CH507960A - Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden - Google Patents
Verfahren zur Herstellung von neuen antidiabetisch wirksamen SulfonamidenInfo
- Publication number
- CH507960A CH507960A CH136368A CH136368A CH507960A CH 507960 A CH507960 A CH 507960A CH 136368 A CH136368 A CH 136368A CH 136368 A CH136368 A CH 136368A CH 507960 A CH507960 A CH 507960A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- cycloalkyl
- ethyl
- optionally substituted
- pyrimidinyl
- Prior art date
Links
- 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 5
- 230000003178 anti-diabetic effect Effects 0.000 title description 3
- 239000003472 antidiabetic agent Substances 0.000 title description 2
- -1 arylmercaptoalkyl Chemical group 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 150000005006 2-aminopyrimidines Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 101000713585 Homo sapiens Tubulin beta-4A chain Proteins 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 102100036788 Tubulin beta-4A chain Human genes 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ADDUTXMPNFDHBN-UHFFFAOYSA-N 5-propylsulfanylpyrimidin-2-amine Chemical compound NC1=NC=C(C=N1)SCCC ADDUTXMPNFDHBN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 1
- YSOMTIHBNLYURM-UHFFFAOYSA-N NC1=NC=C(C=N1)SC(C)C Chemical compound NC1=NC=C(C=N1)SC(C)C YSOMTIHBNLYURM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HLBLNLYCFFWMFF-UHFFFAOYSA-N n-pyrimidin-2-ylbenzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC1=NC=CC=N1 HLBLNLYCFFWMFF-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1361970A CH507961A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967B0090983 DE1670188A1 (de) | 1967-02-01 | 1967-02-01 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507960A true CH507960A (de) | 1971-05-31 |
Family
ID=6985585
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH136368A CH507960A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1361870A CH542855A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1361770A CH542215A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1361970A CH507961A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1361870A CH542855A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1361770A CH542215A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
| CH1361970A CH507961A (de) | 1967-02-01 | 1968-01-30 | Verfahren zur Herstellung von neuen antidiabetisch wirksamen Sulfonamiden |
Country Status (6)
| Country | Link |
|---|---|
| AT (4) | AT280292B (https=) |
| CH (4) | CH507960A (https=) |
| DE (1) | DE1670188A1 (https=) |
| FR (1) | FR1595528A (https=) |
| GB (1) | GB1148287A (https=) |
| NL (1) | NL6801402A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2021962C3 (de) * | 1970-04-28 | 1981-12-24 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Blutzuckersenkende Sulfamoylpyrimidine mit asymmetrischem Kohlenstoffatom |
| DK163123C (da) * | 1978-05-30 | 1992-06-09 | Du Pont | Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse |
-
1967
- 1967-02-01 DE DE1967B0090983 patent/DE1670188A1/de active Pending
-
1968
- 1968-01-30 CH CH136368A patent/CH507960A/de not_active IP Right Cessation
- 1968-01-30 CH CH1361870A patent/CH542855A/de not_active IP Right Cessation
- 1968-01-30 CH CH1361770A patent/CH542215A/de not_active IP Right Cessation
- 1968-01-30 GB GB473568A patent/GB1148287A/en not_active Expired
- 1968-01-30 CH CH1361970A patent/CH507961A/de not_active IP Right Cessation
- 1968-01-31 AT AT94868A patent/AT280292B/de not_active IP Right Cessation
- 1968-01-31 NL NL6801402A patent/NL6801402A/xx unknown
- 1968-01-31 AT AT420269A patent/AT280298B/de active
- 1968-01-31 AT AT420369A patent/AT280299B/de not_active IP Right Cessation
- 1968-01-31 AT AT420169A patent/AT280297B/de not_active IP Right Cessation
- 1968-02-01 FR FR138328A patent/FR1595528A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT280292B (de) | 1970-04-10 |
| FR1595528A (https=) | 1970-06-15 |
| DE1670188A1 (de) | 1971-03-25 |
| AT280298B (de) | 1970-04-10 |
| CH542855A (de) | 1973-11-30 |
| AT280297B (de) | 1970-04-10 |
| CH507961A (de) | 1971-05-31 |
| CH542215A (de) | 1973-11-15 |
| AT280299B (de) | 1970-04-10 |
| GB1148287A (en) | 1969-04-10 |
| NL6801402A (https=) | 1968-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |