HU200746B - Process for producing new, substituted urea derivatives and pharmaceutical compositions, particularly with antiatherosclerotic action, comprising same - Google Patents
Process for producing new, substituted urea derivatives and pharmaceutical compositions, particularly with antiatherosclerotic action, comprising same Download PDFInfo
- Publication number
- HU200746B HU200746B HU83227A HU22783A HU200746B HU 200746 B HU200746 B HU 200746B HU 83227 A HU83227 A HU 83227A HU 22783 A HU22783 A HU 22783A HU 200746 B HU200746 B HU 200746B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- formula
- group
- alkyl
- benzyl
- Prior art date
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- 150000003672 ureas Chemical class 0.000 title claims abstract description 9
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 9
- 230000000879 anti-atherosclerotic effect Effects 0.000 title abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 43
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003335 secondary amines Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- -1 phenoxy, mercapto Chemical class 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 150000003585 thioureas Chemical class 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000006277 halobenzyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000006178 methyl benzyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 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 description 29
- 239000000243 solution Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 239000012230 colorless oil Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 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 description 3
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- 239000003443 antiviral agent Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AVSXSVCZWQODGV-DPAQBDIFSA-N desmosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC=C(C)C)C)[C@@]1(C)CC2 AVSXSVCZWQODGV-DPAQBDIFSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
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- 239000000417 fungicide Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
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- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
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- 229940102213 injectable suspension Drugs 0.000 description 1
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- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
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- 229940126601 medicinal product Drugs 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- 230000003228 microsomal effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940111688 monobasic potassium phosphate Drugs 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 description 1
- VLJJFRIHSLTXSI-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NCC=2C(=CC=CC=2)Cl)=C1 VLJJFRIHSLTXSI-UHFFFAOYSA-N 0.000 description 1
- PUEUFOKKVOOXEW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]butan-1-amine Chemical compound CCCCNCC1=CC=CC=C1Cl PUEUFOKKVOOXEW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical class C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- PERRBGDAOVSLIV-UHFFFAOYSA-N n-butyl-2-chlorobenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1Cl PERRBGDAOVSLIV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- XDUHQPOXLUAVEE-BPMMELMSSA-N oleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDUHQPOXLUAVEE-BPMMELMSSA-N 0.000 description 1
- 238000011369 optimal treatment Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 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
- UKTDAQDTJFLOMR-UHFFFAOYSA-N phenyl n-(4-chloro-2,6-dimethylphenyl)carbamate Chemical compound CC1=CC(Cl)=CC(C)=C1NC(=O)OC1=CC=CC=C1 UKTDAQDTJFLOMR-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 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
- 208000024891 symptom Diseases 0.000 description 1
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- 230000008719 thickening Effects 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/342,698 US4387105A (en) | 1982-01-26 | 1982-01-26 | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas |
| US06/342,693 US4473579A (en) | 1982-01-26 | 1982-01-26 | Antiatherosclerotic tetrasubstituted ureas and thioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU200746B true HU200746B (en) | 1990-08-28 |
Family
ID=26993144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83227A HU200746B (en) | 1982-01-26 | 1983-01-25 | Process for producing new, substituted urea derivatives and pharmaceutical compositions, particularly with antiatherosclerotic action, comprising same |
Country Status (20)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2138804A (en) * | 1983-04-27 | 1984-10-31 | Sumitomo Chemical Co | Fungicidal N-phenylcarbamates |
| GB2149394B (en) * | 1983-07-19 | 1986-09-24 | American Cyanamid Co | Ureas |
| US4818899A (en) * | 1986-12-03 | 1989-04-04 | Minnesota Mining And Manufacturing Company | Second harmonic generation by carbamic acid derivatives |
| EP0344425B1 (en) * | 1988-03-30 | 1993-12-08 | Warner-Lambert Company | N-[[(2,6-disubstituted)phenyl]-N'- arylalkyl] ureas as antihypercholesterolemic and antiatherosclerotic agents |
| US5116848A (en) * | 1988-03-30 | 1992-05-26 | Warner-Lambert Company | N-(((2,6-disubstituted)phenyl)-n-diarylalkyl)ureas as antihyperlipidemic and antiatherosclerotic agents |
| EP0515684A4 (en) * | 1990-02-14 | 1993-04-21 | Chugai Seiyaku Kabushiki Kaisha | Inhibitor of denatured ldl formation |
| US5668136A (en) * | 1990-09-25 | 1997-09-16 | Eisai Co., Ltd. | Trisubstituted benzene derivatives, composition and methods of treatment |
| HUT62558A (en) * | 1991-07-01 | 1993-05-28 | Sandoz Ag | Process for producing n-phenylthiourea derivaties and pharmaceutical compositions comprising same |
| CA2115915A1 (en) * | 1992-07-20 | 1994-02-03 | Kenji Hayashi | Benzene derivatives |
| AU8534198A (en) * | 1997-08-05 | 1999-03-01 | Novo Nordisk A/S | Derivatives of 2,5- and 3,5-disubstituted anilines, their preparation and use |
| TW415942B (en) * | 1997-09-03 | 2000-12-21 | American Home Prod | Novel substituted 1-aryl-3-heteroaryl-thioureas and substituted 1-aryl-3-heteroaryl-isothioureas as antiatherosclerotic agents |
| US6455566B1 (en) | 1997-09-03 | 2002-09-24 | Wyeth | Substituted 1-aryl-3-heteroaryl-thioureas (or isothioureas) as antiatherosclerotic agents |
| WO1999037604A2 (en) * | 1998-01-21 | 1999-07-29 | Zymogenetics, Inc. | Dialkyl ureas as calcitonin mimetics |
| CA2692598A1 (en) * | 2007-07-10 | 2009-01-15 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL92838C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1949-12-06 | |||
| US2688039A (en) * | 1952-02-08 | 1954-08-31 | Ciba Pharm Prod Inc | Halogen-containing di-(substituted phenyl)-thioureas |
| US3326663A (en) * | 1964-09-25 | 1967-06-20 | Shell Oil Co | Herbicidal phenylureas |
| US3335142A (en) * | 1965-07-07 | 1967-08-08 | American Cyanamid Co | Process for the preparation of n, n'-disubstituted ureas |
| US3659012A (en) * | 1969-05-26 | 1972-04-25 | Lilly Co Eli | Methods of treating helminth infections with thiourea derivatives |
| US3728386A (en) * | 1970-07-27 | 1973-04-17 | Exxon Research Engineering Co | N-cycloalkylalkyl and n-cycloalkyl substituted phenyl ureas and halo acetamides |
| US3928437A (en) * | 1970-09-02 | 1975-12-23 | Ciba Geigy Corp | Phenoxy-phenyl, phenylthiophenyl, phenylsulfonylphenyl and phenylaminophenyl diaminothioureas |
| US3856952A (en) * | 1973-03-01 | 1974-12-24 | Pennwalt Corp | Synergistic antimicrobial compositions employing certain n-(phenyl-carbamyl)amino-benzene sulfonyl flourides |
| US3903130A (en) * | 1974-05-03 | 1975-09-02 | Stauffer Chemical Co | 1-Trifluormethylphenyl-3-dicyanophenyl urea |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
-
1982
- 1982-12-05 IL IL67417A patent/IL67417A/xx not_active IP Right Cessation
- 1982-12-22 DE DE19823247581 patent/DE3247581A1/de not_active Withdrawn
- 1982-12-28 KR KR8205843A patent/KR890001808B1/ko not_active Expired
-
1983
- 1983-01-14 GR GR70261A patent/GR77186B/el unknown
- 1983-01-21 AU AU10681/83A patent/AU562699B2/en not_active Ceased
- 1983-01-24 GB GB08301863A patent/GB2113684B/en not_active Expired
- 1983-01-25 NL NL8300269A patent/NL8300269A/nl not_active Application Discontinuation
- 1983-01-25 IE IE146/83A patent/IE54683B1/en not_active IP Right Cessation
- 1983-01-25 DK DK028683A patent/DK160869C/da not_active IP Right Cessation
- 1983-01-25 PT PT76138A patent/PT76138A/pt not_active IP Right Cessation
- 1983-01-25 PL PL1983240284A patent/PL143836B1/pl unknown
- 1983-01-25 SE SE8300370A patent/SE462653B/sv not_active IP Right Cessation
- 1983-01-25 NO NO830238A patent/NO158417C/no unknown
- 1983-01-25 FI FI830247A patent/FI85013C/fi not_active IP Right Cessation
- 1983-01-25 CH CH404/83A patent/CH654571A5/de not_active IP Right Cessation
- 1983-01-25 ES ES519246A patent/ES519246A0/es active Granted
- 1983-01-25 HU HU83227A patent/HU200746B/hu not_active IP Right Cessation
- 1983-01-25 AT AT0023983A patent/AT391313B/de not_active IP Right Cessation
- 1983-01-25 FR FR8301082A patent/FR2521134B1/fr not_active Expired
- 1983-01-25 IT IT47605/83A patent/IT1203647B/it active
-
1984
- 1984-04-11 ES ES531508A patent/ES531508A0/es active Granted
Also Published As
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| Date | Code | Title | Description |
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| HMM4 | Cancellation of final prot. due to non-payment of fee |