DE2548508A1 - Verfahren zur herstellung von d,d'-2,2'-(aethylendiimino)-di-1-butanol- dihydrochlorid - Google Patents
Verfahren zur herstellung von d,d'-2,2'-(aethylendiimino)-di-1-butanol- dihydrochloridInfo
- Publication number
- DE2548508A1 DE2548508A1 DE19752548508 DE2548508A DE2548508A1 DE 2548508 A1 DE2548508 A1 DE 2548508A1 DE 19752548508 DE19752548508 DE 19752548508 DE 2548508 A DE2548508 A DE 2548508A DE 2548508 A1 DE2548508 A1 DE 2548508A1
- Authority
- DE
- Germany
- Prior art keywords
- butanol
- dihydrochloride
- solution
- alkanol
- isopropanol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 43
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 42
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- -1 ethylene diimino Chemical group 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000002956 ash Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229960000285 ethambutol Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- JCBPETKZIGVZRE-SCSAIBSYSA-N (2r)-2-aminobutan-1-ol Chemical compound CC[C@@H](N)CO JCBPETKZIGVZRE-SCSAIBSYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- CDSXYBLXNJGHHR-UHFFFAOYSA-N butan-1-ol dihydrochloride Chemical compound Cl.Cl.C(CCC)O.C(CCC)O CDSXYBLXNJGHHR-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
- 238000004821 distillation Methods 0.000 description 2
- 229960001618 ethambutol hydrochloride Drugs 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 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
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/518,832 US3944616A (en) | 1974-10-29 | 1974-10-29 | Purification of d,d'-2,2'(ethylenediimino)di-1-butanol dihydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2548508A1 true DE2548508A1 (de) | 1976-05-06 |
| DE2548508C2 DE2548508C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-14 |
Family
ID=24065699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752548508 Granted DE2548508A1 (de) | 1974-10-29 | 1975-10-29 | Verfahren zur herstellung von d,d'-2,2'-(aethylendiimino)-di-1-butanol- dihydrochlorid |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0134893A3 (en) * | 1983-05-19 | 1987-11-04 | TAMBURINI SpA | System for composing heavy structure houses to disassemble |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6456231U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1987-10-02 | 1989-04-07 | ||
| US5162214A (en) * | 1991-04-05 | 1992-11-10 | General Atomics International Services Corporation | Cma production utilizing acetate ion exchange from fermentation broth |
| 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 |
| US7456222B2 (en) * | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| US20040033986A1 (en) | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| 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 |
| CN103664652A (zh) * | 2013-09-25 | 2014-03-26 | 南京工业大学 | 一种n，n，n′，n′-四(2-羟基乙基)-乙二胺的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2205269A1 (de) * | 1971-02-11 | 1972-09-07 | American Cyanamid Co., Wayne, N.J. (V.StA.) | Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2569549A (en) * | 1949-03-21 | 1951-10-02 | Du Pont | Imidohalides and process of preparing them and their hydrolysis products |
| AT252890B (de) * | 1961-02-07 | 1967-03-10 | American Cyanamid Co | Verfahren zur Herstellung von neuen Hydroxydiaminen |
| US3553257A (en) * | 1966-09-16 | 1971-01-05 | American Cyanamid Co | Preparation of d-2-amino-1-butanol salts |
| GB1198923A (en) * | 1968-04-18 | 1970-07-15 | Zoja Lab Chim Farm | Process for the Preparation of the Dextrorotatory 2, 2', (Ethylenediimino)-di-1-butanoldihydrochloride |
| DE1768612A1 (de) * | 1968-06-06 | 1971-11-18 | Zoja Lab Chim Farm | Verfahren zur Herstellung von sehr reinem,pharmazeutisch geeignetem rechtsdrehenden 2,2'-(AEthylendiimin)-di-1-butanoldihydrochlorid |
| US3855300A (en) * | 1973-09-05 | 1974-12-17 | Sankyo Chem Ind Ltd | Process for the production of 2-amino-1-butanol |
-
1974
- 1974-10-29 US US05/518,832 patent/US3944616A/en not_active Expired - Lifetime
-
1975
- 1975-09-08 CA CA234,913A patent/CA1065344A/en not_active Expired
- 1975-09-17 GB GB38283/75A patent/GB1516169A/en not_active Expired
- 1975-10-27 PH PH17709A patent/PH13460A/en unknown
- 1975-10-27 JP JP50128414A patent/JPS5926612B2/ja not_active Expired
- 1975-10-28 BE BE161300A patent/BE834930A/xx not_active IP Right Cessation
- 1975-10-29 DE DE19752548508 patent/DE2548508A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2205269A1 (de) * | 1971-02-11 | 1972-09-07 | American Cyanamid Co., Wayne, N.J. (V.StA.) | Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0134893A3 (en) * | 1983-05-19 | 1987-11-04 | TAMBURINI SpA | System for composing heavy structure houses to disassemble |
Also Published As
| Publication number | Publication date |
|---|---|
| PH13460A (en) | 1980-05-15 |
| DE2548508C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-14 |
| JPS5926612B2 (ja) | 1984-06-29 |
| US3944616A (en) | 1976-03-16 |
| AU8472575A (en) | 1977-03-17 |
| GB1516169A (en) | 1978-06-28 |
| CA1065344A (en) | 1979-10-30 |
| JPS5168511A (en) | 1976-06-14 |
| BE834930A (fr) | 1976-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1493579B1 (de) | Verfahren zur Herstellung neuer pharmazeutisch wertvoller Verbindungen | |
| DE2548508C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2205269A1 (de) | Verfahren zur Herstellung von d,d-2,2-(Äthylendiimino)-di-l-butanol-hydrochlorid | |
| DE2022656C3 (de) | 2-(Nicotinoylaminoäthansulfonylamino) pyridin | |
| DE69604513T2 (de) | Verfahren zur Herstellung substituierter Carbodiimide | |
| DE2439284C2 (de) | 2-Phenyl-3-amino-4-acetyl-5-methylpyrrol, dessen Salze und diese Verbindungen enthaltende pharmazeutische Zubereitung | |
| DE1620747C3 (de) | Carbothiamin sowie dessen nichttoxische organische oder anorganische Säureadditionssalze sowie Verfahren zur Herstellung dieser Verbindungen | |
| DE1445415C3 (de) | Substituierte Imidazolidinone, ihre therapeutisch verträglichen Salze und Verfahren zu ihrer Herstellung | |
| DE825840C (de) | Verfahren zur Herstellung substituierter Piperazine | |
| DE948687C (de) | Verfahren zur Herstellung von Dialkylxanthinabkoemlingen | |
| DE1131679B (de) | Verfahren zur Herstellung von Phenthiazinverbindungen | |
| AT232500B (de) | Verfahren zur Herstellung von neuen Phenylalaninderivaten | |
| EP0104352B1 (de) | Verfahren zur Herstellung von O,S-Dimethyl-thiolophosphorsäureamid | |
| DE1770104C3 (de) | 2- [(3,4-Dichlorphenoxy)-methyl] -2-unidazolin und seine Salze | |
| DE2536146A1 (de) | Verfahren zur herstellung von tetramisol | |
| EP0049494A1 (de) | Ester von 7-Hydroxylalkyl-1,3-dimethylxanthinen, Verfahren zu ihrer Herstellung und ihre Verwendung als lipidsenkende Mittel | |
| DE1643890C (de) | alpha- Hy droxy-gamma-methy lmercaptobuttersäure-methylsulfonium-halogenide und Verfahren zu ihrer Herstellung | |
| CH514595A (de) | Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung | |
| DE2925359C3 (de) | Verfahren zur Herstellung von Salzen der (-)cis-1,2-Epoxypropylphosphonsäure | |
| AT329576B (de) | Verfahren zur herstellung von neuen 2- (morpholino- oder homomorpholino) -1- (3-trifluormethylphenyl) -propanderivaten ihren salzen und optischen isomeren | |
| DE2515548A1 (de) | Quaternaere ammoniumsalze von n-dialkylaminoalkyl-n-(2-indanyl)-anilinen und verfahren zu ihrer herstellung | |
| AT374456B (de) | Verfahren zur herstellung von neuen benzolsulfonamidderivaten | |
| DE1037443B (de) | Verfahren zur Herstellung von narkotisch wirkenden Carbamaten | |
| DE1593927A1 (de) | Verfahren zur Herstellung von neuen basischen AEthern | |
| DE1793002B2 (de) | Verfahren zur Herstellung von Äthylendihydrazin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 800 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |