CA1185181A - Derives de l'alkyluree pour le traitement des maladies du metabolisme des graisses, procede de preparation utilisation en pharmacie et procede de preparation des medicaments contenant lesdits derives - Google Patents

Derives de l'alkyluree pour le traitement des maladies du metabolisme des graisses, procede de preparation utilisation en pharmacie et procede de preparation des medicaments contenant lesdits derives

Info

Publication number: CA1185181A
Authority: CA; Canada
Prior art keywords: carbon atoms; alkyl; alkoxy; hydrogen; alkylurea
Prior art date: 1979-11-09
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

Application number

CA000443986A

Other languages

English (en)

Inventor

Hans-Joachim Kabbe

Hans-Peter Krause

Rudiger Sitt

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1979-11-09

Filing date

1983-12-21

Publication date

1985-04-09

1979-11-09 Priority claimed from DE19792945238 external-priority patent/DE2945238A1/de

1980-08-08 Priority claimed from DE19803030024 external-priority patent/DE3030024A1/de

1980-11-07 Priority claimed from CA000364269A external-priority patent/CA1191133A/fr

1983-12-21 Application filed by Bayer AG filed Critical Bayer AG

1985-04-09 Application granted granted Critical

1985-04-09 Publication of CA1185181A publication Critical patent/CA1185181A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title description 9
239000003814 drug Substances 0.000 title description 7
238000002360 preparation method Methods 0.000 title description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 4
201000010099 disease Diseases 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 24
125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
150000002367 halogens Chemical group 0.000 claims abstract description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
150000003254 radicals Chemical class 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 10
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
239000000460 chlorine Substances 0.000 claims abstract description 7
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000004122 cyclic group Chemical group 0.000 claims abstract description 6
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
239000005864 Sulphur Substances 0.000 claims abstract description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
239000011737 fluorine Substances 0.000 claims abstract description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
239000003085 diluting agent Substances 0.000 claims abstract description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
239000000203 mixture Substances 0.000 claims description 22
-1 ali-phatic hydrocarbon radical Chemical class 0.000 claims description 20
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003118 aryl group Chemical group 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 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
150000001875 compounds Chemical class 0.000 description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000546 pharmaceutical excipient Substances 0.000 description 8
241000700159 Rattus Species 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000004006 olive oil Substances 0.000 description 6
235000008390 olive oil Nutrition 0.000 description 6
239000008187 granular material Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000008298 dragée Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000006187 pill Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
241000416162 Astragalus gummifer Species 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000001828 Gelatine Substances 0.000 description 3
235000019759 Maize starch Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920001615 Tragacanth Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
QRWRJDVVXAXGBT-UHFFFAOYSA-N 2-Methylindoline Chemical compound C1=CC=C2NC(C)CC2=C1 QRWRJDVVXAXGBT-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000206672 Gelidium Species 0.000 description 2
208000031226 Hyperlipidaemia Diseases 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
235000010419 agar Nutrition 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
235000012216 bentonite Nutrition 0.000 description 2
229940092782 bentonite Drugs 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
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 2
239000012973 diazabicyclooctane Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229940068917 polyethylene glycols Drugs 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
229940058015 1,3-butylene glycol Drugs 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
KSNRDYQOHXQKAB-UHFFFAOYSA-N 2,2,4-trimethyl-3,4-dihydro-1h-quinoline Chemical compound C1=CC=C2C(C)CC(C)(C)NC2=C1 KSNRDYQOHXQKAB-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
239000004258 Ethoxyquin Substances 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
101100313003 Rattus norvegicus Tanc1 gene Proteins 0.000 description 1
SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
229940093500 ethoxyquin Drugs 0.000 description 1
235000019285 ethoxyquin Nutrition 0.000 description 1
239000010642 eucalyptus oil Substances 0.000 description 1
229940044949 eucalyptus oil Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
229940074076 glycerol formal Drugs 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000003906 humectant Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052742 iron Inorganic materials 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
239000000314 lubricant Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
TUYCIJKMNWFKFB-UHFFFAOYSA-N n,2-dimethyl-2,3-dihydroindole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)NC)C(C)CC2=C1 TUYCIJKMNWFKFB-UHFFFAOYSA-N 0.000 description 1
GTGKSEPRRFBUQM-UHFFFAOYSA-N n-dodecyl-2,2,4-trimethyl-3,4-dihydroquinoline-1-carboxamide Chemical compound C1=CC=C2C(C)CC(C)(C)N(C(=O)NCCCCCCCCCCCC)C2=C1 GTGKSEPRRFBUQM-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil 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
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000443986A 1979-11-09 1983-12-21 Derives de l'alkyluree pour le traitement des maladies du metabolisme des graisses, procede de preparation utilisation en pharmacie et procede de preparation des medicaments contenant lesdits derives Expired CA1185181A (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE19792945238 DE2945238A1 (de)	1979-11-09	1979-11-09	Verwendung von alkylharnstoffderivaten in arzneimitteln zur behandlung von fettstoffwechselstoerungen
DEP2945238.8		1979-11-09
DEP3030024.4		1980-08-08
DE19803030024 DE3030024A1 (de)	1980-08-08	1980-08-08	Alkylharnstoffderivate zur behandlung von erkrankungen des fettstoffwechsels, verfahren zu deren herstellung, deren verwendung in arzneimitteln zur behandlung von festtstoffwechselstoerungen, diese enthaltende arzneimittel und verfahren zur herstellung der arzneimittel
CA000364269A CA1191133A (fr)	1979-11-09	1980-11-07	Derives de l'alkyluree pourle traitement des troubles du metabolisme des lipides, procede de preparation et utilisation dans des composes pharmaceutiques

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000364269A Division CA1191133A (fr)	1979-11-09	1980-11-07	Derives de l'alkyluree pourle traitement des troubles du metabolisme des lipides, procede de preparation et utilisation dans des composes pharmaceutiques

Publications (1)

Publication Number	Publication Date
CA1185181A true CA1185181A (fr)	1985-04-09

Family

ID=27166881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000443986A Expired CA1185181A (fr)	1979-11-09	1983-12-21	Derives de l'alkyluree pour le traitement des maladies du metabolisme des graisses, procede de preparation utilisation en pharmacie et procede de preparation des medicaments contenant lesdits derives

Country Status (1)

Country	Link
CA (1)	CA1185181A (fr)

1983
- 1983-12-21 CA CA000443986A patent/CA1185181A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-04-09	MKEX	Expiry

Publication	Publication Date	Title
US4225591A (en)	1980-09-30	2,6-Diaminonebularines
PL180302B1 (pl)	2001-01-31	Nowe pochodne benzoiloguanidyny, sposób ich wytwarzaniai kompozycje farmaceutyczne. PL PL PL PL
DE69132167T2 (de)	2000-12-14	Kondensierte benzoxa-ringverbindung, deren herstellung sowie diese enthaltendes arzneimittel
US4510156A (en)	1985-04-09	Bisindolyl alkylene ureas lipid absorption-inhibiting agents and their use thereas
EP0327986A2 (fr)	1989-08-16	Médicaments contenant des lactames, lactames substitués et procédé pour leur préparation
EP0287890A1 (fr)	1988-10-26	Pyrroles substitués
US5391552A (en)	1995-02-21	Diphenylpiperazine derivative and drug for circulatory organ containing the same
DE69128477T2 (de)	1998-07-16	Benzopyranderivat
US3818032A (en)	1974-06-18	Substituted 1-phenyl-2,5-dioxo imidazolidines
JPS58128380A (ja)	1983-07-30	新規イミダゾ−ル化合物、それらの製造方法及びそれらからなる抗体外寄生生物、駆虫剤
CA1185181A (fr)	1985-04-09	Derives de l'alkyluree pour le traitement des maladies du metabolisme des graisses, procede de preparation utilisation en pharmacie et procede de preparation des medicaments contenant lesdits derives
DE3782636T2 (de)	1993-04-08	Isoindolin-1-on-derivat und antiarrhythmisches mittel.
DE69103535T2 (de)	1995-01-26	1-Phenylalkyl-3-Phenylharnstoff-Derivate.
US4188323A (en)	1980-02-12	Derivatives of 2-oxazolydone and methods for preparing the same
US4011343A (en)	1977-03-08	Triazapentadienes as acaricides and insecticides
JPH0140027B2 (fr)	1989-08-24
EP0339342A1 (fr)	1989-11-02	N-aminopyrrols N-substitués
US4193994A (en)	1980-03-18	Tetrahydro-s-triazine thiones
EP0095278B1 (fr)	1988-11-30	Dérivés de l'acide 5-oxo-2-pyrrolidinepropanoique et leur production
US4032524A (en)	1977-06-28	1-carbamoyl-5-fluorouracil derivatives
US4320129A (en)	1982-03-16	Pyromellitic diimide complexes
EP0334147A1 (fr)	1989-09-27	Pyrroles disubstitués
GB2084154A (en)	1982-04-07	4-Carbamoyloxy-oxazaphosphorins method of producing them and pharmaceutical preparations containing them
CA1085297A (fr)	1980-09-09	Anthelminthique
FR2489825A1 (fr)	1982-03-12	4-carbamoyloxy-oxazaphosphorines, procede pour leur preparation et compositions pharmaceutiques qui les contiennent