CA1062717A - 1-aryloxy-2-hydroxy-3-alkinylaminopropanes and processes for production thereof - Google Patents
1-aryloxy-2-hydroxy-3-alkinylaminopropanes and processes for production thereofInfo
- Publication number
- CA1062717A CA1062717A CA193,683A CA193683A CA1062717A CA 1062717 A CA1062717 A CA 1062717A CA 193683 A CA193683 A CA 193683A CA 1062717 A CA1062717 A CA 1062717A
- Authority
- CA
- Canada
- Prior art keywords
- group
- carbon atoms
- formula
- compounds
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 63
- 230000008569 process Effects 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 29
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 36
- -1 cyano, amino Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000001475 halogen functional group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 claims description 5
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 8
- 231100000252 nontoxic Toxicity 0.000 claims 4
- 230000003000 nontoxic effect Effects 0.000 claims 4
- 239000012458 free base Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000002140 halogenating effect Effects 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 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 2
- BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 claims 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical group [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 5
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- AEPFLTPVMYFQQQ-UHFFFAOYSA-N 2-(5-amino-2-hydroxy-5-methylhept-6-ynoxy)benzonitrile Chemical compound C(#N)C1=C(OCC(CCC(C#C)(C)N)O)C=CC=C1 AEPFLTPVMYFQQQ-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2309887A DE2309887C2 (de) | 1973-02-28 | 1973-02-28 | 1-Aryloxy-2-hydroxy-3-alkinylaminopropan-Derivate und deren physiologisch verträgliche Säureadditionssalze, pharmazeutische Präparate und Herstellungsverfahren für die Verbindungen |
| DE19742403809 DE2403809C2 (de) | 1974-01-26 | 1974-01-26 | 1-Aryloxy-2-hydroxy-3-alkinylaminopropane und Verfahren zu ihrer Herstellung und pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062717A true CA1062717A (en) | 1979-09-18 |
Family
ID=25764753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA193,683A Expired CA1062717A (en) | 1973-02-28 | 1974-02-27 | 1-aryloxy-2-hydroxy-3-alkinylaminopropanes and processes for production thereof |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3925446A (en, 2012) |
| JP (1) | JPS594417B2 (en, 2012) |
| AT (1) | AT330150B (en, 2012) |
| BG (7) | BG20565A3 (en, 2012) |
| CA (1) | CA1062717A (en, 2012) |
| CH (7) | CH605689A5 (en, 2012) |
| CS (1) | CS186263B2 (en, 2012) |
| DD (1) | DD110652A5 (en, 2012) |
| DK (1) | DK143128C (en, 2012) |
| ES (7) | ES423466A1 (en, 2012) |
| FI (1) | FI62054C (en, 2012) |
| FR (1) | FR2218900B1 (en, 2012) |
| GB (1) | GB1450287A (en, 2012) |
| HU (1) | HU168598B (en, 2012) |
| IE (1) | IE39482B1 (en, 2012) |
| IL (1) | IL44301A (en, 2012) |
| MX (2) | MX4592E (en, 2012) |
| NL (1) | NL169733C (en, 2012) |
| NO (1) | NO138062C (en, 2012) |
| PH (1) | PH9722A (en, 2012) |
| PL (2) | PL91560B1 (en, 2012) |
| SE (1) | SE411897B (en, 2012) |
| SU (1) | SU793381A3 (en, 2012) |
| YU (2) | YU50074A (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038313A (en) * | 1970-01-08 | 1977-07-26 | Ciba-Geigy Corporation | Cycloalkylureido phenoxy propanolamines |
| US4035420A (en) * | 1972-07-06 | 1977-07-12 | Aktiebolaget Hassle | Substituted ureido alkylene phenoxy propanolamines |
| US4078146A (en) * | 1972-07-06 | 1978-03-07 | Aktiebolaget Hassle | Phenoxy propanolamines |
| GB1374366A (en) * | 1972-07-21 | 1974-11-20 | Science Union & Cie | Propanol derivatives and a process for their preparation |
| AT334385B (de) * | 1973-12-20 | 1976-01-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| US4243681A (en) * | 1977-10-11 | 1981-01-06 | Mead Johnson & Company | Alkylthiophenoxypropanolamines and pharmaceutical compositions and uses thereof |
| DE2805404A1 (de) * | 1978-02-09 | 1979-08-16 | Merck Patent Gmbh | 1-aryloxy-3-nitratoalkylamino-2-propanole und verfahren zu ihrer herstellung |
| DE3009047A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
| DE3009036A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
| US4387103A (en) * | 1980-11-28 | 1983-06-07 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3248835A1 (de) * | 1981-06-23 | 1983-06-30 | American Hospital Supply Corp | Zusammensetzungen fuer die behandlung von glaukom |
| US4559359A (en) * | 1981-06-23 | 1985-12-17 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4455317A (en) * | 1981-06-23 | 1984-06-19 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4578403A (en) * | 1981-06-23 | 1986-03-25 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3133719A1 (de) * | 1981-08-26 | 1983-03-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue 1-aryloxy-3-alkinylamino-2-propanole und verfahren zu ihrer herstellung |
| JPH02130007U (en, 2012) * | 1989-03-31 | 1990-10-26 | ||
| BRPI0507670A (pt) * | 2004-02-13 | 2007-07-17 | Warner Lambert Co | moduladores do receptor de androgênio |
| JP5838114B2 (ja) | 2012-04-02 | 2015-12-24 | 株式会社リガク | Ｘ線トポグラフィ装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459782A (en) * | 1963-08-26 | 1969-08-05 | Boehringer Sohn Ingelheim | 1-substituted phenoxy-2-hydroxy-3-isopropylamino-propanes |
| GB1199037A (en) * | 1967-09-27 | 1970-07-15 | Ici Ltd | Alkanolamine Derivatives |
| US3541130A (en) * | 1967-02-06 | 1970-11-17 | Boehringer Sohn Ingelheim | 1-(cyanophenoxy)-2-hydroxy-3-tert.-butylamine propanes |
-
1974
- 1974-02-11 AT AT104774A patent/AT330150B/de not_active IP Right Cessation
- 1974-02-21 ES ES423466A patent/ES423466A1/es not_active Expired
- 1974-02-22 US US444713A patent/US3925446A/en not_active Expired - Lifetime
- 1974-02-25 CS CS7400001369A patent/CS186263B2/cs unknown
- 1974-02-25 FI FI544/74A patent/FI62054C/fi active
- 1974-02-26 DD DD176809A patent/DD110652A5/xx unknown
- 1974-02-26 BG BG026942A patent/BG20565A3/xx unknown
- 1974-02-26 BG BG026943A patent/BG20566A3/xx unknown
- 1974-02-26 HU HUBO1487A patent/HU168598B/hu unknown
- 1974-02-26 BG BG026941A patent/BG20335A3/xx unknown
- 1974-02-26 BG BG026939A patent/BG21208A3/xx unknown
- 1974-02-26 BG BG026940A patent/BG21394A3/xx unknown
- 1974-02-26 BG BG025901A patent/BG20564A3/xx unknown
- 1974-02-26 BG BG026938A patent/BG20334A3/xx unknown
- 1974-02-27 CH CH1485677A patent/CH605689A5/xx not_active IP Right Cessation
- 1974-02-27 YU YU00500/74A patent/YU50074A/xx unknown
- 1974-02-27 CH CH1485577A patent/CH605638A5/xx not_active IP Right Cessation
- 1974-02-27 NO NO740670A patent/NO138062C/no unknown
- 1974-02-27 MX MX745493U patent/MX4592E/es unknown
- 1974-02-27 PL PL1974169115A patent/PL91560B1/pl unknown
- 1974-02-27 CH CH1486077A patent/CH605691A5/xx not_active IP Right Cessation
- 1974-02-27 MX MX745489U patent/MX4588E/es unknown
- 1974-02-27 DK DK105174A patent/DK143128C/da not_active IP Right Cessation
- 1974-02-27 CH CH278074A patent/CH605636A5/xx not_active IP Right Cessation
- 1974-02-27 CH CH1485477A patent/CH605637A5/xx not_active IP Right Cessation
- 1974-02-27 CA CA193,683A patent/CA1062717A/en not_active Expired
- 1974-02-27 SE SE7402622A patent/SE411897B/sv not_active IP Right Cessation
- 1974-02-27 PL PL1974183356A patent/PL93591B1/pl unknown
- 1974-02-27 GB GB894974A patent/GB1450287A/en not_active Expired
- 1974-02-27 PH PH15555*UA patent/PH9722A/en unknown
- 1974-02-27 JP JP49023221A patent/JPS594417B2/ja not_active Expired
- 1974-02-27 CH CH1485977A patent/CH605690A5/xx not_active IP Right Cessation
- 1974-02-27 IL IL44301A patent/IL44301A/en unknown
- 1974-02-28 IE IE428/74A patent/IE39482B1/xx unknown
- 1974-02-28 FR FR7406835A patent/FR2218900B1/fr not_active Expired
- 1974-02-28 NL NLAANVRAGE7402704,A patent/NL169733C/xx not_active IP Right Cessation
- 1974-08-27 CH CH1485877A patent/CH605639A5/xx not_active IP Right Cessation
-
1975
- 1975-01-29 SU SU752100046A patent/SU793381A3/ru active
- 1975-04-04 ES ES436316A patent/ES436316A1/es not_active Expired
- 1975-04-04 ES ES436311A patent/ES436311A1/es not_active Expired
- 1975-04-04 ES ES436315A patent/ES436315A1/es not_active Expired
- 1975-04-04 ES ES436313A patent/ES436313A1/es not_active Expired
- 1975-04-04 ES ES436314A patent/ES436314A1/es not_active Expired
- 1975-04-04 ES ES436312A patent/ES436312A1/es not_active Expired
-
1980
- 1980-04-22 YU YU01095/80A patent/YU109580A/xx unknown
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