ES424272A1 - A PROCEDURE FOR PREPARING THERAPEUTICALLY VA-LIOSA N - (2 - AMINO - 3,5 - DI- BROMOBENZYL) - N - METHYL CYCLOHEXYLAMINE. - Google Patents
A PROCEDURE FOR PREPARING THERAPEUTICALLY VA-LIOSA N - (2 - AMINO - 3,5 - DI- BROMOBENZYL) - N - METHYL CYCLOHEXYLAMINE.Info
- Publication number
- ES424272A1 ES424272A1 ES424272A ES424272A ES424272A1 ES 424272 A1 ES424272 A1 ES 424272A1 ES 424272 A ES424272 A ES 424272A ES 424272 A ES424272 A ES 424272A ES 424272 A1 ES424272 A1 ES 424272A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- amino
- see formula
- dibromobenzyl
- 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.)
- Expired
Links
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- -1 2-amino-3,5-dibromobenzyl Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (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)
Abstract
A method of preparing therapeutically valuable N- (2-amino-3,5-dibromobenzyl) -N-methylcyclyoxylamine, which has the formula **(See formula)** and its acid addition salts, which comprises reacting a 2-amino-3,5-dibromobenzyl alcohol ester derivative having the formula **(See formula)** wherein R1 represents the acidic moiety of an arbitrary organic or inorganic acid, and (1) R2 and R3 each represent hydrogen or (2) R2 represents hydrogen and R3 represents an acyl or sulfonyl radical, or (3) R2 and R3 together with the nitrogen atom form an imino radical of the formula **(See formula)** wherein R4 and R5 are the same or different and each can represent a hydrogen atom or a substituted or unsubstituted alcohol or aryl radical, with N-methylcyclohexylamine having the formula **(See formula)** to form a compound that has the formula **(See formula)** wherein R2 and R3 have the meanings defined above, and if necessary decompose said compound into N- (2-amino-3,5-dibromobenzyl) -N-methylcyclohexylamine (I) and, if desired, convert the compound (I) thus formed into an acid addition salt. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI78673 | 1973-03-15 | ||
| FI2122/73A FI55647C (en) | 1973-07-02 | 1973-07-02 | PROCEDURE FOR THERAPEUTIC PREPARATION OF THERAPEUTIC 2-AMINO-N-CYCLOHEXYL-3,5-DIBROM-N-METHYLBENYLAMINE OCH DESS SYRAADDITIONSSALTER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES424272A1 true ES424272A1 (en) | 1976-05-16 |
Family
ID=26156383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES424272A Expired ES424272A1 (en) | 1973-03-15 | 1974-03-14 | A PROCEDURE FOR PREPARING THERAPEUTICALLY VA-LIOSA N - (2 - AMINO - 3,5 - DI- BROMOBENZYL) - N - METHYL CYCLOHEXYLAMINE. |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5328906B2 (en) |
| AT (1) | AT333249B (en) |
| BG (1) | BG23745A3 (en) |
| CH (1) | CH613938A5 (en) |
| DE (1) | DE2411848A1 (en) |
| ES (1) | ES424272A1 (en) |
| HU (1) | HU166949B (en) |
| NL (1) | NL7403155A (en) |
| NO (1) | NO139558C (en) |
| RO (1) | RO69817A (en) |
| SE (2) | SE396216B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8771807B2 (en) * | 2011-05-24 | 2014-07-08 | Air Products And Chemicals, Inc. | Organoaminosilane precursors and methods for making and using same |
| 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 |
| CN109535010B (en) * | 2018-12-27 | 2021-10-26 | 广州一品红制药有限公司 | Preparation method of bromhexine hydrochloride |
-
1973
- 1973-07-18 SE SE7310071A patent/SE396216B/en unknown
- 1973-07-31 NO NO306373A patent/NO139558C/en unknown
-
1974
- 1974-03-08 NL NL7403155A patent/NL7403155A/xx not_active Application Discontinuation
- 1974-03-12 DE DE2411848A patent/DE2411848A1/en active Pending
- 1974-03-13 BG BG026039A patent/BG23745A3/en unknown
- 1974-03-13 HU HUTO000957 patent/HU166949B/hu unknown
- 1974-03-13 RO RO7800574A patent/RO69817A/en unknown
- 1974-03-14 AT AT212974A patent/AT333249B/en not_active IP Right Cessation
- 1974-03-14 ES ES424272A patent/ES424272A1/en not_active Expired
- 1974-03-15 CH CH366874A patent/CH613938A5/en not_active IP Right Cessation
- 1974-03-15 JP JP2986274A patent/JPS5328906B2/ja not_active Expired
-
1975
- 1975-12-09 SE SE7513882A patent/SE7513882L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA212974A (en) | 1976-03-15 |
| RO69817A (en) | 1980-12-30 |
| BG23745A3 (en) | 1977-10-12 |
| AT333249B (en) | 1976-11-10 |
| SE7513882L (en) | 1975-12-09 |
| JPS5328906B2 (en) | 1978-08-17 |
| DE2411848A1 (en) | 1974-09-26 |
| NL7403155A (en) | 1974-09-17 |
| NO139558C (en) | 1979-04-04 |
| HU166949B (en) | 1975-06-28 |
| NO139558B (en) | 1978-12-27 |
| JPS5046643A (en) | 1975-04-25 |
| CH613938A5 (en) | 1979-10-31 |
| SE396216B (en) | 1977-09-12 |
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