AT327174B - Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen - Google Patents
Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzenInfo
- Publication number
- AT327174B AT327174B AT915174*7A AT915174A AT327174B AT 327174 B AT327174 B AT 327174B AT 915174 A AT915174 A AT 915174A AT 327174 B AT327174 B AT 327174B
- Authority
- AT
- Austria
- Prior art keywords
- group
- hydrogen
- acid addition
- new
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- -1 hydroxy, methyl Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PRJWYFPDHWJLEV-UHFFFAOYSA-N 2-methyl-4-phenylbutan-2-amine Chemical compound CC(C)(N)CCC1=CC=CC=C1 PRJWYFPDHWJLEV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2115926A DE2115926C3 (de) | 1971-04-01 | 1971-04-01 | 1 -(4-Hydroxy-3-dimethylaminosuIfamidophenyI)-2-aminoäthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT327174B true AT327174B (de) | 1976-01-26 |
Family
ID=5803592
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT915174*7A AT327174B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen |
| AT915174*1A ATA915174A (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen |
| AT284472A AT326628B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren säureadditionssalzen |
| AT00895/74A AT320613B (de) | 1971-04-01 | 1972-03-31 | Vzh von neuen sulfamiden |
| AT915074*7A AT327173B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen |
| AT89474*A AT321888B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamidensowie deren saeureadditionssalzen |
| AT89674*A AT321889B (de) | 1971-04-01 | 1974-03-31 | Verfahren zur herstellung von neuen sulfamidensowie deren saeureadditionssalzen |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT915174*1A ATA915174A (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen |
| AT284472A AT326628B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren säureadditionssalzen |
| AT00895/74A AT320613B (de) | 1971-04-01 | 1972-03-31 | Vzh von neuen sulfamiden |
| AT915074*7A AT327173B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamiden und deren saureadditionssalzen |
| AT89474*A AT321888B (de) | 1971-04-01 | 1972-03-31 | Verfahren zur herstellung von neuen sulfamidensowie deren saeureadditionssalzen |
| AT89674*A AT321889B (de) | 1971-04-01 | 1974-03-31 | Verfahren zur herstellung von neuen sulfamidensowie deren saeureadditionssalzen |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4038314A (en, 2012) |
| JP (3) | JPS5735193B1 (en, 2012) |
| AR (6) | AR204905A1 (en, 2012) |
| AT (7) | AT327174B (en, 2012) |
| AU (1) | AU470838B2 (en, 2012) |
| BE (1) | BE781542A (en, 2012) |
| CH (6) | CH580068A5 (en, 2012) |
| DE (1) | DE2115926C3 (en, 2012) |
| DK (1) | DK140836B (en, 2012) |
| ES (4) | ES401332A1 (en, 2012) |
| FI (1) | FI58325C (en, 2012) |
| FR (1) | FR2132372B1 (en, 2012) |
| GB (1) | GB1381184A (en, 2012) |
| IE (1) | IE36240B1 (en, 2012) |
| IL (1) | IL39110A (en, 2012) |
| NL (1) | NL170850C (en, 2012) |
| NO (1) | NO135247C (en, 2012) |
| PH (1) | PH14121A (en, 2012) |
| SE (1) | SE393106B (en, 2012) |
| ZA (1) | ZA722177B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1435721A (en) * | 1972-05-18 | 1976-05-12 | Lilly Industries Ltd | Benzoxazole derivatives |
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
| DE3220598A1 (de) * | 1982-06-01 | 1983-12-01 | Boehringer Ingelheim KG, 6507 Ingelheim | Lipolytische zusammensetzungen und mittel zur behandlung der fettsucht |
| GB8322178D0 (en) * | 1983-08-17 | 1983-09-21 | Sterwin Ag | Preparing aerosol compositions |
| GB8502892D0 (en) * | 1985-02-05 | 1985-03-06 | Sterwin Ag | Aerosol composition |
| NZ226934A (en) * | 1987-11-13 | 1991-01-29 | Glaxo Group Ltd | Phenethanolamine derivatives and pharmaceutical compositions |
| US20040127733A1 (en) | 2002-10-31 | 2004-07-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New beta-agonists, processes for preparing them and their use as pharmaceutical compositions |
| DE10251170A1 (de) * | 2002-10-31 | 2004-05-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102004021779A1 (de) | 2004-04-30 | 2005-11-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| DE102005052127A1 (de) | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue indol-haltige Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US7718822B2 (en) | 2007-08-28 | 2010-05-18 | Sepracor Inc. | Carbamate Stereoisomer |
| CN109535007A (zh) * | 2018-11-07 | 2019-03-29 | 万华化学集团股份有限公司 | 一种二氨基二环己基甲烷同分异构体分离方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3804834A (en) * | 1967-10-16 | 1974-04-16 | Boehringer Sohn Ingelheim | 1-(2',3',4'-trisubstituted-phenyl)-2-amino-alkanols-(1)and salts thereof |
| US3701808A (en) * | 1967-12-21 | 1972-10-31 | Allen & Hanburys Ltd | Phenylethanolamines |
| US3574741A (en) * | 1969-04-14 | 1971-04-13 | Mead Johnson & Co | Sulfonamidophenalkylamines |
| US3711545A (en) * | 1971-02-23 | 1973-01-16 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-sulfamoylaminobenzyl alcohols |
| BE794414A (fr) * | 1972-01-25 | 1973-07-23 | Sandoz Sa | Nouveaux amino-alcools, leur preparation et leur application comme medicament |
-
1971
- 1971-04-01 DE DE2115926A patent/DE2115926C3/de not_active Expired
-
1972
- 1972-01-01 AR AR244859A patent/AR204905A1/es active
- 1972-03-28 NO NO1061/72A patent/NO135247C/no unknown
- 1972-03-29 PH PH13398A patent/PH14121A/en unknown
- 1972-03-29 ES ES401332A patent/ES401332A1/es not_active Expired
- 1972-03-29 DK DK154772AA patent/DK140836B/da not_active IP Right Cessation
- 1972-03-29 IL IL39110A patent/IL39110A/xx unknown
- 1972-03-30 SE SE7204239A patent/SE393106B/xx unknown
- 1972-03-30 CH CH1390375A patent/CH580068A5/xx not_active IP Right Cessation
- 1972-03-30 CH CH1390275A patent/CH572905A5/xx not_active IP Right Cessation
- 1972-03-30 CH CH1647576A patent/CH587237A5/xx not_active IP Right Cessation
- 1972-03-30 CH CH1390475A patent/CH580069A5/xx not_active IP Right Cessation
- 1972-03-30 IE IE415/72A patent/IE36240B1/xx unknown
- 1972-03-30 FI FI915/72A patent/FI58325C/fi active
- 1972-03-30 GB GB1515672A patent/GB1381184A/en not_active Expired
- 1972-03-30 NL NLAANVRAGE7204316,A patent/NL170850C/xx not_active IP Right Cessation
- 1972-03-30 CH CH482372A patent/CH587236A5/xx not_active IP Right Cessation
- 1972-03-30 ZA ZA722177A patent/ZA722177B/xx unknown
- 1972-03-30 AU AU40592/72A patent/AU470838B2/en not_active Expired
- 1972-03-30 CH CH1056976A patent/CH590219A5/xx not_active IP Right Cessation
- 1972-03-31 BE BE781542A patent/BE781542A/xx not_active IP Right Cessation
- 1972-03-31 AT AT915174*7A patent/AT327174B/de active
- 1972-03-31 JP JP3180472A patent/JPS5735193B1/ja active Pending
- 1972-03-31 AT AT915174*1A patent/ATA915174A/de unknown
- 1972-03-31 AT AT284472A patent/AT326628B/de not_active IP Right Cessation
- 1972-03-31 AT AT00895/74A patent/AT320613B/de not_active IP Right Cessation
- 1972-03-31 AT AT915074*7A patent/AT327173B/de not_active IP Right Cessation
- 1972-03-31 FR FR7211614A patent/FR2132372B1/fr not_active Expired
- 1972-03-31 AT AT89474*A patent/AT321888B/de not_active IP Right Cessation
- 1972-10-27 AR AR244858A patent/AR200002A1/es active
- 1972-10-27 AR AR244860A patent/AR200116A1/es active
-
1973
- 1973-10-25 ES ES419936A patent/ES419936A1/es not_active Expired
- 1973-10-25 ES ES419934A patent/ES419934A1/es not_active Expired
- 1973-10-25 ES ES419935A patent/ES419935A1/es not_active Expired
- 1973-11-26 AR AR251170A patent/AR210055A1/es active
- 1973-11-26 AR AR251171A patent/AR209268A1/es active
- 1973-11-26 AR AR251169A patent/AR199809A1/es active
-
1974
- 1974-03-21 US US05/453,438 patent/US4038314A/en not_active Expired - Lifetime
- 1974-03-31 AT AT89674*A patent/AT321889B/de not_active IP Right Cessation
-
1981
- 1981-05-25 JP JP56078170A patent/JPS5929191B2/ja not_active Expired
- 1981-05-25 JP JP56078169A patent/JPS5929190B2/ja not_active Expired
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