CH495950A - Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren Salzen - Google Patents
Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren SalzenInfo
- Publication number
- CH495950A CH495950A CH876668A CH876668A CH495950A CH 495950 A CH495950 A CH 495950A CH 876668 A CH876668 A CH 876668A CH 876668 A CH876668 A CH 876668A CH 495950 A CH495950 A CH 495950A
- Authority
- CH
- Switzerland
- Prior art keywords
- tert
- hydroxy
- compounds
- formula
- optically active
- Prior art date
Links
- 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
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- WSABLXKFAPKFSO-UHFFFAOYSA-N 1,3-ditert-butylurea Chemical compound CC(C)(C)NC(=O)NC(C)(C)C WSABLXKFAPKFSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NSFIAKFOCAEBER-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 230000000059 bradycardiac effect Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HZBOQOXQPRQKTF-UHFFFAOYSA-N bis(4-methylphenyl) 2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1OC(=O)C(O)C(O)C(=O)OC1=CC=C(C)C=C1 HZBOQOXQPRQKTF-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- -1 toluyl tartaric acid Chemical compound 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-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
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JDSHWUSBLSNDSV-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(CCC)NCCC Chemical compound C(C(=O)O)(=O)O.C(CCC)NCCC JDSHWUSBLSNDSV-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
- 239000004593 Epoxy Substances 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
- 208000001871 Tachycardia Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000001778 cardiodepressive effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 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
- 239000012452 mother liquor Substances 0.000 description 1
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- UFNAECVCKNHAKN-UHFFFAOYSA-N pargolol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1OCC#C UFNAECVCKNHAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
-
- 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
- A61K31/13—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
- A61K31/275—Nitriles; Isonitriles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1168070A CH510629A (de) | 1967-06-15 | 1968-06-13 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
| CH1168170A CH509973A (de) | 1967-06-15 | 1968-06-13 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren Salzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967B0093025 DE1593782B2 (de) | 1967-06-15 | 1967-06-15 | 1-nitrilophenoxy- 2- hydroxy -3- tert.butylaminopropane, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495950A true CH495950A (de) | 1970-09-15 |
Family
ID=6986720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH876668A CH495950A (de) | 1967-06-15 | 1968-06-13 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren Salzen |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS51100B1 (en, 2012) |
| AT (8) | AT289081B (en, 2012) |
| BE (1) | BE716647A (en, 2012) |
| BG (6) | BG15038A3 (en, 2012) |
| CH (1) | CH495950A (en, 2012) |
| DE (1) | DE1593782B2 (en, 2012) |
| DK (1) | DK127059B (en, 2012) |
| ES (6) | ES354823A1 (en, 2012) |
| FI (1) | FI48922C (en, 2012) |
| FR (2) | FR1583559A (en, 2012) |
| GB (1) | GB1187546A (en, 2012) |
| IE (1) | IE32373B1 (en, 2012) |
| IL (1) | IL30181A (en, 2012) |
| MY (1) | MY7300288A (en, 2012) |
| NL (2) | NL6808196A (en, 2012) |
| SE (1) | SE355571B (en, 2012) |
| YU (7) | YU33779B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3937834A (en) | 1970-10-02 | 1976-02-10 | Ciba-Geigy Corporation | Pharmaceutical preparations |
| JPS57125772U (en, 2012) * | 1981-01-30 | 1982-08-05 | ||
| DE3744371A1 (de) * | 1987-12-29 | 1989-07-13 | Jacobs Suchard Ag | Verpackung fuer suesswaren |
| DE4014252A1 (de) * | 1990-05-04 | 1991-11-07 | Boehringer Ingelheim Vetmed | Enantiomerentrennung von cimaterol, (-)-cimaterol und dessen verwendung als arzneimittel oder als leistungsfoerderer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301580A (en, 2012) * | 1962-12-11 |
-
0
- NL NL136601D patent/NL136601C/xx active
-
1967
- 1967-06-15 DE DE1967B0093025 patent/DE1593782B2/de active Granted
- 1967-06-17 FR FR1583559D patent/FR1583559A/fr not_active Expired
-
1968
- 1968-06-05 JP JP43038048A patent/JPS51100B1/ja active Pending
- 1968-06-08 ES ES354823A patent/ES354823A1/es not_active Expired
- 1968-06-11 NL NL6808196A patent/NL6808196A/xx unknown
- 1968-06-13 SE SE07980/68A patent/SE355571B/xx unknown
- 1968-06-13 CH CH876668A patent/CH495950A/de not_active IP Right Cessation
- 1968-06-14 AT AT248270A patent/AT289081B/de active
- 1968-06-14 AT AT572568A patent/AT289067B/de not_active IP Right Cessation
- 1968-06-14 AT AT248170A patent/AT289080B/de active
- 1968-06-14 GB GB28529/68A patent/GB1187546A/en not_active Expired
- 1968-06-14 AT AT248370A patent/AT289082B/de not_active IP Right Cessation
- 1968-06-14 AT AT248070A patent/AT289079B/de active
- 1968-06-14 AT AT247870A patent/AT289077B/de active
- 1968-06-14 AT AT247970A patent/AT289078B/de not_active IP Right Cessation
- 1968-06-14 DK DK281968AA patent/DK127059B/da not_active IP Right Cessation
- 1968-06-14 FI FI681664A patent/FI48922C/fi active
- 1968-06-14 IL IL6830181A patent/IL30181A/xx unknown
- 1968-06-14 BE BE716647D patent/BE716647A/xx not_active IP Right Cessation
- 1968-06-14 AT AT247770A patent/AT289076B/de not_active IP Right Cessation
- 1968-06-14 IE IE710/68A patent/IE32373B1/xx unknown
- 1968-06-15 BG BG011628A patent/BG15038A3/bg unknown
- 1968-06-15 BG BG011630A patent/BG15040A3/bg unknown
- 1968-06-15 BG BG011631A patent/BG15041A3/bg unknown
- 1968-06-15 BG BG011629A patent/BG15039A3/bg unknown
- 1968-06-15 BG BG011632A patent/BG15042A3/bg unknown
- 1968-06-15 BG BG011627A patent/BG15037A3/bg unknown
- 1968-09-17 FR FR166464A patent/FR8162M/fr not_active Expired
-
1969
- 1969-06-16 ES ES69368396A patent/ES368396A1/es not_active Expired
- 1969-06-16 ES ES368401A patent/ES368401A1/es not_active Expired
- 1969-06-16 ES ES368395A patent/ES368395A1/es not_active Expired
- 1969-06-16 ES ES368399A patent/ES368399A1/es not_active Expired
- 1969-06-16 ES ES368398A patent/ES368398A1/es not_active Expired
-
1973
- 1973-12-31 MY MY1973288A patent/MY7300288A/xx unknown
-
1974
- 1974-08-21 YU YU2292/74A patent/YU33779B/xx unknown
- 1974-08-21 YU YU2288/74A patent/YU33775B/xx unknown
- 1974-08-21 YU YU2291/74A patent/YU33778B/xx unknown
- 1974-08-21 YU YU2290/74A patent/YU33777B/xx unknown
- 1974-08-21 YU YU2293/74A patent/YU35578B/xx unknown
- 1974-08-21 YU YU2289/74A patent/YU33776B/xx unknown
- 1974-08-21 YU YU2294/74A patent/YU33780B/xx unknown
- 1974-10-17 JP JP49119881A patent/JPS5112613B1/ja active Pending
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