CH513115A - Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanen - Google Patents
Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanenInfo
- Publication number
- CH513115A CH513115A CH333471A CH333471A CH513115A CH 513115 A CH513115 A CH 513115A CH 333471 A CH333471 A CH 333471A CH 333471 A CH333471 A CH 333471A CH 513115 A CH513115 A CH 513115A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- group
- formula
- carbon atoms
- compounds
- Prior art date
Links
- -1 alkylamino propanes Chemical class 0.000 title claims abstract description 27
- 208000001953 Hypotension Diseases 0.000 title abstract 2
- 208000021822 hypotensive Diseases 0.000 title abstract 2
- 230000001077 hypotensive effect Effects 0.000 title abstract 2
- 235000013849 propane Nutrition 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000005336 allyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- OCDHRUIARWXIBR-UHFFFAOYSA-N 2-[(2-prop-2-ynoxyphenoxy)methyl]oxirane Chemical compound C#CCOC1=CC=CC=C1OCC1OC1 OCDHRUIARWXIBR-UHFFFAOYSA-N 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000001294 propane Substances 0.000 description 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- SBLICTZXSBWZKD-UHFFFAOYSA-N 2-[2-hydroxy-3-(pentan-3-ylamino)propoxy]benzonitrile Chemical compound CCC(CC)NCC(O)COC1=CC=CC=C1C#N SBLICTZXSBWZKD-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- MFEDKMBNKNOUPA-UHFFFAOYSA-N (2-bromo-4,7-dimethyl-3-oxo-7-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(C)C(=O)C(Br)C1C2(CS(O)(=O)=O)C MFEDKMBNKNOUPA-UHFFFAOYSA-N 0.000 description 1
- QCSQDMYVUFIBAJ-UHFFFAOYSA-N 2-[2-hydroxy-3-(4-methylpentan-2-ylamino)propoxy]benzonitrile Chemical compound CC(C)CC(C)NCC(O)COC1=CC=CC=C1C#N QCSQDMYVUFIBAJ-UHFFFAOYSA-N 0.000 description 1
- XZGVKQFFWXMHGH-UHFFFAOYSA-N 2-[3-(butan-2-ylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCC(C)NCC(O)COC1=CC=CC=C1C#N XZGVKQFFWXMHGH-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CEZIEIZBVCMDTD-UHFFFAOYSA-N C(#N)C1=C(OCC(CNC(CC(C)(C)C)C)O)C=CC=C1 Chemical compound C(#N)C1=C(OCC(CNC(CC(C)(C)C)C)O)C=CC=C1 CEZIEIZBVCMDTD-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- 239000000150 Sympathomimetic Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/04—Nitro compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0095902 | 1967-12-18 | ||
| DEB0095988 | 1967-12-22 | ||
| CH1874168A CH512427A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513115A true CH513115A (de) | 1971-09-30 |
Family
ID=27177740
Family Applications (10)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH333471A CH513115A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanen |
| CH333871A CH553745A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur herstellung von neuen racemischen oder optisch aktiven 1-phenoxy-2-hydroxy-3-sec.alkylaminopropanen. |
| CH33971A CH513118A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.alkylaminopropanen |
| CH334071A CH526511A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
| CH333771A CH513812A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
| CH333571A CH513116A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanen |
| CH1128871A CH559718A5 (enrdf_load_stackoverflow) | 1967-12-18 | 1968-12-17 | |
| CH333671A CH513117A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.alkylaminopropanen |
| CH1128771A CH583174A5 (enrdf_load_stackoverflow) | 1967-12-18 | 1968-12-17 | |
| CH334171A CH513813A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
Family Applications After (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH333871A CH553745A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur herstellung von neuen racemischen oder optisch aktiven 1-phenoxy-2-hydroxy-3-sec.alkylaminopropanen. |
| CH33971A CH513118A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.alkylaminopropanen |
| CH334071A CH526511A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
| CH333771A CH513812A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
| CH333571A CH513116A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec. -alkylaminopropanen |
| CH1128871A CH559718A5 (enrdf_load_stackoverflow) | 1967-12-18 | 1968-12-17 | |
| CH333671A CH513117A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.alkylaminopropanen |
| CH1128771A CH583174A5 (enrdf_load_stackoverflow) | 1967-12-18 | 1968-12-17 | |
| CH334171A CH513813A (de) | 1967-12-18 | 1968-12-17 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Phenoxy-2-hydroxy-3-sec.-alkylaminopropanen |
Country Status (1)
| Country | Link |
|---|---|
| CH (10) | CH513115A (enrdf_load_stackoverflow) |
-
1968
- 1968-12-17 CH CH333471A patent/CH513115A/de not_active IP Right Cessation
- 1968-12-17 CH CH333871A patent/CH553745A/xx not_active IP Right Cessation
- 1968-12-17 CH CH33971A patent/CH513118A/de not_active IP Right Cessation
- 1968-12-17 CH CH334071A patent/CH526511A/de not_active IP Right Cessation
- 1968-12-17 CH CH333771A patent/CH513812A/de not_active IP Right Cessation
- 1968-12-17 CH CH333571A patent/CH513116A/de not_active IP Right Cessation
- 1968-12-17 CH CH1128871A patent/CH559718A5/xx not_active IP Right Cessation
- 1968-12-17 CH CH333671A patent/CH513117A/de not_active IP Right Cessation
- 1968-12-17 CH CH1128771A patent/CH583174A5/xx not_active IP Right Cessation
- 1968-12-17 CH CH334171A patent/CH513813A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH513117A (de) | 1971-09-30 |
| CH513116A (de) | 1971-09-30 |
| CH526511A (de) | 1972-08-15 |
| CH513813A (de) | 1971-10-15 |
| CH559718A5 (enrdf_load_stackoverflow) | 1975-03-14 |
| CH513812A (de) | 1971-10-15 |
| CH583174A5 (enrdf_load_stackoverflow) | 1976-12-31 |
| CH513118A (de) | 1971-09-30 |
| CH553745A (de) | 1974-09-13 |
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