SE8003874L - PROCEDURE FOR PREPARING BROMHEXINE AND AGENTS FOR USING THE PROCEDURE - Google Patents
PROCEDURE FOR PREPARING BROMHEXINE AND AGENTS FOR USING THE PROCEDUREInfo
- Publication number
- SE8003874L SE8003874L SE8003874A SE8003874A SE8003874L SE 8003874 L SE8003874 L SE 8003874L SE 8003874 A SE8003874 A SE 8003874A SE 8003874 A SE8003874 A SE 8003874A SE 8003874 L SE8003874 L SE 8003874L
- Authority
- SE
- Sweden
- Prior art keywords
- procedure
- agents
- benzoxazin
- cyclohexylamine
- dihydro
- Prior art date
Links
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 title abstract 2
- 229960003870 bromhexine Drugs 0.000 title 1
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 abstract 1
- RQJFMNQNCRVVFJ-UHFFFAOYSA-N 6,8-dibromo-1,4-dihydro-3,1-benzoxazin-2-one Chemical compound N1C(=O)OCC2=CC(Br)=CC(Br)=C21 RQJFMNQNCRVVFJ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 1
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
N-(2-amino-3,5-dibromobenzyl)- N-methyl-cyclohexylamine, the hydrochloride of which has the formula <IMAGE> is prepared by brominating 1,4- dihydro-2H-3,1-benzoxazin-2-one with free bromine to form the hitherto unknown intermediate 6,8-dibromo- 1,4-dihydro-2H-3,1-benzoxazin-2- one, and reacting this with N-methyl- cyclohexylamine to bromhexin. Preferably, the reaction takes place by heating in N-monomethylformamide to the boiling point of the latter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK230079A DK145714C (en) | 1979-06-01 | 1979-06-01 | METHOD FOR PREPARING N- (2-AMINO-3,5-DIBROMBENZYL) -N-METYLYCYLOHEXYLAMINE |
| DK230179A DK145718C (en) | 1979-06-01 | 1979-06-01 | DIBROME COMPOUND USE AS INTERMEDIATE IN THE PREPARATION OF N- (2-AMINO-3,5-DIBROMBENZYL) -N-METYLCYCLOHEXYLAMINE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8003874L true SE8003874L (en) | 1980-12-02 |
| SE433847B SE433847B (en) | 1984-06-18 |
Family
ID=26066477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8003874A SE433847B (en) | 1979-06-01 | 1980-05-23 | PROCEDURE FOR PREPARING BROMHEXIN |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT371800B (en) |
| CH (1) | CH642617A5 (en) |
| DE (1) | DE3020604A1 (en) |
| ES (1) | ES492005A0 (en) |
| FI (1) | FI68808C (en) |
| GB (1) | GB2053900B (en) |
| IE (1) | IE49820B1 (en) |
| KE (1) | KE3302A (en) |
| NL (1) | NL8003153A (en) |
| NO (2) | NO148372C (en) |
| SE (1) | SE433847B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2881955B1 (en) | 2005-02-11 | 2007-05-11 | Oreal | COSMETIC NANOEMULSION CONTAINING HYDROXYL UREA COMPOUND |
| CN102775316B (en) * | 2012-08-17 | 2013-06-12 | 夏智红 | Bromhexine hydrochloride compound and medicine composition thereof |
| CN102924295B (en) * | 2012-10-09 | 2014-10-29 | 石家庄东方药业有限公司 | Bromhexine hydrochloride crystal as well as preparation method and application of crystal |
| CN103145564B (en) * | 2013-03-15 | 2014-06-18 | 湖北美林药业有限公司 | Bromhexine hydrochloride compound and pharmaceutical composition thereof |
-
1980
- 1980-05-23 IE IE1081/80A patent/IE49820B1/en unknown
- 1980-05-23 SE SE8003874A patent/SE433847B/en not_active IP Right Cessation
- 1980-05-27 FI FI801705A patent/FI68808C/en not_active IP Right Cessation
- 1980-05-29 GB GB8017619A patent/GB2053900B/en not_active Expired
- 1980-05-30 NL NL8003153A patent/NL8003153A/en not_active Application Discontinuation
- 1980-05-30 CH CH423780A patent/CH642617A5/en not_active IP Right Cessation
- 1980-05-30 DE DE19803020604 patent/DE3020604A1/en not_active Withdrawn
- 1980-05-30 NO NO801617A patent/NO148372C/en unknown
- 1980-05-30 ES ES492005A patent/ES492005A0/en active Granted
- 1980-05-30 AT AT0288580A patent/AT371800B/en not_active IP Right Cessation
-
1982
- 1982-11-26 NO NO823977A patent/NO148415C/en unknown
-
1983
- 1983-07-11 KE KE3302A patent/KE3302A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8104185A1 (en) | 1981-04-01 |
| CH642617A5 (en) | 1984-04-30 |
| NL8003153A (en) | 1980-12-03 |
| NO801617L (en) | 1980-12-02 |
| IE49820B1 (en) | 1985-12-25 |
| GB2053900B (en) | 1983-04-20 |
| NO148372C (en) | 1983-09-28 |
| AT371800B (en) | 1983-07-25 |
| IE801081L (en) | 1980-12-01 |
| FI801705A7 (en) | 1980-12-02 |
| NO148415C (en) | 1983-10-12 |
| NO823977L (en) | 1980-12-02 |
| ATA288580A (en) | 1982-12-15 |
| SE433847B (en) | 1984-06-18 |
| NO148372B (en) | 1983-06-20 |
| ES492005A0 (en) | 1981-04-01 |
| NO148415B (en) | 1983-06-27 |
| KE3302A (en) | 1983-08-19 |
| FI68808C (en) | 1985-11-11 |
| DE3020604A1 (en) | 1980-12-11 |
| GB2053900A (en) | 1981-02-11 |
| FI68808B (en) | 1985-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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