SK1012003A3 - Process for the preparation of imidazopyridines - Google Patents

Process for the preparation of imidazopyridines Download PDF

Info

Publication number: SK1012003A3
Authority: SK; Slovakia
Prior art keywords: hydrogen; compound; formula; halogen; alkyl
Prior art date: 2000-08-17

Application number

SK101-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Max Rey

Armin Rossler

Giusep Derungs

Jae Kyoung Pak

Original Assignee

Cilag Ag

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.)

2000-08-17

Filing date

2001-08-17

Publication date

2003-07-01

2001-08-17 Application filed by Cilag Ag filed Critical Cilag Ag

2003-07-01 Publication of SK1012003A3 publication Critical patent/SK1012003A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims description 8
150000005232 imidazopyridines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 39
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 17
150000002367 halogens Chemical class 0.000 claims abstract description 17
150000002431 hydrogen Chemical class 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
239000012345 acetylating agent Substances 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
239000012346 acetyl chloride Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
235000019253 formic acid Nutrition 0.000 claims 1
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 abstract description 2
239000002249 anxiolytic agent Substances 0.000 abstract description 2
230000000949 anxiolytic effect Effects 0.000 abstract description 2
229940005530 anxiolytics Drugs 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 4
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
IGJYZHOQYHTURH-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1h-imidazole Chemical compound CC1=CC(C)=CC=C1C1=NC=CN1 IGJYZHOQYHTURH-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002912 oxalic acid derivatives Chemical class 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61P25/22—Anxiolytics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK101-2003A 2000-08-17 2001-08-17 Process for the preparation of imidazopyridines SK1012003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/EP2000/008021 WO2002014306A1 (en)	2000-08-17	2000-08-17	Process for the preparation of imidazopyridines
PCT/EP2001/009519 WO2002014316A1 (en)	2000-08-17	2001-08-17	Process for the preparation of imidazopyridines

Publications (1)

Publication Number	Publication Date
SK1012003A3 true SK1012003A3 (en)	2003-07-01

Family

ID=8164061

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK101-2003A SK1012003A3 (en)	2000-08-17	2001-08-17	Process for the preparation of imidazopyridines

Country Status (9)

Country	Link
US (1)	US6841679B2 (de)
JP (1)	JP2004506634A (de)
AT (1)	ATE262526T1 (de)
AU (2)	AU2000264428A1 (de)
CA (1)	CA2417821A1 (de)
CZ (1)	CZ294416B6 (de)
DE (1)	DE60102478D1 (de)
SK (1)	SK1012003A3 (de)
WO (2)	WO2002014306A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004058758A1 (en)	2002-12-18	2004-07-15	Mallinckrodt Inc.	Synthesis of heteroaryl acetamides
ATE489385T1 (de)	2005-08-24	2010-12-15	Elder Pharmaceuticals Ltd	Verfahren zur herstellung von imidazopyridinen
US20080145425A1 (en) *	2006-12-15	2008-06-19	Pliva Research & Development Limited	Pharmaceutical composition of zolpidem
IN2012MU03517A (de) *	2012-12-13	2015-06-26	Alembic Pharmaceuticals Ltd

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2492382A1 (fr) *	1980-10-22	1982-04-23	Synthelabo	Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique
FR2600650B1 (fr) *	1986-06-27	1988-09-09	Synthelabo	Procede de preparation d'imidazopyridines et composes intermediaires

2000
- 2000-08-17 WO PCT/EP2000/008021 patent/WO2002014306A1/en not_active Ceased
- 2000-08-17 AU AU2000264428A patent/AU2000264428A1/en not_active Abandoned
2001
- 2001-08-17 SK SK101-2003A patent/SK1012003A3/sk unknown
- 2001-08-17 AU AU2002212143A patent/AU2002212143A1/en not_active Abandoned
- 2001-08-17 AT AT01980251T patent/ATE262526T1/de not_active IP Right Cessation
- 2001-08-17 JP JP2002519456A patent/JP2004506634A/ja active Pending
- 2001-08-17 US US10/344,713 patent/US6841679B2/en not_active Expired - Fee Related
- 2001-08-17 CZ CZ2003321A patent/CZ294416B6/cs not_active IP Right Cessation
- 2001-08-17 CA CA002417821A patent/CA2417821A1/en not_active Abandoned
- 2001-08-17 DE DE60102478T patent/DE60102478D1/de not_active Expired - Lifetime
- 2001-08-17 WO PCT/EP2001/009519 patent/WO2002014316A1/en not_active Ceased

Also Published As

Publication number	Publication date
WO2002014306A1 (en)	2002-02-21
CA2417821A1 (en)	2002-02-21
CZ2003321A3 (cs)	2003-06-18
WO2002014316A1 (en)	2002-02-21
DE60102478D1 (de)	2004-04-29
ATE262526T1 (de)	2004-04-15
AU2002212143A1 (en)	2002-02-25
US6841679B2 (en)	2005-01-11
AU2000264428A1 (en)	2002-02-25
CZ294416B6 (cs)	2004-12-15
US20040072861A1 (en)	2004-04-15
JP2004506634A (ja)	2004-03-04

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