KR900701848A - 신규한 폴리삭카리이드의 에스테르 - Google Patents
신규한 폴리삭카리이드의 에스테르Info
- Publication number
- KR900701848A KR900701848A KR1019900700072A KR900700072A KR900701848A KR 900701848 A KR900701848 A KR 900701848A KR 1019900700072 A KR1019900700072 A KR 1019900700072A KR 900700072 A KR900700072 A KR 900700072A KR 900701848 A KR900701848 A KR 900701848A
- Authority
- KR
- South Korea
- Prior art keywords
- alcohol
- ester
- salt
- salts
- hygiene
- Prior art date
Links
- 229920001282 polysaccharide Polymers 0.000 title claims 2
- 239000005017 polysaccharide Substances 0.000 title claims 2
- 150000004676 glycans Chemical class 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 33
- -1 heterocyclic alcohols Chemical class 0.000 claims 32
- 229920001284 acidic polysaccharide Polymers 0.000 claims 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 17
- 150000004805 acidic polysaccharides Chemical class 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000001931 aliphatic group Chemical group 0.000 claims 9
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 7
- 125000002723 alicyclic group Chemical group 0.000 claims 7
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 7
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 7
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 150000007529 inorganic bases Chemical class 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 150000007530 organic bases Chemical class 0.000 claims 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 229920002472 Starch Polymers 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 235000019698 starch Nutrition 0.000 claims 5
- 239000008107 starch Substances 0.000 claims 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 150000001298 alcohols Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 235000013877 carbamide Nutrition 0.000 claims 3
- 229920003064 carboxyethyl cellulose Polymers 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 239000003381 stabilizer Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229930013930 alkaloid Natural products 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000002921 anti-spasmodic effect Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000003218 coronary vasodilator agent Substances 0.000 claims 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 2
- 239000006260 foam Substances 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 230000000147 hypnotic effect Effects 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 239000003158 myorelaxant agent Substances 0.000 claims 2
- 125000001421 myristyl 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])[H] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229950000688 phenothiazine Drugs 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- 239000000932 sedative agent Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 150000007970 thio esters Chemical class 0.000 claims 2
- 150000003568 thioethers Chemical class 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 claims 2
- 239000005526 vasoconstrictor agent Substances 0.000 claims 2
- FQTLCLSUCSAZDY-UHFFFAOYSA-N (+) E(S) nerolidol Natural products CC(C)=CCCC(C)=CCCC(C)(O)C=C FQTLCLSUCSAZDY-UHFFFAOYSA-N 0.000 claims 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims 1
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 1
- MADORZDTLHDDEN-UHFFFAOYSA-N 1-piperidin-1-ylethanol Chemical compound CC(O)N1CCCCC1 MADORZDTLHDDEN-UHFFFAOYSA-N 0.000 claims 1
- KEVKXUZQHIMSCM-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanol Chemical compound CC(O)N1CCCC1 KEVKXUZQHIMSCM-UHFFFAOYSA-N 0.000 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims 1
- 229920002101 Chitin Polymers 0.000 claims 1
- 239000004380 Cholic acid Substances 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims 1
- 239000005792 Geraniol Substances 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims 1
- FQTLCLSUCSAZDY-ATGUSINASA-N Nerolidol Chemical compound CC(C)=CCC\C(C)=C\CC[C@](C)(O)C=C FQTLCLSUCSAZDY-ATGUSINASA-N 0.000 claims 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 239000000674 adrenergic antagonist Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical group 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005237 alkyleneamino group Chemical group 0.000 claims 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 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
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- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000003474 anti-emetic effect Effects 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 claims 1
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 claims 1
- 239000000924 antiasthmatic agent Substances 0.000 claims 1
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 239000002111 antiemetic agent Substances 0.000 claims 1
- 229940125683 antiemetic agent Drugs 0.000 claims 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 claims 1
- 229960005475 antiinfective agent Drugs 0.000 claims 1
- 239000003430 antimalarial agent Substances 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940124575 antispasmodic agent Drugs 0.000 claims 1
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- 239000000010 aprotic solvent Substances 0.000 claims 1
- 150000003974 aralkylamines Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
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- 235000014633 carbohydrates Nutrition 0.000 claims 1
- 239000000919 ceramic Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 claims 1
- 235000019416 cholic acid Nutrition 0.000 claims 1
- 229960002471 cholic acid Drugs 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 239000000064 cholinergic agonist Substances 0.000 claims 1
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- 239000002537 cosmetic Substances 0.000 claims 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims 1
- 235000013365 dairy product Nutrition 0.000 claims 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
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- 239000004744 fabric Substances 0.000 claims 1
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- 229940043259 farnesol Drugs 0.000 claims 1
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- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 229940113087 geraniol Drugs 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 241000411851 herbal medicine Species 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 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 claims 1
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- 238000007918 intramuscular administration Methods 0.000 claims 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 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 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 claims 1
- 229910052757 nitrogen Chemical group 0.000 claims 1
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- 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 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 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 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 150000004804 polysaccharides Chemical class 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 229940125723 sedative agent Drugs 0.000 claims 1
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- 159000000000 sodium salts Chemical group 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
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- 150000003431 steroids Chemical class 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
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- 238000006467 substitution reaction Methods 0.000 claims 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
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- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (46)
- 에틸렌 또는 프로필렌 글리콜과의 카르복시메틸셀롤로오즈 부분 에스테르 및 메틸 또는 벤질 알콜과의 카르복시메틸스타치 부분 에스테르를 제외한 지방족, 아르지방족 지환식 및 이종환식 알콜과의 카르복시메틸 셀룰로오즈, 카르복시메틸스타치 및 카르복시메틸키틴 중에서 선택된 산성 폴리삭카라이드의 전체 또는 부분에스테르와 상기 부분 에스테르와 무기 또는 유기 염기와의 염.
- 제1항에 있어서, 상기 지방족 알콜은 탄소원자수가 34이하이고, 아미노, 하이드록시, 메르캅토, 알데하이도, 케토, 카르복시, 하이드로카르빌 및 디하이드로카르빌아미노, 에테르, 에스테르, 티오에테르, 티오에스테르, 아세탄, 케탈, 카르발콕시기, 카르바미드 및 탄소원자수가 6이하인 하이드로카르빌 라디칼을 갖는 알킬기가 치환된 카르바미드기 중에서 선택된 관능기 1 또는 2개가 치환되거나 치환되지 않으며, 이러한 지방족 알콜은 그의 탄소원자쇄에 산소, 황 또는 질소와 같은 이종원자가 삽입되거나 삽입되지 않은 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제2항에 있어서, 상기 지방족 알콜은 탄소원자수가 12이하이고, 상기 하이드로카르빌 라디칼은 탄소원자수가 4이하이며, 상기 아미노 또는 치환된 카르바미드기는 탄소원자수가 8이하인 알킬렌아미노기나 알킬렌카르바미드일 수 있는 것임을 특징으로 하는 산성 폴리삭카라이드의 에스테르와 그의 염.
- 제3항에 있어서, 상기 알콜은 에틸 프로필, 이소프로필 또는 n-부틸, 이소부틸, t-부틸 알콜이나아밀, 펜틸, 헥실 또는 옥틸 알콜인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제3항에 있어서, 상기 알콜은 글리세린인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제3항에 있어서, 상기 에스테르화 되는 알콜은 타르트론 알콜 젖산, 글리콜산, 알산, 타르타르산 또는 구연산인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테드와 그의 염.
- 제3항에 있어서, 상기 에스테르화 되는 알콜은 아미노에탄올, 아미노프로판올, n-아미노부탄올 또는 그의 아미노 부분에서의 디메틸 또는 디에틸 유도체나, 혹은 콜린, 피롤리디닐에탄올, 피페리디닐에탈올, 피페라지닐에탄을 또는 그에 상응하는 n-프로필 또는 n-부틸 알콜의 유도체나, 혹은 모노티오에틸렌글리콜 또는 그의 메르캅토 부분에서의 저급 알킬 유도체인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제3항에 있어서, 상기 에스테르화 되는 알콜 성분은 세틸, 미리실 알콜, 시트로넬롤, 게라니올, 네롤, 네롤리돌, 리날로올, 파르네솔 및 피톨 중에서 선택된 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제1항에 있어서, 상기 아르지방족 알콜은 오직 하나의 벤젠기를 함유하며, 그의 지방족 쇄의 탄소원자수가 4이하이고, 그의 벤젠기에는 1내지 3개의 메틸 또는 히드록시기나 할로겐 원자가 치환되거나 치환되지 않으며, 그의 지방족 쇄에는 아미노기, 모노- 또는 디에틸기, 피롤리닌기 또는 피페리딘기가 치환되거나 치환되지 않은 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제9항에 있어서, 상기 알콜은 벤질 알콜, 페네틸 알콜, 에페드린 및 아드레날린 중에서 선택된 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제1항에 있어서, 상기 지환식 알콜 또는 지방족-지환식 또는 이종환식 알콜은 각각 탄소원자수가 34이하인 단일환식 또는 다중환식 탄소화물로부터 유도된 것으로서 아미노, 하이드록시, 메르캅토, 알데하이드, 케토, 카르복시, 하이드로카르빌 디하이드로카르빌아미노, 에테르, 에스테르, 티오에테르, 티오에스테르, 아세탈, 케탈, 카르발콕시, 카르바이드 및 탄소원자수가 6이하인 하이드로카르빌 라디칼을 갖는 알킬기가 치환, 카르바미드 중에서 선택된 관능기 1 또는 2개가 치환되거나 치환되지 않으며, 그의 탄소원자 쇄에중에서 선택된 이종원자가 삽입되거나 삽입되지 않으며, 방향족 구조를 포함하는 하나 이상의 결합을 갖거나 갖지 않는 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제11항에 있어서, 상기 알콜은 탄소원자수가 12이하인 단일환식이며, 그 환은 탄소원자수가 5내지 7이고 1내지 3개의 저급알킬기가 치환되거나 치환되지 않은 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제11항 있어서, 상기 다중환식 알콜은 스테린, 콜산 또는 스테로이드 알콜인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제11항에 있어서, 상기 알콜은, 알카로이드, 페네틸아민, 페노티아진 약물, 티오크산테넨, 진경제, 진정제, 진통제, 진통제, 최면제, 식욕저하제, 안정제, 근육이완제, 관상혈관확장제, 아드레날린 차단제, 마취성 길항제, 항종양제, 항생제, 항바이러스제, 말초혈관확정제, 탄산 탈수효소 억제제, 항천식제, 항감염제 및 설파미드 중에서 선택된 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제1항 내지 제14항중 어느 한 항에 있어서, 카르복시기 모두가 알콜로 에스테르화 된 것임을 된 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르.
- 제1항 내지 제14항중 어느 한 항에 있어서, 카르복실기중 5내지 95%가 에스테르화된 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르와 그의 염.
- 제1항 내지 제14항 및 제16항중 어느 한 항에 있어서, 상기 무기염은 알카리 금속, 알카리 토금속, 마그네슘 또는 알루미늄인 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제17항에 있어서, 상기 염은 나트륨염 또는 암모늄염인 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제l항 내지 제16항중 어느 한 항에 있어서, 상기 유기염기는 지방족, 아르지방족, 지환식 또는 이중환식 아민 염기인 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제19항에 있어서, 상기 아민은 치료학적으로 허용가능한 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제2O항에 있어서, 상기 아민은 알카로이드, 펩타이드, 페노티아진, 벤조디아제핀, 티오크산테넨, 호르몬, 비타민, 진경제, 진정제, 진토제, 마취제, 최면제, 식용저하제, 안정제, 근육이완제, 관상혈관확장제, 항종양제, 항생제, 항균제, 항바이러스제, 항말라리아제, 탄산 탈수효소 억제제, 비스테로이드계 항감염제, 혈관수축제, 콜린작동성 아고니스트, 콜린작동성 차단제, 아드레날린, 아고니스트, 아드레날린 차단제 및 마취성 길항제 중에서 선택된 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제2O항에 있어서, 상기 아민은 약제학적으로 불할성이며 탄소원자수가 8이하인 모노-, 디- 및 트리알킬아민, 지방족 부분의 탄소원자수가 8이하이고 방향족 부분으로서는 1내지 3개의 메틸기나 할로겐 원자 또는 하이드록시기가 치환되거나 치환되어 있지 않은 하나의 벤질기를 갖는 아르알킬아민, 탄소원자수가 4내지 6이고 탄소원자들 사이에 O 및 S중에서 선택된 이종원자가 삽입되거나 삽입되어 있지 않은 환을 갖는 알킬렌아민 및 그들에 아미노 또는 하이드록시기가 치환되어 있는 아민중에서 선택된 것임을 특징으로 하는 산성 폴리삭카라이드 부분 에스테르의 염.
- 제1항에 있어서, 상기 에스테르는 에틸, 이소프로필, 벤질, P-브로모-벤질 및 미리스틸 중에서 선택된 화합물과의 카르복시에틸키틴, 에스테르인 것임을 특징으로 하는 산성 폴리삭카라이드 에스테르.
- 제1항에 있어서, 상기 에스테르는 에틸, 이소프로필, 벤질, P-브로보-벤질 및 미리스틸 중에서 선택된 화합물과의 카르복지에틸셀룰로오즈 에스테르인 것임을 특징으로 하는 산성 폴리삭카라이드부분 에스테르.
- 유효성분으로서 에틸렌 또는 프로필렌 글리콜과의 카르복시메틸셀룰로오즈 부분 에스테르나 혹은 메틸 또는 벤질 알콜과의 카르복시메틸스타치 부분 에스테르나 혹은 그들의 약제학적으로 허영가능한 염과 이와 함께 약제학적으로 허용가능한 부형제를 함유하는 약제 조성물.
- 제2항 내지 제23항중 어느 한 항에 따른 에스테르 또는 염을 유효성분으로서 함유하는 약제 조성물.
- 제25항 또는 제26항에 있어서, 약제 조성물은 비경구투여용인 것임을 특징으로 하는 약제 조성물.
- (1)약제학적으로 유효한 물질 또는 약제학적으로 유효한 물질들의 복합물과 (2)카르복시메틸 셀룰로오즈 나카르복시메틸키틴 또는 카르복시메틸 스타치의 전체 또는 부분 에스테르나 혹은 상기 부분 에스테르와 유기 또는 무기 염기와의 염으로 이루어진 부형제로 이루어진 약제 조성물 또는 의약.
- 알콜과의 카르복시메틸셀룰로오즈나 카르복시에틸키틴 또는 카르복시메틸스타치의 전체 또는 부분 에스테르와 상기 부분 에스테르와 유기 또는 무기염기와의 염으로 이루어지되 상기 알콜 및 염들 중 적어도 하나이상은 치료학적으로 유효한 것인 약제 조성물 또는 의약.
- 제28항 또는 제29항에 있어서, 상기 유효한 물질은 국부적인 용도에 사용되는 것임을 특징으로 하는 약제 조성물 또는 의약.
- 지방족, 아르지방족, 지환식 및 이종환식 알콜과의 카르복시에틸셀룰로오즈, 카르복시메틸스타치 및 카르복시에틸키틴 중에서 선택된 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 상기 부분 에스테르와 무기 또는 유기 염기와의 염을 사용하여 치료하는 방법.
- 지방족, 아르지방족, 지환식 및 이종환식 알콜과의 카르복시에틸셀룰로오즈, 카르복시에틸스타치 및 카르복시메틸키틴 중에서 선택된 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 상기 부분 에스테르와 무기 또는 유기 염기염기와의 염을 사용하여 화장품을 제조하는 방법.
- 지방족, 아르지방족, 지환식 및 이종환식 알콜과의 카르복시메틸셀룰로오즈, 카르복시메틸스타치 및 카르복시메틸키틴 중에서 선택된 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 상기 부분에스테르와 무기 또는 유기염기와의 염을 (1)식품업, (2)제지업, (3)접착제, (4)인쇄, (5)직물염색, (6)위생용품, 의료품 및 외과용품의 제조, (7)캡슐 및 마이크로캡슐 제조용 본초약물, (8)효소 고정용 생물학, (9)유약, 광택제, 거품 억제제, 유제품 및 세라익과 계면활성제 산업에서의 안정화제용 유화제에 사용하는 방법.
- 지방족, 아르지방족, 지환식 및 이종환식 알콜과의 카르복시메틸셀룰로오즈, 카르복시메틸스타치 및 카르복시메틸키틴 중에서 선택된 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 상기 부분 에스테르와 무기 또는 유기 염기와의 염을 함유하는 위생용품 또는 외과용품.
- 제34항에 있어서, 제2항 내지 제24항중 어느 한항에 따른 산성 폴리삭카라이드의 전체 또는 부분 에스테르를 함유하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 필름 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 실 형태인 것임을 특징으로 하는 위생용품 또는 외과용폼.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 외과수술용 봉합실 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 피부의학상 인공피부 용도의 필름 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 의약의 피하주입용 캡슐 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 피하주사, 근육주사 또는 정맥주사용 캡슐 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생용품 또는 외과용품은 일정시간이 경과된 후에는 제거되어지는 고형 삽입제 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 제34항 또는 제35항에 있어서, 상기 위생품 또는 외과용품은 상처 및 병소 투약용 스폰지 형태인 것임을 특징으로 하는 위생용품 또는 외과용품.
- 폴리삭카라이드의 4급 암모늄 염을 비양자성 용매중에서 에테르와제로 처리하고, 경우에 따라 자유 카르복시기를 염화시키는 것임을 특징으로 하는 산성 폴리삭카라이드의 전체 또는 부분 에스테르와그의 염의 제조 방법.
- 제44항에 있어서, 상기 용매는 디메틸설폭사이드인 것임을 특징으로 하는 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 그의 염의 제조방법.
- 제44항에 있어서, 상기 4급 암모늄 염은 저급 테트라알킬 암모늄 염인 것임을 특징으로 하는 산성 폴리삭카라이드의 전체 또는 부분 에스테르와 그의 염의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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IT47963A/88 | 1988-05-13 | ||
IT47963/88A IT1219942B (it) | 1988-05-13 | 1988-05-13 | Esteri polisaccaridici |
PCT/EP1989/000520 WO1989010940A1 (en) | 1988-05-13 | 1989-05-12 | New polysaccharide esters |
JP90-68492 | 1990-06-29 | ||
JP90-117740 | 1990-11-13 | ||
JP90-117739 | 1990-11-13 |
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KR900701848A true KR900701848A (ko) | 1990-12-04 |
KR940011646B1 KR940011646B1 (ko) | 1994-12-22 |
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KR1019920700072A KR940011646B1 (ko) | 1988-05-13 | 1991-06-27 | 슬롯 절연자성 쐐기 |
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US (2) | US5122598A (ko) |
EP (2) | EP0615979A3 (ko) |
JP (1) | JP2958373B2 (ko) |
KR (1) | KR940011646B1 (ko) |
AT (1) | ATE114322T1 (ko) |
AU (1) | AU629551B2 (ko) |
CA (1) | CA1336087C (ko) |
DE (1) | DE68919435T2 (ko) |
DK (1) | DK10890A (ko) |
ES (1) | ES2063779T3 (ko) |
FI (1) | FI900187A0 (ko) |
HU (1) | HU208440B (ko) |
IL (1) | IL90273A (ko) |
IT (1) | IT1219942B (ko) |
NZ (1) | NZ229099A (ko) |
WO (1) | WO1989010940A1 (ko) |
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IT1219942B (it) * | 1988-05-13 | 1990-05-24 | Fidia Farmaceutici | Esteri polisaccaridici |
IL98087A (en) * | 1990-05-04 | 1996-11-14 | Perio Prod Ltd | Preparation for dispensing drugs in the colon |
ES2048133T3 (es) * | 1990-05-04 | 2000-01-16 | Perio Prod Ltd | Sistema de descarga de farmacos para el colon. |
DE4022944A1 (de) * | 1990-07-19 | 1992-01-23 | Merck Patent Gmbh | Sucralfat-kautablette |
EP0544000B1 (en) * | 1990-08-17 | 1997-05-02 | Drug Delivery System Institute, Ltd. | N-acetylcarboxymethylchitosan derivative and production thereof |
GB9109757D0 (en) * | 1991-05-04 | 1991-06-26 | Procter & Gamble | Cosmetic compositions |
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IT1254119B (it) * | 1991-09-13 | 1995-09-08 | Fidia | Esteri di derivati carbossilici di polisaccaridi |
IT1263755B (it) * | 1991-09-16 | 1996-08-29 | Fidia Spa | Uso di esteri della colina con polisaccaridi acidi come agenti antiulcera e gastroprotettivi |
EP0571671B1 (en) * | 1992-05-26 | 1997-09-17 | The Procter & Gamble Company | A Pharmaceutical composition in powder form |
US5648074A (en) * | 1993-05-25 | 1997-07-15 | Allergan | Compositions and methods for disinfecting contact lenses and reducing proteinaceous deposit formation |
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DE957938C (de) * | 1957-01-24 | Henkel S. Cie GmbH, Dusseldorf-Holthausen | Verfahren zur Herstellung der Ester von Celluloseathercarbonsauren | |
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IT1219942B (it) * | 1988-05-13 | 1990-05-24 | Fidia Farmaceutici | Esteri polisaccaridici |
-
1988
- 1988-05-13 IT IT47963/88A patent/IT1219942B/it active
-
1989
- 1989-05-12 CA CA000599556A patent/CA1336087C/en not_active Expired - Fee Related
- 1989-05-12 JP JP1505459A patent/JP2958373B2/ja not_active Expired - Lifetime
- 1989-05-12 AT AT89108628T patent/ATE114322T1/de not_active IP Right Cessation
- 1989-05-12 NZ NZ229099A patent/NZ229099A/en unknown
- 1989-05-12 ES ES89108628T patent/ES2063779T3/es not_active Expired - Lifetime
- 1989-05-12 HU HU893005A patent/HU208440B/hu not_active IP Right Cessation
- 1989-05-12 WO PCT/EP1989/000520 patent/WO1989010940A1/en active Application Filing
- 1989-05-12 EP EP94107393A patent/EP0615979A3/en not_active Withdrawn
- 1989-05-12 IL IL9027389A patent/IL90273A/en not_active IP Right Cessation
- 1989-05-12 EP EP89108628A patent/EP0342557B1/en not_active Expired - Lifetime
- 1989-05-12 DE DE68919435T patent/DE68919435T2/de not_active Expired - Fee Related
- 1989-05-12 AU AU35718/89A patent/AU629551B2/en not_active Ceased
- 1989-05-12 US US07/350,920 patent/US5122598A/en not_active Expired - Fee Related
-
1990
- 1990-01-12 DK DK010890A patent/DK10890A/da not_active Application Discontinuation
- 1990-01-12 FI FI900187A patent/FI900187A0/fi not_active IP Right Cessation
-
1991
- 1991-06-27 KR KR1019920700072A patent/KR940011646B1/ko not_active Application Discontinuation
-
1992
- 1992-04-02 US US07/862,370 patent/US5466461A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AU3571889A (en) | 1989-11-29 |
DE68919435D1 (de) | 1995-01-05 |
US5122598A (en) | 1992-06-16 |
IL90273A (en) | 1995-11-27 |
IL90273A0 (en) | 1989-12-15 |
JPH02504164A (ja) | 1990-11-29 |
NZ229099A (en) | 1992-02-25 |
ATE114322T1 (de) | 1994-12-15 |
KR940011646B1 (ko) | 1994-12-22 |
CA1336087C (en) | 1995-06-27 |
IT8847963A0 (it) | 1988-05-13 |
AU629551B2 (en) | 1992-10-08 |
ES2063779T3 (es) | 1995-01-16 |
WO1989010940A1 (en) | 1989-11-16 |
EP0342557B1 (en) | 1994-11-23 |
US5466461A (en) | 1995-11-14 |
HU208440B (en) | 1993-10-28 |
FI900187A0 (fi) | 1990-01-12 |
EP0615979A2 (en) | 1994-09-21 |
DE68919435T2 (de) | 1995-07-06 |
DK10890D0 (da) | 1990-01-12 |
DK10890A (da) | 1990-03-12 |
HU893005D0 (en) | 1990-07-28 |
IT1219942B (it) | 1990-05-24 |
HUT53127A (en) | 1990-09-28 |
EP0342557A1 (en) | 1989-11-23 |
JP2958373B2 (ja) | 1999-10-06 |
EP0615979A3 (en) | 1994-12-28 |
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