NO317395B1 - Alfa-aryl - eller heteroaryl-substituerte amid-ester ACAT-inhibitorer - Google Patents
Alfa-aryl - eller heteroaryl-substituerte amid-ester ACAT-inhibitorer Download PDFInfo
- Publication number
- NO317395B1 NO317395B1 NO19962078A NO962078A NO317395B1 NO 317395 B1 NO317395 B1 NO 317395B1 NO 19962078 A NO19962078 A NO 19962078A NO 962078 A NO962078 A NO 962078A NO 317395 B1 NO317395 B1 NO 317395B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- ester
- methylethyl
- bis
- carbonyl
- Prior art date
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- -1 amide ester Chemical class 0.000 title claims description 49
- 239000003112 inhibitor Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
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- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
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- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 230000011164 ossification Effects 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
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZAVZXDSKDPYPRI-UHFFFAOYSA-N tetradecan-2-yl 3-[2,6-di(propan-2-yl)anilino]-3-oxopropanoate Chemical compound CCCCCCCCCCCCC(C)OC(=O)CC(=O)NC1=C(C(C)C)C=CC=C1C(C)C ZAVZXDSKDPYPRI-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
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- 230000002477 vacuolizing effect Effects 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/29—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/156,225 US5420339A (en) | 1993-11-22 | 1993-11-22 | Alpha-aryl or heteroaryl-substituted amide ester ACAT inhibitors |
| PCT/US1994/012299 WO1995014657A1 (fr) | 1993-11-22 | 1994-10-26 | Inhibiteurs de l'acat constitues d'ester d'amides a substitution alpha-aryle ou heteroaryle |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962078D0 NO962078D0 (no) | 1996-05-21 |
| NO962078L NO962078L (no) | 1996-05-21 |
| NO317395B1 true NO317395B1 (no) | 2004-10-25 |
Family
ID=22558652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962078A NO317395B1 (no) | 1993-11-22 | 1996-05-21 | Alfa-aryl - eller heteroaryl-substituerte amid-ester ACAT-inhibitorer |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5420339A (fr) |
| EP (1) | EP0730571A1 (fr) |
| JP (1) | JPH09505584A (fr) |
| AU (1) | AU8092794A (fr) |
| CA (1) | CA2176042C (fr) |
| NO (1) | NO317395B1 (fr) |
| WO (1) | WO1995014657A1 (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6699910B2 (en) | 2000-10-11 | 2004-03-02 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| US20040122091A1 (en) * | 2000-10-11 | 2004-06-24 | Esperion Therapeutics, Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| IL155215A0 (en) | 2000-10-11 | 2003-11-23 | Esperion Therapeutics Inc | Ether compounds and compositions for cholesterol management and related uses |
| CN1479721A (zh) | 2000-10-11 | 2004-03-03 | ͨ��ҽ�ƹ�˾ | 用于胆固醇治疗和相关应用的亚砜和双亚砜化合物和组合物 |
| US7304093B2 (en) * | 2000-10-11 | 2007-12-04 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| EP1363879A2 (fr) | 2000-10-11 | 2003-11-26 | Esperion Therapeutics Inc. | Composes et compositions de sulfure et de disulfure pour le traitement du cholesterol et utilisations associees |
| HUP0400708A3 (en) * | 2000-12-07 | 2007-10-29 | Cv Therapeutics | Substituted 1,3,5-triazine and pyrimidine derivatives, their use and pharmaceutical compositions containing them |
| US20040072903A1 (en) * | 2001-05-08 | 2004-04-15 | Auerbach Bruce Jeffrey | Carboxyalkylether-acat inhibitors combinations |
| US20040192771A1 (en) * | 2001-10-11 | 2004-09-30 | Dasseux Jean-Louis Henri | Ether compounds and compositions for cholesterol management and related uses |
| US20040204502A1 (en) * | 2001-10-11 | 2004-10-14 | Dasseux Jean-Louis Henri | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| US20050020694A1 (en) * | 2001-10-11 | 2005-01-27 | Dasseux Jean-Louis Henri | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| MXPA04009831A (es) * | 2002-04-10 | 2004-12-07 | Esperion Therapeutics Inc | Imitaciones de la coenzima-a de acilo, composiciones de las mismas y metodos de manejo del colesterol y usos relacionados. |
| SI2404890T1 (sl) * | 2003-01-23 | 2017-12-29 | Esperion Therapeutics Inc. | Hidroksilne spojine in sestavki za uravnavanje holesterola in sorodne uporabe |
| EP1701931B1 (fr) | 2003-12-24 | 2018-10-10 | Esperion Therapeutics, Inc. | Dérivés cétoniques, compositions pour maintenir le taux de cholèstèrol et leurs utilisations |
| MX2017011499A (es) | 2015-03-13 | 2018-03-26 | Esperion Therapeutics Inc | Combinaciones de dosis fija y formulaciones que comprenden ácido 8-hidroxi-2,2,14,14 tetrametilpentadecanodioico (etc1002) y ezetimiba y métodos para tratar o reducir el riesgo de enfermedad cardiovascular. |
| MA41793A (fr) | 2015-03-16 | 2018-01-23 | Esperion Therapeutics Inc | Associations de doses fixes comprenant du etc1002 et une ou plusieurs statines permettant de traiter ou de réduire un risque cardiovasculaire |
| KR20220024816A (ko) | 2019-06-21 | 2022-03-03 | 에스페리온 테라피유틱스 인코포레이티드 | 벰페도산 및 그의 조성물을 제조하는 방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955111A (en) * | 1957-01-28 | 1960-10-04 | Bofors Ab | Synthesis of n-alkyl-piperidine and n-alkyl-pyrrolidine-alpha-carboxylic acid amides |
| AT211821B (de) * | 1959-11-26 | 1960-11-10 | Heilmittelwerke Wien Ges Mit B | Verfahren zur Herstellung Alkylaminoacetaryliden |
| DD132430A1 (de) * | 1977-07-18 | 1978-09-27 | Heinz Stopsack | Verfahren zur herstellung von halbestern und halbamiden substituierter malonsaeuren |
| EP0269656B1 (fr) * | 1986-03-31 | 1993-12-29 | Rhone Poulenc Nederland B.V. | Nouveaux composes derives de l'acide malonique et compositions les contenant pour retarder la croissance des plantes |
| US5123951A (en) * | 1986-03-31 | 1992-06-23 | Rhone-Poulenc Nederland B.V. | Synergistic plant growth regulator compositions |
| JPH0363648A (ja) * | 1989-08-01 | 1991-03-19 | Fuji Photo Film Co Ltd | 熱現像カラー感光材料 |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| AU7745991A (en) * | 1990-04-11 | 1991-10-30 | Warner-Lambert Company | Amide ester acat inhibitors |
| DE4114733A1 (de) * | 1991-05-06 | 1992-11-12 | Huels Chemische Werke Ag | Verfahren zur herstellung von substituierten malonesteraniliden und malonsaeure-monoaniliden |
| US5366987A (en) * | 1991-08-22 | 1994-11-22 | Warner-Lambert Company | Isoxazolyl-substituted alkyl amide ACAT inhibitors |
-
1993
- 1993-11-22 US US08/156,225 patent/US5420339A/en not_active Expired - Lifetime
-
1994
- 1994-10-26 EP EP94932061A patent/EP0730571A1/fr not_active Ceased
- 1994-10-26 AU AU80927/94A patent/AU8092794A/en not_active Abandoned
- 1994-10-26 WO PCT/US1994/012299 patent/WO1995014657A1/fr not_active Application Discontinuation
- 1994-10-26 JP JP7515071A patent/JPH09505584A/ja active Pending
- 1994-10-26 CA CA002176042A patent/CA2176042C/fr not_active Expired - Fee Related
-
1995
- 1995-03-06 US US08/398,704 patent/US5502198A/en not_active Expired - Fee Related
-
1996
- 1996-05-21 NO NO19962078A patent/NO317395B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995014657A1 (fr) | 1995-06-01 |
| US5502198A (en) | 1996-03-26 |
| NO962078D0 (no) | 1996-05-21 |
| CA2176042A1 (fr) | 1995-06-01 |
| NO962078L (no) | 1996-05-21 |
| US5420339A (en) | 1995-05-30 |
| EP0730571A1 (fr) | 1996-09-11 |
| CA2176042C (fr) | 2005-03-29 |
| AU8092794A (en) | 1995-06-13 |
| JPH09505584A (ja) | 1997-06-03 |
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