IL94874A - ]a-)טרט, בוטיל אמינומתיל(-3,4- דיכלורובנזיל[ תיואצטאמיד, הכנתן ותכשירי רוקחות המכילים אותו - Google Patents
]a-)טרט, בוטיל אמינומתיל(-3,4- דיכלורובנזיל[ תיואצטאמיד, הכנתן ותכשירי רוקחות המכילים אותוInfo
- Publication number
- IL94874A IL94874A IL9487490A IL9487490A IL94874A IL 94874 A IL94874 A IL 94874A IL 9487490 A IL9487490 A IL 9487490A IL 9487490 A IL9487490 A IL 9487490A IL 94874 A IL94874 A IL 94874A
- Authority
- IL
- Israel
- Prior art keywords
- tert
- preparation
- thioacetamide
- dichlorobenzyl
- alpha
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 9
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 title abstract description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 230000001737 promoting effect Effects 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 10
- 235000021050 feed intake Nutrition 0.000 claims description 4
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- 230000037406 food intake Effects 0.000 abstract description 4
- 235000012631 food intake Nutrition 0.000 abstract description 4
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 241001465754 Metazoa Species 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000006052 feed supplement Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 206010021113 Hypothermia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- IWUXJCHIHHGRFR-UHFFFAOYSA-N ethanethioamide;hydrochloride Chemical compound Cl.CC(N)=S IWUXJCHIHHGRFR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 hydrogen salts Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- OCRODJQDEQDAOM-UHFFFAOYSA-N n-butylethanethioamide Chemical compound CCCCNC(C)=S OCRODJQDEQDAOM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Animal Husbandry (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Nutrition Science (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8908480A FR2648814B1 (fr) | 1989-06-26 | 1989-06-26 | L'alpha (tert-butyl-aminomethyl-3,4-dichlorobenzyl)thioacetamide, son procede de preparation et son application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL94874A0 IL94874A0 (en) | 1991-04-15 |
| IL94874A true IL94874A (he) | 1994-07-31 |
Family
ID=9383122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9487490A IL94874A (he) | 1989-06-26 | 1990-06-26 | ]a-)טרט, בוטיל אמינומתיל(-3,4- דיכלורובנזיל[ תיואצטאמיד, הכנתן ותכשירי רוקחות המכילים אותו |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5621011A (he) |
| EP (1) | EP0406088B1 (he) |
| JP (1) | JP2859935B2 (he) |
| CN (1) | CN1031998C (he) |
| AT (1) | ATE102921T1 (he) |
| AU (1) | AU630710B2 (he) |
| CA (1) | CA2019749C (he) |
| DE (1) | DE69007352T2 (he) |
| DK (1) | DK0406088T3 (he) |
| ES (1) | ES2053137T3 (he) |
| FR (1) | FR2648814B1 (he) |
| HK (1) | HK1007428A1 (he) |
| IE (1) | IE64078B1 (he) |
| IL (1) | IL94874A (he) |
| LT (1) | LT2241B (he) |
| LV (2) | LV5231A3 (he) |
| NZ (1) | NZ234239A (he) |
| PT (1) | PT94484B (he) |
| SU (1) | SU1736337A3 (he) |
| UA (1) | UA26311C2 (he) |
| ZA (1) | ZA904959B (he) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506268A (en) * | 1993-06-11 | 1996-04-09 | Nps Pharmaceuticals, Inc. | Use of isovaleramide as a mild anxiolytic and sedative agent |
| FR2734264B1 (fr) * | 1995-05-19 | 1997-08-01 | Lafon Labor | Utilisation de derives d'alpha-aminomethyl-3,4-dichlorobenzyl-thioacetamide pour la fabrication d'un medicament inhibant la recapture de la dopamine et nouveaux composes pour cette utilisation |
| EP2990036B1 (de) * | 2014-07-30 | 2019-04-10 | Symrise AG | Hydroxyflavone als Appetitanreger |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3624143A (en) * | 1968-05-10 | 1971-11-30 | Merck & Co Inc | Compounds of the class {62 -aralkylthio-substituted-{60 -amino acids |
| US4534874A (en) * | 1983-11-21 | 1985-08-13 | Ciba-Geigy Corporation | Anti-oxidative, anti-thermal, and anti-actinic degradation amides of hydroxyphenylalkylthio alkanoic acids, compositions, and method of use therefor |
| FR2561646B1 (fr) * | 1984-03-23 | 1987-10-09 | Lafon Labor | Derives d'acide (a-(alkylaminomethyl)-benzyl)-thioacetique, procede de preparation et utilisation en therapeutique |
| FI864901A7 (fi) * | 1985-12-06 | 1987-06-07 | Ciba Geigy Ag | Hydroxitioetrar. |
| US4843071A (en) * | 1986-12-05 | 1989-06-27 | Serotonin Industries Of Charleston | Method and composition for treating obesity, drug abuse, and narcolepsy |
-
1989
- 1989-06-26 FR FR8908480A patent/FR2648814B1/fr not_active Expired - Lifetime
-
1990
- 1990-06-25 CA CA002019749A patent/CA2019749C/en not_active Expired - Lifetime
- 1990-06-25 SU SU904830498A patent/SU1736337A3/ru active
- 1990-06-25 ES ES90401801T patent/ES2053137T3/es not_active Expired - Lifetime
- 1990-06-25 DK DK90401801.7T patent/DK0406088T3/da active
- 1990-06-25 PT PT94484A patent/PT94484B/pt not_active IP Right Cessation
- 1990-06-25 EP EP90401801A patent/EP0406088B1/fr not_active Expired - Lifetime
- 1990-06-25 DE DE69007352T patent/DE69007352T2/de not_active Expired - Fee Related
- 1990-06-25 UA UA4830498A patent/UA26311C2/uk unknown
- 1990-06-25 AT AT90401801T patent/ATE102921T1/de not_active IP Right Cessation
- 1990-06-25 IE IE233690A patent/IE64078B1/en not_active IP Right Cessation
- 1990-06-26 ZA ZA904959A patent/ZA904959B/xx unknown
- 1990-06-26 AU AU57867/90A patent/AU630710B2/en not_active Ceased
- 1990-06-26 JP JP2165834A patent/JP2859935B2/ja not_active Expired - Fee Related
- 1990-06-26 NZ NZ234239A patent/NZ234239A/en unknown
- 1990-06-26 IL IL9487490A patent/IL94874A/he unknown
- 1990-06-26 CN CN90103322A patent/CN1031998C/zh not_active Expired - Lifetime
-
1993
- 1993-06-07 LT LTRP627A patent/LT2241B/xx not_active IP Right Cessation
- 1993-06-08 LV LV930494A patent/LV5231A3/xx unknown
-
1995
- 1995-06-29 US US08/496,452 patent/US5621011A/en not_active Expired - Lifetime
-
1996
- 1996-07-19 LV LV960290A patent/LV5820B4/xx unknown
-
1998
- 1998-06-25 HK HK98106621A patent/HK1007428A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| LT2241B (lt) | 1993-11-15 |
| DE69007352D1 (de) | 1994-04-21 |
| IE902336A1 (en) | 1991-01-16 |
| UA26311C2 (uk) | 1999-08-30 |
| FR2648814A1 (fr) | 1990-12-28 |
| IL94874A0 (en) | 1991-04-15 |
| PT94484B (pt) | 1997-02-28 |
| JPH03148254A (ja) | 1991-06-25 |
| CA2019749A1 (en) | 1990-12-26 |
| PT94484A (pt) | 1991-02-08 |
| FR2648814B1 (fr) | 1991-10-18 |
| CA2019749C (en) | 2002-02-05 |
| CN1048381A (zh) | 1991-01-09 |
| DK0406088T3 (da) | 1994-04-05 |
| ES2053137T3 (es) | 1994-07-16 |
| AU630710B2 (en) | 1992-11-05 |
| LV5231A3 (lv) | 1993-10-10 |
| DE69007352T2 (de) | 1994-08-18 |
| CN1031998C (zh) | 1996-06-12 |
| HK1007428A1 (en) | 1999-04-09 |
| AU5786790A (en) | 1991-01-03 |
| EP0406088B1 (fr) | 1994-03-16 |
| IE902336L (en) | 1990-12-26 |
| LV5820A4 (lv) | 1997-04-20 |
| LV5820B4 (lv) | 1997-08-20 |
| ATE102921T1 (de) | 1994-04-15 |
| SU1736337A3 (ru) | 1992-05-23 |
| ZA904959B (en) | 1992-02-26 |
| JP2859935B2 (ja) | 1999-02-24 |
| EP0406088A1 (fr) | 1991-01-02 |
| NZ234239A (en) | 1991-07-26 |
| US5621011A (en) | 1997-04-15 |
| IE64078B1 (en) | 1995-07-12 |
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