DE3503279C2 - - Google Patents
Info
- Publication number
- DE3503279C2 DE3503279C2 DE3503279A DE3503279A DE3503279C2 DE 3503279 C2 DE3503279 C2 DE 3503279C2 DE 3503279 A DE3503279 A DE 3503279A DE 3503279 A DE3503279 A DE 3503279A DE 3503279 C2 DE3503279 C2 DE 3503279C2
- Authority
- DE
- Germany
- Prior art keywords
- metoclopramide
- c12oh
- mcp
- hcl
- amount
- 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
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 48
- 229960004503 metoclopramide Drugs 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000001298 alcohols Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 aliphatic monocarboxylic acids Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 17
- 210000003491 skin Anatomy 0.000 description 17
- 150000002009 diols Chemical class 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 15
- 239000003814 drug Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000499 gel Substances 0.000 description 12
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000004907 flux Effects 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 235000013772 propylene glycol Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000036765 blood level Effects 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241000282560 Macaca mulatta Species 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 6
- 150000004040 pyrrolidinones Chemical class 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 210000000038 chest Anatomy 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- 241000282693 Cercopithecidae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 210000000481 breast Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 230000036470 plasma concentration Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007910 systemic administration Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- IOUUIFSIQMVYKP-UHFFFAOYSA-N Tetradecyl acetate Chemical compound CCCCCCCCCCCCCCOC(C)=O IOUUIFSIQMVYKP-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910002056 binary alloy Inorganic materials 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 229940078812 myristyl myristate Drugs 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- LSTDYDRCKUBPDI-UHFFFAOYSA-N palmityl acetate Chemical compound CCCCCCCCCCCCCCCCOC(C)=O LSTDYDRCKUBPDI-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229940080693 reglan Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 1
- WJTCHBVEUFDSIK-NWDGAFQWSA-N (2r,5s)-1-benzyl-2,5-dimethylpiperazine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC=CC=C1 WJTCHBVEUFDSIK-NWDGAFQWSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- BNXZHVUCNYMNOS-UHFFFAOYSA-N 1-butylpyrrolidin-2-one Chemical compound CCCCN1CCCC1=O BNXZHVUCNYMNOS-UHFFFAOYSA-N 0.000 description 1
- UKFTXWKNVSVVCJ-UHFFFAOYSA-N 2-[(6-hydrazinylpyridazin-3-yl)-(2-hydroxyethyl)amino]ethanol;hydron;dichloride Chemical class Cl.Cl.NNC1=CC=C(N(CCO)CCO)N=N1 UKFTXWKNVSVVCJ-UHFFFAOYSA-N 0.000 description 1
- CAYHVMBQBLYQMT-UHFFFAOYSA-N 2-decyltetradecan-1-ol Chemical compound CCCCCCCCCCCCC(CO)CCCCCCCCCC CAYHVMBQBLYQMT-UHFFFAOYSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241001340526 Chrysoclista linneella Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940049297 cetyl acetate Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 229940009493 gel-one Drugs 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 description 1
- 229960005287 lincomycin Drugs 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N octan-4-ol Chemical compound CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical group O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 208000018556 stomach disease Diseases 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/576,087 US4605670A (en) | 1984-02-01 | 1984-02-01 | Method for percutaneously administering metoclopramide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3503279A1 DE3503279A1 (de) | 1985-08-08 |
| DE3503279C2 true DE3503279C2 (OSRAM) | 1989-03-09 |
Family
ID=24302934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853503279 Granted DE3503279A1 (de) | 1984-02-01 | 1985-01-31 | Pharmazeutisches mittel zur perkutanen verabreichung von metoclopramid |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4605670A (OSRAM) |
| JP (1) | JPS60161918A (OSRAM) |
| CA (1) | CA1252049A (OSRAM) |
| CH (1) | CH667810A5 (OSRAM) |
| DE (1) | DE3503279A1 (OSRAM) |
| DK (1) | DK43385A (OSRAM) |
| FR (1) | FR2558729B1 (OSRAM) |
| GB (1) | GB2153223B (OSRAM) |
| NL (1) | NL8403618A (OSRAM) |
| SE (1) | SE465452B (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10134607A1 (de) * | 2001-07-17 | 2003-02-06 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit langanhaltender kühlender Wirkung |
| DE10134603A1 (de) * | 2001-07-17 | 2003-02-06 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit langanhaltender kühlender Wirkung |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5128376A (en) * | 1983-07-01 | 1992-07-07 | Nitto Denko Corporation | Method for percutaneously administering physiologically active agents using an adjuvant a solvent and a diol moderator |
| US5256647A (en) * | 1986-01-31 | 1993-10-26 | Whitby Research, Inc. | Compositions comprising 1-substituted azacycloalkanes |
| EP0257063B1 (en) * | 1986-01-31 | 1992-06-17 | WHITBY RESEARCH, Inc. | Compositions comprising 1-substituted azacycloalkanes and their uses |
| US4992422A (en) * | 1986-01-31 | 1991-02-12 | Whitby Research, Inc. | Compositions comprising 1-substituted azacycloalkanes |
| US5204339A (en) * | 1986-01-31 | 1993-04-20 | Whitby Research, Inc. | Penetration enhancers for transdermal delivery of systemic agents |
| US5142044A (en) * | 1986-04-23 | 1992-08-25 | Whitby Research, Inc. | Penetration enhancers for transdermal delivery of systemic agents |
| CA1319613C (en) * | 1986-10-07 | 1993-06-29 | Gevork Minaskanian | Penetration enhancers for transdermal delivery of systemic agents |
| US4863970A (en) * | 1986-11-14 | 1989-09-05 | Theratech, Inc. | Penetration enhancement with binary system of oleic acid, oleins, and oleyl alcohol with lower alcohols |
| US4880632A (en) * | 1987-09-08 | 1989-11-14 | The United States Of America | Prevention of fescue toxicosis |
| US4879275A (en) * | 1987-09-30 | 1989-11-07 | Nelson Research & Development Co. | Penetration enhancers for transdermal delivery of systemic agent |
| US4920101A (en) * | 1987-09-30 | 1990-04-24 | Nelson Research & Development Co. | Compositions comprising 1-oxo- or thiohydrocarbyl substituted azacycloaklkanes |
| US5234992A (en) * | 1989-02-09 | 1993-08-10 | Alza Corporation | Electrotransport adhesive |
| US4956171A (en) * | 1989-07-21 | 1990-09-11 | Paco Pharmaceutical Services, Inc. | Transdermal drug delivery using a dual permeation enhancer and method of performing the same |
| DE69009946T2 (de) * | 1989-12-04 | 1994-11-03 | Searle & Co | System zur transdermalen Albuterol Applikation. |
| US5814599A (en) * | 1995-08-04 | 1998-09-29 | Massachusetts Insitiute Of Technology | Transdermal delivery of encapsulated drugs |
| US5736580A (en) * | 1994-11-14 | 1998-04-07 | Alza Croporation | Composition, device, and method for electrotransport agent delivery |
| US5990179A (en) * | 1995-04-28 | 1999-11-23 | Alza Corporation | Composition and method of enhancing electrotransport agent delivery |
| US5985316A (en) * | 1995-04-28 | 1999-11-16 | Alza Corporation | Composition and method of enhancing electrotransport agent delivery |
| US6041253A (en) * | 1995-12-18 | 2000-03-21 | Massachusetts Institute Of Technology | Effect of electric field and ultrasound for transdermal drug delivery |
| US5947921A (en) * | 1995-12-18 | 1999-09-07 | Massachusetts Institute Of Technology | Chemical and physical enhancers and ultrasound for transdermal drug delivery |
| US6002961A (en) * | 1995-07-25 | 1999-12-14 | Massachusetts Institute Of Technology | Transdermal protein delivery using low-frequency sonophoresis |
| EP2921111A1 (en) | 1995-08-29 | 2015-09-23 | Nitto Denko Corporation | Microporation of human skin for drug delivery and monitoring applications |
| EP0925088A2 (en) | 1996-06-28 | 1999-06-30 | Sontra Medical, L.P. | Ultrasound enhancement of transdermal transport |
| US6071865A (en) * | 1997-04-16 | 2000-06-06 | Pickering; Douglas James | Nail polish remover |
| US7066884B2 (en) | 1998-01-08 | 2006-06-27 | Sontra Medical, Inc. | System, method, and device for non-invasive body fluid sampling and analysis |
| US8287483B2 (en) | 1998-01-08 | 2012-10-16 | Echo Therapeutics, Inc. | Method and apparatus for enhancement of transdermal transport |
| US6173202B1 (en) | 1998-03-06 | 2001-01-09 | Spectrx, Inc. | Method and apparatus for enhancing flux rates of a fluid in a microporated biological tissue |
| US20040171980A1 (en) | 1998-12-18 | 2004-09-02 | Sontra Medical, Inc. | Method and apparatus for enhancement of transdermal transport |
| US6225269B1 (en) | 2000-08-22 | 2001-05-01 | Bradley M. Baker | Nail polish remover |
| ES2294026T3 (es) | 2000-09-06 | 2008-04-01 | Ap Pharma, Inc. | Polimeros degradables de poliacetal. |
| US20030152630A1 (en) * | 2001-05-11 | 2003-08-14 | Ng Steven Y. | PEG-POE, PEG-POE-PEG, and POE-PEG-POE block copolymers |
| US6590059B2 (en) * | 2001-05-11 | 2003-07-08 | Ap Pharma, Inc. | Bioerodible polyorthoesters from dioxolane-based diketene acetals |
| FR2826246A1 (fr) | 2001-06-26 | 2002-12-27 | Oreal | Essoreur a montage simplifie |
| US6524606B1 (en) * | 2001-11-16 | 2003-02-25 | Ap Pharma, Inc. | Bioerodible polyorthoesters containing amine groups |
| JP2006516047A (ja) | 2002-10-28 | 2006-06-15 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | マグネットクランプを備えた経皮アッセイ |
| US20040241223A1 (en) * | 2003-05-27 | 2004-12-02 | David Wong | Oral dosage forms for macromolecular drugs |
| US20050158329A1 (en) * | 2004-01-21 | 2005-07-21 | Ghosh Swapan K. | Novel phytol derived immunoadjuvants and their use in vaccine formulations |
| US20060094944A1 (en) | 2004-10-28 | 2006-05-04 | Sontra Medical Corporation | System and method for analyte sampling and analysis with error correction |
| JP5006196B2 (ja) * | 2005-08-01 | 2012-08-22 | 久光製薬株式会社 | 経皮または経粘膜投与のためのアジュバントおよび製剤 |
| US7432069B2 (en) | 2005-12-05 | 2008-10-07 | Sontra Medical Corporation | Biocompatible chemically crosslinked hydrogels for glucose sensing |
| WO2008109739A1 (en) | 2007-03-07 | 2008-09-12 | Echo Therapeutics, Inc. | Transdermal analyte monitoring systems and methods for analyte detection |
| AU2008245585B2 (en) | 2007-04-27 | 2011-10-06 | Echo Therapeutics, Inc. | Skin permeation device for analyte sensing or transdermal drug delivery |
| WO2009143175A2 (en) | 2008-05-19 | 2009-11-26 | Children's Medical Center Corporation | Sensory-specific local anesthesia and prolonged duration local anesthesia |
| WO2010101625A2 (en) | 2009-03-02 | 2010-09-10 | Seventh Sense Biosystems, Inc. | Oxygen sensor |
| US9041541B2 (en) | 2010-01-28 | 2015-05-26 | Seventh Sense Biosystems, Inc. | Monitoring or feedback systems and methods |
| US9033898B2 (en) | 2010-06-23 | 2015-05-19 | Seventh Sense Biosystems, Inc. | Sampling devices and methods involving relatively little pain |
| EP2408372B1 (en) | 2009-03-02 | 2019-01-09 | Seventh Sense Biosystems, Inc. | Devices associated with blood sampling |
| US8952152B2 (en) | 2009-03-24 | 2015-02-10 | Proteus S.A. | Methods for purifying phycotoxins, pharmaceutical compositions containing purified phycotoxins, and methods of use thereof |
| WO2011017520A1 (en) | 2009-08-05 | 2011-02-10 | Wake Forest University Health Sciences | Compositions and methods for inducing apoptosis in prostate cancer cells |
| EP2593014B1 (en) | 2010-07-16 | 2015-11-04 | Seventh Sense Biosystems, Inc. | Low-pressure environment for fluid transfer devices |
| WO2012021801A2 (en) | 2010-08-13 | 2012-02-16 | Seventh Sense Biosystems, Inc. | Systems and techniques for monitoring subjects |
| EP2992827B1 (en) | 2010-11-09 | 2017-04-19 | Seventh Sense Biosystems, Inc. | Systems and interfaces for blood sampling |
| EP2702406B1 (en) | 2011-04-29 | 2017-06-21 | Seventh Sense Biosystems, Inc. | Plasma or serum production and removal of fluids under reduced pressure |
| US20130158468A1 (en) | 2011-12-19 | 2013-06-20 | Seventh Sense Biosystems, Inc. | Delivering and/or receiving material with respect to a subject surface |
| AU2012249692A1 (en) | 2011-04-29 | 2013-11-14 | Seventh Sense Biosystems, Inc. | Delivering and/or receiving fluids |
| EP3106092A3 (en) | 2011-04-29 | 2017-03-08 | Seventh Sense Biosystems, Inc. | Systems and methods for collecting fluid from a subject |
| JP6313420B2 (ja) | 2013-03-15 | 2018-04-18 | ザ チルドレンズ メディカル センター コーポレイション | 持続する局所麻酔のためのネオサキシトキシン併用製剤 |
| EP3064218B1 (en) | 2013-10-31 | 2019-06-19 | Hisamitsu Pharmaceutical Co., Inc. | Adjuvant composition |
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|---|---|---|---|---|
| US3472931A (en) * | 1969-01-17 | 1969-10-14 | Foster Milburn Co | Percutaneous absorption with lower alkyl amides |
| US3551554A (en) * | 1968-08-16 | 1970-12-29 | Crown Zellerbach Corp | Enhancing tissue penetration of physiologically active agents with dmso |
| US3969516A (en) * | 1974-12-19 | 1976-07-13 | Nelson Research & Development Company | Composition and method for treatment of acne |
| US3989816A (en) * | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
| US4017641A (en) * | 1975-01-31 | 1977-04-12 | The Procter & Gamble Company | Skin moisturizing compositions containing 2-pyrrolidinone |
| GB1504302A (en) * | 1974-08-23 | 1978-03-15 | Fisons Ltd | Sedative method and composition |
| US4202888A (en) * | 1976-07-12 | 1980-05-13 | Kali-Chemie Pharma Gmbh. | Readily enterally absorbable pharmaceutical compositions of cardiac glycosides and preparation thereof |
| EP0043738A2 (en) * | 1980-07-09 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Penetrating topical pharmaceutical compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1022719A (fr) * | 1950-08-01 | 1953-03-09 | Produits tels que crèmes, pommades, pâtes, laits, etc., destinés à être appliqués sur la peau | |
| GB708384A (en) * | 1951-03-16 | 1954-05-05 | Imhausen & Co Gmbh | Drug solutions and process for the manufacture thereof |
| NL281225A (OSRAM) * | 1961-07-20 | |||
| FR2001768A1 (fr) * | 1968-02-12 | 1969-10-03 | Gillette Co | Compositions pour l'application topique de medicaments sur la peau |
| US3964482A (en) * | 1971-05-17 | 1976-06-22 | Alza Corporation | Drug delivery device |
| US3957994A (en) * | 1974-12-19 | 1976-05-18 | Nelson Research & Development Company | Topical anti-inflammatory composition and method of use |
| US4444762A (en) * | 1980-04-04 | 1984-04-24 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacyclopentan-2-ones |
| JPS57134413A (en) * | 1981-02-14 | 1982-08-19 | Nitto Electric Ind Co Ltd | Percutaneous absorbable drug and product containing the same |
| US4440777A (en) * | 1981-07-07 | 1984-04-03 | Merck & Co., Inc. | Use of eucalyptol for enhancing skin permeation of bio-affecting agents |
| US4411893A (en) * | 1981-08-14 | 1983-10-25 | Minnesota Mining And Manufacturing Company | Topical medicament preparations |
| JPS5855411A (ja) * | 1981-09-28 | 1983-04-01 | Nitto Electric Ind Co Ltd | 基剤組成物および外用医薬組成物 |
-
1984
- 1984-02-01 US US06/576,087 patent/US4605670A/en not_active Expired - Fee Related
- 1984-08-24 JP JP59175206A patent/JPS60161918A/ja active Pending
- 1984-11-23 SE SE8405929A patent/SE465452B/sv not_active IP Right Cessation
- 1984-11-28 NL NL8403618A patent/NL8403618A/nl not_active Application Discontinuation
- 1984-11-29 CA CA000468965A patent/CA1252049A/en not_active Expired
- 1984-12-03 GB GB08430458A patent/GB2153223B/en not_active Expired
-
1985
- 1985-01-31 DK DK43385A patent/DK43385A/da not_active Application Discontinuation
- 1985-01-31 DE DE19853503279 patent/DE3503279A1/de active Granted
- 1985-01-31 CH CH439/85A patent/CH667810A5/de not_active IP Right Cessation
- 1985-02-01 FR FR8501459A patent/FR2558729B1/fr not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3551554A (en) * | 1968-08-16 | 1970-12-29 | Crown Zellerbach Corp | Enhancing tissue penetration of physiologically active agents with dmso |
| US3472931A (en) * | 1969-01-17 | 1969-10-14 | Foster Milburn Co | Percutaneous absorption with lower alkyl amides |
| GB1504302A (en) * | 1974-08-23 | 1978-03-15 | Fisons Ltd | Sedative method and composition |
| US3969516A (en) * | 1974-12-19 | 1976-07-13 | Nelson Research & Development Company | Composition and method for treatment of acne |
| US4017641A (en) * | 1975-01-31 | 1977-04-12 | The Procter & Gamble Company | Skin moisturizing compositions containing 2-pyrrolidinone |
| US3989816A (en) * | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
| US4202888A (en) * | 1976-07-12 | 1980-05-13 | Kali-Chemie Pharma Gmbh. | Readily enterally absorbable pharmaceutical compositions of cardiac glycosides and preparation thereof |
| EP0043738A2 (en) * | 1980-07-09 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Penetrating topical pharmaceutical compositions |
Non-Patent Citations (1)
| Title |
|---|
| GRAFFNER, C. et al., Br. J. Clin. Pharmac. 8, 1979, S.469-474 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10134607A1 (de) * | 2001-07-17 | 2003-02-06 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit langanhaltender kühlender Wirkung |
| DE10134603A1 (de) * | 2001-07-17 | 2003-02-06 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit langanhaltender kühlender Wirkung |
Also Published As
| Publication number | Publication date |
|---|---|
| DK43385D0 (da) | 1985-01-31 |
| SE8405929L (sv) | 1985-08-02 |
| GB2153223B (en) | 1987-06-24 |
| FR2558729A1 (fr) | 1985-08-02 |
| US4605670A (en) | 1986-08-12 |
| GB2153223A (en) | 1985-08-21 |
| JPS60161918A (ja) | 1985-08-23 |
| DK43385A (da) | 1985-08-02 |
| GB8430458D0 (en) | 1985-01-09 |
| SE8405929D0 (sv) | 1984-11-23 |
| FR2558729B1 (fr) | 1988-10-28 |
| DE3503279A1 (de) | 1985-08-08 |
| NL8403618A (nl) | 1985-09-02 |
| CA1252049A (en) | 1989-04-04 |
| CH667810A5 (de) | 1988-11-15 |
| SE465452B (sv) | 1991-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |