CH468979A - Verfahren zur Herstellung von Benzolsulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von BenzolsulfonylharnstoffenInfo
- Publication number
- CH468979A CH468979A CH49867A CH4986764A CH468979A CH 468979 A CH468979 A CH 468979A CH 49867 A CH49867 A CH 49867A CH 4986764 A CH4986764 A CH 4986764A CH 468979 A CH468979 A CH 468979A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- formula
- molecular weight
- low molecular
- benzenesulfonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- -1 organic acid radical Chemical class 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- NQOJWOIPQBVKKX-UHFFFAOYSA-N cyclooctane Chemical compound [CH]1CCCCCCC1 NQOJWOIPQBVKKX-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 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
- 239000003472 antidiabetic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IMMFXSGHFKGGMO-UHFFFAOYSA-N n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]acetamide Chemical compound C1=CC(CCNC(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 IMMFXSGHFKGGMO-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940127003 anti-diabetic drug Drugs 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38953A DE1188078B (de) | 1963-02-07 | 1963-02-07 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH128064A CH448050A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH468979A true CH468979A (de) | 1969-02-28 |
Family
ID=7097559
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH49867A CH468979A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH50067A CH449604A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH128064A CH448050A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH49967A CH449603A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH50067A CH449604A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH128064A CH448050A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| CH49967A CH449603A (de) | 1963-02-07 | 1964-02-04 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Country Status (9)
| Country | Link |
|---|---|
| AT (4) | AT257628B (enrdf_load_stackoverflow) |
| BE (1) | BE643527A (enrdf_load_stackoverflow) |
| BR (1) | BR6456764D0 (enrdf_load_stackoverflow) |
| CH (4) | CH468979A (enrdf_load_stackoverflow) |
| DE (1) | DE1188078B (enrdf_load_stackoverflow) |
| DK (4) | DK111817B (enrdf_load_stackoverflow) |
| FR (2) | FR1384309A (enrdf_load_stackoverflow) |
| GB (1) | GB1052113A (enrdf_load_stackoverflow) |
| NL (1) | NL6400975A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH505829A (de) * | 1968-03-14 | 1971-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkylbenzolsulfonamids |
| BE754597A (fr) * | 1969-08-08 | 1971-02-08 | Geigy Ag J R | Alkyl-benzene-sulfonamides et medicaments contenant de tels composes |
-
0
- GB GB1052113D patent/GB1052113A/en active Active
-
1963
- 1963-02-07 DE DEF38953A patent/DE1188078B/de active Pending
-
1964
- 1964-02-04 CH CH49867A patent/CH468979A/de unknown
- 1964-02-04 CH CH50067A patent/CH449604A/de unknown
- 1964-02-04 CH CH128064A patent/CH448050A/de unknown
- 1964-02-04 CH CH49967A patent/CH449603A/de unknown
- 1964-02-05 AT AT33166A patent/AT257628B/de active
- 1964-02-05 AT AT33066A patent/AT254897B/de active
- 1964-02-05 AT AT33266A patent/AT257629B/de active
- 1964-02-05 AT AT92964A patent/AT253521B/de active
- 1964-02-06 DK DK58664AA patent/DK111817B/da unknown
- 1964-02-06 NL NL6400975A patent/NL6400975A/xx unknown
- 1964-02-07 BR BR156764/64A patent/BR6456764D0/pt unknown
- 1964-02-07 FR FR962976A patent/FR1384309A/fr not_active Expired
- 1964-02-07 BE BE643527A patent/BE643527A/xx unknown
- 1964-05-06 FR FR973506A patent/FR3497M/fr active Active
-
1965
- 1965-03-26 DK DK158765AA patent/DK117292B/da unknown
- 1965-03-26 DK DK158665AA patent/DK117224B/da unknown
- 1965-03-26 DK DK158865AA patent/DK117293B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT257628B (de) | 1967-10-10 |
| AT257629B (de) | 1967-10-10 |
| CH449603A (de) | 1968-01-15 |
| DE1188078B (de) | 1965-03-04 |
| AT254897B (de) | 1967-06-12 |
| GB1052113A (enrdf_load_stackoverflow) | |
| BE643527A (enrdf_load_stackoverflow) | 1964-08-07 |
| DK117293B (da) | 1970-04-13 |
| AT253521B (de) | 1967-04-10 |
| DK117292B (da) | 1970-04-13 |
| FR3497M (fr) | 1965-08-23 |
| DK111817B (da) | 1968-10-14 |
| FR1384309A (fr) | 1965-01-04 |
| CH449604A (de) | 1968-01-15 |
| CH448050A (de) | 1967-12-15 |
| DK117224B (da) | 1970-03-31 |
| NL6400975A (enrdf_load_stackoverflow) | 1964-08-10 |
| BR6456764D0 (pt) | 1973-08-14 |
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