JP2002308835A - テルビナフィンの製造方法 - Google Patents
テルビナフィンの製造方法Info
- Publication number
- JP2002308835A JP2002308835A JP2002056007A JP2002056007A JP2002308835A JP 2002308835 A JP2002308835 A JP 2002308835A JP 2002056007 A JP2002056007 A JP 2002056007A JP 2002056007 A JP2002056007 A JP 2002056007A JP 2002308835 A JP2002308835 A JP 2002308835A
- Authority
- JP
- Japan
- Prior art keywords
- terbinafine
- mmol
- copper
- palladium
- base
- 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
- 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 claims abstract description 26
- 229960002722 terbinafine Drugs 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 9
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical group CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical group CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229960000699 terbinafine hydrochloride Drugs 0.000 description 3
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- ZDHCSCQGRLSOQG-UHFFFAOYSA-N 2-chloroethenamine Chemical compound NC=CCl ZDHCSCQGRLSOQG-UHFFFAOYSA-N 0.000 description 1
- 101100408296 Autographa californica nuclear polyhedrosis virus AC24 gene Proteins 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 241001068914 Melicope knudsenii Species 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- IHJICFFGQVAWEV-UHFFFAOYSA-N [Li].CC(C)(C)C#C Chemical group [Li].CC(C)(C)C#C IHJICFFGQVAWEV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical class CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910000080 stannane Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- -1 vinyl halide Chemical class 0.000 description 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI000430A ITMI20010430A1 (it) | 2001-03-02 | 2001-03-02 | Metodo per la sintesi di terbinafina |
| IT2001A000430 | 2001-03-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002308835A true JP2002308835A (ja) | 2002-10-23 |
| JP2002308835A5 JP2002308835A5 (OSRAM) | 2005-08-25 |
Family
ID=11447087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002056007A Pending JP2002308835A (ja) | 2001-03-02 | 2002-03-01 | テルビナフィンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6515181B2 (OSRAM) |
| EP (1) | EP1236709B1 (OSRAM) |
| JP (1) | JP2002308835A (OSRAM) |
| AT (1) | ATE380171T1 (OSRAM) |
| CA (1) | CA2373813A1 (OSRAM) |
| DE (1) | DE60223862T2 (OSRAM) |
| IT (1) | ITMI20010430A1 (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006508156A (ja) * | 2002-11-29 | 2006-03-09 | ディファルマ・ソシエタ・ペル・アチオニ | 触媒として白金を用いたテルビナフィンの製造方法 |
| JP2007504110A (ja) * | 2003-08-29 | 2007-03-01 | ノバルティス アクチエンゲゼルシャフト | テルビナフィンの精製法 |
| JP2008501784A (ja) * | 2004-06-09 | 2008-01-24 | エッフェ．イー．エッセ． ファブリカ イタリアーナ シンテーティチ エッセ．ペー．アー． | テルビナフィンおよびその誘導体を合成するための方法 |
| JP2008531513A (ja) * | 2005-02-25 | 2008-08-14 | ノバルティス アクチエンゲゼルシャフト | 精製方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7244703B2 (en) * | 2001-06-22 | 2007-07-17 | Bentley Pharmaceuticals, Inc. | Pharmaceutical compositions and methods for peptide treatment |
| US20050197512A1 (en) * | 2003-08-29 | 2005-09-08 | Ulrich Beutler | Purification process |
| EP1706128B1 (en) | 2003-12-08 | 2010-07-21 | CPEX Pharmaceuticals, Inc. | Pharmaceutical compositions and methods for insulin treatment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4755538A (en) * | 1987-04-14 | 1988-07-05 | The B. F. Goodrich Company | Skinless porous particle PVC resin and process for producing same |
| NZ280065A (en) * | 1995-09-20 | 1998-04-27 | Apotex Inc | Preparation of n-alkyl-n-(1-naphthylmethyl)alk-2-en-4-ynylamine derivatives |
-
2001
- 2001-03-02 IT IT2001MI000430A patent/ITMI20010430A1/it unknown
-
2002
- 2002-02-22 DE DE60223862T patent/DE60223862T2/de not_active Expired - Fee Related
- 2002-02-22 AT AT02003969T patent/ATE380171T1/de not_active IP Right Cessation
- 2002-02-22 EP EP02003969A patent/EP1236709B1/en not_active Expired - Lifetime
- 2002-02-28 US US10/085,699 patent/US6515181B2/en not_active Expired - Fee Related
- 2002-02-28 CA CA002373813A patent/CA2373813A1/en not_active Abandoned
- 2002-03-01 JP JP2002056007A patent/JP2002308835A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006508156A (ja) * | 2002-11-29 | 2006-03-09 | ディファルマ・ソシエタ・ペル・アチオニ | 触媒として白金を用いたテルビナフィンの製造方法 |
| JP2007504110A (ja) * | 2003-08-29 | 2007-03-01 | ノバルティス アクチエンゲゼルシャフト | テルビナフィンの精製法 |
| KR101233024B1 (ko) * | 2003-08-29 | 2013-02-13 | 노파르티스 아게 | 테르비나핀의 정제 방법 |
| JP2008501784A (ja) * | 2004-06-09 | 2008-01-24 | エッフェ．イー．エッセ． ファブリカ イタリアーナ シンテーティチ エッセ．ペー．アー． | テルビナフィンおよびその誘導体を合成するための方法 |
| JP2008531513A (ja) * | 2005-02-25 | 2008-08-14 | ノバルティス アクチエンゲゼルシャフト | 精製方法 |
| JP2012176960A (ja) * | 2005-02-25 | 2012-09-13 | Novartis Ag | 精製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6515181B2 (en) | 2003-02-04 |
| DE60223862D1 (de) | 2008-01-17 |
| EP1236709A3 (en) | 2003-11-26 |
| US20020123651A1 (en) | 2002-09-05 |
| EP1236709B1 (en) | 2007-12-05 |
| CA2373813A1 (en) | 2002-09-02 |
| DE60223862T2 (de) | 2008-03-20 |
| ATE380171T1 (de) | 2007-12-15 |
| ITMI20010430A1 (it) | 2002-09-02 |
| EP1236709A2 (en) | 2002-09-04 |
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