NO330010B1 - Nye derivater av pyridyletanol (fenyl-etyl) aminer som inhibitorer av kolesterolbiosyntese, fremgangsmater for deres fremstilling, anvendelse av forbindelsene og farmasoytiske preparater som inneholder dem - Google Patents
Nye derivater av pyridyletanol (fenyl-etyl) aminer som inhibitorer av kolesterolbiosyntese, fremgangsmater for deres fremstilling, anvendelse av forbindelsene og farmasoytiske preparater som inneholder dem Download PDFInfo
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- NO330010B1 NO330010B1 NO20050833A NO20050833A NO330010B1 NO 330010 B1 NO330010 B1 NO 330010B1 NO 20050833 A NO20050833 A NO 20050833A NO 20050833 A NO20050833 A NO 20050833A NO 330010 B1 NO330010 B1 NO 330010B1
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- formula
- compounds
- pyridyl
- ethanol
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title claims abstract description 106
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 47
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 11
- PPHIIIRFJKDTLG-UHFFFAOYSA-N 1-pyridin-2-ylethanol Chemical class CC(O)C1=CC=CC=N1 PPHIIIRFJKDTLG-UHFFFAOYSA-N 0.000 title abstract description 19
- 150000001412 amines Chemical class 0.000 title abstract description 19
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 title abstract description 4
- 239000003112 inhibitor Substances 0.000 title description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000003446 ligand Substances 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 201000005577 familial hyperlipidemia Diseases 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Chemical group 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 108010085082 sigma receptors Proteins 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- PBHVAENVSMGNPF-UHFFFAOYSA-N 2-[2-phenylethyl(propyl)amino]-1-pyridin-3-ylethanol Chemical group C=1C=CN=CC=1C(O)CN(CCC)CCC1=CC=CC=C1 PBHVAENVSMGNPF-UHFFFAOYSA-N 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- -1 ethyl-N-propylamino Chemical group 0.000 abstract description 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
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- CGSJXLIKVBJVRY-XTGBIJOFSA-N zymosterol Chemical compound C([C@@]12C)C[C@H](O)C[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@H]21 CGSJXLIKVBJVRY-XTGBIJOFSA-N 0.000 description 1
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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200200177A SI21268A (sl) | 2002-07-17 | 2002-07-17 | Novi derivati piridiletanol (feniletil) aminov kot inhibitorjev biosinteze holesterola, postopki za njihovo pripravo in farmacevtski pripravki, ki jih vsebujejo |
| SI200200287A SI21368A (sl) | 2002-11-28 | 2002-11-28 | Novi derivati piridiletanol (feniletil) aminov kot inhibitorjev biosinteze holesterola, postopki za njihovo pripravo in farmacevtski pripravki, ki jih vsebujejo |
| PCT/SI2003/000021 WO2004007456A1 (en) | 2002-07-17 | 2003-07-09 | Novel derivatives of pyridylethanol (phenylethyl) amines as inhibitors of cholesterol biosynthesis, processes for their preparation, and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20050833L NO20050833L (no) | 2005-04-18 |
| NO330010B1 true NO330010B1 (no) | 2011-02-07 |
Family
ID=30117598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20050833A NO330010B1 (no) | 2002-07-17 | 2005-02-16 | Nye derivater av pyridyletanol (fenyl-etyl) aminer som inhibitorer av kolesterolbiosyntese, fremgangsmater for deres fremstilling, anvendelse av forbindelsene og farmasoytiske preparater som inneholder dem |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7560474B2 (pl) |
| EP (1) | EP1546105A1 (pl) |
| JP (1) | JP4567448B2 (pl) |
| KR (1) | KR100645412B1 (pl) |
| CN (1) | CN1297540C (pl) |
| AU (1) | AU2003248614B2 (pl) |
| BR (1) | BR0312945A (pl) |
| CA (1) | CA2493004A1 (pl) |
| EC (1) | ECSP055546A (pl) |
| IL (1) | IL166191A (pl) |
| MX (1) | MXPA05000663A (pl) |
| NO (1) | NO330010B1 (pl) |
| NZ (1) | NZ537635A (pl) |
| PL (1) | PL373429A1 (pl) |
| RU (1) | RU2309949C2 (pl) |
| WO (1) | WO2004007456A1 (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3328365A1 (en) * | 2015-07-31 | 2018-06-06 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma receptor ligands in dyslipidemia |
| EP3838287A3 (en) | 2016-07-27 | 2021-07-28 | Case Western Reserve University | Compounds and methods of promoting myelination |
| EP3810777A4 (en) | 2018-06-21 | 2022-03-30 | Yumanity Therapeutics, Inc. | COMPOSITIONS AND METHODS FOR THE TREATMENT AND PREVENTION OF NEUROLOGICAL DISORDERS |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2786846A (en) * | 1953-06-01 | 1957-03-26 | Reilly Tar & Chem Corp | Process of alkylating pyridines |
| US2792403A (en) * | 1955-01-05 | 1957-05-14 | Univ Michigan | 2-pyridylethyl-phenylethylalkylamines |
| NL6707290A (pl) * | 1966-05-28 | 1967-11-29 | ||
| GB1417029A (en) * | 1973-03-07 | 1975-12-10 | Pfizer Ltd | Quinazoline-derived amines |
| JPS5840539B2 (ja) * | 1976-03-31 | 1983-09-06 | 大塚製薬株式会社 | α−置換アミノアルカノイルオキシインド−ル誘導体 |
| DE2817494A1 (de) * | 1977-05-03 | 1978-11-09 | Continental Pharma | Aminoalkohol-derivat |
| ZA821436B (en) * | 1981-03-06 | 1983-02-23 | Beecham Group Plc | Secondary amines |
| CA1287061C (en) * | 1986-06-27 | 1991-07-30 | Roche Holding Ltd. | Pyridine ethanolamine derivatives |
| ZA874449B (en) * | 1986-06-27 | 1987-12-28 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Pyridine ethanolamine derivatives |
| DE3729284A1 (de) * | 1987-09-02 | 1989-03-23 | Thomae Gmbh Dr K | Neue heteroarylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| EP0507863A4 (en) * | 1989-12-28 | 1993-07-07 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| GB2305665A (en) * | 1995-09-26 | 1997-04-16 | Merck & Co Inc | Selective ß3 agonists for the treatment of diabetes aand obesity |
| GB9812709D0 (en) * | 1998-06-13 | 1998-08-12 | Glaxo Group Ltd | Chemical compounds |
| AUPP796798A0 (en) * | 1998-12-30 | 1999-01-28 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| DZ3493A1 (fr) * | 2001-03-29 | 2002-10-10 | Lilly Co Eli | N-(2-arylethyl)benzylamines comme antagonistes du recepteur 5-ht6 |
-
2003
- 2003-07-09 AU AU2003248614A patent/AU2003248614B2/en not_active Ceased
- 2003-07-09 NZ NZ537635A patent/NZ537635A/en not_active IP Right Cessation
- 2003-07-09 WO PCT/SI2003/000021 patent/WO2004007456A1/en active Application Filing
- 2003-07-09 KR KR1020057000707A patent/KR100645412B1/ko not_active IP Right Cessation
- 2003-07-09 JP JP2004521370A patent/JP4567448B2/ja not_active Expired - Fee Related
- 2003-07-09 EP EP03764285A patent/EP1546105A1/en not_active Withdrawn
- 2003-07-09 CA CA002493004A patent/CA2493004A1/en not_active Abandoned
- 2003-07-09 RU RU2005104420/04A patent/RU2309949C2/ru not_active IP Right Cessation
- 2003-07-09 CN CNB038168502A patent/CN1297540C/zh not_active Expired - Fee Related
- 2003-07-09 MX MXPA05000663A patent/MXPA05000663A/es active IP Right Grant
- 2003-07-09 US US10/521,294 patent/US7560474B2/en not_active Expired - Fee Related
- 2003-07-09 BR BR0312945-4A patent/BR0312945A/pt not_active Withdrawn
- 2003-07-09 PL PL03373429A patent/PL373429A1/pl not_active Application Discontinuation
-
2005
- 2005-01-06 IL IL166191A patent/IL166191A/en not_active IP Right Cessation
- 2005-01-17 EC EC2005005546A patent/ECSP055546A/es unknown
- 2005-02-16 NO NO20050833A patent/NO330010B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003248614A1 (en) | 2004-02-02 |
| MXPA05000663A (es) | 2005-09-20 |
| ECSP055546A (es) | 2005-05-30 |
| US20050256172A1 (en) | 2005-11-17 |
| WO2004007456A1 (en) | 2004-01-22 |
| NZ537635A (en) | 2006-11-30 |
| RU2309949C2 (ru) | 2007-11-10 |
| CN1297540C (zh) | 2007-01-31 |
| EP1546105A1 (en) | 2005-06-29 |
| BR0312945A (pt) | 2005-07-12 |
| PL373429A1 (pl) | 2005-08-22 |
| CA2493004A1 (en) | 2004-01-22 |
| JP4567448B2 (ja) | 2010-10-20 |
| IL166191A (en) | 2010-12-30 |
| NO20050833L (no) | 2005-04-18 |
| RU2005104420A (ru) | 2005-10-10 |
| US7560474B2 (en) | 2009-07-14 |
| KR20050026480A (ko) | 2005-03-15 |
| CN1668594A (zh) | 2005-09-14 |
| KR100645412B1 (ko) | 2006-11-15 |
| IL166191A0 (en) | 2006-01-15 |
| JP2005538081A (ja) | 2005-12-15 |
| AU2003248614B2 (en) | 2007-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |