CA2610890A1 - Novel 2-azetidinone derivatives and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia - Google Patents
Novel 2-azetidinone derivatives and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia Download PDFInfo
- Publication number
- CA2610890A1 CA2610890A1 CA002610890A CA2610890A CA2610890A1 CA 2610890 A1 CA2610890 A1 CA 2610890A1 CA 002610890 A CA002610890 A CA 002610890A CA 2610890 A CA2610890 A CA 2610890A CA 2610890 A1 CA2610890 A1 CA 2610890A1
- Authority
- CA
- Canada
- Prior art keywords
- solvate
- formula
- compound
- salt
- pharmaceutically acceptable
- Prior art date
- 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
Links
- 238000011282 treatment Methods 0.000 title abstract description 40
- 230000001906 cholesterol absorption Effects 0.000 title abstract description 29
- 239000003112 inhibitor Substances 0.000 title abstract description 23
- 208000031226 Hyperlipidaemia Diseases 0.000 title abstract description 5
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 287
- 239000012453 solvate Substances 0.000 claims abstract description 278
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- 229940002612 prodrug Drugs 0.000 claims abstract description 141
- 239000000651 prodrug Substances 0.000 claims abstract description 141
- 238000000034 method Methods 0.000 claims abstract description 60
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- 230000008569 process Effects 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
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- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 34
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
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- 150000001412 amines Chemical class 0.000 claims description 7
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims description 6
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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- 150000002431 hydrogen Chemical group 0.000 description 22
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- 125000000623 heterocyclic group Chemical group 0.000 description 18
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229950005772 tosifen Drugs 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- AHYHTSYNOHNUSH-HXFGRODQSA-N trandolaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)C(O)=O)CC1=CC=CC=C1 AHYHTSYNOHNUSH-HXFGRODQSA-N 0.000 description 1
- 229960002651 trandolaprilat Drugs 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
- 230000008733 trauma Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229950001407 trifenagrel Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 229950005696 utibapril Drugs 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 230000006492 vascular dysfunction Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 229960002647 warfarin sodium Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229950009999 zabicipril Drugs 0.000 description 1
- 229950005973 zabiciprilat Drugs 0.000 description 1
- DFKDOZMCHOGOBR-NCSQYGPNSA-N zaragozic acid A Chemical group C([C@@H](C)[C@H](OC(C)=O)C(=C)CC[C@]12[C@H](O)[C@H]([C@](O2)(C(O)=O)[C@@](O)([C@H](O1)C(O)=O)C(O)=O)OC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)C1=CC=CC=C1 DFKDOZMCHOGOBR-NCSQYGPNSA-N 0.000 description 1
- DFKDOZMCHOGOBR-UHFFFAOYSA-N zaragozic acid A Natural products O1C(C(O)(C(O2)C(O)=O)C(O)=O)(C(O)=O)C(OC(=O)C=CC(C)CC(C)CC)C(O)C21CCC(=C)C(OC(C)=O)C(C)CC1=CC=CC=C1 DFKDOZMCHOGOBR-UHFFFAOYSA-N 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
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- UQWLOWFDKAFKAP-WXHSDQCUSA-N zofenoprilat Chemical compound C1[C@@H](C(O)=O)N(C(=O)[C@@H](CS)C)C[C@H]1SC1=CC=CC=C1 UQWLOWFDKAFKAP-WXHSDQCUSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0501425-3 | 2005-06-20 | ||
SE0501425 | 2005-06-20 | ||
PCT/SE2006/000741 WO2006137782A1 (en) | 2005-06-20 | 2006-06-19 | Novel 2-azetidinone derivatives and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2610890A1 true CA2610890A1 (en) | 2006-12-28 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA002610890A Abandoned CA2610890A1 (en) | 2005-06-20 | 2006-06-19 | Novel 2-azetidinone derivatives and their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia |
Country Status (18)
Families Citing this family (18)
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WO2005061452A1 (en) | 2003-12-23 | 2005-07-07 | Astrazeneca Ab | Diphenylazetidinone derivates possessing cholesterol absorption inhibitory activity |
UY29607A1 (es) | 2005-06-20 | 2007-01-31 | Astrazeneca Ab | Compuestos quimicos |
AR057072A1 (es) | 2005-06-22 | 2007-11-14 | Astrazeneca Ab | Compuestos quimicos derivados de 2-azetidinona, formulacion farmaceutica y un proceso de preparacion del compuesto |
SA06270191B1 (ar) * | 2005-06-22 | 2010-03-29 | استرازينيكا ايه بي | مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم |
TW200811098A (en) | 2006-04-27 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
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US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
WO2012120055A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
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TW200806623A (en) | 2005-10-05 | 2008-02-01 | Merck & Co Inc | Anti-hypercholesterolemic compounds |
AR057575A1 (es) | 2005-11-15 | 2007-12-05 | Takeda Pharmaceutical | Metodo para tratar hiperlipidemia |
DE102005055726A1 (de) | 2005-11-23 | 2007-08-30 | Sanofi-Aventis Deutschland Gmbh | Hydroxy-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
US7498431B2 (en) | 2005-12-01 | 2009-03-03 | Bomi Patel Framroze | Process for the preparation of chiral azetidinones |
HU0501164D0 (en) | 2005-12-20 | 2006-02-28 | Richter Gedeon Vegyeszet | New industrial process for the production of ezetimibe |
BRPI0620255A2 (pt) | 2005-12-21 | 2011-11-08 | Schering Corp | uso de agentes redutores de colesterol e/ou antagonista/agonista inverso do receptor de h3 |
TW200811098A (en) * | 2006-04-27 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
US20080070890A1 (en) * | 2006-09-15 | 2008-03-20 | Burnett Duane A | Spirocyclic Azetidinone Compounds and Methods of Use Thereof |
EP2133347A4 (en) * | 2007-03-06 | 2010-03-17 | Teijin Pharma Ltd | 1-BIARYLAZETIDINONDERIVATE |
-
2006
- 2006-06-16 UY UY29607A patent/UY29607A1/es unknown
- 2006-06-19 JP JP2008518077A patent/JP2008546766A/ja active Pending
- 2006-06-19 WO PCT/SE2006/000741 patent/WO2006137782A1/en active Application Filing
- 2006-06-19 CN CNA2006800264766A patent/CN101228123A/zh active Pending
- 2006-06-19 RU RU2007147338/04A patent/RU2007147338A/ru not_active Application Discontinuation
- 2006-06-19 CA CA002610890A patent/CA2610890A1/en not_active Abandoned
- 2006-06-19 US US11/993,033 patent/US7863265B2/en not_active Expired - Fee Related
- 2006-06-19 EP EP06747933A patent/EP1896407A4/en not_active Withdrawn
- 2006-06-19 BR BRPI0612254A patent/BRPI0612254A2/pt not_active IP Right Cessation
- 2006-06-19 KR KR1020087001031A patent/KR20080019710A/ko not_active Application Discontinuation
- 2006-06-19 MX MX2007016483A patent/MX2007016483A/es not_active Application Discontinuation
- 2006-06-19 AU AU2006259949A patent/AU2006259949A1/en not_active Abandoned
- 2006-06-20 AR ARP060102624A patent/AR054484A1/es unknown
- 2006-06-20 TW TW095122114A patent/TW200730493A/zh unknown
-
2007
- 2007-11-28 IL IL187736A patent/IL187736A0/en unknown
- 2007-11-28 NO NO20076137A patent/NO20076137L/no not_active Application Discontinuation
- 2007-11-30 ZA ZA200710415A patent/ZA200710415B/xx unknown
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2008
- 2008-01-17 EC EC2008008114A patent/ECSP088114A/es unknown
Also Published As
Publication number | Publication date |
---|---|
JP2008546766A (ja) | 2008-12-25 |
WO2006137782A1 (en) | 2006-12-28 |
TW200730493A (en) | 2007-08-16 |
ZA200710415B (en) | 2008-10-29 |
AR054484A1 (es) | 2007-06-27 |
IL187736A0 (en) | 2008-08-07 |
CN101228123A (zh) | 2008-07-23 |
RU2007147338A (ru) | 2009-07-27 |
BRPI0612254A2 (pt) | 2016-09-06 |
NO20076137L (no) | 2008-01-18 |
KR20080019710A (ko) | 2008-03-04 |
US7863265B2 (en) | 2011-01-04 |
MX2007016483A (es) | 2008-03-10 |
EP1896407A4 (en) | 2010-06-16 |
AU2006259949A1 (en) | 2006-12-28 |
UY29607A1 (es) | 2007-01-31 |
ECSP088114A (es) | 2008-02-20 |
US20100216759A1 (en) | 2010-08-26 |
EP1896407A1 (en) | 2008-03-12 |
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