CY1443A - Pharmaceutical preparations for topical application which contain salts jof alkanecarboxylic acids,novel carboxylic acid salts and the production thereof - Google Patents
Pharmaceutical preparations for topical application which contain salts jof alkanecarboxylic acids,novel carboxylic acid salts and the production thereof Download PDFInfo
- Publication number
- CY1443A CY1443A CY1443A CY144389A CY1443A CY 1443 A CY1443 A CY 1443A CY 1443 A CY1443 A CY 1443A CY 144389 A CY144389 A CY 144389A CY 1443 A CY1443 A CY 1443A
- Authority
- CY
- Cyprus
- Prior art keywords
- formula
- hydrogen
- topical application
- group
- lower alkyl
- Prior art date
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- 230000000699 topical effect Effects 0.000 title claims description 71
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 45
- 150000003839 salts Chemical class 0.000 title claims description 21
- 239000002253 acid Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000007513 acids Chemical class 0.000 title description 3
- 150000001734 carboxylic acid salts Chemical class 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- -1 3-pyrrolin-1-yl Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 69
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 239000004480 active ingredient Substances 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 239000012050 conventional carrier Substances 0.000 claims description 21
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 19
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 17
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 229940049953 phenylacetate Drugs 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 8
- 241000534944 Thia Species 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- CHLFQJAVIKSLEU-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetate;morpholin-4-ium Chemical compound C1COCC[NH2+]1.[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl CHLFQJAVIKSLEU-UHFFFAOYSA-N 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- YJTNNVDTCOMTRV-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanoate;morpholin-4-ium Chemical compound C1COCC[NH2+]1.C1=C(C(C)C([O-])=O)C=CC2=CC(OC)=CC=C21 YJTNNVDTCOMTRV-UHFFFAOYSA-N 0.000 claims description 2
- IKEVKIVGQHWKOU-UHFFFAOYSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate;morpholin-4-ium Chemical compound C1COCC[NH2+]1.CC1=C(CC([O-])=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 IKEVKIVGQHWKOU-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000011369 resultant mixture Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- NJTLAOVYRDBVEY-UHFFFAOYSA-M 2-[2-(2,6-dichloroanilino)phenyl]acetate;tris(hydroxymethyl)-methylazanium Chemical compound OC[N+](C)(CO)CO.[O-]C(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl NJTLAOVYRDBVEY-UHFFFAOYSA-M 0.000 claims 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 claims 1
- ZTBJNAWSWPEWAH-UHFFFAOYSA-N diethylazanium;2-(6-methoxynaphthalen-2-yl)propanoate Chemical compound CC[NH2+]CC.C1=C(C(C)C([O-])=O)C=CC2=CC(OC)=CC=C21 ZTBJNAWSWPEWAH-UHFFFAOYSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- 235000014113 dietary fatty acids Nutrition 0.000 description 22
- 239000000194 fatty acid Substances 0.000 description 22
- 229930195729 fatty acid Natural products 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 239000000499 gel Substances 0.000 description 12
- 239000002304 perfume Substances 0.000 description 12
- 239000002674 ointment Substances 0.000 description 11
- 229940035676 analgesics Drugs 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000005662 Paraffin oil Substances 0.000 description 7
- 239000006210 lotion Substances 0.000 description 7
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZQVZPANTCLRASL-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetate;diethylazanium Chemical compound CCNCC.OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl ZQVZPANTCLRASL-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000004530 micro-emulsion Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920001214 Polysorbate 60 Polymers 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 229960000541 cetyl alcohol Drugs 0.000 description 4
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 4
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 229940114930 potassium stearate Drugs 0.000 description 4
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SDOFMBGMRVAJNF-SLPGGIOYSA-N (2r,3r,4r,5s)-6-aminohexane-1,2,3,4,5-pentol Chemical compound NC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO SDOFMBGMRVAJNF-SLPGGIOYSA-N 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
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- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 2
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 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 2
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- 239000000155 melt Substances 0.000 description 2
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- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
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- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
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- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 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 1
- 239000003701 inert diluent Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940057429 sorbitan isostearate Drugs 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8105822A GB2093693B (en) | 1981-02-24 | 1981-02-24 | Pharmaceutical preparations for topical application which contain salts of alkanecarboxylic acids novel carboxylic acid salts and the production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1443A true CY1443A (en) | 1989-03-10 |
Family
ID=10519933
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1443A CY1443A (en) | 1981-02-24 | 1989-03-10 | Pharmaceutical preparations for topical application which contain salts jof alkanecarboxylic acids,novel carboxylic acid salts and the production thereof |
| CY1444A CY1444A (en) | 1981-02-24 | 1989-03-10 | Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1444A CY1444A (en) | 1981-02-24 | 1989-03-10 | Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US4407824A (en, 2012) |
| AT (1) | AT370721B (en, 2012) |
| CA (1) | CA1180008A (en, 2012) |
| CY (2) | CY1443A (en, 2012) |
| FR (2) | FR2500751A1 (en, 2012) |
| GB (2) | GB2093693B (en, 2012) |
| HK (1) | HK83888A (en, 2012) |
| KE (1) | KE3820A (en, 2012) |
| LU (1) | LU83945A1 (en, 2012) |
| NL (1) | NL193216C (en, 2012) |
| SE (2) | SE448088B (en, 2012) |
| SG (1) | SG33388G (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
| FR2526427A1 (fr) * | 1982-05-04 | 1983-11-10 | Bouchara Emile | Nouveau sel d'indometacine, son procede de preparation et les compositions pharmaceutiques en renfermant |
| US4437053A (en) * | 1982-05-10 | 1984-03-13 | Diasonics (Nmr) Inc. | Gradient power supply |
| CH655656B (en, 2012) * | 1982-10-07 | 1986-05-15 | ||
| ES8407042A1 (es) * | 1982-10-08 | 1984-09-01 | Espinos & Bofill Lab Sa | Procedimiento para la obtencion de un nuevo derivado del sulpiride. |
| JPS59137408A (ja) * | 1983-01-27 | 1984-08-07 | Taisho Pharmaceut Co Ltd | 軟膏 |
| JPS59139315A (ja) * | 1983-01-31 | 1984-08-10 | Taisho Pharmaceut Co Ltd | クリ−ム剤 |
| CH643138A5 (de) * | 1983-08-29 | 1984-05-30 | Mepha Ag | Indomethacin enthaltende, gelartige salbe. |
| DE3381733D1 (de) * | 1983-12-08 | 1990-08-16 | Toko Yakuhin Kogyo Kk | Gelpraeparate zur externen applikation. |
| US4670254A (en) * | 1983-12-09 | 1987-06-02 | Toko Yakuhin Industry Co., Ltd. | Gel preparations for topical application of diclofenac sodium |
| DE3423589A1 (de) * | 1984-06-27 | 1986-01-09 | Wella Ag, 6100 Darmstadt | Oxidationshaarfaerbemittel auf basis einer niedrigviskosen traegermasse |
| IT1178411B (it) * | 1984-09-06 | 1987-09-09 | Sigma Tau Ind Farmaceuti | Sale di d,l-lisina dell'acido 1-(4-clorobenzoil)-5-metossi-2-metil-1h-indol-3 acetico, procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono |
| CA1265288A (en) * | 1984-11-22 | 1990-01-30 | E. I. Du Pont De Nemours And Company | Curable fluoroelastomer composition |
| US4980084A (en) * | 1985-09-11 | 1990-12-25 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Water rinsable petroleum jelly compositions |
| US4690774A (en) * | 1985-09-11 | 1987-09-01 | Chesebrough Pond's Inc. | Novel translucent water in oil emulsions |
| US4832858A (en) * | 1987-02-19 | 1989-05-23 | Chesebrough-Pond's Inc. | Water dispersible petroleum jelly compositions |
| US4960892A (en) * | 1988-06-10 | 1990-10-02 | American Home Products Corporation | Naphthalenepropionic acid derivatives as anti-inflammatory/anti-allergic agents |
| TW225536B (en, 2012) * | 1990-08-23 | 1994-06-21 | Ciba Geigy Ag | |
| US5444076A (en) * | 1990-11-26 | 1995-08-22 | Roemmers S.A.I.C.F. | Pharmaceutical preparation for topical application |
| AU2259692A (en) * | 1991-07-03 | 1993-02-11 | Sano Corporation | Composition and method for transdermal delivery of diclofenac |
| US6117907A (en) * | 1993-04-14 | 2000-09-12 | Sher; Neal A. | Topical treatment of ocular pain after corneal surgery |
| JP3526887B2 (ja) * | 1993-04-23 | 2004-05-17 | 帝國製薬株式会社 | 消炎鎮痛外用貼付剤 |
| FI100692B (fi) * | 1994-05-24 | 1998-02-13 | Leiras Oy | Menetelmä farmaseuttisten koostumusten valmistamiseksi, jolloin koostu mukset pohjautuvat mikroemulsiogeeleihin sekä uusia mikroemulsioihin p ohjautuvia geelejä |
| ATE178884T1 (de) * | 1994-06-29 | 1999-04-15 | Novartis Erfind Verwalt Gmbh | Salze von 2-((2,6- dichlorophenyl)amin>phenylacetoxyessigsäure mit organischen basischen kationen |
| RU2128989C1 (ru) * | 1997-03-05 | 1999-04-20 | Закрытое акционерное общество "Химмедсинтез" | Композиция антимикробного, противовоспалительного и регенерационного действия |
| US20030060657A1 (en) * | 1998-04-28 | 2003-03-27 | Russinsky Limited | Process for the preparation of Aceclofenac |
| RU2177314C2 (ru) * | 2000-03-22 | 2001-12-27 | Кривошеин Юрий Семенович | Состав с антисептическими, репаративными и болеутоляющими свойствами |
| TWI290464B (en) | 2000-09-01 | 2007-12-01 | Novartis Consumer Health Sa | Treatment of burns |
| DE10114561A1 (de) * | 2001-03-24 | 2002-09-26 | Wella Ag | Verwendung von Mitteln enthaltend Kreatin, Kreatin und/oder deren Derivaten zur Verstärkung und Strukturverbesserung von keratinischen Fasern |
| ITMI20020986A1 (it) * | 2002-05-10 | 2003-11-10 | Acraf | Composizione a base di diclofenac per il trattamento topico di affezioni del cavo orofaringeo |
| AR042206A1 (es) | 2002-11-26 | 2005-06-15 | Novartis Ag | Acidos fenilaceticos y derivados |
| ITMI20030269A1 (it) * | 2003-02-14 | 2004-08-15 | Advance Holdings Ltd | Sale di cetilpiridino di un agente antiinfiammatorio |
| FR2854802B1 (fr) * | 2003-05-12 | 2005-06-24 | Galderma Res & Dev | Procede de preparation d'une formulation contenant un principe actif microdose |
| EP2055298A1 (en) | 2007-10-30 | 2009-05-06 | Novartis AG | Topical composition |
| US11000495B2 (en) | 2014-09-10 | 2021-05-11 | GSK Consumer Healthcare S.A. | Topical diclofenac sodium compositions |
| CN116143647A (zh) * | 2023-03-03 | 2023-05-23 | 长沙晶易医药科技股份有限公司 | 双氯芬酸二乙胺的新晶型及其制备方法 |
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| US514839A (en) * | 1894-02-13 | sergeant | ||
| GB971700A (en) * | 1961-02-02 | 1964-09-30 | Boots Pure Drug Co Ltd | Anti-Inflammatory Agents |
| AT290523B (de) * | 1962-01-05 | 1971-06-11 | Merck & Co Inc | Verfahren zur Herstellung neuer α-(3-Indolyl)-carbonsäuren |
| US3558690A (en) * | 1965-04-08 | 1971-01-26 | Gelgy Chemical Corp | Substituted derivatives of 2-anilinophenylacetic acids and a process of preparation |
| CH470349A (de) * | 1966-10-07 | 1969-03-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
| US3896157A (en) * | 1967-01-13 | 1975-07-22 | Syntex Corp | Dihydo 2-naphthylacetic acid derivatives |
| US4048330A (en) * | 1967-01-13 | 1977-09-13 | Syntex Corporation | Compositions containing 2-(6'-substituted-2'-naphthyl)acetic acid esters used for treating inflammation, pain or pyrexia |
| CA960689A (en) * | 1967-01-13 | 1975-01-07 | Syntex Corporation | 2-naphthyl acetic acid derivatives and compositions |
| FR1546478A (fr) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
| US3592902A (en) * | 1967-04-13 | 1971-07-13 | Sumitomo Chemical Co | Injection |
| NL6817965A (en, 2012) * | 1967-12-20 | 1969-06-24 | ||
| US3641040A (en) * | 1968-03-27 | 1972-02-08 | Ciba Geigy Corp | Tertiary amino phenyl acetic acids |
| US3637767A (en) * | 1968-07-30 | 1972-01-25 | Syntex Corp | 2-(6'-methoxynaphth-2'-yl)propylene oxide and 5'-halo derivatives |
| BR6915470D0 (pt) * | 1969-03-24 | 1973-03-13 | Syntex Corp | Processo para preparar derivados de acido 2-(6'substituido 2'naftil)propionico e de seus sais |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| US3647858A (en) * | 1970-05-01 | 1972-03-07 | Merck & Co Inc | Process for preparing 1-benzylidene-3-indenyl acetic acids |
| US4033816A (en) | 1973-06-18 | 1977-07-05 | The Upjohn Company | Process for inhibiting platelet aggregation |
| US3936528A (en) * | 1974-02-13 | 1976-02-03 | Syntex Corporation | Analgesic formulations having enhanced therapeutic activity |
| ES423834A1 (es) * | 1974-03-02 | 1976-06-01 | Roger Lab | Procedimiento de obtencion de una nueva sal de piperacina del acido (1 - p - clorobenzoil - 2 - metil - 5 - metoxi - 3- indolil) acetico. |
| US4031243A (en) * | 1975-07-03 | 1977-06-21 | Juste, S.A. Quimico-Farmaceutica | 2-(4-Isobutyl phenyl)butyric acid, salts thereof, and pharmaceutical compositions containing the same |
| PT66660B (en) * | 1976-06-12 | 1978-11-13 | Ciba Geigy Ag | Process for the production of a derivative of phenylacetic |
| LU77316A1 (en, 2012) * | 1977-05-11 | 1979-01-19 | ||
| JPS549240A (en) * | 1977-06-23 | 1979-01-24 | Asahi Chem Ind Co Ltd | New derivative of phenylglycolic acid, its preparation and analgesic and antiinflammatory agent contining it as effective component |
| GB2023000B (en) * | 1978-06-17 | 1982-10-13 | Kowa Co | Antinflammatory analgesic gelled ointments |
| BE871335A (fr) * | 1978-10-18 | 1979-04-18 | Bago Sa Labor | Derives solubles des acides 2-anilino-aryl-carboxyliques substitues utiles par la voie buccale comme agents anti-inflammatoires. |
| LU83138A1 (de) * | 1981-02-16 | 1981-09-11 | T Eckert | Topische pharmazeutische praeparate,enthaltend salze von alkancarbonsaeuren sowie neue carbonsaeuresalze und verfahren zu ihrer herstellung |
-
1981
- 1981-02-16 AT AT0070981A patent/AT370721B/de not_active IP Right Cessation
- 1981-02-17 SE SE8101064A patent/SE448088B/sv not_active IP Right Cessation
- 1981-02-19 CA CA000371271A patent/CA1180008A/en not_active Expired
- 1981-02-20 US US06/236,097 patent/US4407824A/en not_active Expired - Lifetime
- 1981-02-24 GB GB8105822A patent/GB2093693B/en not_active Expired
- 1981-02-25 NL NL8100917A patent/NL193216C/nl not_active IP Right Cessation
- 1981-02-27 FR FR8103932A patent/FR2500751A1/fr active Granted
- 1981-10-09 FR FR8119055A patent/FR2514348A1/fr active Granted
-
1982
- 1982-02-15 LU LU83945A patent/LU83945A1/de unknown
- 1982-05-25 SE SE8203228A patent/SE8203228L/xx unknown
-
1983
- 1983-07-27 US US06/517,606 patent/US4551475A/en not_active Expired - Lifetime
-
1984
- 1984-07-16 GB GB08418021A patent/GB2143528B/en not_active Expired
-
1985
- 1985-08-14 US US06/765,416 patent/US4619926A/en not_active Expired - Lifetime
-
1988
- 1988-02-18 US US07/156,770 patent/US4784808A/en not_active Expired - Lifetime
- 1988-05-27 SG SG33388A patent/SG33388G/en unknown
- 1988-06-07 KE KE3820A patent/KE3820A/xx unknown
- 1988-10-13 HK HK838/88A patent/HK83888A/xx not_active IP Right Cessation
-
1989
- 1989-03-10 CY CY1443A patent/CY1443A/en unknown
- 1989-03-10 CY CY1444A patent/CY1444A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2143528B (en) | 1985-10-02 |
| SE8203228L (sv) | 1982-08-18 |
| GB2093693B (en) | 1985-10-02 |
| SG33388G (en) | 1988-09-30 |
| CY1444A (en) | 1989-03-10 |
| FR2500751B1 (en, 2012) | 1984-12-28 |
| ATA70981A (de) | 1982-09-15 |
| FR2514348A1 (fr) | 1983-04-15 |
| KE3820A (en) | 1988-09-09 |
| US4407824A (en) | 1983-10-04 |
| CA1180008A (en) | 1984-12-27 |
| US4619926A (en) | 1986-10-28 |
| FR2514348B1 (en, 2012) | 1984-12-14 |
| NL8100917A (nl) | 1982-09-16 |
| AT370721B (de) | 1983-04-25 |
| NL193216B (nl) | 1998-11-02 |
| HK83888A (en) | 1988-10-21 |
| FR2500751A1 (fr) | 1982-09-03 |
| US4551475A (en) | 1985-11-05 |
| GB2143528A (en) | 1985-02-13 |
| GB8418021D0 (en) | 1984-08-22 |
| NL193216C (nl) | 1999-03-03 |
| LU83945A1 (de) | 1982-12-13 |
| SE8101064L (sv) | 1982-08-18 |
| GB2093693A (en) | 1982-09-08 |
| US4784808A (en) | 1988-11-15 |
| SE448088B (sv) | 1987-01-19 |
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