LT2002103A - Method for the preparation of (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethanamine (terbinafine) - Google Patents
Method for the preparation of (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethanamine (terbinafine)Info
- Publication number
- LT2002103A LT2002103A LT2002103A LT2002103A LT2002103A LT 2002103 A LT2002103 A LT 2002103A LT 2002103 A LT2002103 A LT 2002103A LT 2002103 A LT2002103 A LT 2002103A LT 2002103 A LT2002103 A LT 2002103A
- Authority
- LT
- Lithuania
- Prior art keywords
- naphthalenemethanamine
- methyl
- hepten
- terbinafine
- ynyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 229960002722 terbinafine Drugs 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 239000000543 intermediate Substances 0.000 abstract 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 abstract 1
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The method for the preparation of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl))-N-methyl-1-naphthalenemethanamine (terbinafine) from N-methyl-1-naphthalenemethanamine and (E)-1,3-dichlorpropene and by subsequent reaction with 3,3-dimethylbut-1-yne characterised in that the whole reaction sequence is carried out without any isolation of intermediates. All sequential reactions are carried out in the solvent system common for the whole reaction sequence and inert to the reactants and intermediates presentin the process. The method according to the present invention may also include additional purification steps.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SK520-2000A SK5202000A3 (en) | 2000-04-07 | 2000-04-07 | Method for the preparation of (e)-n-(6,6-dimethyl-2-hepten-4- inyl)-n-methyl-1-naphthalenemethylamine (terbinaphin) |
Publications (2)
Publication Number | Publication Date |
---|---|
LT2002103A true LT2002103A (en) | 2003-05-26 |
LT5051B LT5051B (en) | 2003-08-25 |
Family
ID=20435846
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LT2002103A LT5051B (en) | 2000-04-07 | 2002-09-19 | Method for the preparation of (e)-n-(6,6-dimethyl-2-hepten-4-ynyl)-n-methyl-1-naphthalenemethanamine (terbinafine) |
Country Status (7)
Country | Link |
---|---|
AU (1) | AU2001248998A1 (en) |
EE (1) | EE200200583A (en) |
HU (1) | HUP0302919A3 (en) |
LT (1) | LT5051B (en) |
LV (1) | LV12955B (en) |
SK (1) | SK5202000A3 (en) |
WO (1) | WO2001077064A1 (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100459275B1 (en) * | 2001-12-28 | 2004-12-03 | 주식회사유한양행 | A PROCESS FOR THE PREPARATION OF TERBINAFINE OR HCl SALT THEREOF |
KR20030066186A (en) * | 2002-02-05 | 2003-08-09 | 한솔케미언스 주식회사 | Process for preparation of Terbinafin |
ITMI20022534A1 (en) | 2002-11-29 | 2004-05-30 | Dinamite Dipharma S P A | PROCEDURE FOR THE PREPARATION OF TERBINAFINA BY USING PLATINUM AS A CATALYST. |
EP1951700A2 (en) * | 2005-10-31 | 2008-08-06 | Janssen Pharmaceutica N.V. | Novel processes for the preparation of piperazinyl and diazapanyl benzamide derivatives |
MY151028A (en) * | 2005-10-31 | 2014-03-31 | Janssen Pharmaceutica Nv | Novel processes for the preparation of cyclopropyl-amide derivatives |
CN101624328B (en) * | 2009-07-31 | 2011-12-14 | 山东铂源化学有限公司 | Method for synthesizing (E)-1-chlorine-6, 6-dimethyl-2-heptylene-4-alkyne |
CN104725240B (en) * | 2015-02-12 | 2017-05-24 | 吉林修正药业新药开发有限公司 | Method for preparing terbinafine hydrochloride Z-shaped isomer |
CN105016966A (en) * | 2015-07-31 | 2015-11-04 | 江苏恒润制药有限公司 | Preparation method of (E)-1-chloro-6,6-dimethyl-2-heptene-4-alkyne |
CN111153807B (en) * | 2020-01-16 | 2023-01-06 | 河南豫辰药业股份有限公司 | Preparation method of N, N-dimethylamino chloropropane hydrochloride |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19975055I1 (en) | 1979-08-22 | 2000-01-27 | Novartis Ag | Propenylamines Process for their preparation pharmaceutical compositions containing them and their use as medicines |
CH678527A5 (en) | 1989-06-22 | 1991-09-30 | Sandoz Ag | Trans(E)-N-(1-naphthyl:methyl)-heptenyl-amine prepn. - by simultaneously converting crude mixt. contg. cis and trans isomers to salt and precipitating trans isomer |
JP3116364B2 (en) | 1989-10-02 | 2000-12-11 | 萬有製薬株式会社 | Method for producing enyne derivatives |
NZ280065A (en) | 1995-09-20 | 1998-04-27 | Apotex Inc | Preparation of n-alkyl-n-(1-naphthylmethyl)alk-2-en-4-ynylamine derivatives |
-
2000
- 2000-04-07 SK SK520-2000A patent/SK5202000A3/en unknown
-
2001
- 2001-04-05 WO PCT/SK2001/000008 patent/WO2001077064A1/en not_active Application Discontinuation
- 2001-04-05 EE EEP200200583A patent/EE200200583A/en unknown
- 2001-04-05 HU HU0302919A patent/HUP0302919A3/en unknown
- 2001-04-05 AU AU2001248998A patent/AU2001248998A1/en not_active Abandoned
-
2002
- 2002-09-19 LT LT2002103A patent/LT5051B/en not_active IP Right Cessation
- 2002-11-06 LV LVP-02-193A patent/LV12955B/en unknown
Also Published As
Publication number | Publication date |
---|---|
LV12955B (en) | 2003-04-20 |
AU2001248998A1 (en) | 2001-10-23 |
SK5202000A3 (en) | 2001-12-03 |
LT5051B (en) | 2003-08-25 |
WO2001077064A1 (en) | 2001-10-18 |
EE200200583A (en) | 2004-04-15 |
HUP0302919A2 (en) | 2003-12-29 |
WO2001077064A8 (en) | 2002-01-03 |
HUP0302919A3 (en) | 2004-09-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM9A | Lapsed patents |
Effective date: 20040405 |