYSA-N 0.000 description 1
- TYILRWKOBWOVII-UHFFFAOYSA-N n-tert-butyl-2-hydroxy-2-phenylacetamide Chemical compound CC(C)(C)NC(=O)C(O)C1=CC=CC=C1 TYILRWKOBWOVII-UHFFFAOYSA-N 0.000 description 1
- 229960005250 naloxone hydrochloride Drugs 0.000 description 1
- RGPDIGOSVORSAK-STHHAXOLSA-N naloxone hydrochloride Chemical compound Cl.O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C RGPDIGOSVORSAK-STHHAXOLSA-N 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000003401 opiate antagonist Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000024 polymyxin B Polymers 0.000 description 1
- 229960005266 polymyxin b Drugs 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39374182A | 1982-06-30 | 1982-06-30 | |
| US495159 | 1983-05-17 | ||
| US393741 | 1995-02-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5921654A JPS5921654A (ja) | 1984-02-03 |
| JPH0410466B2 true JPH0410466B2 (el) | 1992-02-25 |
Family
ID=23556042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11944383A Granted JPS5921654A (ja) | 1982-06-30 | 1983-06-30 | フエニルアルフア−アシルオキシアセトアミド誘導体及びその組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5921654A (el) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8416638D0 (en) * | 1984-06-29 | 1984-08-01 | Beecham Group Plc | Topical treatment and composition |
-
1983
- 1983-06-30 JP JP11944383A patent/JPS5921654A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5921654A (ja) | 1984-02-03 |
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