ZA200408273B - Method for manufacture of sertindole - Google Patents

Method for manufacture of sertindole Download PDF

Info

Publication number: ZA200408273B
Authority: ZA; South Africa
Prior art keywords: chloro; indole; copper; ethylenediamine; reaction
Prior art date: 2002-03-27

Application number

ZA200408273A

Other languages

English (en)

Inventor

Jacopo Zanon

Marco Villa

Francesco Ciardella

Original Assignee

Lundbeck & Co As H

Priority date (The priority date 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 date listed.)

2002-03-27

Filing date

2004-10-13

Publication date

2006-07-26

2004-10-13 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2006-07-26 Publication of ZA200408273B publication Critical patent/ZA200408273B/en

Links

238000000034 method Methods 0.000 title claims description 39
238000004519 manufacturing process Methods 0.000 title claims description 25
GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 title claims description 13
229960000652 sertindole Drugs 0.000 title claims description 13
238000006243 chemical reaction Methods 0.000 claims description 25
150000001879 copper Chemical class 0.000 claims description 20
239000003446 ligand Substances 0.000 claims description 19
MYTGFBZJLDLWQG-UHFFFAOYSA-N 5-chloro-1h-indole Chemical compound ClC1=CC=C2NC=CC2=C1 MYTGFBZJLDLWQG-UHFFFAOYSA-N 0.000 claims description 17
JYEKQDWSLSXYTJ-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C=C1 JYEKQDWSLSXYTJ-UHFFFAOYSA-N 0.000 claims description 14
239000002585 base Substances 0.000 claims description 14
230000003197 catalytic effect Effects 0.000 claims description 13
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 10
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 10
229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 8
229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 8
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 8
239000010949 copper Substances 0.000 claims description 8
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
-1 Cul Inorganic materials 0.000 claims description 5
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical class C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 5
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical group FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
KGNQDBQYEBMPFZ-UHFFFAOYSA-N 1-fluoro-4-iodobenzene Chemical compound FC1=CC=C(I)C=C1 KGNQDBQYEBMPFZ-UHFFFAOYSA-N 0.000 claims description 3
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
238000006254 arylation reaction Methods 0.000 description 6
229910052802 copper Inorganic materials 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
JDOHKGNGBGUGTR-UHFFFAOYSA-N 1-(4-fluorophenyl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=CC=C2C=C1 JDOHKGNGBGUGTR-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000561 anti-psychotic effect Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
150000003346 selenoethers Chemical class 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000006887 Ullmann reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
150000001500 aryl chlorides Chemical class 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
208000010877 cognitive disease Diseases 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
230000010354 integration Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Indole Compounds (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

ZA200408273A 2002-03-27 2004-10-13 Method for manufacture of sertindole ZA200408273B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DKPA200200480		2002-03-27

Publications (1)

Publication Number	Publication Date
ZA200408273B true ZA200408273B (en)	2006-07-26

Family

ID=37952025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200408273A ZA200408273B (en)	2002-03-27	2004-10-13	Method for manufacture of sertindole

Country Status (17)

Country	Link
EP (2)	EP1661887A1 (ja)
JP (1)	JP2005531519A (ja)
KR (1)	KR20040095332A (ja)
CN (1)	CN100528863C (ja)
AR (1)	AR039116A1 (ja)
AU (1)	AU2003215528B2 (ja)
BR (1)	BR0308627A (ja)
CA (1)	CA2480239C (ja)
CO (1)	CO5611197A2 (ja)
EA (1)	EA007009B1 (ja)
ME (1)	MEP6008A (ja)
NZ (1)	NZ535533A (ja)
PL (1)	PL371585A1 (ja)
RS (1)	RS85004A (ja)
UA (1)	UA78300C2 (ja)
WO (1)	WO2003080597A1 (ja)
ZA (1)	ZA200408273B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2494142A1 (en) *	2002-08-02	2004-02-12	Rhodia Pharma Solutions Inc.	Copper catalyzed arylation
RU2436490C2 (ru)	2006-07-07	2011-12-20	Пласт 2000 С.Р.Л.	Заварочный аппарат (варианты)
CN101591330B (zh) *	2009-06-29	2013-03-06	上海医药工业研究院	舍吲哚晶型及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE58370B1 (en) *	1985-04-10	1993-09-08	Lundbeck & Co As H	Indole derivatives
US6335463B1 (en) *	1997-05-09	2002-01-01	H. Lundbeck A/S	Method of manufacturing sertindole
WO1999018057A1 (en) *	1997-10-06	1999-04-15	Massachusetts Institute Of Technology	Preparation of diaryl ether by condensation reactions

2003
- 2003-03-24 AR ARP030101015A patent/AR039116A1/es unknown
- 2003-03-26 AU AU2003215528A patent/AU2003215528B2/en not_active Ceased
- 2003-03-26 PL PL03371585A patent/PL371585A1/xx not_active Application Discontinuation
- 2003-03-26 NZ NZ535533A patent/NZ535533A/en not_active IP Right Cessation
- 2003-03-26 RS YU85004A patent/RS85004A/sr unknown
- 2003-03-26 CN CNB038070111A patent/CN100528863C/zh not_active Expired - Fee Related
- 2003-03-26 UA UA20041008714A patent/UA78300C2/uk unknown
- 2003-03-26 WO PCT/DK2003/000208 patent/WO2003080597A1/en not_active Application Discontinuation
- 2003-03-26 KR KR10-2004-7015339A patent/KR20040095332A/ko not_active Application Discontinuation
- 2003-03-26 EA EA200401261A patent/EA007009B1/ru not_active IP Right Cessation
- 2003-03-26 CA CA2480239A patent/CA2480239C/en not_active Expired - Fee Related
- 2003-03-26 ME MEP-60/08A patent/MEP6008A/xx unknown
- 2003-03-26 EP EP05023338A patent/EP1661887A1/en not_active Withdrawn
- 2003-03-26 BR BR0308627-5A patent/BR0308627A/pt not_active IP Right Cessation
- 2003-03-26 EP EP03744772A patent/EP1490353A1/en not_active Ceased
- 2003-03-26 JP JP2003578351A patent/JP2005531519A/ja active Pending
2004
- 2004-10-13 CO CO04102837A patent/CO5611197A2/es not_active Application Discontinuation
- 2004-10-13 ZA ZA200408273A patent/ZA200408273B/en unknown

Also Published As

Publication number	Publication date
CO5611197A2 (es)	2006-02-28
BR0308627A (pt)	2005-02-15
KR20040095332A (ko)	2004-11-12
CN1642942A (zh)	2005-07-20
MEP6008A (xx)	2010-02-10
WO2003080597A1 (en)	2003-10-02
JP2005531519A (ja)	2005-10-20
EP1661887A1 (en)	2006-05-31
AR039116A1 (es)	2005-02-09
EP1490353A1 (en)	2004-12-29
EA007009B1 (ru)	2006-06-30
AU2003215528B2 (en)	2009-05-28
UA78300C2 (en)	2007-03-15
NZ535533A (en)	2007-01-26
CN100528863C (zh)	2009-08-19
CA2480239C (en)	2010-11-23
EA200401261A1 (ru)	2005-02-24
AU2003215528A1 (en)	2003-10-08
CA2480239A1 (en)	2003-10-02
PL371585A1 (en)	2005-06-27
RS85004A (en)	2006-12-15

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