CH406184A - Verfahren zur Herstellung von Mercaptonen und Verwendung derselben - Google Patents
Verfahren zur Herstellung von Mercaptonen und Verwendung derselbenInfo
- Publication number
- CH406184A CH406184A CH6233058A CH6233058A CH406184A CH 406184 A CH406184 A CH 406184A CH 6233058 A CH6233058 A CH 6233058A CH 6233058 A CH6233058 A CH 6233058A CH 406184 A CH406184 A CH 406184A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- radical
- urea
- benzenesulfonyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000008280 blood Substances 0.000 claims description 11
- 210000004369 blood Anatomy 0.000 claims description 11
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 9
- 229960003151 mercaptamine Drugs 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000002019 disulfides Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003673 urethanes Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229940100389 Sulfonylurea Drugs 0.000 description 9
- -1 aminobenzenesulphonyl group Chemical group 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- DVTYAUOYHFTJHI-UHFFFAOYSA-N 1-(4-ethylphenyl)sulfonyl-3-(2-sulfanylethyl)urea Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCS DVTYAUOYHFTJHI-UHFFFAOYSA-N 0.000 description 3
- WVACFTUPNPFQMQ-UHFFFAOYSA-N 1-cyclohexylsulfonyl-3-(2-sulfanylethyl)urea Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NCCS WVACFTUPNPFQMQ-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 2
- 229940099500 cystamine Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 229940127017 oral antidiabetic Drugs 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KLHUBDSZIPFYGP-UHFFFAOYSA-N (4-chlorophenyl)sulfonyl-methylcarbamic acid Chemical compound CN(C(O)=O)S(=O)(=O)C1=CC=C(C=C1)Cl KLHUBDSZIPFYGP-UHFFFAOYSA-N 0.000 description 1
- HVXMFWHVRQYLLE-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)sulfonyl-3-(2-sulfanylethyl)urea Chemical compound CC=1C=C(C=CC1C)S(=O)(=O)NC(=O)NCCS HVXMFWHVRQYLLE-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
- 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
- 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
- AFUNFTWQTLZMNW-UHFFFAOYSA-N CCOC(NCS(C1CCCCC1)(=O)=O)=O Chemical compound CCOC(NCS(C1CCCCC1)(=O)=O)=O AFUNFTWQTLZMNW-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LOWQEDSQFHBDHF-UHFFFAOYSA-N N-(benzenesulfonylcarbamoyl)acetamide Chemical compound C(C)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 LOWQEDSQFHBDHF-UHFFFAOYSA-N 0.000 description 1
- CPQUAOFWFOGARR-UHFFFAOYSA-N N-(benzenesulfonylcarbamoyl)butanamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)NC(CCC)=O CPQUAOFWFOGARR-UHFFFAOYSA-N 0.000 description 1
- QKMZRTPNTOPHPH-UHFFFAOYSA-N N-(cyclohexylsulfonylcarbamoyl)acetamide Chemical compound C1(CCCCC1)S(=O)(=O)NC(=O)NC(C)=O QKMZRTPNTOPHPH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JAVYWSYYOFLJMT-UHFFFAOYSA-N O=C(NCCS)N=S(=O)=O Chemical compound O=C(NCCS)N=S(=O)=O JAVYWSYYOFLJMT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HWCQNZGRHUPEBP-UHFFFAOYSA-N ethyl N-(3,4-dimethoxyphenyl)sulfonyl-N-methylcarbamate Chemical compound CCOC(=O)N(C)S(=O)(=O)C1=CC(OC)=C(OC)C=C1 HWCQNZGRHUPEBP-UHFFFAOYSA-N 0.000 description 1
- CEHNDPXHFFJGHW-UHFFFAOYSA-N ethyl N-(4-chlorophenyl)sulfonyl-N-methylcarbamate Chemical compound CN(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Cl CEHNDPXHFFJGHW-UHFFFAOYSA-N 0.000 description 1
- KWHXRPOBVUXTNC-UHFFFAOYSA-N ethyl N-(4-methoxyphenyl)sulfonyl-N-methylcarbamate Chemical compound COC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C KWHXRPOBVUXTNC-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
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical class CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical class CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 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
- CDQYMWJDKABVFK-UHFFFAOYSA-N n-(oxomethylidene)cyclohexanesulfonamide Chemical compound O=C=NS(=O)(=O)C1CCCCC1 CDQYMWJDKABVFK-UHFFFAOYSA-N 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0023644 | 1957-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH406184A true CH406184A (de) | 1966-01-31 |
Family
ID=7090927
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6233058A CH406184A (de) | 1957-07-31 | 1958-07-28 | Verfahren zur Herstellung von Mercaptonen und Verwendung derselben |
| CH1503163A CH393304A (de) | 1957-07-31 | 1958-07-28 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1503163A CH393304A (de) | 1957-07-31 | 1958-07-28 | Verfahren zur Herstellung von Sulfonylharnstoffen |
Country Status (2)
| Country | Link |
|---|---|
| CH (2) | CH406184A (da) |
| DK (3) | DK104167C (da) |
-
1958
- 1958-07-23 DK DK169959A patent/DK104167C/da active
- 1958-07-23 DK DK169859A patent/DK106847C/da active
- 1958-07-23 DK DK169759A patent/DK104934C/da active
- 1958-07-28 CH CH6233058A patent/CH406184A/de unknown
- 1958-07-28 CH CH1503163A patent/CH393304A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK104167C (da) | 1966-04-18 |
| DK106847C (da) | 1967-03-28 |
| CH393304A (de) | 1965-06-15 |
| DK104934C (da) | 1966-07-25 |
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