DE1593782B2 - 1-nitrilophenoxy- 2- hydroxy -3- tert.butylaminopropane, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate - Google Patents
1-nitrilophenoxy- 2- hydroxy -3- tert.butylaminopropane, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparateInfo
- Publication number
- DE1593782B2 DE1593782B2 DE1967B0093025 DEB0093025A DE1593782B2 DE 1593782 B2 DE1593782 B2 DE 1593782B2 DE 1967B0093025 DE1967B0093025 DE 1967B0093025 DE B0093025 A DEB0093025 A DE B0093025A DE 1593782 B2 DE1593782 B2 DE 1593782B2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- tert
- choh
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 tert-butyl halide Chemical class 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- 238000000297 Sandmeyer reaction Methods 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000003944 halohydrins Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 150000004707 phenolate Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 description 1
- OVBICQMTCPFEBS-SATRDZAXSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bi Chemical compound CC(O)=O.CC(O)=O.C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OVBICQMTCPFEBS-SATRDZAXSA-N 0.000 description 1
- WSABLXKFAPKFSO-UHFFFAOYSA-N 1,3-ditert-butylurea Chemical compound CC(C)(C)NC(=O)NC(C)(C)C WSABLXKFAPKFSO-UHFFFAOYSA-N 0.000 description 1
- BLOZPOZETDEMRB-UHFFFAOYSA-N 1-(4-aminophenoxy)-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C(N)C=C1 BLOZPOZETDEMRB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-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
- LJQGARKSJMMQBX-UHFFFAOYSA-N 2-methyl-n-propylpropan-2-amine Chemical compound CCCNC(C)(C)C LJQGARKSJMMQBX-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 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
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 108700032141 ganirelix Proteins 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NXQMNKUGGYNLBY-UHFFFAOYSA-N toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 description 1
- 229950000245 toliprolol Drugs 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 (59)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL136601D NL136601C (en, 2012) | 1967-06-15 | ||
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 |
FR1583559D FR1583559A (en, 2012) | 1967-06-15 | 1967-06-17 | |
US700376A US3541130A (en) | 1967-02-06 | 1968-01-25 | 1-(cyanophenoxy)-2-hydroxy-3-tert.-butylamine propanes |
JP43038048A JPS51100B1 (en, 2012) | 1967-06-15 | 1968-06-05 | |
ES354823A ES354823A1 (es) | 1967-06-15 | 1968-06-08 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi-3-ter-butilamino propanos sustituidos. |
NL6808196A NL6808196A (en, 2012) | 1967-06-15 | 1968-06-11 | |
YU135068A YU33262B (en) | 1967-06-15 | 1968-06-12 | Postopek za pripravo novih substiturnih 1-fenoksi -2-hidroksi-3-terc. butilamino-propanov |
SE07980/68A SE355571B (en, 2012) | 1967-06-15 | 1968-06-13 | |
CH1167570A CH509253A (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 |
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 |
CH1167670A CH509254A (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 |
CH1167970A CH509257A (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 |
CH1167770A CH509255A (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 |
CH1167870A CH509256A (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 |
IE710/68A IE32373B1 (en) | 1967-06-15 | 1968-06-14 | Propanolamine derivatives |
BE716647D BE716647A (en, 2012) | 1967-06-15 | 1968-06-14 | |
AT572568A AT289067B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
GB28529/68A GB1187546A (en) | 1967-06-15 | 1968-06-14 | Propanolamine derivatives |
DK281968AA DK127059B (da) | 1967-06-15 | 1968-06-14 | Analogifremgangsmåde til fremstilling af substituerede 1-phenoxy-2-hydroxy-3-tert.butylaminopropaner eller salte heraf eller de tilsvarende optisk aktive antipoder. |
IL6830181A IL30181A (en) | 1967-06-15 | 1968-06-14 | 1-(substituted phenoxy)-2-hydroxy-3-tertiary butylaminopropanes,their preparation and pharmaceutical compositions containing them |
AT247870A AT289077B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
AT247770A AT289076B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
AT248170A AT289080B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
FI681664A FI48922C (fi) | 1967-06-15 | 1968-06-14 | Menetelmä farmaseuttisesti vaikuttavien uusien, sekä raseemisten että optisesti aktiivisten substituoitujen 1-fenoksi-2-hydroksi-3-tert.buty yliaminopropaanien ja niiden suolojen valmistamiseksi. |
AT248270A AT289081B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
AT247970A AT289078B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy- oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.butylaminopropanen und deren Salzen |
AT248370A AT289082B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren Salzen |
AT248070A AT289079B (de) | 1967-06-15 | 1968-06-14 | Verfahren zur Herstellung von neuen racemischen oder optisch aktiven 1-Nitrilophenoxy-oder 1-Alkinyloxyphenoxy-2-hydroxy-3-tert.-butylaminopropanen und deren Salzen |
BG011628A BG15038A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови заместени 1-фенокси -2- хидрокси -3- терц.бутиламинопропани и техните соли |
BG011627A BG15037A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови заместени 1-фенокси-2-хидрокси- -3-терц. бутиламинопропани и техните соли |
BG011632A BG15042A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови-заместени 1-фенокси-2-хидрокси-3-терц. бутиламино пропани и техните соли |
BG011631A BG15041A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови заместени 1-фенокси 2-хидрокси-3-терц. бутиламино-пропани и техните соли |
BG011629A BG15039A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови заместени 1-фенокси-2-хидрокси- -3-терц.бутиламинопропани и техните соли |
BG011630A BG15040A3 (bg) | 1967-06-15 | 1968-06-15 | Метод за получаване на нови заместени 1-фенокси-2-хидрокси -3-терц.бутиламинопропани и техните соли |
FR166464A FR8162M (en, 2012) | 1967-06-15 | 1968-09-17 | |
ES368395A ES368395A1 (es) | 1967-06-15 | 1969-06-16 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi - 3-ter-butilaminopropanos sustituidos. |
ES368401A ES368401A1 (es) | 1967-06-15 | 1969-06-16 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi - 3-ter-butilaminopropanos sustituidos. |
ES368398A ES368398A1 (es) | 1967-06-15 | 1969-06-16 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi - 3-ter-butilaminopropanos sustituidos. |
ES69368396A ES368396A1 (es) | 1967-06-15 | 1969-06-16 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi - 3-ter-butilaminopropanos sustituidos. |
ES368399A ES368399A1 (es) | 1967-06-15 | 1969-06-16 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi - 3-ter-butilamino propanos sustituidos. |
GB3825170A GB1318533A (en) | 1967-06-15 | 1970-08-07 | 3-2-cyanophenoxy-2-hydroxy-n-ethyl-propylamine |
NL7111854.A NL158171B (nl) | 1967-06-15 | 1971-08-27 | Werkwijze voor het op op zichzelf bekende wijze bereiden van een 1-(2- propargyloxyfenoxy) 3-alkylamino 2-propanol, werkwijze voor het bereiden van preparaten die deze verbinding bevatten, alsmede de verkregen gevormde preparaten. |
US408743A US3868460A (en) | 1967-02-06 | 1973-10-23 | Therapeutic compositions and method |
MY1973288A MY7300288A (en) | 1967-06-15 | 1973-12-31 | Propanolamine derivatives |
YU2293/74A YU35578B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert. butyl amino propanes |
YU2292/74A YU33779B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
YU2291/74A YU33778B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
YU2294/74A YU33780B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
YU2290/74A YU33777B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
YU2289/74A YU33776B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
YU2288/74A YU33775B (en) | 1967-06-15 | 1974-08-21 | Process for preparing novel substituted 1-phenoxy-2-hydroxy-3-tert.-butylamino-propanes |
US05/502,634 US3940489A (en) | 1967-02-06 | 1974-09-03 | Therapeutic compositions and method |
JP49119881A JPS5112613B1 (en, 2012) | 1967-06-15 | 1974-10-17 | |
US05/564,308 US3961071A (en) | 1967-02-06 | 1975-04-02 | Therapeutic compositions and method |
US05/571,790 US4039685A (en) | 1967-02-06 | 1975-04-25 | 1-phenoxy-2-hydroxy-3-tert.-butylamino propane antiarrhythmic compounds |
US05/656,000 US4036988A (en) | 1967-02-06 | 1976-02-06 | Therapeutic compositions and method |
IT7949447A IT7949447A0 (it) | 1967-02-06 | 1979-06-18 | 1-cianofenossi-2-idrossi-3-terz.butilamminopropani loro sali eprocedimento di preparazione |
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 (2)
Publication Number | Publication Date |
---|---|
DE1593782A1 DE1593782A1 (de) | 1972-04-20 |
DE1593782B2 true DE1593782B2 (de) | 1976-09-09 |
Family
ID=6986720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1967B0093025 Granted DE1593782B2 (de) | 1967-02-06 | 1967-06-15 | 1-nitrilophenoxy- 2- hydroxy -3- tert.butylaminopropane, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
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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C3 | Grant after two publication steps (3rd publication) | ||
E77 | Valid patent as to the heymanns-index 1977 |