BE569963A - - Google Patents
Info
- Publication number
- BE569963A BE569963A BE569963DA BE569963A BE 569963 A BE569963 A BE 569963A BE 569963D A BE569963D A BE 569963DA BE 569963 A BE569963 A BE 569963A
- Authority
- BE
- Belgium
- Prior art keywords
- sulfonyl
- formula
- ethyl
- acyl
- urea
- Prior art date
Links
- 150000002019 disulfides Chemical class 0.000 claims description 17
- UFULAYFCSOUIOV-UHFFFAOYSA-N Cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 14
- 229940119025 Cysteamine Drugs 0.000 claims description 14
- 229960003151 Mercaptamine Drugs 0.000 claims description 14
- 230000000875 corresponding Effects 0.000 claims description 14
- -1 cystamine acyl-ureas Chemical class 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000002218 hypoglycaemic Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229940099500 Cystamine Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 235000013877 carbamide Nutrition 0.000 claims description 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000003673 urethanes Chemical class 0.000 claims description 3
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 230000002194 synthesizing Effects 0.000 claims 2
- 230000000844 anti-bacterial Effects 0.000 claims 1
- 239000004202 carbamide Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 13
- 239000000155 melt Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 210000004369 Blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl N-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 3
- XLCDSNFXNIFAJK-UHFFFAOYSA-N 2-sulfanylethylurea Chemical compound NC(=O)NCCS XLCDSNFXNIFAJK-UHFFFAOYSA-N 0.000 description 2
- DVTYAUOYHFTJHI-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCS Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCS DVTYAUOYHFTJHI-UHFFFAOYSA-N 0.000 description 2
- HVXMFWHVRQYLLE-UHFFFAOYSA-N CC=1C=C(C=CC1C)S(=O)(=O)NC(=O)NCCS Chemical compound CC=1C=C(C=CC1C)S(=O)(=O)NC(=O)NCCS HVXMFWHVRQYLLE-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- MPJIXDYXBDYRCZ-UHFFFAOYSA-N ethyl N-(benzenesulfonyl)-N-methylcarbamate Chemical class CCOC(=O)N(C)S(=O)(=O)C1=CC=CC=C1 MPJIXDYXBDYRCZ-UHFFFAOYSA-N 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NTFFTFGUNKNQQA-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-(2-sulfanylethyl)urea Chemical compound CC1=CC=C(S(=O)(=O)NC(=O)NCCS)C=C1 NTFFTFGUNKNQQA-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-N-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- JVPKRFXSEHQJRU-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC(O)=O Chemical compound C(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC(O)=O JVPKRFXSEHQJRU-UHFFFAOYSA-N 0.000 description 1
- ARAHQDBOLBKARK-UHFFFAOYSA-N C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C ARAHQDBOLBKARK-UHFFFAOYSA-N 0.000 description 1
- CPQUAOFWFOGARR-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NC(=O)NC(CCC)=O Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)NC(CCC)=O CPQUAOFWFOGARR-UHFFFAOYSA-N 0.000 description 1
- VYHPPHNKGCWGKG-UHFFFAOYSA-N C1(CCCCC1)N(C(=O)OC(C)S(=O)(=O)C)C Chemical compound C1(CCCCC1)N(C(=O)OC(C)S(=O)(=O)C)C VYHPPHNKGCWGKG-UHFFFAOYSA-N 0.000 description 1
- MVVBXRLEWUHVLJ-UHFFFAOYSA-N C1(CCCCC1)S(=O)(=O)N(C(=O)OCC)C Chemical compound C1(CCCCC1)S(=O)(=O)N(C(=O)OCC)C MVVBXRLEWUHVLJ-UHFFFAOYSA-N 0.000 description 1
- WVACFTUPNPFQMQ-UHFFFAOYSA-N C1(CCCCC1)S(=O)(=O)NC(=O)NCCS Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NCCS WVACFTUPNPFQMQ-UHFFFAOYSA-N 0.000 description 1
- JATUCKOGEZIRGJ-UHFFFAOYSA-N C12SC2C=CC2(C(C)C)C1S2 Chemical compound C12SC2C=CC2(C(C)C)C1S2 JATUCKOGEZIRGJ-UHFFFAOYSA-N 0.000 description 1
- AUASHCDCDOYZFR-UHFFFAOYSA-N CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)C Chemical compound CC=1C=C(C=CC1)S(=O)(=O)N(C(=O)OCC)C AUASHCDCDOYZFR-UHFFFAOYSA-N 0.000 description 1
- INIXPPCUQCQUJG-UHFFFAOYSA-N CCOC(=O)N(C)S(=O)(=O)C1=CC(C)=C(C)C=C1 Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC(C)=C(C)C=C1 INIXPPCUQCQUJG-UHFFFAOYSA-N 0.000 description 1
- IOMDJMXTAGBAQQ-UHFFFAOYSA-N CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)C(C)C Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)C(C)C IOMDJMXTAGBAQQ-UHFFFAOYSA-N 0.000 description 1
- CEHNDPXHFFJGHW-UHFFFAOYSA-N CN(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Cl Chemical compound CN(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Cl CEHNDPXHFFJGHW-UHFFFAOYSA-N 0.000 description 1
- XWQXWXZSAIORQC-UHFFFAOYSA-N COC(NS(=O)(=O)C1=CC(=C(C=C1)C)C)=O Chemical compound COC(NS(=O)(=O)C1=CC(=C(C=C1)C)C)=O XWQXWXZSAIORQC-UHFFFAOYSA-N 0.000 description 1
- XTPNRFBDHIQAAI-UHFFFAOYSA-N COC(NS(=O)(=O)C1CCCCC1)=O Chemical compound COC(NS(=O)(=O)C1CCCCC1)=O XTPNRFBDHIQAAI-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N N-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N N-(p-Tolylsulfonyl)-N'-butylcarbamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- GKRZNOGGALENQJ-UHFFFAOYSA-N N-carbamoylacetamide Chemical compound CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003178 anti-diabetic Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 description 1
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl N-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 1
- CXLBYPJSAWOYSI-UHFFFAOYSA-N ethyl N-methyl-N-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC=C(C)C=C1 CXLBYPJSAWOYSI-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- MIMJFNVDBPUTPB-UHFFFAOYSA-N potassium hexacyanoferrate(3-) Chemical compound [K+].[K+].[K+].N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N MIMJFNVDBPUTPB-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569963A true BE569963A (no) |
Family
ID=188714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569963D BE569963A (no) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569963A (no) |
-
0
- BE BE569963D patent/BE569963A/fr unknown
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