UA81036C2 - Intermediate for the preparation of therapeutically active imidazopyridines - Google Patents

Intermediate for the preparation of therapeutically active imidazopyridines Download PDF

Info

Publication number: UA81036C2
Authority: UA; Ukraine
Prior art keywords: formula; compound; acid; naphthalene disulfonic; carried out
Prior art date: 2003-05-14

Application number

UAA200511529A

Other languages

English (en)

Ukrainian (uk)

Inventor

Bernd Mueller

Original Assignee

Altana Pharma 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.)

2003-05-14

Filing date

2004-05-13

Publication date

2007-11-26

2004-05-13 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2007-11-26 Publication of UA81036C2 publication Critical patent/UA81036C2/uk

Links

238000002360 preparation method Methods 0.000 title abstract description 3
150000005232 imidazopyridines Chemical class 0.000 title 1
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 34
239000000654 additive Substances 0.000 claims description 14
230000000996 additive effect Effects 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
-1 for example Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZGLUKQQSWABKDH-UHFFFAOYSA-N 5-amino-1-methyl-3h-indol-2-one Chemical compound NC1=CC=C2N(C)C(=O)CC2=C1 ZGLUKQQSWABKDH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

UAA200511529A 2003-05-14 2004-05-13 Intermediate for the preparation of therapeutically active imidazopyridines UA81036C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP03010785		2003-05-14
PCT/EP2004/050780 WO2004101566A1 (en)	2003-05-14	2004-05-13	Novel intermediate for the preparation of therapeutically active imidazopyridines

Publications (1)

Publication Number	Publication Date
UA81036C2 true UA81036C2 (en)	2007-11-26

Family

ID=33442723

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200511529A UA81036C2 (en)	2003-05-14	2004-05-13	Intermediate for the preparation of therapeutically active imidazopyridines

Country Status (27)

Country	Link
US (1)	US20060235228A1 (de)
EP (1)	EP1631571B1 (de)
JP (1)	JP2007502852A (de)
KR (1)	KR20060012593A (de)
CN (1)	CN100361991C (de)
AR (1)	AR044288A1 (de)
AT (1)	ATE393155T1 (de)
AU (1)	AU2004238570A1 (de)
BR (1)	BRPI0410084A (de)
CA (1)	CA2525038A1 (de)
CL (1)	CL2004001019A1 (de)
DE (1)	DE602004013311D1 (de)
EA (1)	EA008746B1 (de)
EC (1)	ECSP056055A (de)
GE (1)	GEP20084394B (de)
IS (1)	IS8163A (de)
MX (1)	MXPA05011859A (de)
MY (1)	MY141657A (de)
NO (1)	NO20055755L (de)
NZ (1)	NZ543913A (de)
PE (1)	PE20050155A1 (de)
RS (1)	RS20050824A (de)
SA (1)	SA04250092B1 (de)
TW (1)	TW200503701A (de)
UA (1)	UA81036C2 (de)
WO (1)	WO2004101566A1 (de)
ZA (1)	ZA200507741B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SG11201800591TA (en)	2015-07-30	2018-02-27	Takeda Pharmaceuticals Co	Tablet
US20230060797A1 (en) *	2021-09-02	2023-03-02	Jcr Pharmaceuticals Co., Ltd.	Therapeutic compound for neuronal ceroid lipofuscinosis

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2011078C3 (de) *	1970-03-09	1974-11-14	Goedecke Ag, 1000 Berlin	Verfahren zur Reinigung von Hexetidin
NZ510610A (en) *	1998-09-23	2003-07-25	Altana Pharma Ag	Tetrahydropyridoethers
CA2404474A1 (en) *	2000-03-29	2001-10-04	Altana Pharma Ag	Prodrugs of imidazopyridine derivatives

2004
- 2004-04-26 SA SA4250092A patent/SA04250092B1/ar unknown
- 2004-05-03 RS YUP-2005/0824A patent/RS20050824A/sr unknown
- 2004-05-11 PE PE2004000485A patent/PE20050155A1/es not_active Application Discontinuation
- 2004-05-11 MY MYPI20041747A patent/MY141657A/en unknown
- 2004-05-11 AR ARP040101591A patent/AR044288A1/es not_active Application Discontinuation
- 2004-05-12 CL CL200401019A patent/CL2004001019A1/es unknown
- 2004-05-13 EP EP04741560A patent/EP1631571B1/de not_active Expired - Lifetime
- 2004-05-13 MX MXPA05011859A patent/MXPA05011859A/es not_active Application Discontinuation
- 2004-05-13 JP JP2006530186A patent/JP2007502852A/ja not_active Withdrawn
- 2004-05-13 DE DE602004013311T patent/DE602004013311D1/de not_active Expired - Fee Related
- 2004-05-13 US US10/555,793 patent/US20060235228A1/en not_active Abandoned
- 2004-05-13 CN CNB200480011797XA patent/CN100361991C/zh not_active Expired - Fee Related
- 2004-05-13 BR BRPI0410084-0A patent/BRPI0410084A/pt not_active IP Right Cessation
- 2004-05-13 CA CA002525038A patent/CA2525038A1/en not_active Abandoned
- 2004-05-13 GE GEAP20049113A patent/GEP20084394B/en unknown
- 2004-05-13 WO PCT/EP2004/050780 patent/WO2004101566A1/en not_active Ceased
- 2004-05-13 KR KR1020057021015A patent/KR20060012593A/ko not_active Withdrawn
- 2004-05-13 AU AU2004238570A patent/AU2004238570A1/en not_active Abandoned
- 2004-05-13 UA UAA200511529A patent/UA81036C2/uk unknown
- 2004-05-13 AT AT04741560T patent/ATE393155T1/de not_active IP Right Cessation
- 2004-05-13 NZ NZ543913A patent/NZ543913A/en unknown
- 2004-05-13 EA EA200501691A patent/EA008746B1/ru not_active IP Right Cessation
- 2004-05-14 TW TW093113749A patent/TW200503701A/zh unknown
2005
- 2005-09-26 ZA ZA200507741A patent/ZA200507741B/xx unknown
- 2005-09-28 EC EC2005006055A patent/ECSP056055A/es unknown
- 2005-12-01 IS IS8163A patent/IS8163A/is unknown
- 2005-12-05 NO NO20055755A patent/NO20055755L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
TW200503701A (en)	2005-02-01
ZA200507741B (en)	2008-08-27
JP2007502852A (ja)	2007-02-15
KR20060012593A (ko)	2006-02-08
WO2004101566A1 (en)	2004-11-25
NZ543913A (en)	2008-02-29
SA04250092B1 (ar)	2008-05-04
DE602004013311D1 (de)	2008-06-05
GEP20084394B (en)	2008-06-10
AR044288A1 (es)	2005-09-07
NO20055755L (no)	2005-12-05
BRPI0410084A (pt)	2006-05-16
AU2004238570A1 (en)	2004-11-25
RS20050824A (sr)	2007-12-31
ATE393155T1 (de)	2008-05-15
MXPA05011859A (es)	2006-02-17
EA200501691A1 (ru)	2006-06-30
CN100361991C (zh)	2008-01-16
IS8163A (is)	2005-12-01
PE20050155A1 (es)	2005-03-22
WO2004101566A8 (en)	2007-04-26
CN1780839A (zh)	2006-05-31
EP1631571B1 (de)	2008-04-23
CL2004001019A1 (es)	2005-03-04
EP1631571A1 (de)	2006-03-08
ECSP056055A (es)	2006-01-27
MY141657A (en)	2010-05-31
US20060235228A1 (en)	2006-10-19
EA008746B1 (ru)	2007-08-31
CA2525038A1 (en)	2004-11-25

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