ES401235A1 - Aminopropanol derivative - Google Patents
Aminopropanol derivativeInfo
- Publication number
- ES401235A1 ES401235A1 ES401235A ES401235A ES401235A1 ES 401235 A1 ES401235 A1 ES 401235A1 ES 401235 A ES401235 A ES 401235A ES 401235 A ES401235 A ES 401235A ES 401235 A1 ES401235 A1 ES 401235A1
- Authority
- ES
- Spain
- Prior art keywords
- dichlorophenoxy
- tert
- propanol
- reacted
- butylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 7
- GZFSQWVTRGNOJS-UHFFFAOYSA-N 1-amino-3-(2,5-dichlorophenoxy)propan-2-ol Chemical compound NCC(O)COC1=CC(Cl)=CC=C1Cl GZFSQWVTRGNOJS-UHFFFAOYSA-N 0.000 abstract 2
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 abstract 2
- -1 2,5-dichlorophenoxy Chemical group 0.000 abstract 2
- BKYYOPSMOZNITO-UHFFFAOYSA-N 2-[(2,5-dichlorophenoxy)methyl]oxirane Chemical compound ClC1=CC=C(Cl)C(OCC2OC2)=C1 BKYYOPSMOZNITO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- XYCMOTOFHFTUIU-UHFFFAOYSA-N cloranolol Chemical compound CC(C)(C)NCC(O)COC1=CC(Cl)=CC=C1Cl XYCMOTOFHFTUIU-UHFFFAOYSA-N 0.000 abstract 2
- 238000001640 fractional crystallisation Methods 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-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-KBPBESRZSA-N 0.000 abstract 1
- MTWBUKBMYJXKNU-UHFFFAOYSA-N 1-chloro-3-(2,5-dichlorophenoxy)propan-2-ol Chemical compound ClCC(O)COC1=CC(Cl)=CC=C1Cl MTWBUKBMYJXKNU-UHFFFAOYSA-N 0.000 abstract 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 abstract 1
- PZMYHLFQJXHHLD-UHFFFAOYSA-N 2-methyl-n-(oxiran-2-ylmethyl)propan-2-amine Chemical compound CC(C)(C)NCC1CO1 PZMYHLFQJXHHLD-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- YLJQSXXOUNWETA-UHFFFAOYSA-M sodium;2,5-dichlorophenolate Chemical compound [Na+].[O-]C1=CC(Cl)=CC=C1Cl YLJQSXXOUNWETA-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy 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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary 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)
- Epoxy Compounds (AREA)
Abstract
Procedure for the preparation of 1- (2,5-dichlorophenoxy) -3-tert-butylamino-2-propanol and its salts, particularly for the preparation of 1- (2,5-dichlorophenoxy) -3-tert-butylamino-2- racemic and optically active propanol and its salts, characterized in that a/1- (2,5-Dichlorophenoxy) -2,3-epoxypropane is reacted with tert-butylamine, or b/1- (2,5-diolorophenoxy) -3-chloro-2-propanol is reacted with tert-butylamine, or c/sodium 2,5-dichlorophenolate is reacted with 1-halo-3-tert-butylamino-2-propanol, or d/2,5-dichlorophenol is reacted with 1,2-epoxy-3-tert-butylaminopropane, or e/a diastereomeric salt pair of (±) - 1- (2,5-dichlorophenoxy) -3-tert-butylamino-2-propanol formed with (-) or (+) - dibenzoyltartaric acid is subjected to fractional crystallization in a low molecular weight alcohol at a temperature above 40ºC, or f/2,5-dichlorophenol is reacted with epichlorohydrin, 1- (2,5-dichlorophenoxy) -2,3-epoxypropane or 1- (2,5-dichlorophenoxy) -3-chloro-2-propanol is reacted obtained with ammonia, the 1- (2,5-dichlorophenoxy) -3-amino-2-propanol obtained in its diastereomeric salt pair is converted with (-) or (+) - dibenzoyltartramide, the obtained salt pair is subjected to fractional crystallization and (-) and (+) - 1- (2,5-dichlorophenoxy) -3-amino-2-propanol is alkylated on the nitrogen atom with tert-butyl halide, and, if desired, the free base obtained by any of the processes obtained is converted to its acid addition salt, or the salt is converted to the free base. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUGO001156 | 1971-03-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES401235A1 true ES401235A1 (en) | 1975-02-16 |
Family
ID=10996691
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES401235A Expired ES401235A1 (en) | 1971-03-17 | 1972-03-11 | Aminopropanol derivative |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS5310581B1 (en) |
AT (1) | AT316515B (en) |
AU (1) | AU461159B2 (en) |
BE (1) | BE780719A (en) |
CA (1) | CA1002537A (en) |
CH (1) | CH569692A5 (en) |
CS (1) | CS163270B2 (en) |
DK (1) | DK133872B (en) |
ES (1) | ES401235A1 (en) |
FI (1) | FI55025C (en) |
FR (1) | FR2130284B1 (en) |
GB (1) | GB1337921A (en) |
IL (1) | IL38870A (en) |
NL (1) | NL170626C (en) |
NO (1) | NO134836C (en) |
PL (1) | PL88985B1 (en) |
SE (1) | SE384021B (en) |
SU (1) | SU496721A3 (en) |
YU (1) | YU35435B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU172137B (en) | 1976-03-02 | 1978-06-28 | Gyogyszerkutato Intezet | Process for preparing substituted derivatives of the phenoxy-propanolamine |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1236523C2 (en) * | 1962-02-15 | 1975-06-12 | Sanol-Arzneimittel Dr. Schwarz Gmbh, 4019 Monheim | PROCESS FOR THE PRODUCTION OF BASIC PHENYLAETHERS AND THEIR SALTS |
-
1972
- 1972-02-29 CH CH283272A patent/CH569692A5/xx not_active IP Right Cessation
- 1972-03-01 AT AT170072A patent/AT316515B/en not_active IP Right Cessation
- 1972-03-02 IL IL38870A patent/IL38870A/en unknown
- 1972-03-06 AU AU39659/72A patent/AU461159B2/en not_active Expired
- 1972-03-07 CS CS1504A patent/CS163270B2/cs unknown
- 1972-03-08 FI FI611/72A patent/FI55025C/en active
- 1972-03-10 YU YU639/72A patent/YU35435B/en unknown
- 1972-03-11 ES ES401235A patent/ES401235A1/en not_active Expired
- 1972-03-13 SU SU1758614A patent/SU496721A3/en active
- 1972-03-14 NL NLAANVRAGE7203323,A patent/NL170626C/en not_active IP Right Cessation
- 1972-03-15 BE BE780719A patent/BE780719A/en not_active IP Right Cessation
- 1972-03-15 SE SE7203354A patent/SE384021B/en unknown
- 1972-03-15 PL PL1972154080A patent/PL88985B1/pl unknown
- 1972-03-15 FR FR7209048A patent/FR2130284B1/fr not_active Expired
- 1972-03-16 NO NO855/72A patent/NO134836C/no unknown
- 1972-03-16 JP JP2692872A patent/JPS5310581B1/ja active Pending
- 1972-03-16 GB GB1233472A patent/GB1337921A/en not_active Expired
- 1972-03-16 CA CA137,222A patent/CA1002537A/en not_active Expired
- 1972-03-16 DK DK123772AA patent/DK133872B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
BE780719A (en) | 1972-07-03 |
NL170626C (en) | 1982-12-01 |
JPS5310581B1 (en) | 1978-04-14 |
SE384021B (en) | 1976-04-12 |
GB1337921A (en) | 1973-11-21 |
FI55025B (en) | 1979-01-31 |
AU461159B2 (en) | 1975-04-29 |
DK133872B (en) | 1976-08-02 |
NO134836C (en) | 1976-12-21 |
DE2213044A1 (en) | 1972-09-28 |
YU35435B (en) | 1981-02-28 |
DE2213044B2 (en) | 1977-05-26 |
NL170626B (en) | 1982-07-01 |
IL38870A (en) | 1975-08-31 |
IL38870A0 (en) | 1972-05-30 |
NL7203323A (en) | 1972-09-19 |
CH569692A5 (en) | 1975-11-28 |
CA1002537A (en) | 1976-12-28 |
NO134836B (en) | 1976-09-13 |
AU3965972A (en) | 1973-09-13 |
CS163270B2 (en) | 1975-08-29 |
FR2130284A1 (en) | 1972-11-03 |
FR2130284B1 (en) | 1975-10-10 |
DK133872C (en) | 1976-12-27 |
FI55025C (en) | 1979-05-10 |
YU63972A (en) | 1980-06-30 |
SU496721A3 (en) | 1975-12-25 |
PL88985B1 (en) | 1976-10-30 |
AT316515B (en) | 1974-07-10 |
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