CA2411065A1 - Thiazolidinedione salt for treatment of diabetes mellitus - Google Patents

Thiazolidinedione salt for treatment of diabetes mellitus Download PDF

Info

Publication number: CA2411065A1
Authority: CA; Canada
Prior art keywords: hydrobromide; solvate; methyl; thiazolidine; pyridyl
Prior art date: 2000-06-08
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.): Abandoned

Application number

CA002411065A

Other languages

English (en)

French (fr)

Inventor

Andrew Simon Craig

Tim Chien Ting Ho

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Ltd

Original Assignee

Individual

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.)

2000-06-08

Filing date

2001-06-08

Publication date

2001-12-13

2001-06-08 Application filed by Individual filed Critical Individual

2001-12-13 Publication of CA2411065A1 publication Critical patent/CA2411065A1/en

Status Abandoned legal-status Critical Current

Links

206010012601 diabetes mellitus Diseases 0.000 title claims description 20
238000011282 treatment Methods 0.000 title claims description 11
150000001467 thiazolidinediones Chemical class 0.000 title description 2
239000012453 solvate Substances 0.000 claims abstract description 32
150000001875 compounds Chemical class 0.000 claims abstract description 30
-1 compound 5-[4-[2-(N-methyl-N-(2- pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione hydrobromide Chemical class 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims abstract description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 9
MSOPDKKENJARPF-UHFFFAOYSA-N 5-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;hydrobromide Chemical compound Br.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O MSOPDKKENJARPF-UHFFFAOYSA-N 0.000 claims description 8
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 8
238000000634 powder X-ray diffraction Methods 0.000 claims description 8
238000011321 prophylaxis Methods 0.000 claims description 7
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 6
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239000008186 active pharmaceutical agent Substances 0.000 description 4
239000007810 chemical reaction solvent Substances 0.000 description 4
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IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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HWKCRWVVWLVDRA-UHFFFAOYSA-O CN(CCOC1=CC=C(C[S+](CC(N2)=O)C2=O)C=C1)C1=NC=CC=C1.Br Chemical compound CN(CCOC1=CC=C(C[S+](CC(N2)=O)C2=O)C=C1)C1=NC=CC=C1.Br HWKCRWVVWLVDRA-UHFFFAOYSA-O 0.000 description 1
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
208000007342 Diabetic Nephropathies Diseases 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
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IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
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206010060378 Hyperinsulinaemia Diseases 0.000 description 1
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235000010643 Leucaena leucocephala Nutrition 0.000 description 1
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238000005481 NMR spectroscopy Methods 0.000 description 1
206010029164 Nephrotic syndrome Diseases 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
206010036049 Polycystic ovaries Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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238000000862 absorption spectrum Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
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239000002671 adjuvant Substances 0.000 description 1
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239000008168 almond oil Substances 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
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238000013461 design Methods 0.000 description 1
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HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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235000011167 hydrochloric acid Nutrition 0.000 description 1
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230000000055 hyoplipidemic effect Effects 0.000 description 1
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230000035879 hyperinsulinaemia Effects 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
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239000002687 nonaqueous vehicle Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
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235000005985 organic acids Nutrition 0.000 description 1
235000020830 overeating Nutrition 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
201000010065 polycystic ovary syndrome Diseases 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000003893 regulation of appetite Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000007789 sealing Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Endocrinology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

CA002411065A 2000-06-08 2001-06-08 Thiazolidinedione salt for treatment of diabetes mellitus Abandoned CA2411065A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0014006.1		2000-06-08
GBGB0014006.1A GB0014006D0 (en)	2000-06-08	2000-06-08	Novel pharmaceutical
PCT/GB2001/002567 WO2001094344A1 (en)	2000-06-08	2001-06-08	Thiazolidinedione salt for treatment of diabetes mellitus

Publications (1)

Publication Number	Publication Date
CA2411065A1 true CA2411065A1 (en)	2001-12-13

Family

ID=9893257

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002411065A Abandoned CA2411065A1 (en)	2000-06-08	2001-06-08	Thiazolidinedione salt for treatment of diabetes mellitus

Country Status (23)

Country	Link
EP (1)	EP1296980A1 (cs)
JP (1)	JP2003535862A (cs)
KR (1)	KR20030007918A (cs)
CN (1)	CN1443186A (cs)
AP (1)	AP2002002673A0 (cs)
AU (1)	AU2001264078A1 (cs)
BG (1)	BG107357A (cs)
BR (1)	BR0111536A (cs)
CA (1)	CA2411065A1 (cs)
CZ (1)	CZ20023966A3 (cs)
DZ (1)	DZ3382A1 (cs)
EA (1)	EA200300005A1 (cs)
GB (1)	GB0014006D0 (cs)
HU (1)	HUP0301137A3 (cs)
IL (1)	IL153279A0 (cs)
MA (1)	MA25753A1 (cs)
MX (1)	MXPA02012100A (cs)
NO (1)	NO20025883L (cs)
OA (1)	OA12284A (cs)
PL (1)	PL360592A1 (cs)
SK (1)	SK17142002A3 (cs)
WO (1)	WO2001094344A1 (cs)
ZA (1)	ZA200209954B (cs)

Families Citing this family (5)

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USRE39384E1 (en)	1993-09-01	2006-11-07	Smithkline Beecham P.L.C.	Substituted thiazolidinedione derivatives
DE102005034406A1 (de) *	2005-07-22	2007-02-01	Ratiopharm Gmbh	Neue Salze von Rosiglitazon
EP2016076A2 (en) *	2007-01-22	2009-01-21	Teva Pharmaceutical Industries Ltd.	Polymorphic forms of rosiglitazone hydrobromide and processes for preparation thereof
EP1956018A1 (de) *	2007-02-06	2008-08-13	Boehringer Ingelheim Pharma GmbH & Co. KG	Verfahren zur Herstellung eines Benzimidazolderivats
WO2010021745A2 (en) *	2008-08-21	2010-02-25	Teva Pharmaceutical Industries Ltd.	Polymorphic forms of rosiglitazone hydrobromide and processes for their preparation

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GB9218830D0 (en) *	1992-09-05	1992-10-21	Smithkline Beecham Plc	Novel compounds

2000
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2001
- 2001-06-08 WO PCT/GB2001/002567 patent/WO2001094344A1/en not_active Ceased
- 2001-06-08 BR BR0111536-7A patent/BR0111536A/pt not_active IP Right Cessation
- 2001-06-08 AU AU2001264078A patent/AU2001264078A1/en not_active Abandoned
- 2001-06-08 AP APAP/P/2002/002673A patent/AP2002002673A0/en unknown
- 2001-06-08 MX MXPA02012100A patent/MXPA02012100A/es unknown
- 2001-06-08 CZ CZ20023966A patent/CZ20023966A3/cs unknown
- 2001-06-08 EP EP01938400A patent/EP1296980A1/en not_active Withdrawn
- 2001-06-08 JP JP2002501893A patent/JP2003535862A/ja active Pending
- 2001-06-08 CA CA002411065A patent/CA2411065A1/en not_active Abandoned
- 2001-06-08 CN CN01813190A patent/CN1443186A/zh active Pending
- 2001-06-08 DZ DZ013382A patent/DZ3382A1/xx active
- 2001-06-08 HU HU0301137A patent/HUP0301137A3/hu unknown
- 2001-06-08 EA EA200300005A patent/EA200300005A1/ru unknown
- 2001-06-08 OA OA1200200370A patent/OA12284A/en unknown
- 2001-06-08 IL IL15327901A patent/IL153279A0/xx unknown
- 2001-06-08 KR KR1020027016721A patent/KR20030007918A/ko not_active Withdrawn
- 2001-06-08 PL PL36059201A patent/PL360592A1/xx not_active Application Discontinuation
- 2001-06-08 SK SK1714-2002A patent/SK17142002A3/sk not_active Application Discontinuation
2002
- 2002-12-04 MA MA26933A patent/MA25753A1/fr unknown
- 2002-12-05 BG BG107357A patent/BG107357A/bg unknown
- 2002-12-06 NO NO20025883A patent/NO20025883L/no not_active Application Discontinuation
- 2002-12-09 ZA ZA200209954A patent/ZA200209954B/en unknown

Also Published As

Publication number	Publication date
BG107357A (bg)	2003-08-29
PL360592A1 (en)	2004-09-20
CN1443186A (zh)	2003-09-17
AU2001264078A1 (en)	2001-12-17
CZ20023966A3 (cs)	2003-04-16
BR0111536A (pt)	2003-07-01
JP2003535862A (ja)	2003-12-02
GB0014006D0 (en)	2000-08-02
NO20025883D0 (no)	2002-12-06
EA200300005A1 (ru)	2003-04-24
DZ3382A1 (fr)	2001-12-13
MXPA02012100A (es)	2003-04-25
AP2002002673A0 (en)	2002-12-31
KR20030007918A (ko)	2003-01-23
MA25753A1 (fr)	2003-04-01
ZA200209954B (en)	2003-10-10
IL153279A0 (en)	2003-07-06
EP1296980A1 (en)	2003-04-02
WO2001094344A1 (en)	2001-12-13
HUP0301137A2 (hu)	2003-08-28
NO20025883L (no)	2003-02-03
HUP0301137A3 (en)	2005-04-28
OA12284A (en)	2003-11-10
SK17142002A3 (sk)	2003-10-07

Legal Events

Date	Code	Title	Description
2006-06-08	FZDE	Discontinued

Publication	Publication Date	Title
EP1305312B1 (en)	2008-04-23	Tartrate salts of thiazolidinedione derivative
US20050107440A1 (en)	2005-05-19	Rosiglitazone edisylates and their use as antidiabetics
CA2411065A1 (en)	2001-12-13	Thiazolidinedione salt for treatment of diabetes mellitus
CA2421213A1 (en)	2002-03-14	The hydrochloride salt of 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione
EP1305311B1 (en)	2008-01-16	Tartrate salt of thiazolidinedione derivative
AU2001262550B2 (en)	2004-04-22	5-(4-(2-(n-methyl-n-(2-pyridyl)amino)ethoxy)benzyl)thiazolidine-2,4-dione hydriodide as pharmaceutical
WO2002020517A1 (en)	2002-03-14	A thiazolidinedione derivative and its use as antidiabetic
EP1305310B1 (en)	2008-02-20	Tartrate salts of thiazolidinedione derivative
AU2001292034B2 (en)	2005-04-21	A thiazolidinedione derivative and its use as antidiabetic
US20030162815A1 (en)	2003-08-28	Thiazolidinedione salt for treatment of diabetes mellitus
AU2001262550A1 (en)	2002-03-07	5-(4-(2-(n-methyl-n-(2-pyridyl)amino)ethoxy)benzyl)thiazolidine-2,4-dione hydriodide as pharmaceutical
HK1105818A (en)	2008-02-22	A thiazolidinedione derivative and its use as antidiabetic
HK1057360B (en)	2009-01-23	Tartrate salts of thiazolidinedione derivative
HK1057359B (en)	2009-03-27	Tartrate salts of thiazolidinedione derivative