FR2494698A1 - Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant - Google Patents
Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant Download PDFInfo
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- FR2494698A1 FR2494698A1 FR8024750A FR8024750A FR2494698A1 FR 2494698 A1 FR2494698 A1 FR 2494698A1 FR 8024750 A FR8024750 A FR 8024750A FR 8024750 A FR8024750 A FR 8024750A FR 2494698 A1 FR2494698 A1 FR 2494698A1
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- Prior art keywords
- radical
- amino
- formula
- carbon atoms
- hydrogen atom
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims description 13
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- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- 150000007524 organic acids Chemical class 0.000 claims abstract description 7
- 235000005985 organic acids Nutrition 0.000 claims abstract description 6
- -1 alkyl radical Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 20
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- 235000001014 amino acid Nutrition 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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- 238000000034 method Methods 0.000 claims description 14
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- 125000002252 acyl group Chemical group 0.000 claims description 12
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- 125000006239 protecting group Chemical group 0.000 claims description 12
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- 125000003277 amino group Chemical group 0.000 claims description 5
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- AMLJWLYRONUCKO-UHFFFAOYSA-N n-(6-amino-5-iodopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(I)C(N)=N1 AMLJWLYRONUCKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
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- 150000003431 steroids Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
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- 238000006243 chemical reaction Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
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- 239000013078 crystal Substances 0.000 description 6
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- 239000002775 capsule Substances 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
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- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
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- 230000002498 deadly effect Effects 0.000 description 1
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- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- CAGRHEDHVJKNBB-UHFFFAOYSA-N dihydroxyphosphanyl ethyl hydrogen phosphite Chemical compound CCOP(O)OP(O)O CAGRHEDHVJKNBB-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-LUJOEAJASA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 101150118163 h gene Proteins 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 230000001024 immunotherapeutic effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UBOIQDHHVMFACX-UHFFFAOYSA-N n,n-dimethylmethanamine;dihydrate Chemical compound O.O.CN(C)C UBOIQDHHVMFACX-UHFFFAOYSA-N 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- SILPHWBUAUNNKU-UHFFFAOYSA-M sodium;ethyl acetate;acetate Chemical compound [Na+].CC([O-])=O.CCOC(C)=O SILPHWBUAUNNKU-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0027—Azides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024750A FR2494698A1 (fr) | 1980-11-21 | 1980-11-21 | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| US06/292,791 US4424218A (en) | 1979-08-17 | 1981-08-14 | Novel 3 α-amino steroids |
| SE8105995A SE451456B (sv) | 1980-11-21 | 1981-10-09 | Nya 3-aminosubstituerade steroider och deras salter, sett for framstellning derav och kompositioner innehallande dem |
| HU813135A HU184896B (en) | 1980-11-21 | 1981-10-26 | Process for producing new 3-alpha-amino-substituted-steroide derivatives |
| IL64224A IL64224A0 (en) | 1980-11-21 | 1981-11-06 | New 3-amino substituted steroid derivatives and their salts,process for preparing them,use as medicaments and compositions containing them |
| ZA817806A ZA817806B (en) | 1980-11-21 | 1981-11-11 | 3-substituted amino steroid derivatives and their salts,process for preparing them,their use as medicaments and the compositions containing them |
| AT0497081A AT389703B (de) | 1980-11-21 | 1981-11-18 | Verfahren zur herstellung von neuen 3-amino-substituierten steroidderivaten und von deren salzen |
| KR1019810004462A KR880001239B1 (ko) | 1980-11-21 | 1981-11-18 | 3-아미드 치환 스테로이드 유도체의 제조방법 |
| FI813677A FI77871C (fi) | 1980-11-21 | 1981-11-19 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3-aminosubstituerade steroidderivat. |
| IE2732/81A IE52188B1 (en) | 1980-11-21 | 1981-11-20 | New 3-amino steroid compounds,their production and pharmaceutical compositions containing them |
| SU813355225A SU1327789A3 (ru) | 1980-11-21 | 1981-11-20 | Способ получени стероидных производных с замещенной 3-аминогруппой или их кислото-аддитивных солей |
| PT74015A PT74015B (fr) | 1980-11-21 | 1981-11-20 | Procede de preparation de nouveaux derives steroides 3-amino substitue |
| AU77723/81A AU546100B2 (en) | 1980-11-21 | 1981-11-20 | 3-amino substituted steroid derivatives |
| JP56185540A JPS57116099A (en) | 1980-11-21 | 1981-11-20 | Novel 3-amino substituted steroid derivative, salt, manufacture, use as drug and composition containing same |
| NL8105260A NL8105260A (nl) | 1980-11-21 | 1981-11-20 | Nieuwe 3-aminogesubstitueerde steroied-derivaten en de zouten daarvan, werkwijze ter bereiding daarvan, de toepassing daarvan als geneesmiddelen en preparaten, die deze verbindingen bevatten. |
| CH7459/81A CH651056A5 (fr) | 1980-11-21 | 1981-11-20 | Derives steroides 3-amino substitue et leurs sels, procedes de preparation et medicaments les renfermant. |
| DK514981A DK161093C (da) | 1980-11-21 | 1981-11-20 | Analogifremgangsmaade til fremstilling af 3-aminosubstituerede steroidderivater |
| IT49746/81A IT1172086B (it) | 1980-11-21 | 1981-11-20 | Derivati steroidei 3-ammino-sostituiti e loro sali relativo procedimento di produzione e loro impiego come medicamenti |
| LU83781A LU83781A1 (fr) | 1980-11-21 | 1981-11-20 | Nouveaux derives steroides 3-amino substitue et leurs selsprocede de preparation application a tire de medicaments et compositions les renfermant |
| BE0/206612A BE891201A (fr) | 1980-11-21 | 1981-11-20 | Nouveaux derives steroides 3-amino substitue et leurs sels, procede de preparation, applicatiion a titre de medicaments et compositions les renfermant |
| CA000390559A CA1175415A (fr) | 1980-11-21 | 1981-11-20 | Procede de preparation de nouveaux derives steroides 3-amino substitue |
| DE19813146117 DE3146117A1 (de) | 1980-11-21 | 1981-11-20 | "neue 3-amino-substituierte steroidderivate, deren salze, deren herstellungsverfahren, deren verwendung als arzneimittel und die sie enthaltenden zusammensetzungen" |
| ES507309A ES507309A0 (es) | 1980-11-21 | 1981-11-20 | Procedimiento de preparacion de nuevos derivados esteroides sustituidos con amino en posicion 3. |
| GB8135218A GB2087894B (en) | 1980-11-21 | 1981-11-23 | Immunotherapeutic 3-(substituted amino) steroids of the pregnane and 19-norpregnane series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024750A FR2494698A1 (fr) | 1980-11-21 | 1980-11-21 | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2494698A1 true FR2494698A1 (fr) | 1982-05-28 |
| FR2494698B1 FR2494698B1 (enrdf_load_stackoverflow) | 1983-06-24 |
Family
ID=9248226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8024750A Granted FR2494698A1 (fr) | 1979-08-17 | 1980-11-21 | Nouveaux derives steroides 3-amino substitues, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
Country Status (23)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9084800B2 (en) * | 2011-11-07 | 2015-07-21 | Natreon, Inc. | Indolealkylamino-withasteroid conjugates and method of use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE647858A (enrdf_load_stackoverflow) * | 1964-05-13 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2430467A (en) * | 1944-02-11 | 1947-11-11 | Glidden Co | 3-amino-derivatives of steroids and method of making same |
| US2781342A (en) * | 1952-05-17 | 1957-02-12 | Upjohn Co | Steroid enamines |
| FR1311761A (fr) * | 1959-09-12 | 1962-12-14 | Clin Byla Ets | Composés aminés de la série des stéroïdes et procédé de préparation de tels composés |
| GB962324A (en) * | 1959-09-12 | 1964-07-01 | Clin Byla Ets | Steroid compounds and production thereof |
| NL103735C (enrdf_load_stackoverflow) * | 1961-02-17 | |||
| US3503959A (en) * | 1962-03-30 | 1970-03-31 | Sterling Drug Inc | 3-amino steroids |
| US3196168A (en) * | 1964-02-18 | 1965-07-20 | American Home Prod | Aminoaroyl aminosteroids |
| US3196169A (en) * | 1964-11-03 | 1965-07-20 | American Home Prod | Aminoacyl aminosteroids |
| BE672238A (enrdf_load_stackoverflow) * | 1965-11-12 | 1966-03-01 | ||
| BE811304R (fr) * | 1973-10-24 | 1974-06-17 | Pr0cede de preparation du (20 s) 3 beta -n-dimethylamino | |
| FR2463777A1 (fr) * | 1979-08-17 | 1981-02-27 | Roussel Uclaf | Nouveaux derives du 5a-pregnan-20-ol, leur procede de preparation et leur application comme medicaments |
-
1980
- 1980-11-21 FR FR8024750A patent/FR2494698A1/fr active Granted
-
1981
- 1981-10-09 SE SE8105995A patent/SE451456B/sv not_active IP Right Cessation
- 1981-10-26 HU HU813135A patent/HU184896B/hu unknown
- 1981-11-06 IL IL64224A patent/IL64224A0/xx not_active IP Right Cessation
- 1981-11-11 ZA ZA817806A patent/ZA817806B/xx unknown
- 1981-11-18 KR KR1019810004462A patent/KR880001239B1/ko not_active Expired
- 1981-11-18 AT AT0497081A patent/AT389703B/de not_active IP Right Cessation
- 1981-11-19 FI FI813677A patent/FI77871C/fi not_active IP Right Cessation
- 1981-11-20 CH CH7459/81A patent/CH651056A5/fr not_active IP Right Cessation
- 1981-11-20 DE DE19813146117 patent/DE3146117A1/de not_active Ceased
- 1981-11-20 SU SU813355225A patent/SU1327789A3/ru active
- 1981-11-20 AU AU77723/81A patent/AU546100B2/en not_active Ceased
- 1981-11-20 NL NL8105260A patent/NL8105260A/nl not_active Application Discontinuation
- 1981-11-20 BE BE0/206612A patent/BE891201A/fr not_active IP Right Cessation
- 1981-11-20 IT IT49746/81A patent/IT1172086B/it active
- 1981-11-20 JP JP56185540A patent/JPS57116099A/ja active Granted
- 1981-11-20 IE IE2732/81A patent/IE52188B1/en unknown
- 1981-11-20 ES ES507309A patent/ES507309A0/es active Granted
- 1981-11-20 PT PT74015A patent/PT74015B/pt unknown
- 1981-11-20 CA CA000390559A patent/CA1175415A/fr not_active Expired
- 1981-11-20 LU LU83781A patent/LU83781A1/fr unknown
- 1981-11-20 DK DK514981A patent/DK161093C/da not_active IP Right Cessation
- 1981-11-23 GB GB8135218A patent/GB2087894B/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE647858A (enrdf_load_stackoverflow) * | 1964-05-13 |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/65 * |
Also Published As
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Legal Events
| Date | Code | Title | Description |
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| ST | Notification of lapse |