ZA200401796B - Benzothiazepine derivatives for the treatment of hyperlipidaemia. - Google Patents

Benzothiazepine derivatives for the treatment of hyperlipidaemia. Download PDF

Info

Publication number: ZA200401796B
Authority: ZA; South Africa
Prior art keywords: formula; solvate; compound; salt; pharmaceutically acceptable
Prior art date: 2001-09-07

Application number

ZA200401796A

Other languages

English (en)

Inventor

Ingemar Starke

David Blomberg

Mikael Ulf Johan Dahlstrom

Original Assignee

Astrazeneca Ab

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.)

2001-09-07

Filing date

2004-03-04

Publication date

2005-04-08

2004-03-04 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2005-04-08 Publication of ZA200401796B publication Critical patent/ZA200401796B/en

Links

238000011282 treatment Methods 0.000 title claims description 37
208000031226 Hyperlipidaemia Diseases 0.000 title description 7
150000007657 benzothiazepines Chemical class 0.000 title description 7
229940085242 benzothiazepine derivative selective calcium channel blockers with direct cardiac effects Drugs 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 130
-1 nitro, cyano, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims description 129
150000003839 salts Chemical class 0.000 claims description 102
239000012453 solvate Substances 0.000 claims description 94
229910052739 hydrogen Inorganic materials 0.000 claims description 84
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238000000034 method Methods 0.000 claims description 53
239000000651 prodrug Substances 0.000 claims description 49
229940002612 prodrug Drugs 0.000 claims description 49
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 39
230000008569 process Effects 0.000 claims description 38
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
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125000001424 substituent group Chemical group 0.000 claims description 26
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241001465754 Metazoa Species 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 24
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238000005804 alkylation reaction Methods 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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238000003556 assay Methods 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
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150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
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239000006071 cream Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
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230000002452 interceptive effect Effects 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
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159000000003 magnesium salts Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
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150000007522 mineralic acids Chemical class 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
238000005897 peptide coupling reaction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
108010080180 poststatin Proteins 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
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238000011200 topical administration Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
125000001425 triazolyl group Chemical group 0.000 description 1
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Steroid Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

ZA200401796A 2001-09-07 2004-03-04 Benzothiazepine derivatives for the treatment of hyperlipidaemia. ZA200401796B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB0121621.7A GB0121621D0 (en)	2001-09-07	2001-09-07	Chemical compounds

Publications (1)

Publication Number	Publication Date
ZA200401796B true ZA200401796B (en)	2005-04-08

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ID=9921649

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ZA200401796A ZA200401796B (en)	2001-09-07	2004-03-04	Benzothiazepine derivatives for the treatment of hyperlipidaemia.

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Country	Link
US (1)	US7125864B2 (de)
EP (1)	EP1427713B1 (de)
JP (1)	JP4494780B2 (de)
KR (1)	KR20040031057A (de)
CN (1)	CN1639140A (de)
AT (1)	ATE454379T1 (de)
AU (1)	AU2002331927B2 (de)
BR (1)	BR0212344A (de)
CA (1)	CA2459457A1 (de)
DE (1)	DE60235019D1 (de)
ES (1)	ES2337559T3 (de)
GB (1)	GB0121621D0 (de)
IL (1)	IL160689A0 (de)
MX (1)	MXPA04002189A (de)
NO (1)	NO20040954L (de)
NZ (1)	NZ531797A (de)
UY (1)	UY27437A1 (de)
WO (1)	WO2003022825A1 (de)
ZA (1)	ZA200401796B (de)

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- 2001-09-07 GB GBGB0121621.7A patent/GB0121621D0/en not_active Ceased
2002
- 2002-09-05 IL IL16068902A patent/IL160689A0/xx unknown
- 2002-09-05 MX MXPA04002189A patent/MXPA04002189A/es active IP Right Grant
- 2002-09-05 AT AT02767623T patent/ATE454379T1/de not_active IP Right Cessation
- 2002-09-05 CA CA002459457A patent/CA2459457A1/en not_active Abandoned
- 2002-09-05 DE DE60235019T patent/DE60235019D1/de not_active Expired - Lifetime
- 2002-09-05 WO PCT/GB2002/004043 patent/WO2003022825A1/en not_active Ceased
- 2002-09-05 JP JP2003526900A patent/JP4494780B2/ja not_active Expired - Fee Related
- 2002-09-05 EP EP02767623A patent/EP1427713B1/de not_active Expired - Lifetime
- 2002-09-05 CN CNA028221079A patent/CN1639140A/zh active Pending
- 2002-09-05 AU AU2002331927A patent/AU2002331927B2/en not_active Ceased
- 2002-09-05 NZ NZ531797A patent/NZ531797A/en unknown
- 2002-09-05 US US10/489,009 patent/US7125864B2/en not_active Expired - Fee Related
- 2002-09-05 BR BR0212344-4A patent/BR0212344A/pt not_active IP Right Cessation
- 2002-09-05 ES ES02767623T patent/ES2337559T3/es not_active Expired - Lifetime
- 2002-09-05 KR KR10-2004-7003331A patent/KR20040031057A/ko not_active Ceased
- 2002-09-06 UY UY27437A patent/UY27437A1/es unknown
2004
- 2004-03-04 NO NO20040954A patent/NO20040954L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
ES2337559T3 (es)	2010-04-27
EP1427713A1 (de)	2004-06-16
IL160689A0 (en)	2004-08-31
ATE454379T1 (de)	2010-01-15
JP2005503401A (ja)	2005-02-03
AU2002331927B2 (en)	2008-02-21
JP4494780B2 (ja)	2010-06-30
NZ531797A (en)	2005-11-25
CN1639140A (zh)	2005-07-13
US7125864B2 (en)	2006-10-24
GB0121621D0 (en)	2001-10-31
EP1427713B1 (de)	2010-01-06
NO20040954L (no)	2004-03-04
MXPA04002189A (es)	2004-06-29
CA2459457A1 (en)	2003-03-20
WO2003022825A1 (en)	2003-03-20
BR0212344A (pt)	2004-10-19
DE60235019D1 (de)	2010-02-25
UY27437A1 (es)	2003-04-30
KR20040031057A (ko)	2004-04-09
US20050032776A1 (en)	2005-02-10

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KR20040031057A (ko)	2004-04-09	고지혈증의 치료를 위한 벤조티아제핀 유도체
NZ536105A (en)	2007-06-29	Benzothiadiazepine derivatives, processes for their preparation and pharmaceutical compositions containing them
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AU2002329386A1 (en)	2003-03-24	Benzothiepine ileal bile acid transport inhibitors
AU2002321579A1 (en)	2003-03-18	Benzothiazepine derivatives
HK1056732B (en)	2007-09-21	1,5 benzothiazepines and their use as antihyperlipidemics