CA1239150A - Anti-atherosclerotic trisubstituted ureas - Google Patents
Anti-atherosclerotic trisubstituted ureasInfo
- Publication number
- CA1239150A CA1239150A CA000459032A CA459032A CA1239150A CA 1239150 A CA1239150 A CA 1239150A CA 000459032 A CA000459032 A CA 000459032A CA 459032 A CA459032 A CA 459032A CA 1239150 A CA1239150 A CA 1239150A
- Authority
- CA
- Canada
- Prior art keywords
- urea
- chloro
- phenyl
- compound
- hydrogen
- 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.)
- Expired
Links
- 150000003672 ureas Chemical class 0.000 title abstract description 13
- 235000013877 carbamide Nutrition 0.000 title description 36
- 230000000879 anti-atherosclerotic effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- -1 4-(trifluormethyl)phenyl Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- QKJLDOBXDUVGEE-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-[[4-(2,2-dimethylpropyl)phenyl]methyl]-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CC(C)(C)C)C=C1 QKJLDOBXDUVGEE-UHFFFAOYSA-N 0.000 claims description 3
- JCLZLZKUISPXDC-UHFFFAOYSA-N 4-chloro-2,6-dimethylaniline Chemical compound CC1=CC(Cl)=CC(C)=C1N JCLZLZKUISPXDC-UHFFFAOYSA-N 0.000 claims description 3
- RLMPWGAJKNLQIO-UHFFFAOYSA-N n-[[4-(2,2-dimethylpropyl)phenyl]methyl]heptan-1-amine Chemical compound CCCCCCCNCC1=CC=C(CC(C)(C)C)C=C1 RLMPWGAJKNLQIO-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- HNENEALJPWJWJY-UHFFFAOYSA-N 2,4-difluoro-1-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C(F)=C1 HNENEALJPWJWJY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- CIDIAEUJFUABCA-UHFFFAOYSA-N 3-(4-chloro-2,6-dimethylphenyl)-1-[[4-(2,2-dimethylpropyl)phenyl]methyl]-1-heptylurea Chemical compound CC=1C=C(Cl)C=C(C)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CC(C)(C)C)C=C1 CIDIAEUJFUABCA-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- MXMKGZGXZKHNOH-UHFFFAOYSA-N (4-chloro-2,6-dimethyl-3-phenylphenyl) carbamate Chemical compound C(N)(OC1=C(C(=C(C=C1C)Cl)C1=CC=CC=C1)C)=O MXMKGZGXZKHNOH-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 21
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 21
- 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 abstract description 17
- 235000012000 cholesterol Nutrition 0.000 abstract description 8
- 241000124008 Mammalia Species 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 abstract description 2
- 230000003143 atherosclerotic effect Effects 0.000 abstract description 2
- 230000008901 benefit Effects 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000003902 lesion Effects 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 50
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 30
- 239000004202 carbamide Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- SBBRRSKIPTXBCO-UHFFFAOYSA-N (2,4-difluorophenyl)urea Chemical compound NC(=O)NC1=CC=C(F)C=C1F SBBRRSKIPTXBCO-UHFFFAOYSA-N 0.000 description 8
- MPBYIGCMFBGXSZ-UHFFFAOYSA-N (4-chloro-2-methylphenyl)urea Chemical compound CC1=CC(Cl)=CC=C1NC(N)=O MPBYIGCMFBGXSZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- PODOAIWAYUVDEF-UHFFFAOYSA-N (2,4,6-trichlorophenyl)urea Chemical compound NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl PODOAIWAYUVDEF-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JZJOAYCSUKDTOP-UHFFFAOYSA-N (4-chloro-2,6-dimethylphenyl)urea Chemical compound CC1=CC(Cl)=CC(C)=C1NC(N)=O JZJOAYCSUKDTOP-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- 241000208422 Rhododendron Species 0.000 description 4
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000005911 diet Nutrition 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000000023 Kugelrohr distillation Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- YTRQFSDWAXHJCC-UHFFFAOYSA-N chloroform;phenol Chemical compound ClC(Cl)Cl.OC1=CC=CC=C1 YTRQFSDWAXHJCC-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CGCOVQSKNBEYNN-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C(F)(F)F)C=C1 CGCOVQSKNBEYNN-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- 150000002632 lipids Chemical class 0.000 description 2
- 230000004903 negative regulation of intestinal cholesterol absorption Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 2
- PFVQTLVDWFDABZ-UHFFFAOYSA-N (2,4,6-trifluorophenyl)urea Chemical compound NC(=O)NC1=C(F)C=C(F)C=C1F PFVQTLVDWFDABZ-UHFFFAOYSA-N 0.000 description 1
- PSQBZUHTEQVVIQ-UHFFFAOYSA-N (4-chloro-2,5-dimethylphenyl)urea Chemical compound CC1=CC(NC(N)=O)=C(C)C=C1Cl PSQBZUHTEQVVIQ-UHFFFAOYSA-N 0.000 description 1
- NJBOMSIZOJJCDU-UHFFFAOYSA-N 1-heptyl-3-(2,4,6-trifluorophenyl)urea Chemical compound CCCCCCCNC(=O)NC1=C(F)C=C(F)C=C1F NJBOMSIZOJJCDU-UHFFFAOYSA-N 0.000 description 1
- BJSVKBGQDHUBHZ-UHFFFAOYSA-N 2,4,6-trifluoroaniline Chemical compound NC1=C(F)C=C(F)C=C1F BJSVKBGQDHUBHZ-UHFFFAOYSA-N 0.000 description 1
- RYJIUCWUVTUWGF-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)-n-heptylbenzamide Chemical compound CCCCCCCNC(=O)C1=CC=C(CC(C)(C)C)C=C1 RYJIUCWUVTUWGF-UHFFFAOYSA-N 0.000 description 1
- XSNKOUWZXGZYPF-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)benzoic acid Chemical compound CC(C)(C)CC1=CC=C(C(O)=O)C=C1 XSNKOUWZXGZYPF-UHFFFAOYSA-N 0.000 description 1
- XEGGPWMGBNKOQH-UHFFFAOYSA-N 4-(2,2-dimethylpropyl)benzoyl chloride Chemical compound CC(C)(C)CC1=CC=C(C(Cl)=O)C=C1 XEGGPWMGBNKOQH-UHFFFAOYSA-N 0.000 description 1
- VWYKSJIPZHRLNO-UHFFFAOYSA-N 4-chloro-2,6-dimethylphenol Chemical compound CC1=CC(Cl)=CC(C)=C1O VWYKSJIPZHRLNO-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
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- XNVHLZNMYBIIDA-UHFFFAOYSA-N phenyl n-(2,4,6-trifluorophenyl)carbamate Chemical compound FC1=CC(F)=CC(F)=C1NC(=O)OC1=CC=CC=C1 XNVHLZNMYBIIDA-UHFFFAOYSA-N 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51532183A | 1983-07-19 | 1983-07-19 | |
| US515,321 | 1983-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1239150A true CA1239150A (en) | 1988-07-12 |
Family
ID=24050874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000459032A Expired CA1239150A (en) | 1983-07-19 | 1984-07-17 | Anti-atherosclerotic trisubstituted ureas |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS6041655A (forum.php) |
| AT (1) | AT394191B (forum.php) |
| BE (1) | BE900178A (forum.php) |
| CA (1) | CA1239150A (forum.php) |
| FR (1) | FR2549473B1 (forum.php) |
| GB (1) | GB2149394B (forum.php) |
| NL (1) | NL8402272A (forum.php) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH642342A5 (fr) * | 1979-09-13 | 1984-04-13 | Firmenich & Cie | Procede pour la preparation de muscone. |
| US5003106A (en) * | 1983-07-19 | 1991-03-26 | American Cyanamid Company | Antiatherosclerotic ureas and thioureas |
| US5248688A (en) * | 1986-09-10 | 1993-09-28 | Dudrick Medical Research Fund I, Ltd. | Method and substrate composition for treating atherosclerosis |
| US5032608A (en) * | 1986-09-10 | 1991-07-16 | Dudrick Stanley J | Method and substrate composition for treating atherosclerosis |
| US4994465A (en) * | 1989-02-17 | 1991-02-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic trisubstituted urea compounds |
| GB9020841D0 (en) * | 1990-09-25 | 1990-11-07 | Wellcome Found | Anti-atherosclerotic aryl compounds |
| KR0169501B1 (ko) * | 1990-11-26 | 1999-03-20 | 우에하라 아키라 | 아닐리드 유도체 |
| US5420164A (en) * | 1991-04-04 | 1995-05-30 | Yoshitomi Pharmaceutical Industries, Ltd. | Cycloalkylurea compounds |
| AU660346B2 (en) * | 1991-12-25 | 1995-06-22 | Taisho Pharmaceutical Co., Ltd. | Anilide derivative |
| JPH05320143A (ja) * | 1992-03-18 | 1993-12-03 | Mochida Pharmaceut Co Ltd | 新規ピリミジン誘導体 |
| US5378728A (en) * | 1992-11-03 | 1995-01-03 | Sandoz Ltd. | Benzoic acid derivatives as antidiabetic agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5224104B2 (forum.php) * | 1974-10-07 | 1977-06-29 | ||
| JPS5461149A (en) * | 1977-10-20 | 1979-05-17 | Kumiai Chem Ind Co Ltd | 3-chloro-4-fluorophenyl urea derivative, its preparation and herbicide containing the same |
| US4387105A (en) * | 1982-01-26 | 1983-06-07 | American Cyanamid Company | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas |
| IL67417A (en) * | 1982-01-26 | 1989-10-31 | American Cyanamid Co | Antiatherosclerotic substituted ureas,process for their preparation and pharmaceutical compositions containing them |
| US4387106A (en) * | 1982-01-26 | 1983-06-07 | American Cyanamid Company | Method of treating atherosclerosis with di(aralkyl)ureas and di(aralkyl)thioureas |
-
1984
- 1984-07-05 GB GB08417126A patent/GB2149394B/en not_active Expired
- 1984-07-17 AT AT0231284A patent/AT394191B/de not_active IP Right Cessation
- 1984-07-17 CA CA000459032A patent/CA1239150A/en not_active Expired
- 1984-07-18 BE BE0/213345A patent/BE900178A/fr not_active IP Right Cessation
- 1984-07-18 NL NL8402272A patent/NL8402272A/nl not_active Application Discontinuation
- 1984-07-18 JP JP59147751A patent/JPS6041655A/ja active Granted
- 1984-07-19 FR FR8411471A patent/FR2549473B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA231284A (de) | 1991-08-15 |
| GB8417126D0 (en) | 1984-08-08 |
| JPH0585543B2 (forum.php) | 1993-12-07 |
| FR2549473A1 (fr) | 1985-01-25 |
| BE900178A (fr) | 1985-01-18 |
| AT394191B (de) | 1992-02-10 |
| JPS6041655A (ja) | 1985-03-05 |
| GB2149394B (en) | 1986-09-24 |
| GB2149394A (en) | 1985-06-12 |
| NL8402272A (nl) | 1985-02-18 |
| FR2549473B1 (fr) | 1988-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |