CA1291132C - Urees et thiourees substituees anti-atherosclerotiques - Google Patents

Urees et thiourees substituees anti-atherosclerotiques

Info

Publication number: CA1291132C
Authority: CA; Canada
Prior art keywords: benzyl; formula; compound; urea; butyl
Prior art date: 1982-01-26
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 - Fee Related

Application number

CA 420024

Other languages

English (en)

Inventor

Vern Gordon Devries

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1982-01-26

Filing date

1983-01-21

Publication date

1991-10-22

1983-01-21 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1991-10-22 Application granted granted Critical

1991-10-22 Publication of CA1291132C publication Critical patent/CA1291132C/fr

Status Expired - Fee Related legal-status Critical Current

Links

230000000879 anti-atherosclerotic effect Effects 0.000 title claims abstract description 11
235000013877 carbamide Nutrition 0.000 title abstract description 68
150000003585 thioureas Chemical class 0.000 title abstract description 20
150000003672 ureas Chemical class 0.000 title abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 67
-1 nitro, cyano, phenyl Chemical group 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 14
230000008569 process Effects 0.000 claims abstract description 13
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
125000003944 tolyl group Chemical group 0.000 claims abstract description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
239000001301 oxygen Substances 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 5
229910052717 sulfur Chemical group 0.000 claims abstract 5
239000011593 sulfur Chemical group 0.000 claims abstract 5
241000124008 Mammalia Species 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
150000003335 secondary amines Chemical class 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 9
150000004982 aromatic amines Chemical class 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000004953 trihalomethyl group Chemical group 0.000 claims description 5
QUOBVYPFBJUOAJ-UHFFFAOYSA-N 1-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1 QUOBVYPFBJUOAJ-UHFFFAOYSA-N 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000006277 halobenzyl group Chemical group 0.000 claims description 3
125000006178 methyl benzyl group Chemical group 0.000 claims description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
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229910052796 boron Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
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LIEOQKOTIYVPKN-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,4,6-trimethylphenyl)urea Chemical compound CC=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 LIEOQKOTIYVPKN-UHFFFAOYSA-N 0.000 claims 3
CQCRPHVZWXLSLZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 CQCRPHVZWXLSLZ-UHFFFAOYSA-N 0.000 claims 3
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
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125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 2
SXJYSIBLFGQAND-UHFFFAOYSA-N 1-isocyanato-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(N=C=O)=C1 SXJYSIBLFGQAND-UHFFFAOYSA-N 0.000 claims 1
VXGQDFOHLMAZIV-UHFFFAOYSA-N 1-phenylpentan-2-amine Chemical compound CCCC(N)CC1=CC=CC=C1 VXGQDFOHLMAZIV-UHFFFAOYSA-N 0.000 claims 1
HJHZRZFONUPQAA-UHFFFAOYSA-N 2-isocyanato-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C(C)=C1 HJHZRZFONUPQAA-UHFFFAOYSA-N 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000001589 carboacyl group Chemical group 0.000 abstract description 2
125000006193 alkinyl group Chemical group 0.000 abstract 2
125000004432 carbon atom Chemical group C* 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
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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 description 42
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
235000012000 cholesterol Nutrition 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000543 intermediate Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
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Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA 420024 1982-01-26 1983-01-21 Urees et thiourees substituees anti-atherosclerotiques Expired - Fee Related CA1291132C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US34269282A	1982-01-26	1982-01-26
US342,692		1982-01-26

Publications (1)

Publication Number	Publication Date
CA1291132C true CA1291132C (fr)	1991-10-22

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ID=23342878

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 420024 Expired - Fee Related CA1291132C (fr)	1982-01-26	1983-01-21	Urees et thiourees substituees anti-atherosclerotiques

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CA (1)	CA1291132C (fr)

1983
- 1983-01-21 CA CA 420024 patent/CA1291132C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2000-10-23	MKLA	Lapsed

Publication	Publication Date	Title
US4473579A (en)	1984-09-25	Antiatherosclerotic tetrasubstituted ureas and thioureas
US4387105A (en)	1983-06-07	Methods of treating atherosclerosis with dialkylureas and dialkylthioureas
US4387106A (en)	1983-06-07	Method of treating atherosclerosis with di(aralkyl)ureas and di(aralkyl)thioureas
US4623662A (en)	1986-11-18	Antiatherosclerotic ureas and thioureas
US5612377A (en)	1997-03-18	Method of inhibiting leukotriene biosynthesis
EP0196184B1 (fr)	1992-09-16	Dérivés arylés
US5015644A (en)	1991-05-14	Antihyperlipidemic and antiatherosclerotic urea and carbamate compounds
SU873878A3 (ru)	1981-10-15	Способ получени производных гидантоина
US4397868A (en)	1983-08-09	Method of treating atherosclerosis with trisubstituted ureas
KR20020089347A (ko)	2002-11-29	전립선암, 탈모증 및 기타 과안드로겐 증후군의 치료 및진단용 안드로겐 수용체 억제제
WO2000037430A2 (fr)	2000-06-29	Utilisation de suppresseurs du recepteur androgenique
CH646154A5 (de)	1984-11-15	Imidazol-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
CS655889A3 (en)	1992-11-18	Anti-atherosclerotic active compounds, pharmaceuticals containing suchcompounds and process for preparing thereof
IE54683B1 (en)	1990-01-03	Antiatherosclerotic substituted ureas
US5003106A (en)	1991-03-26	Antiatherosclerotic ureas and thioureas
CA1255299A (fr)	1989-06-06	Derives de guanidinothiazole renfermant des ponts alcoylene; preparation et utilisation comme medicaments
CA1239150A (fr)	1988-07-12	Urees trisubstituees anti-atherosclerotiques
US4413011A (en)	1983-11-01	Substituted 2,2-dimethyl-5-phenoxypentanoic acid benzamides as anti-arteriosclerotic agents and method
US5668157A (en)	1997-09-16	Cyanoguanidines as K-channel blockers
CA2010184A1 (fr)	1990-08-17	Composes d'uree trisubstitues ayant des proprietes antihyperlipidemiques et antiatherosclerotiques
US4977188A (en)	1990-12-11	Method of treating inflammation
US4450272A (en)	1984-05-22	Antiatherosclerotic 1-piperazine-thicarboxamides
EP0557787B1 (fr)	2000-05-24	Dérivés d'imidazolylphénol, médicaments les contenant et un procédé de préparation de ces composés et médicaments
US4666932A (en)	1987-05-19	Formamidine derivatives and pharmaceutical use
GB2139621A (en)	1984-11-14	Pyridyl n-oxides