IE34946B1 - Alpha-aminoalkyl-4-hydroxy-3-ureidobenzyl alcohols - Google Patents
Alpha-aminoalkyl-4-hydroxy-3-ureidobenzyl alcoholsInfo
- Publication number
- IE34946B1 IE34946B1 IE163/71A IE16371A IE34946B1 IE 34946 B1 IE34946 B1 IE 34946B1 IE 163/71 A IE163/71 A IE 163/71A IE 16371 A IE16371 A IE 16371A IE 34946 B1 IE34946 B1 IE 34946B1
- Authority
- IE
- Ireland
- Prior art keywords
- benzyloxy
- acetophenone
- bromo
- methylureido
- prepared
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1286225 Benzyl alcohol derivatives SMITH KLINE & FRENCH LABORATORIES 19 April 1971 [17 Feb 1970] 22115/71 Heading C2C The invention comprises novel benzyl alcohol derivatives, pharmaceutically acceptable acid addition salts thereof, and the corresponding novel aminobenzyloxyphenones of the formulµ wherein R is H, C 1-5 alkIl, phenyl, dimethylaminoethyl, or dimethylaminopropyl; R 1 is C 3-5 alkyl C 3-6 cycloalkyl, C 3-6 cycloalkylmethyl or a radical of the formula R 2 is H, CH3 or CH 2 CH 3 ; R 3 and R 4 each are H, OH or OCH3 and R 5 is H or CH 3 , the compounds of the above formulµ are prepared by reacting the appropriate 4-benzyloxy-α-bromophenones with the corresponding N-benzylamines of the formula followed by, if desired, catalytic hydrogenation. 4 - Benzyloxy - α - bromo - 3 - ureidoawtophenone is obtained by brominating 4-benzyloxy-3- ureido-ecetophenone resulting from the action of ammonia on 4-benzyloxy-3-isocyantoacetophenone which is prepared by reacting 3-amino-4-benzyloxyacetophenone with phosgene. 4 - Benzyloxy - - bromo - 3 - (N<SP>1</SP> - methylureido)-acetophenone is made by brominating 4- benzyloxy 3-(N<SP>1</SP>-methylureido)-acetophenone obtained by treating the above named isocyanate with methylamine. By similar processes 4- benzyloxy - 3 - (N<SP>1</SP> - phenylureido) - acetophenone, 4 - benzyloxy - α - bromo - 3 - (N<SP>1</SP> - phenylureido)- acetophenone, 4 -beizyloxy - 3 -isocyantobutyro - phenone, 4 -benzyloxy- 3 -ureidobutyrophenone, 4- benzyloxy-3-(N,N<SP>1</SP>-dimethylureido)-acetophenone, 4 - benzyloxy - α - bromo - 3 - (N,N<SP>1</SP> - dimethylureido)-acetophenone, and 4 -bemyloxy-α-bromo-3- 3-ureidoobutyrophenone are prepared. 4 - Benzyloxy- α - bromo - 3 - (N- methylureido)-acetophenone is made by brominating 4- benzyloxy- 3- (N-methylureido ) -acetoph enone resulting from the action of sodium cyanate on 4-benzyloxy- 3 -methylaminoccetophenane, which is prepared by hydrolysing 4-benzyloxy-3-(N-methylformamido)-acetophenone, obtained by methylating 4-benzyloxy- 3 -formamidoacetophenone resulting from reaction between ethyl formate and 3-amino-4-benzyloxyacetophenone. Pharmaceutical compositions, having #- adrenergic stimulating activity and suitable for oral or parenteral administration, contain the above novel benzyl alcohol derivative together with suitable pharmaceutical carriers.
[GB1286225A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1215170A | 1970-02-17 | 1970-02-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34946L IE34946L (en) | 1971-08-17 |
| IE34946B1 true IE34946B1 (en) | 1975-10-01 |
Family
ID=21753623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE163/71A IE34946B1 (en) | 1970-02-17 | 1971-02-11 | Alpha-aminoalkyl-4-hydroxy-3-ureidobenzyl alcohols |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5323293B1 (en) |
| BE (1) | BE762504A (en) |
| BR (1) | BR7101084D0 (en) |
| CA (1) | CA992987A (en) |
| CH (1) | CH554317A (en) |
| CY (1) | CY826A (en) |
| DE (1) | DE2106620C3 (en) |
| DK (1) | DK129788B (en) |
| ES (1) | ES388339A1 (en) |
| FI (1) | FI53701C (en) |
| FR (1) | FR2081517B1 (en) |
| GB (1) | GB1286225A (en) |
| IE (1) | IE34946B1 (en) |
| IL (2) | IL36077A (en) |
| IT (1) | IT1045479B (en) |
| KE (1) | KE2565A (en) |
| LU (1) | LU62598A1 (en) |
| MY (1) | MY7500241A (en) |
| NL (1) | NL169179C (en) |
| PH (2) | PH10013A (en) |
| SE (1) | SE361035B (en) |
| ZA (1) | ZA71417B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4867235A (en) * | 1971-12-17 | 1973-09-13 | ||
| US4404224A (en) * | 1981-12-02 | 1983-09-13 | American Cyanamid Company | Alkanesulfonanilide derivatives and pharmaceutically acceptable acid addition salts thereof for increasing the growth rate and/or improving the lean meat to fat ratio of warm blooded animals |
| GB8426200D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1214012A (en) * | 1967-12-21 | 1970-11-25 | Allen & Hanburys Ltd | Phenylethanolamines |
-
1971
- 1971-01-22 ZA ZA710417A patent/ZA71417B/en unknown
- 1971-01-27 IL IL36077A patent/IL36077A/en unknown
- 1971-01-29 DK DK41771AA patent/DK129788B/en unknown
- 1971-01-29 PH PH12136A patent/PH10013A/en unknown
- 1971-02-02 SE SE01256/71A patent/SE361035B/xx unknown
- 1971-02-04 BE BE762504A patent/BE762504A/en not_active IP Right Cessation
- 1971-02-08 FR FR7104110A patent/FR2081517B1/fr not_active Expired
- 1971-02-08 FI FI335/71A patent/FI53701C/en active
- 1971-02-11 IE IE163/71A patent/IE34946B1/en unknown
- 1971-02-12 DE DE2106620A patent/DE2106620C3/en not_active Expired
- 1971-02-13 IT IT20544/71A patent/IT1045479B/en active
- 1971-02-15 LU LU62598D patent/LU62598A1/xx unknown
- 1971-02-16 ES ES388339A patent/ES388339A1/en not_active Expired
- 1971-02-16 NL NLAANVRAGE7102039,A patent/NL169179C/en not_active IP Right Cessation
- 1971-02-16 JP JP705171A patent/JPS5323293B1/ja active Pending
- 1971-02-16 CH CH225471A patent/CH554317A/en not_active IP Right Cessation
- 1971-02-16 CA CA105,486A patent/CA992987A/en not_active Expired
- 1971-02-17 BR BR1084/71A patent/BR7101084D0/en unknown
- 1971-04-19 GB GB22115/71A patent/GB1286225A/en not_active Expired
- 1971-04-19 CY CY826A patent/CY826A/en unknown
-
1973
- 1973-12-07 IL IL43774A patent/IL43774A0/en unknown
-
1974
- 1974-05-06 PH PH15808A patent/PH10684A/en unknown
-
1975
- 1975-09-09 KE KE2565*UA patent/KE2565A/en unknown
- 1975-12-30 MY MY241/75A patent/MY7500241A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1286225A (en) | 1972-08-23 |
| MY7500241A (en) | 1975-12-31 |
| KE2565A (en) | 1975-09-19 |
| BE762504A (en) | 1971-08-04 |
| NL169179C (en) | 1982-06-16 |
| DK129788B (en) | 1974-11-18 |
| PH10684A (en) | 1977-08-10 |
| DE2106620C3 (en) | 1980-03-20 |
| NL169179B (en) | 1982-01-18 |
| ES388339A1 (en) | 1974-02-01 |
| NL7102039A (en) | 1971-08-19 |
| SE361035B (en) | 1973-10-15 |
| JPS5323293B1 (en) | 1978-07-13 |
| DK129788C (en) | 1975-04-28 |
| FI53701B (en) | 1978-03-31 |
| PH10013A (en) | 1976-07-13 |
| FR2081517B1 (en) | 1974-08-30 |
| IT1045479B (en) | 1980-05-10 |
| FI53701C (en) | 1978-07-10 |
| IE34946L (en) | 1971-08-17 |
| IL43774A0 (en) | 1974-03-14 |
| IL36077A0 (en) | 1971-03-24 |
| DE2106620B2 (en) | 1979-08-02 |
| FR2081517A1 (en) | 1971-12-03 |
| CY826A (en) | 1976-03-19 |
| IL36077A (en) | 1974-12-31 |
| CA992987A (en) | 1976-07-13 |
| CH554317A (en) | 1974-09-30 |
| DE2106620A1 (en) | 1971-08-26 |
| LU62598A1 (en) | 1971-08-19 |
| ZA71417B (en) | 1971-10-27 |
| BR7101084D0 (en) | 1973-04-05 |
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