JPH0469129B2 - - Google Patents
Info
- Publication number
- JPH0469129B2 JPH0469129B2 JP59213152A JP21315284A JPH0469129B2 JP H0469129 B2 JPH0469129 B2 JP H0469129B2 JP 59213152 A JP59213152 A JP 59213152A JP 21315284 A JP21315284 A JP 21315284A JP H0469129 B2 JPH0469129 B2 JP H0469129B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydrochloride
- phosphate ester
- salt
- phosphate
- 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
- -1 phosphate ester Chemical class 0.000 claims description 40
- 239000004615 ingredient Substances 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 14
- 229960001047 methyl salicylate Drugs 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229960001067 hydrocortisone acetate Drugs 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000003623 enhancer Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
- 229940098465 tincture Drugs 0.000 description 4
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 3
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000208293 Capsicum Species 0.000 description 3
- 235000002566 Capsicum Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 229960000458 allantoin Drugs 0.000 description 3
- 239000001390 capsicum minimum Substances 0.000 description 3
- 239000000679 carrageenan Substances 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 229940113118 carrageenan Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 3
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000131283 Cantharis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 2
- 239000000006 Nitroglycerin Substances 0.000 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 description 2
- 241000700159 Rattus Species 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- XWCYDHJOKKGVHC-UHFFFAOYSA-N Vitamin A2 Chemical compound OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C XWCYDHJOKKGVHC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 210000001015 abdomen Anatomy 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KVYGGMBOZFWZBQ-UHFFFAOYSA-N benzyl nicotinate Chemical compound C=1C=CN=CC=1C(=O)OCC1=CC=CC=C1 KVYGGMBOZFWZBQ-UHFFFAOYSA-N 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- 229960000199 bismuth subgallate Drugs 0.000 description 2
- JAONZGLTYYUPCT-UHFFFAOYSA-K bismuth subgallate Chemical compound OC(=O)C1=CC(O)=C2O[Bi](O)OC2=C1 JAONZGLTYYUPCT-UHFFFAOYSA-K 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 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
- 229940105847 calamine Drugs 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- DNTGGZPQPQTDQF-XBXARRHUSA-N crotamiton Chemical compound C/C=C/C(=O)N(CC)C1=CC=CC=C1C DNTGGZPQPQTDQF-XBXARRHUSA-N 0.000 description 2
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 229960000520 diphenhydramine Drugs 0.000 description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 description 2
- 239000003676 hair preparation Substances 0.000 description 2
- 229910052864 hemimorphite Inorganic materials 0.000 description 2
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 2
- 229960004068 hexachlorophene Drugs 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[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 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- AHXDSVSZEZHDLV-UHFFFAOYSA-N mesulfen Chemical compound CC1=CC=C2SC3=CC(C)=CC=C3SC2=C1 AHXDSVSZEZHDLV-UHFFFAOYSA-N 0.000 description 2
- 229960005479 mesulfen Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
- 229940033663 thimerosal Drugs 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 229940041603 vitamin k 3 Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- MRAMPOPITCOOIN-VIFPVBQESA-N (2r)-n-(3-ethoxypropyl)-2,4-dihydroxy-3,3-dimethylbutanamide Chemical compound CCOCCCNC(=O)[C@H](O)C(C)(C)CO MRAMPOPITCOOIN-VIFPVBQESA-N 0.000 description 1
- OAJLVMGLJZXSGX-CXGXMSGESA-L (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-methanidyloxolane-3,4-diol;cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 1-[3-[(4z,9z,14z)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8 Chemical compound [Co+3].O[C@@H]1[C@H](O)[C@@H]([CH2-])O[C@H]1N1C2=NC=NC(N)=C2N=C1.O([C@H]1[C@H]([C@H](O[C@@H]1CO)N1C2=CC(C)=C(C)C=C2N=C1)O)P([O-])(=O)OC(C)CNC(=O)CCC1(C)C(CC(N)=O)C2[N-]\C1=C(C)/C(C(C\1(C)C)CCC(N)=O)=N/C/1=C\C(C(C/1(CC(N)=O)C)CCC(N)=O)=N\C\1=C(C)/C1=NC2(C)C(C)(CC(N)=O)C1CCC(N)=O OAJLVMGLJZXSGX-CXGXMSGESA-L 0.000 description 1
- YYCQZBJGQVVGMS-ZSCHJXSPSA-N (2s)-2,6-diaminohexanoic acid;ditetradecyl hydrogen phosphate Chemical compound NCCCC[C@H](N)C(O)=O.CCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCC YYCQZBJGQVVGMS-ZSCHJXSPSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
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- 239000011747 thiamine hydrochloride Substances 0.000 description 1
- UIERGBJEBXXIGO-UHFFFAOYSA-N thiamine mononitrate Chemical compound [O-][N+]([O-])=O.CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N UIERGBJEBXXIGO-UHFFFAOYSA-N 0.000 description 1
- HZSAJDVWZRBGIF-UHFFFAOYSA-M thiamine(1+) monophosphate(2-) Chemical compound CC1=C(CCOP([O-])([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N HZSAJDVWZRBGIF-UHFFFAOYSA-M 0.000 description 1
- 229960003279 thiopental Drugs 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 229930188428 trichomycin Natural products 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- HLDCSYXMVXILQC-UHFFFAOYSA-N xenysalate Chemical compound CCN(CC)CCOC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1O HLDCSYXMVXILQC-UHFFFAOYSA-N 0.000 description 1
- 229960003434 xenysalate Drugs 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- 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 description 1
- ZNVKGUVDRSSWHV-UHFFFAOYSA-L zinc;4-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=C(S([O-])(=O)=O)C=C1.OC1=CC=C(S([O-])(=O)=O)C=C1 ZNVKGUVDRSSWHV-UHFFFAOYSA-L 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59213152A JPS6191137A (ja) | 1984-10-11 | 1984-10-11 | 外用薬剤組成物 |
| EP85111872A EP0179277B1 (en) | 1984-10-11 | 1985-09-19 | Medical composition for external application |
| DE8585111872T DE3565937D1 (en) | 1984-10-11 | 1985-09-19 | Medical composition for external application |
| US06/778,226 US4686211A (en) | 1984-10-11 | 1985-09-20 | Medical composition for external application |
| ES547738A ES8701683A1 (es) | 1984-10-11 | 1985-10-09 | Un procedimiento para la preparacion de una composicion terapeutica que contiene un fosfato de dialquilo. |
| MYPI87000383A MY100022A (en) | 1984-10-11 | 1987-03-26 | Medical composition for external application |
| HK336/91A HK33691A (en) | 1984-10-11 | 1991-05-02 | Medical composition for external application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59213152A JPS6191137A (ja) | 1984-10-11 | 1984-10-11 | 外用薬剤組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6191137A JPS6191137A (ja) | 1986-05-09 |
| JPH0469129B2 true JPH0469129B2 (enExample) | 1992-11-05 |
Family
ID=16634426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59213152A Granted JPS6191137A (ja) | 1984-10-11 | 1984-10-11 | 外用薬剤組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4686211A (enExample) |
| EP (1) | EP0179277B1 (enExample) |
| JP (1) | JPS6191137A (enExample) |
| DE (1) | DE3565937D1 (enExample) |
| ES (1) | ES8701683A1 (enExample) |
| HK (1) | HK33691A (enExample) |
| MY (1) | MY100022A (enExample) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01151516A (ja) * | 1987-12-08 | 1989-06-14 | Shionogi & Co Ltd | ビタミンｅ配合外用剤 |
| GB8828017D0 (en) * | 1988-12-01 | 1989-01-05 | Unilever Plc | Topical composition |
| GB8828014D0 (en) * | 1988-12-01 | 1989-01-05 | Unilever Plc | Topical composition |
| GB8828013D0 (en) * | 1988-12-01 | 1989-01-05 | Unilever Plc | Topical composition |
| GB8828020D0 (en) * | 1988-12-01 | 1989-01-05 | Unilever Plc | Topical composition |
| GB8828018D0 (en) * | 1988-12-01 | 1989-01-05 | Unilever Plc | Topical composition |
| US4906454A (en) * | 1989-02-23 | 1990-03-06 | The Procter & Gamble Company | Deodorant compositions containing specific piroctone salts and perfumes |
| US5262165A (en) * | 1992-02-04 | 1993-11-16 | Schering Corporation | Transdermal nitroglycerin patch with penetration enhancers |
| GB9003199D0 (en) * | 1990-02-13 | 1990-04-11 | Unilever Plc | Topical composition |
| US5565207A (en) * | 1990-09-19 | 1996-10-15 | Pola Kasei Kogyo Kabushiki Kaisha | Scalp moisturizer and external skin preparation |
| GB9101986D0 (en) * | 1991-01-30 | 1991-03-13 | Smith & Nephew | Pharmaceutical compositions |
| US5409911A (en) * | 1992-09-11 | 1995-04-25 | Merck & Co., Inc. | Prostaglandin analog for treating osteoporosis |
| TW251302B (enExample) * | 1992-12-28 | 1995-07-11 | Kao Corp | |
| US5665742A (en) * | 1994-05-31 | 1997-09-09 | Kao Corporation | Bath medicine composition and its use in inhibiting the generation of body odor |
| US5543430A (en) * | 1994-10-05 | 1996-08-06 | Kaesemeyer; W. H. | Method and formulation of stimulating nitric oxide synthesis |
| US5968983A (en) * | 1994-10-05 | 1999-10-19 | Nitrosystems, Inc | Method and formulation for treating vascular disease |
| US20110196039A9 (en) * | 1994-10-05 | 2011-08-11 | Kaesemeyer Wayne H | Controlled release arginine formulations |
| US6239172B1 (en) * | 1997-04-10 | 2001-05-29 | Nitrosystems, Inc. | Formulations for treating disease and methods of using same |
| US5560913A (en) * | 1995-01-27 | 1996-10-01 | The Procter & Gamble Company | Pharmaceutical compositions |
| US6605751B1 (en) * | 1997-11-14 | 2003-08-12 | Acrymed | Silver-containing compositions, devices and methods for making |
| WO1999039575A2 (en) * | 1998-02-09 | 1999-08-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Synergistic biocidal activity of ternary complexes of negatively -charged biocides (component a), transition metal ions (component b), and neutral chelators (component c) |
| US5972920A (en) * | 1998-02-12 | 1999-10-26 | Dermalogix Partners, Inc. | Formulation containing a carrier, active ingredient, and surfactant for treating skin disorders |
| US6121253A (en) * | 1998-11-20 | 2000-09-19 | Merck Frosst Canada & Co. | Prostaglandin conjugates for treating or preventing bone disease |
| US6254294B1 (en) * | 1999-08-09 | 2001-07-03 | Sigrid G. Muhar | Pharmaceutical kit |
| FR2799369B1 (fr) * | 1999-10-08 | 2001-12-21 | Oreal | Association d'escine et de sulfate de dextran et son utilisation |
| EP1244476B1 (en) * | 1999-12-30 | 2006-05-31 | Acrymed | Methods and compositions for improved delivery devices |
| US7758888B2 (en) * | 2000-04-21 | 2010-07-20 | Sol-Gel Technologies Ltd. | Composition exhibiting enhanced formulation stability and delivery of topical active ingredients |
| US20040097472A1 (en) * | 2000-11-14 | 2004-05-20 | West Simon Michael | Complexes of phosphate derivatives |
| AUPR549901A0 (en) | 2001-06-06 | 2001-07-12 | Vital Health Sciences Pty Ltd | Topical formulation containing tocopheryl phosphates |
| EP1254909A1 (de) * | 2001-04-30 | 2002-11-06 | Cognis Iberia, S.L. | Phosphorsäureester |
| MXPA04000654A (es) * | 2001-07-27 | 2004-03-19 | Vital Health Sciences Pty Ltd | Terapia dermica usando derivados de fosfato de agente de transferencia de electrones. |
| WO2003049774A1 (en) * | 2001-12-13 | 2003-06-19 | Vital Health Sciences Pty Ltd | Transdermal transport of compounds |
| US6833139B1 (en) * | 2002-01-09 | 2004-12-21 | Ferndale Laboratories, Inc. | Composition and method for the treatment of anorectal disorders |
| CN1678277B (zh) * | 2002-07-29 | 2010-05-05 | 艾克里麦德公司 | 治疗皮肤病的方法和组合物 |
| AU2002950713A0 (en) * | 2002-08-09 | 2002-09-12 | Vital Health Sciences Pty Ltd | Carrier |
| JP4690305B2 (ja) * | 2003-01-17 | 2011-06-01 | バイタル ヘルス サイエンシズ プロプライアタリー リミティド | 抗増殖性質を有する化合物 |
| AU2003901815A0 (en) * | 2003-04-15 | 2003-05-01 | Vital Health Sciences Pty Ltd | Phosphate derivatives |
| RU2477136C2 (ru) * | 2004-03-03 | 2013-03-10 | Вайтал Хэлф Сайнсис Пти Лтд | Алкалоидные составы |
| US20050282870A1 (en) * | 2004-06-16 | 2005-12-22 | Carter Stephen G | Peripherally-acting vasodilators |
| CN102783499A (zh) * | 2004-07-30 | 2012-11-21 | 金伯利-克拉克环球有限公司 | 抗微生物的装置和组合物 |
| EP2789235B1 (en) * | 2004-07-30 | 2015-12-23 | Avent, Inc. | Method of preparing silver nanoparticles |
| US8361553B2 (en) | 2004-07-30 | 2013-01-29 | Kimberly-Clark Worldwide, Inc. | Methods and compositions for metal nanoparticle treated surfaces |
| US9289378B2 (en) * | 2004-09-20 | 2016-03-22 | Avent, Inc. | Antimicrobial amorphous compositions |
| JP2008531602A (ja) * | 2005-03-03 | 2008-08-14 | バイタル ヘルス サイエンシズ プロプライアタリー リミティド | 抗癌特性を有する化合物 |
| US9168216B2 (en) * | 2005-06-17 | 2015-10-27 | Vital Health Sciences Pty. Ltd. | Carrier comprising one or more di and/or mono-(electron transfer agent) phosphate derivatives or complexes thereof |
| BRPI0614143A2 (pt) | 2005-08-02 | 2012-11-20 | Sol Gel Technologies Ltd | processo para revestir um material particulado insolével em Água, sàlido, com um àxido metÁlico, material particulado revestido, composiÇço, mÉtodo para o tratamento de uma condiÇço superficial em um induvÍduo, e, uso de material particulado revestido |
| US20090005348A1 (en) * | 2005-12-23 | 2009-01-01 | Vital Health Sciences Pty Ltd | Compounds Having Cytokine Modulating Properties |
| WO2007127236A2 (en) * | 2006-04-28 | 2007-11-08 | Acrymed, Inc. | Antimicrobial site dressings |
| EA200970724A1 (ru) | 2007-02-01 | 2010-02-26 | Сол-Джел Текнолоджиз Лтд. | Композиции для местного применения, содержащие пероксид и ретиноид |
| ES2763829T3 (es) * | 2007-02-01 | 2020-06-01 | Sol Gel Tech Ltd | Método para preparar partículas que comprenden un revestimiento de óxido de metal |
| JP2010235523A (ja) * | 2009-03-31 | 2010-10-21 | Kao Corp | 水性毛髪洗浄剤 |
| WO2011094814A1 (en) | 2010-02-05 | 2011-08-11 | Phosphagenics Limited | Carrier comprising non-neutralised tocopheryl phosphate |
| CA2794734C (en) | 2010-03-30 | 2017-12-12 | Phosphagenics Limited | Transdermal delivery patch |
| WO2012122586A1 (en) | 2011-03-15 | 2012-09-20 | Phosphagenics Limited | New composition |
| US9687465B2 (en) | 2012-11-27 | 2017-06-27 | Sol-Gel Technologies Ltd. | Compositions for the treatment of rosacea |
| US10973761B2 (en) | 2015-12-09 | 2021-04-13 | Phosphagenics Limited | Pharmaceutical formulation |
| JP7198754B2 (ja) | 2016-12-21 | 2023-01-04 | アベーチョ バイオテクノロジー リミテッド | 方法 |
| HUE073201T2 (hu) | 2017-07-12 | 2026-01-28 | Sol Gel Tech Ltd | Kapszulázott tretinoint tartalmazó készítmények |
| JP2019043853A (ja) * | 2017-08-30 | 2019-03-22 | 旭化成株式会社 | 経皮吸収促進剤、経皮吸収促進助剤、及び経皮製剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046886A (en) * | 1975-01-17 | 1977-09-06 | The Procter & Gamble Company | Dermatological compositions |
| US4130643A (en) * | 1976-01-12 | 1978-12-19 | The Procter & Gamble Company | Dermatological compositions |
-
1984
- 1984-10-11 JP JP59213152A patent/JPS6191137A/ja active Granted
-
1985
- 1985-09-19 EP EP85111872A patent/EP0179277B1/en not_active Expired
- 1985-09-19 DE DE8585111872T patent/DE3565937D1/de not_active Expired
- 1985-09-20 US US06/778,226 patent/US4686211A/en not_active Expired - Fee Related
- 1985-10-09 ES ES547738A patent/ES8701683A1/es not_active Expired
-
1987
- 1987-03-26 MY MYPI87000383A patent/MY100022A/en unknown
-
1991
- 1991-05-02 HK HK336/91A patent/HK33691A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MY100022A (en) | 1989-04-20 |
| ES8701683A1 (es) | 1986-12-01 |
| EP0179277B1 (en) | 1988-11-02 |
| JPS6191137A (ja) | 1986-05-09 |
| EP0179277A1 (en) | 1986-04-30 |
| US4686211A (en) | 1987-08-11 |
| ES547738A0 (es) | 1986-12-01 |
| HK33691A (en) | 1991-05-10 |
| DE3565937D1 (en) | 1988-12-08 |
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