FI68808C - Foerfarande foer framstaellning av bromhexin och en ny dibromfoerening foer anvaendning som mellanprodukt vid foerfarandet - Google Patents
Foerfarande foer framstaellning av bromhexin och en ny dibromfoerening foer anvaendning som mellanprodukt vid foerfarandet Download PDFInfo
- Publication number
- FI68808C FI68808C FI801705A FI801705A FI68808C FI 68808 C FI68808 C FI 68808C FI 801705 A FI801705 A FI 801705A FI 801705 A FI801705 A FI 801705A FI 68808 C FI68808 C FI 68808C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- benzoxazin
- dihydro
- methylcyclohexylamine
- dibromo
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 15
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 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 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 claims description 4
- -1 Dibromo compound Chemical class 0.000 claims description 4
- 229960003870 bromhexine Drugs 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- UCDKONUHZNTQPY-UHFFFAOYSA-N bromhexine hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N UCDKONUHZNTQPY-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK230179 | 1979-06-01 | ||
| DK230179A DK145718C (da) | 1979-06-01 | 1979-06-01 | Dibromforbindelse til anvendelse som mellemprodukt ved fremstilling af n-(2-amino-3,5-dibrombenzyl)-n-metylcyclohexylamin |
| DK230079 | 1979-06-01 | ||
| DK230079A DK145714C (da) | 1979-06-01 | 1979-06-01 | Fremgangsmaade til fremstilling af n-(2-amino-3,5-dibrombenzyl)-n-metylcyklohexylamin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI801705A7 FI801705A7 (fi) | 1980-12-02 |
| FI68808B FI68808B (fi) | 1985-07-31 |
| FI68808C true FI68808C (fi) | 1985-11-11 |
Family
ID=26066477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801705A FI68808C (fi) | 1979-06-01 | 1980-05-27 | Foerfarande foer framstaellning av bromhexin och en ny dibromfoerening foer anvaendning som mellanprodukt vid foerfarandet |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT371800B (de) |
| CH (1) | CH642617A5 (de) |
| DE (1) | DE3020604A1 (de) |
| ES (1) | ES8104185A1 (de) |
| FI (1) | FI68808C (de) |
| GB (1) | GB2053900B (de) |
| IE (1) | IE49820B1 (de) |
| KE (1) | KE3302A (de) |
| NL (1) | NL8003153A (de) |
| NO (2) | NO148372C (de) |
| SE (1) | SE433847B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2881955B1 (fr) | 2005-02-11 | 2007-05-11 | Oreal | Nanoemulsion cosmetique contenant un compose d'uree hydroxyle |
| CN102775316B (zh) * | 2012-08-17 | 2013-06-12 | 夏智红 | 一种盐酸溴己新化合物及其药物组合物 |
| CN102924295B (zh) * | 2012-10-09 | 2014-10-29 | 石家庄东方药业有限公司 | 一种盐酸溴己新晶体及其制备方法和用途 |
| CN103145564B (zh) * | 2013-03-15 | 2014-06-18 | 湖北美林药业有限公司 | 盐酸溴己新化合物及其药物组合物 |
-
1980
- 1980-05-23 IE IE1081/80A patent/IE49820B1/en unknown
- 1980-05-23 SE SE8003874A patent/SE433847B/sv not_active IP Right Cessation
- 1980-05-27 FI FI801705A patent/FI68808C/fi not_active IP Right Cessation
- 1980-05-29 GB GB8017619A patent/GB2053900B/en not_active Expired
- 1980-05-30 NO NO801617A patent/NO148372C/no unknown
- 1980-05-30 ES ES492005A patent/ES8104185A1/es not_active Expired
- 1980-05-30 DE DE19803020604 patent/DE3020604A1/de not_active Withdrawn
- 1980-05-30 AT AT0288580A patent/AT371800B/de not_active IP Right Cessation
- 1980-05-30 CH CH423780A patent/CH642617A5/de not_active IP Right Cessation
- 1980-05-30 NL NL8003153A patent/NL8003153A/nl not_active Application Discontinuation
-
1982
- 1982-11-26 NO NO823977A patent/NO148415C/no unknown
-
1983
- 1983-07-11 KE KE3302A patent/KE3302A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE801081L (en) | 1980-12-01 |
| AT371800B (de) | 1983-07-25 |
| NL8003153A (nl) | 1980-12-03 |
| IE49820B1 (en) | 1985-12-25 |
| GB2053900A (en) | 1981-02-11 |
| ES492005A0 (es) | 1981-04-01 |
| NO148415C (no) | 1983-10-12 |
| FI801705A7 (fi) | 1980-12-02 |
| NO801617L (no) | 1980-12-02 |
| GB2053900B (en) | 1983-04-20 |
| NO148372B (no) | 1983-06-20 |
| DE3020604A1 (de) | 1980-12-11 |
| ATA288580A (de) | 1982-12-15 |
| SE8003874L (sv) | 1980-12-02 |
| ES8104185A1 (es) | 1981-04-01 |
| SE433847B (sv) | 1984-06-18 |
| NO148415B (no) | 1983-06-27 |
| KE3302A (en) | 1983-08-19 |
| CH642617A5 (de) | 1984-04-30 |
| FI68808B (fi) | 1985-07-31 |
| NO148372C (no) | 1983-09-28 |
| NO823977L (no) | 1980-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A/S GEA |