HU180520B - Process for producing 17-alpha-alkinyl derivatives of 17-beta-hydroxy-andorst-4-ene-3-one - Google Patents
Process for producing 17-alpha-alkinyl derivatives of 17-beta-hydroxy-andorst-4-ene-3-one Download PDFInfo
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- HU180520B HU180520B HU79RO1032A HURO001032A HU180520B HU 180520 B HU180520 B HU 180520B HU 79RO1032 A HU79RO1032 A HU 79RO1032A HU RO001032 A HURO001032 A HU RO001032A HU 180520 B HU180520 B HU 180520B
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- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 68
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 20
- -1 17β-hydroxyandrost-4-en-3-one acetylene derivatives Chemical class 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 14
- 238000005886 esterification reaction Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 150000004057 1,4-benzoquinones Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 150000000475 acetylene derivatives Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000001589 carboacyl group Chemical group 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
- 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 claims 3
- 238000011200 topical administration Methods 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testosterone Natural products O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
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- 239000000047 product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 0 C*C1(CC(*2C3)(C22C33CC4)O)[C@](*)(CC#*)CCC1C2C=C(*)C3=CC4=O Chemical compound C*C1(CC(*2C3)(C22C33CC4)O)[C@](*)(CC#*)CCC1C2C=C(*)C3=CC4=O 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
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- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- IQUXBKUKXDWZLA-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IQUXBKUKXDWZLA-VMXHOPILSA-N 0.000 description 1
- DJPXTHIJILUPOE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-8,9,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 DJPXTHIJILUPOE-VMXHOPILSA-N 0.000 description 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
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- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7823851A FR2433536A1 (fr) | 1978-08-16 | 1978-08-16 | Nouveaux derives de l'androst 4-ene, leur procede de preparation et leur application comme medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180520B true HU180520B (en) | 1983-03-28 |
Family
ID=9211827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79RO1032A HU180520B (en) | 1978-08-16 | 1979-07-24 | Process for producing 17-alpha-alkinyl derivatives of 17-beta-hydroxy-andorst-4-ene-3-one |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4232015A (en, 2012) |
| JP (1) | JPS5528982A (en, 2012) |
| AT (1) | AT368520B (en, 2012) |
| AU (1) | AU524232B2 (en, 2012) |
| BE (1) | BE878256A (en, 2012) |
| CH (1) | CH641814A5 (en, 2012) |
| DE (1) | DE2933258A1 (en, 2012) |
| FR (1) | FR2433536A1 (en, 2012) |
| GB (1) | GB2029833B (en, 2012) |
| HU (1) | HU180520B (en, 2012) |
| IE (1) | IE48931B1 (en, 2012) |
| IT (1) | IT1164040B (en, 2012) |
| NL (1) | NL7906214A (en, 2012) |
| PT (1) | PT70060A (en, 2012) |
| SE (1) | SE435186B (en, 2012) |
| ZA (1) | ZA793967B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4424218A (en) | 1979-08-17 | 1984-01-03 | Roussel Uclaf | Novel 3 α-amino steroids |
| FR2468617A1 (fr) * | 1979-10-26 | 1981-05-08 | Roussel Uclaf | Nouveaux derives acetyleniques chlores de l'androst-4-ene leur procede de preparation, et leur application a titre de medicament et les compositions pharmaceutiques les renfermant |
| US4383947A (en) * | 1981-07-24 | 1983-05-17 | The Upjohn Company | Introduction of a fluorine atom |
| US4488995A (en) * | 1984-02-06 | 1984-12-18 | E. R. Squibb & Sons, Inc. | Androstene-17β-alkylthiomethyl ethers |
| US6740646B2 (en) * | 2002-01-16 | 2004-05-25 | Biotest Laboratories, Llc | Bioavailable prodrugs of androgenic steroids and related method |
| JP4636847B2 (ja) * | 2004-10-13 | 2011-02-23 | 株式会社ロッテ | 全粒粉からなる小麦粉の加工方法及びその加工方法により得られた加工小麦粉並びにその加工小麦粉を使用した食品 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2740798A (en) * | 1953-05-25 | 1956-04-03 | Searle & Co | 11 beta-hydroxy-17-ethynyl testosterone and esters thereof |
| US3010957A (en) * | 1958-11-26 | 1961-11-28 | Schering Corp | Ethinyl androstadienes |
| FR1349113A (fr) * | 1959-01-28 | 1964-01-17 | Upjohn Co | Procédé de fabrication de 6-fluoro-11 oxygéné-17-bêta-hydroxy-17 alpha-alkynyl inférieur-4-androstène-3-ones et leurs dérivés acylés |
| GB1081494A (en) * | 1965-09-14 | 1967-08-31 | British Drug Houses Ltd | 17ª-(alka-1',3'-diynyl)-steroids |
| US3793308A (en) * | 1972-11-08 | 1974-02-19 | Upjohn Co | 4-spiro(cyclopropyl)androstenes and process for their production |
| SE7801152L (sv) * | 1977-02-22 | 1978-08-23 | Roussel Uclaf | Sett att framstella 17alfa-acetylen-derivat av androst-4-en |
-
1978
- 1978-08-16 FR FR7823851A patent/FR2433536A1/fr active Granted
-
1979
- 1979-07-04 SE SE7905865A patent/SE435186B/sv not_active IP Right Cessation
- 1979-07-24 HU HU79RO1032A patent/HU180520B/hu not_active IP Right Cessation
- 1979-08-02 ZA ZA00793967A patent/ZA793967B/xx unknown
- 1979-08-06 US US06/063,939 patent/US4232015A/en not_active Expired - Lifetime
- 1979-08-13 PT PT70060A patent/PT70060A/pt unknown
- 1979-08-14 AT AT0553479A patent/AT368520B/de not_active IP Right Cessation
- 1979-08-14 IT IT50049/79A patent/IT1164040B/it active
- 1979-08-14 BE BE0/196747A patent/BE878256A/fr not_active IP Right Cessation
- 1979-08-15 NL NL7906214A patent/NL7906214A/nl not_active Application Discontinuation
- 1979-08-15 CH CH749079A patent/CH641814A5/fr not_active IP Right Cessation
- 1979-08-15 AU AU49958/79A patent/AU524232B2/en not_active Ceased
- 1979-08-16 JP JP10363879A patent/JPS5528982A/ja active Granted
- 1979-08-16 IE IE1578/79A patent/IE48931B1/en not_active IP Right Cessation
- 1979-08-16 DE DE19792933258 patent/DE2933258A1/de active Granted
- 1979-08-16 GB GB7928508A patent/GB2029833B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2933258A1 (de) | 1980-02-28 |
| AT368520B (de) | 1982-10-25 |
| IT7950049A0 (it) | 1979-08-14 |
| SE435186B (sv) | 1984-09-10 |
| PT70060A (fr) | 1979-09-01 |
| JPS5528982A (en) | 1980-02-29 |
| FR2433536B1 (en, 2012) | 1981-07-24 |
| AU524232B2 (en) | 1982-09-09 |
| AU4995879A (en) | 1980-03-06 |
| SE7905865L (sv) | 1980-02-17 |
| FR2433536A1 (fr) | 1980-03-14 |
| US4232015A (en) | 1980-11-04 |
| IT1164040B (it) | 1987-04-08 |
| NL7906214A (nl) | 1980-02-19 |
| ATA553479A (de) | 1982-02-15 |
| IE48931B1 (en) | 1985-06-26 |
| ZA793967B (en) | 1980-07-30 |
| GB2029833A (en) | 1980-03-26 |
| JPS636559B2 (en, 2012) | 1988-02-10 |
| IE791578L (en) | 1980-02-16 |
| CH641814A5 (fr) | 1984-03-15 |
| GB2029833B (en) | 1983-04-27 |
| BE878256A (fr) | 1980-02-14 |
| DE2933258C2 (en, 2012) | 1990-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |