NO324691B1 - Pyrimidin-4-on derivater, farmasoytisk sammensetning inneholdende en slik forbindelse, samt anvendelse av forbindelsene - Google Patents
Pyrimidin-4-on derivater, farmasoytisk sammensetning inneholdende en slik forbindelse, samt anvendelse av forbindelsene Download PDFInfo
- Publication number
- NO324691B1 NO324691B1 NO20023828A NO20023828A NO324691B1 NO 324691 B1 NO324691 B1 NO 324691B1 NO 20023828 A NO20023828 A NO 20023828A NO 20023828 A NO20023828 A NO 20023828A NO 324691 B1 NO324691 B1 NO 324691B1
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- thio
- fluorobenzyl
- diethylamino
- benzyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 120
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title claims 4
- 102000016752 1-Alkyl-2-acetylglycerophosphocholine Esterase Human genes 0.000 claims description 24
- 108010024976 Asparaginase Proteins 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- -1 2-(diethylamino)ethyl Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 201000001320 Atherosclerosis Diseases 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000009862 primary prevention Effects 0.000 claims description 4
- 230000009863 secondary prevention Effects 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 12
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 2
- CSRCAGFFMKTXHX-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsulfanyl]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound O=C1C(C)=C(C)NC(SCC=2C=CC(F)=CC=2)=N1 CSRCAGFFMKTXHX-UHFFFAOYSA-N 0.000 claims 1
- UYQPJJFISLQLNF-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsulfanyl]-5-(hydroxymethyl)-1h-pyrimidin-6-one Chemical compound N1C(=O)C(CO)=CN=C1SCC1=CC=C(F)C=C1 UYQPJJFISLQLNF-UHFFFAOYSA-N 0.000 claims 1
- CXDLFOGIFAUZPC-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylsulfanyl]-5-propyl-1h-pyrimidin-6-one Chemical compound N1C(=O)C(CCC)=CN=C1SCC1=CC=C(F)C=C1 CXDLFOGIFAUZPC-UHFFFAOYSA-N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- AGSVBXDKVVPCCX-UHFFFAOYSA-N 5-ethoxy-2-[(4-fluorophenyl)methylsulfanyl]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(OCC)=CN=C1SCC1=CC=C(F)C=C1 AGSVBXDKVVPCCX-UHFFFAOYSA-N 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- CQBYREFQWDUSJY-UHFFFAOYSA-N n',n'-diethyl-n-[[4-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCN(CC)CC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 CQBYREFQWDUSJY-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- 239000000543 intermediate Substances 0.000 description 122
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
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- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 9
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
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- A61P9/08—Vasodilators for multiple indications
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
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- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0003636A GB0003636D0 (en) | 2000-02-16 | 2000-02-16 | Novel compounds |
GB0101437A GB0101437D0 (en) | 2001-01-19 | 2001-01-19 | Novel Compounds |
PCT/EP2001/001515 WO2001060805A1 (en) | 2000-02-16 | 2001-02-13 | Pyrimidine-4-one derivatives as ldl-pla2 inhibitors |
Publications (3)
Publication Number | Publication Date |
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NO20023828D0 NO20023828D0 (no) | 2002-08-13 |
NO20023828L NO20023828L (no) | 2002-09-30 |
NO324691B1 true NO324691B1 (no) | 2007-12-03 |
Family
ID=26243663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20023828A NO324691B1 (no) | 2000-02-16 | 2002-08-13 | Pyrimidin-4-on derivater, farmasoytisk sammensetning inneholdende en slik forbindelse, samt anvendelse av forbindelsene |
Country Status (32)
Country | Link |
---|---|
US (10) | US20020103213A1 (bg) |
EP (2) | EP1686119B1 (bg) |
JP (1) | JP4095804B2 (bg) |
KR (1) | KR100781425B1 (bg) |
CN (1) | CN1179952C (bg) |
AR (1) | AR030190A1 (bg) |
AT (2) | ATE437862T1 (bg) |
AU (2) | AU2001235466B2 (bg) |
BG (1) | BG66014B1 (bg) |
BR (1) | BRPI0108396B1 (bg) |
CA (1) | CA2400554C (bg) |
CO (1) | CO5271661A1 (bg) |
CY (2) | CY1105649T1 (bg) |
CZ (1) | CZ304450B6 (bg) |
DE (2) | DE60139429D1 (bg) |
DK (2) | DK1686119T3 (bg) |
ES (2) | ES2330552T3 (bg) |
GC (1) | GC0000221A (bg) |
HK (1) | HK1053466A1 (bg) |
HU (1) | HU229479B1 (bg) |
IL (2) | IL151236A (bg) |
MX (1) | MXPA02008062A (bg) |
MY (1) | MY135732A (bg) |
NO (1) | NO324691B1 (bg) |
NZ (1) | NZ520752A (bg) |
PL (1) | PL209824B1 (bg) |
PT (2) | PT1263740E (bg) |
SI (2) | SI1686119T1 (bg) |
SK (1) | SK287296B6 (bg) |
TW (1) | TW550259B (bg) |
UA (1) | UA73762C2 (bg) |
WO (1) | WO2001060805A1 (bg) |
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CN104840963B (zh) * | 2015-05-26 | 2018-02-16 | 河北东康生物科技有限公司 | 含脂蛋白相关性磷脂酶a2抑制剂的药物组合物及应用 |
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