CH510631A - Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen - Google Patents
Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanenInfo
- Publication number
- CH510631A CH510631A CH1373770A CH1373770A CH510631A CH 510631 A CH510631 A CH 510631A CH 1373770 A CH1373770 A CH 1373770A CH 1373770 A CH1373770 A CH 1373770A CH 510631 A CH510631 A CH 510631A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- alkyl
- group
- phenoxy
- adrenolytics
- Prior art date
Links
- 208000001953 Hypotension Diseases 0.000 title abstract 3
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract 3
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract 3
- 208000021822 hypotensive Diseases 0.000 title abstract 3
- 230000002959 anti-hypotensive effect Effects 0.000 title abstract 2
- -1 phenoxy hydroxy Chemical group 0.000 title description 11
- 230000001077 hypotensive effect Effects 0.000 title 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- TYXJXOCZTIPTFO-UHFFFAOYSA-N 1-(tert-butylamino)-3-[3-(hydroxymethyl)phenoxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC(CO)=C1 TYXJXOCZTIPTFO-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VFLPZPDGVMHHNJ-UHFFFAOYSA-N 3-[2-hydroxy-3-(propan-2-ylamino)propoxy]-4-methoxybenzonitrile Chemical compound COC1=C(OCC(CNC(C)C)O)C=C(C=C1)C#N VFLPZPDGVMHHNJ-UHFFFAOYSA-N 0.000 description 2
- QAIHVGXGYVRHCY-UHFFFAOYSA-N 3-methoxy-4-(oxiran-2-ylmethoxy)benzonitrile Chemical compound COC1=CC(C#N)=CC=C1OCC1OC1 QAIHVGXGYVRHCY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WOFJRZLKWHCFCL-UHFFFAOYSA-N [3-(oxiran-2-ylmethoxy)phenyl]methanol Chemical compound OCC1=CC=CC(OCC2OC2)=C1 WOFJRZLKWHCFCL-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- CDNNMNLILHWPMH-UHFFFAOYSA-N methyl 2-(oxiran-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1OC1 CDNNMNLILHWPMH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 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
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- SCLDWGHNIIKRGZ-UHFFFAOYSA-N 1-(2-amino-5-methoxyphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound NC1=C(OCC(CNC(C)C)O)C=C(C=C1)OC SCLDWGHNIIKRGZ-UHFFFAOYSA-N 0.000 description 1
- IJOZLEKFOBXYFP-UHFFFAOYSA-N 1-[2-(aminomethyl)-4-chlorophenoxy]-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C(Cl)C=C1CN IJOZLEKFOBXYFP-UHFFFAOYSA-N 0.000 description 1
- WGJVNJGGPWONPI-UHFFFAOYSA-N 1-[2-(hydroxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CO WGJVNJGGPWONPI-UHFFFAOYSA-N 0.000 description 1
- YRSLUHURHMRNES-UHFFFAOYSA-N 1-[3-(aminomethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound NCC=1C=C(OCC(CNC(C)C)O)C=CC1 YRSLUHURHMRNES-UHFFFAOYSA-N 0.000 description 1
- KRTIALANBMISKJ-UHFFFAOYSA-N 1-[3-(hydroxymethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(CO)=C1 KRTIALANBMISKJ-UHFFFAOYSA-N 0.000 description 1
- GBFAXKYFMYXKAC-UHFFFAOYSA-N 1-[4-(aminomethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound NCC1=CC=C(OCC(CNC(C)C)O)C=C1 GBFAXKYFMYXKAC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- WOIUAXCQCROIIH-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methoxybenzonitrile Chemical compound COC1=C(OCC(CNC(C)C)O)C(=CC=C1)C#N WOIUAXCQCROIIH-UHFFFAOYSA-N 0.000 description 1
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- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NZIYLLHOEIBFDE-UHFFFAOYSA-N methyl 2-[3-(tert-butylamino)-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(O)CNC(C)(C)C NZIYLLHOEIBFDE-UHFFFAOYSA-N 0.000 description 1
- GVMPCQYYYYFGMV-UHFFFAOYSA-N methyl 4-(oxiran-2-ylmethoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCC1OC1 GVMPCQYYYYFGMV-UHFFFAOYSA-N 0.000 description 1
- SZAYMQLNVXIKNC-UHFFFAOYSA-N methyl 4-[3-(tert-butylamino)-2-hydroxypropoxy]benzoate Chemical compound COC(=O)C1=CC=C(OCC(O)CNC(C)(C)C)C=C1 SZAYMQLNVXIKNC-UHFFFAOYSA-N 0.000 description 1
- OKRJGUKZYSEUOY-UHFFFAOYSA-N n-propan-2-ylbutan-1-amine Chemical group CCCCNC(C)C OKRJGUKZYSEUOY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 238000001556 precipitation Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 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
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-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
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
- A61K31/14—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
-
- 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
- A61K31/185—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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0091070 | 1967-02-06 | ||
| CH153968A CH506482A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH510631A true CH510631A (de) | 1971-07-31 |
Family
ID=6985633
Family Applications (10)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1373770A CH510631A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374370A CH511212A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374070A CH510634A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374470A CH510636A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374170A CH510635A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1373870A CH510632A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH153968A CH506482A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374570A CH510637A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374270A CH521310A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1373970A CH510633A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
Family Applications After (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1374370A CH511212A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374070A CH510634A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374470A CH510636A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374170A CH510635A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1373870A CH510632A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH153968A CH506482A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374570A CH510637A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1374270A CH521310A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
| CH1373970A CH510633A (de) | 1967-02-06 | 1968-02-01 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE710400A (cs) |
| BG (2) | BG15028A3 (cs) |
| CH (10) | CH510631A (cs) |
| DE (1) | DE1593762A1 (cs) |
| ES (9) | ES349847A1 (cs) |
| FI (1) | FI49496C (cs) |
| FR (2) | FR1566349A (cs) |
| GB (1) | GB1227480A (cs) |
| IE (1) | IE32353B1 (cs) |
| IL (1) | IL29416A (cs) |
| NL (2) | NL139236B (cs) |
| SE (1) | SE359292B (cs) |
| YU (4) | YU32762B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA945172A (en) * | 1969-02-21 | 1974-04-09 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| JPS4875539A (cs) * | 1972-01-12 | 1973-10-11 | ||
| JPS49245A (cs) * | 1972-04-17 | 1974-01-05 | ||
| DE2839475A1 (de) * | 1978-09-11 | 1980-03-20 | Dolorgiet Arzneimittelfabrik | Isopropylamin-verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| 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 |
| DE3407695A1 (de) * | 1984-03-02 | 1985-09-12 | Röhm Pharma GmbH, 6108 Weiterstadt | Pteridinverbindungen mit pharmazeutischer wirksamkeit |
| US4665094A (en) * | 1985-08-29 | 1987-05-12 | Merck & Co., Inc. | Oculoselective beta-blockers for treatment of elevated intraocular pressure |
-
1967
- 1967-02-06 DE DE19671593762 patent/DE1593762A1/de active Pending
-
1968
- 1968-01-27 ES ES349847A patent/ES349847A1/es not_active Expired
- 1968-02-01 CH CH1373770A patent/CH510631A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374370A patent/CH511212A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374070A patent/CH510634A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374470A patent/CH510636A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374170A patent/CH510635A/de not_active IP Right Cessation
- 1968-02-01 CH CH1373870A patent/CH510632A/de not_active IP Right Cessation
- 1968-02-01 CH CH153968A patent/CH506482A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374570A patent/CH510637A/de not_active IP Right Cessation
- 1968-02-01 CH CH1374270A patent/CH521310A/de not_active IP Right Cessation
- 1968-02-01 CH CH1373970A patent/CH510633A/de not_active IP Right Cessation
- 1968-02-05 YU YU0252/68*7A patent/YU32762B/xx unknown
- 1968-02-05 IL IL6829416A patent/IL29416A/xx unknown
- 1968-02-06 NL NL686801661A patent/NL139236B/xx unknown
- 1968-02-06 BG BG011427A patent/BG15028A3/bg unknown
- 1968-02-06 SE SE01539/68A patent/SE359292B/xx unknown
- 1968-02-06 BG BG011429A patent/BG15030A3/bg unknown
- 1968-02-06 IE IE152/68A patent/IE32353B1/xx unknown
- 1968-02-06 BE BE710400D patent/BE710400A/xx unknown
- 1968-02-06 GB GB1227480D patent/GB1227480A/en not_active Expired
- 1968-02-06 FR FR1566349D patent/FR1566349A/fr not_active Expired
- 1968-02-06 FI FI680290A patent/FI49496C/fi active
- 1968-02-06 FR FR138848A patent/FR8040M/fr not_active Expired
-
1969
- 1969-07-15 ES ES69369544A patent/ES369544A1/es not_active Expired
- 1969-07-15 ES ES369539A patent/ES369539A1/es not_active Expired
- 1969-07-15 ES ES369540A patent/ES369540A1/es not_active Expired
- 1969-07-15 ES ES369537A patent/ES369537A1/es not_active Expired
- 1969-07-15 ES ES69369543A patent/ES369543A1/es not_active Expired
- 1969-07-15 ES ES369538A patent/ES369538A1/es not_active Expired
- 1969-07-15 ES ES369541A patent/ES369541A1/es not_active Expired
- 1969-07-15 ES ES369542A patent/ES369542A1/es not_active Expired
-
1973
- 1973-02-08 NL NL7301803A patent/NL7301803A/xx unknown
- 1973-06-05 YU YU1493/73A patent/YU32761B/xx unknown
- 1973-06-05 YU YU01494/73A patent/YU149473A/xx unknown
- 1973-06-05 YU YU1498/73A patent/YU32763B/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |