DE2205269A1 - Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid - Google Patents
Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochloridInfo
- Publication number
- DE2205269A1 DE2205269A1 DE19722205269 DE2205269A DE2205269A1 DE 2205269 A1 DE2205269 A1 DE 2205269A1 DE 19722205269 DE19722205269 DE 19722205269 DE 2205269 A DE2205269 A DE 2205269A DE 2205269 A1 DE2205269 A1 DE 2205269A1
- Authority
- DE
- Germany
- Prior art keywords
- butanol
- ethylenediimino
- amino
- mixture
- alkanol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- JCBPETKZIGVZRE-SCSAIBSYSA-N (2r)-2-aminobutan-1-ol Chemical compound CC[C@@H](N)CO JCBPETKZIGVZRE-SCSAIBSYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- -1 ethylenediimino Chemical group 0.000 claims description 3
- AEUTYOVWOVBAKS-RGURZIINSA-N (2s)-2-[2-(1-hydroxybutan-2-ylamino)ethylamino]butan-1-ol Chemical compound CCC(CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-RGURZIINSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 150000003840 hydrochlorides Chemical class 0.000 claims 2
- COGRWEZMVVEGEK-UHFFFAOYSA-N 4-hydroxybutyl-[2-(4-hydroxybutylazaniumyl)ethyl]azanium;dichloride Chemical compound [Cl-].[Cl-].OCCCC[NH2+]CC[NH2+]CCCCO COGRWEZMVVEGEK-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- CDSXYBLXNJGHHR-UHFFFAOYSA-N butan-1-ol dihydrochloride Chemical compound Cl.Cl.C(CCC)O.C(CCC)O CDSXYBLXNJGHHR-UHFFFAOYSA-N 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 18
- 229960000285 ethambutol Drugs 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229960001618 ethambutol hydrochloride Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- 235000014510 cooky Nutrition 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/14—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11472571A | 1971-02-11 | 1971-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2205269A1 true DE2205269A1 (de) | 1972-09-07 |
Family
ID=22357058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722205269 Pending DE2205269A1 (de) | 1971-02-11 | 1972-02-04 | Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3769347A (enExample) |
| AU (1) | AU465934B2 (enExample) |
| BE (1) | BE779220A (enExample) |
| BG (1) | BG22805A3 (enExample) |
| CA (1) | CA990310A (enExample) |
| CH (1) | CH564508A5 (enExample) |
| CS (1) | CS158576B2 (enExample) |
| CY (1) | CY862A (enExample) |
| DD (1) | DD95011A5 (enExample) |
| DE (1) | DE2205269A1 (enExample) |
| DK (1) | DK136213B (enExample) |
| ES (1) | ES399693A1 (enExample) |
| FR (1) | FR2143635B1 (enExample) |
| GB (1) | GB1345478A (enExample) |
| HK (1) | HK48376A (enExample) |
| HU (1) | HU162518B (enExample) |
| KE (1) | KE2644A (enExample) |
| MY (1) | MY7600231A (enExample) |
| NL (1) | NL7201498A (enExample) |
| PL (1) | PL77439B1 (enExample) |
| RO (1) | RO60604A (enExample) |
| SE (1) | SE384501B (enExample) |
| SU (1) | SU522792A3 (enExample) |
| ZA (1) | ZA72346B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2548508A1 (de) * | 1974-10-29 | 1976-05-06 | American Cyanamid Co | Verfahren zur herstellung von d,d'-2,2'-(aethylendiimino)-di-1-butanol- dihydrochlorid |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5318006B2 (enExample) * | 1973-09-28 | 1978-06-13 | ||
| US3944618A (en) * | 1976-02-20 | 1976-03-16 | American Cyanamid Company | Synthesis of ethambutol |
| US20040033986A1 (en) * | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| US7456222B2 (en) | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| CN101404986B (zh) * | 2002-05-17 | 2011-09-28 | 赛奎拉公司 | 用于诊断和治疗感染性疾病的组合物和制药方法 |
| US7884097B2 (en) * | 2003-09-05 | 2011-02-08 | Sequella, Inc. | Methods and compositions comprising diamines as new anti-tubercular therapeutics |
| WO2009136965A1 (en) * | 2008-05-06 | 2009-11-12 | Sequella, Inc. | Compositions and methods comprising capuramycin analogues |
| JP2013124236A (ja) * | 2011-12-15 | 2013-06-24 | Sumitomo Chemical Co Ltd | ハロゲン化アルキルアミンのハロゲン化水素酸塩の製造方法 |
| CN103772214B (zh) * | 2012-10-25 | 2016-04-20 | 北大方正集团有限公司 | 制备乙胺丁醇和盐酸乙胺丁醇的方法 |
| CN108218724B (zh) * | 2016-12-21 | 2021-02-19 | 武汉武药制药有限公司 | 一种合成盐酸乙胺丁醇的方法 |
| CN108218723B (zh) * | 2016-12-21 | 2020-11-27 | 武汉武药制药有限公司 | 一种制备盐酸乙胺丁醇的工艺 |
| CN110143887A (zh) * | 2018-02-12 | 2019-08-20 | 武汉武药制药有限公司 | 一种盐酸乙胺丁醇的制备方法 |
-
1971
- 1971-02-11 US US00114725A patent/US3769347A/en not_active Expired - Lifetime
-
1972
- 1972-01-18 ZA ZA720346A patent/ZA72346B/xx unknown
- 1972-01-19 CA CA132,777A patent/CA990310A/en not_active Expired
- 1972-01-20 AU AU38131/72A patent/AU465934B2/en not_active Expired
- 1972-01-24 GB GB331972A patent/GB1345478A/en not_active Expired
- 1972-01-24 CY CY862A patent/CY862A/xx unknown
- 1972-02-01 RO RO69625A patent/RO60604A/ro unknown
- 1972-02-02 SU SU1743920A patent/SU522792A3/ru active
- 1972-02-04 NL NL7201498A patent/NL7201498A/xx active Search and Examination
- 1972-02-04 DE DE19722205269 patent/DE2205269A1/de active Pending
- 1972-02-10 DD DD160795A patent/DD95011A5/xx unknown
- 1972-02-10 BG BG019685A patent/BG22805A3/xx unknown
- 1972-02-10 DK DK61672AA patent/DK136213B/da not_active IP Right Cessation
- 1972-02-10 CH CH189072A patent/CH564508A5/xx not_active IP Right Cessation
- 1972-02-10 CS CS86072*#A patent/CS158576B2/cs unknown
- 1972-02-10 BE BE779220A patent/BE779220A/xx not_active IP Right Cessation
- 1972-02-10 PL PL1972153426A patent/PL77439B1/pl unknown
- 1972-02-10 SE SE7201592A patent/SE384501B/xx unknown
- 1972-02-11 ES ES399693A patent/ES399693A1/es not_active Expired
- 1972-02-11 HU HUAE354A patent/HU162518B/hu unknown
- 1972-02-11 FR FR7204717A patent/FR2143635B1/fr not_active Expired
-
1976
- 1976-06-15 KE KE2644A patent/KE2644A/xx unknown
- 1976-07-29 HK HK483/76*UA patent/HK48376A/xx unknown
- 1976-12-30 MY MY231/76A patent/MY7600231A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2548508A1 (de) * | 1974-10-29 | 1976-05-06 | American Cyanamid Co | Verfahren zur herstellung von d,d'-2,2'-(aethylendiimino)-di-1-butanol- dihydrochlorid |
Also Published As
| Publication number | Publication date |
|---|---|
| HU162518B (enExample) | 1973-03-28 |
| KE2644A (en) | 1976-06-25 |
| BE779220A (fr) | 1972-08-10 |
| FR2143635B1 (enExample) | 1976-04-16 |
| NL7201498A (enExample) | 1972-08-15 |
| AU465934B2 (en) | 1975-10-09 |
| CH564508A5 (enExample) | 1975-07-31 |
| SU522792A3 (ru) | 1976-07-25 |
| FR2143635A1 (enExample) | 1973-02-09 |
| DD95011A5 (enExample) | 1973-01-12 |
| RO60604A (enExample) | 1976-08-15 |
| BG22805A3 (bg) | 1977-04-20 |
| ES399693A1 (es) | 1975-07-01 |
| DK136213C (enExample) | 1978-02-13 |
| PL77439B1 (enExample) | 1975-04-30 |
| DK136213B (da) | 1977-09-05 |
| ZA72346B (en) | 1972-09-27 |
| AU3813172A (en) | 1973-07-26 |
| CY862A (en) | 1976-12-17 |
| US3769347A (en) | 1973-10-30 |
| CA990310A (en) | 1976-06-01 |
| HK48376A (en) | 1976-08-06 |
| CS158576B2 (enExample) | 1974-11-25 |
| MY7600231A (en) | 1976-12-31 |
| SE384501B (sv) | 1976-05-10 |
| GB1345478A (en) | 1974-01-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2205269A1 (de) | Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid | |
| DE2021829C2 (de) | Polyfluorierte quaternäre Ammoniumsalze und deren Herstellung | |
| DE2548508C2 (enExample) | ||
| DE3729530C2 (enExample) | ||
| DE1593289C3 (de) | Katalytisches Verfahren zum Hydrieren von aromatischen Verbindungen | |
| DE2748535C3 (de) | Verfahren zur Herstellung von gemischten Polyiminoderivaten von Aluminium und Magnesium und von Magnesiumamiden | |
| DE2164392C3 (de) | Verfahren zur Hertstellung von 5-(4-Aminobutyl)-hydantoin oder dessen Mischung mit 1-Ureido-5-amino-capronamid | |
| DE2449607A1 (de) | Verfahren zur herstellung von benzolderivaten mit einer isocyanatmethyl gruppe | |
| DE1768535A1 (de) | Verfahren zur Trennung von Isomergemischen | |
| DE2410330C2 (de) | Verfahren zur Herstellung von Äthylendiamin mit niedrigem Wassergehalt | |
| EP0088471A1 (de) | Verfahren zur Herstellung von grobkristallinem, reinem Kaliumchlorid | |
| DE866647C (de) | Verfahren zur Herstellung von sekundaeren 1, 3-Alkendiaminen | |
| DE2826842C2 (de) | Verfahren zum Abtrennen von Laurent- Säure (1-Naphthylamin-5-sulfonsäure) aus einem Gemisch von Laurent- und Peri-Säure (1-Naphthylamin-8-sulfonsäure) | |
| EP0781761A1 (de) | Verfahren und Vorrichtung zur Reinigung von handelsüblichem Diphenyl-p-phenylendiamin (DPPD) | |
| DE1418334B1 (de) | Verfahren zur Herstellung von 1,2,3,4,7,7-Hexachlorbicyclo[2,2,1]-2,5-heptadien aus Hexachlorcyclopentadien und Acetylen | |
| AT252896B (de) | Verfahren zur Herstellung von optisch aktivem Lysin | |
| DE2715518C2 (enExample) | ||
| AT372939B (de) | Verfahren zur herstellung von (d)-(-)-phydroxyphenylglycylchlorid-hydrochlorid | |
| EP0086745A1 (de) | Verfahren zur Herstellung einer sehr reinen Handelsform von 4,2',4'-Trichlor-2-hydroxydiphenyläther | |
| CH615437A5 (enExample) | ||
| DE613263C (de) | Verfahren zur Gewinnung von Betaninhydrochlorid aus Schlempen u. dgl. Stoffen | |
| DE2744440A1 (de) | Gemisch aus polycyclischen aromatischen polycarbonsaeuren und verfahren zur herstellung desselben | |
| DE2355735C3 (de) | Verfahren zum Gewinnen eines Fuchsinsalzes | |
| CH323905A (de) | Verfahren zur Herstellung aromatischer Isocyanate | |
| DE1793549A1 (de) | Substituierte Dibenzocycloheptene und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |