SU613724A3 - Способ получени 8-тиометил-эрголинов или их солей - Google Patents
Способ получени 8-тиометил-эрголинов или их солейInfo
- Publication number
- SU613724A3 SU613724A3 SU752140862A SU2140862A SU613724A3 SU 613724 A3 SU613724 A3 SU 613724A3 SU 752140862 A SU752140862 A SU 752140862A SU 2140862 A SU2140862 A SU 2140862A SU 613724 A3 SU613724 A3 SU 613724A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- solution
- found
- calculated
- sodium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000003839 salts Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 16
- 239000000243 solution Substances 0.000 claims 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 11
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 8
- 239000000047 product Substances 0.000 claims 7
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 238000001953 recrystallisation Methods 0.000 claims 6
- 238000004809 thin layer chromatography Methods 0.000 claims 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 5
- 239000012434 nucleophilic reagent Substances 0.000 claims 5
- -1 p-toluenesulfonyl Chemical group 0.000 claims 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 238000001704 evaporation Methods 0.000 claims 3
- 230000008020 evaporation Effects 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 2
- 239000012298 atmosphere Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 239000011976 maleic acid Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- PICOUKBMCJHPHB-NTVGDFDMSA-N C1=CC([C@@H]2[C@H](NCC(C2)CS)C2)=C3C2=CNC3=C1 Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)CS)C2)=C3C2=CNC3=C1 PICOUKBMCJHPHB-NTVGDFDMSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 241000507581 Ergene Species 0.000 claims 1
- 101150038870 NAA20 gene Proteins 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- WUPZNKGVDMHMBS-UHFFFAOYSA-N azane;dihydrate Chemical compound [NH4+].[NH4+].[OH-].[OH-] WUPZNKGVDMHMBS-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000002026 chloroform extract Substances 0.000 claims 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000011097 chromatography purification Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 claims 1
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 claims 1
- RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US477136A US3901894A (en) | 1974-06-06 | 1974-06-06 | 8-thiomethylergolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU613724A3 true SU613724A3 (ru) | 1978-06-30 |
Family
ID=23894677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752140862A SU613724A3 (ru) | 1974-06-06 | 1975-06-05 | Способ получени 8-тиометил-эрголинов или их солей |
Country Status (27)
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147789A (en) * | 1974-03-14 | 1979-04-03 | Sandoz Ltd. | 6-Methyl-8-thiomethyl-ergolene derivatives |
| US3959288A (en) * | 1974-12-13 | 1976-05-25 | Eli Lilly And Company | 8-Oxymethylergolines and process therefor |
| JPS5283894A (en) * | 1976-01-01 | 1977-07-13 | Lilly Co Eli | 88thiomethyl ergoline |
| GB1549829A (en) * | 1976-05-26 | 1979-08-08 | Farmaceutici Italia | 10'-methoxy-1',6'-dimethylergoline-8'-beta-methyl-amino(or thio)-pyrazines |
| IT1192260B (it) * | 1977-07-05 | 1988-03-31 | Simes | Derivati di ergoline-2-tioeteri e loro solfossidi |
| US4166182A (en) * | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4180582A (en) * | 1978-02-08 | 1979-12-25 | Eli Lilly And Company | 6-n-Propyl-8-methoxy-methyl or methylmercaptomethylergolines and related compounds as prolactin inhibitors and to treat Parkinson's syndrome |
| US4202979A (en) * | 1979-01-11 | 1980-05-13 | Eli Lilly And Company | 6-Ethyl(or allyl)-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4246265A (en) * | 1979-10-01 | 1981-01-20 | Eli Lilly And Company | 6-n-Propyl-8α-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4382940A (en) * | 1979-12-06 | 1983-05-10 | Farmitalia Carlo Erba S.P.A. | Ercoline derivatives and therapeutic compositions having CNS affecting activity |
| DE3216870A1 (de) * | 1982-05-03 | 1983-11-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische zubereitungen mit zytostatischer wirkung |
| FR2526797A1 (fr) * | 1982-05-12 | 1983-11-18 | Roussel Uclaf | Nouveaux derives de l'acide 9-oxalysergique, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| CH649998A5 (de) * | 1982-08-09 | 1985-06-28 | Sandoz Ag | Ergolinderivate, ein verfahren zu ihrer herstellung und heilmittel, enthaltend diese ergolinderivate als wirkstoff. |
| GB8427536D0 (en) * | 1984-10-31 | 1984-12-05 | Lilly Industries Ltd | Ergoline derivatives |
| US4675322A (en) * | 1984-12-10 | 1987-06-23 | Eli Lilly And Company | 1-Substituted-6-n-propyl-8β-methylthio-methylergolines |
| US4801712A (en) * | 1985-06-24 | 1989-01-31 | Eli Lilly And Company | 2-Alkyl(or phenyl)thio-6-n-alkylergolines are dopamine D-1 antagonists without D-2 agonist activity |
| FR2589734B1 (fr) * | 1985-11-13 | 1988-09-02 | Roussel Uclaf | Utilisation de derives de l'ergoline a l'obtention d'un medicament a visee geriatrique |
| HU196394B (en) * | 1986-06-27 | 1988-11-28 | Richter Gedeon Vegyeszet | Process for preparing 2-halogenated ergoline derivatives |
| CZ305160B6 (cs) * | 2001-06-08 | 2015-05-27 | Ipsen Pharma S.A.S. | Chimérické somatostatin-dopaminové analogy |
| US7019140B2 (en) * | 2002-03-15 | 2006-03-28 | Antibioticos S.P.A. | Process for the synthesis of pergolide |
| HK1213486A1 (zh) | 2012-11-01 | 2016-07-08 | Ipsen Pharma S.A.S. | 促生长素抑制素类似物及其二聚体 |
| TWI523863B (zh) | 2012-11-01 | 2016-03-01 | 艾普森藥品公司 | 體抑素－多巴胺嵌合體類似物 |
| AU2015320975B2 (en) | 2014-09-25 | 2020-10-08 | Boehringer Ingelheim Vetmedica Gmbh | Combination treatment of SGLT2 inhibitors and dopamine agonists for preventing metabolic disorders in equine animals |
| WO2019234069A1 (en) | 2018-06-08 | 2019-12-12 | Boehringer Ingelheim Vetmedica Gmbh | Liquid pharmaceutical compositions comprising pergolide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE712054A (enrdf_load_stackoverflow) * | 1967-03-16 | 1968-07-15 | ||
| DE1935556A1 (de) * | 1969-07-12 | 1971-01-21 | Hoechst Ag | Verfahren zur Herstellung von Lysergol |
| JPS5012398A (enrdf_load_stackoverflow) * | 1973-06-08 | 1975-02-07 |
-
1974
- 1974-06-06 US US477136A patent/US3901894A/en not_active Expired - Lifetime
-
1975
- 1975-05-16 JP JP50059191A patent/JPS582946B2/ja not_active Expired
- 1975-06-03 NL NLAANVRAGE7506584,A patent/NL180911C/xx not_active IP Right Cessation
- 1975-06-03 DE DE19752524575 patent/DE2524575A1/de not_active Ceased
- 1975-06-03 GB GB23869/75A patent/GB1505296A/en not_active Expired
- 1975-06-03 PH PH17225A patent/PH10992A/en unknown
- 1975-06-03 CA CA228,332A patent/CA1071623A/en not_active Expired
- 1975-06-03 SE SE7506327A patent/SE420095B/xx not_active IP Right Cessation
- 1975-06-03 IE IE1221/75A patent/IE41474B1/en unknown
- 1975-06-03 CS CS753882A patent/CS199591B2/cs unknown
- 1975-06-03 HU HU75EI623A patent/HU173590B/hu unknown
- 1975-06-04 PL PL1975180897A patent/PL95738B1/pl unknown
- 1975-06-04 AU AU81827/75A patent/AU507574B2/en not_active Expired
- 1975-06-04 DK DK249975A patent/DK144160C/da not_active IP Right Cessation
- 1975-06-04 IL IL47424A patent/IL47424A/xx unknown
- 1975-06-04 BG BG030188A patent/BG24812A3/xx unknown
- 1975-06-05 SU SU752140862A patent/SU613724A3/ru active
- 1975-06-05 AT AT427975A patent/AT344333B/de not_active IP Right Cessation
- 1975-06-05 ZA ZA3638A patent/ZA753638B/xx unknown
- 1975-06-05 YU YU01455/75A patent/YU145575A/xx unknown
- 1975-06-05 FR FR7517652A patent/FR2273542A1/fr active Granted
- 1975-06-05 BE BE1006709A patent/BE829887A/xx not_active IP Right Cessation
- 1975-06-05 RO RO7582445A patent/RO77543A/ro unknown
- 1975-06-06 CH CH731075A patent/CH617196A5/de not_active IP Right Cessation
- 1975-06-06 ES ES438313A patent/ES438313A1/es not_active Expired
- 1975-06-06 AR AR259118A patent/AR210736A1/es active
-
1976
- 1976-06-05 DD DD186472A patent/DD120438A5/xx unknown
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