CH509991A - Sulphonamides and process for the manufacture thereof - Google Patents
Sulphonamides and process for the manufacture thereofInfo
- Publication number
- CH509991A CH509991A CH787469A CH787469A CH509991A CH 509991 A CH509991 A CH 509991A CH 787469 A CH787469 A CH 787469A CH 787469 A CH787469 A CH 787469A CH 509991 A CH509991 A CH 509991A
- Authority
- CH
- Switzerland
- Prior art keywords
- groups
- toluenesulfonyl
- symbol
- preparation
- sodium borohydride
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
(A) Cpds. of the formulae:- (I) R1 = H R2 = OH, or together with R' = keto R3 = phenyl opt. subst. by one or more halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino, diacylimido, or lower alkoxy and/or halogen substd. benzamidoethyl; 5-6 membered nitrogen heterocycle attached by the nitrogen atom n = 3 or 4. (B) N-(p-Chlorobenzenesulphonyl)-3,5-dimethyl-1-pyrazole carboxamide. Cpds. I and VI have blood-sugar depressing activity.
Description
Verfahren zur Herstellung von Sulfonamiden
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von Sulfonylharnstoffderivaten der Formel I
EMI1.1
in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylaminooder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man ein entsprechendes o-Oxo-cyclopentylbzw. -cyclohexyl-Derivat reduziert.
Die erfindungsgemässe Reduktion kann z.B. durch Behandlung mit einem komplexen Metalhydrid, wie Natriumborhydrid, bewerkstelligt werden.
Unter niederen Alkylgruppen, die in durch das Symbol R repräsentierten Resten enthalten sind, sollen geradkettige oder verzweigte Alkylgruppen mitl -6 Kohlenstoff- atomen verstanden werden. Beispiele dafür sind Methyl, Äthyl, Propyl, Isopropyl, Butyl, Pentyl, Hexyl und deren Isomeren. Ein durch das Symbol R dargestelltes Halogenphenyl ist vorzugsweise Chlorphenyl. Eine durch das Symbol R dargestellte Acylaminophenylgruppe kann aliphatische oder aromatische Acylreste enthalten. Beispiele für solche Gruppen sinl Acetaminophenyl oder Benzoylaminophenyl. Eine Diacylimidophenylgruppe ist beispielsweise die Phthalimidophenylgruppe.
Die erfindungsgemäss erhältlichen Verbindungen der allgemeinen Formel I zeichnen sich durch eine aussergewöhnliche blutzuckersenkende Aktivität bei oraler Applikation aus. Die Verbindungen haben eine kurze Verweilzeit im Organismus und werden weitgehend unverändert ausgeschieden. Sie können daher als Heilmittel in Form pharmazeutischer Präparate Verwendung finden, welche sie in Mischung mit einem geeigneten pharmazeutischen, organischen oder anorganischen inerten Trägermaterial enthalten.
Beispiel
10 g 1 -(p-Toluolsulfonyl)-3-(2'-oxocyclohexyl)-ham stoff werden in 120 ml Natronlauge (1,4 g NaOH) gelöst, mit 3 g Natriumborhydrid (ca. 70%ig) versetzt und 15 Stunden bei 200 gerührt. Die Reaktionslösung wird vorsichtig mit verdünnter Essigsäure angesäuert. Der Niederschlag wird abfiltriert und aus Äthanol/Wasser umkristallisiert. Man erhält 1 -(p-Toluolsulfonyl)-3-(2'-hydroxycy- clohexyl)-harnstoff.
PATENTANSPRUCH
Verfahren zur Herstellung von Sulfonylharnstoffderi- vaten der Formel
T
EMI1.2
in der R Phenyl, das durch Halogen, Niederalkyl-, Niederalkoxy-, Niederalkylthio-, Acetyl-, Amino-, Acylamino oder Diacylimidogruppen substituiert sein kann, und n die Zahl 3 oder 4 bedeutet, dadurch gekennzeichnet, dass man ein entsprechendes o-Oxo-cyclopentyl-bzw. -cyclohexyl-Derivat reduziert.
UNTERANSPRÜCHE
1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man 1-(p-Toluolsulfonyl)-3-(2'-oxocyclohe- xyl)-harnstoff reduziert.
2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man mittels Natriumborhydrid reduziert.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of sulfonamides
The present invention relates to a process for the preparation of sulfonylurea derivatives of the formula I.
EMI1.1
in which R is phenyl, which may be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4.
The inventive method is characterized in that a corresponding o-oxo-cyclopentylbzw. -cyclohexyl derivative reduced.
The reduction according to the invention can e.g. by treatment with a complex metal hydride such as sodium borohydride.
Lower alkyl groups contained in radicals represented by the symbol R are to be understood as meaning straight-chain or branched alkyl groups with 1-6 carbon atoms. Examples are methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl and their isomers. Halophenyl represented by the symbol R is preferably chlorophenyl. An acylaminophenyl group represented by the symbol R may contain aliphatic or aromatic acyl groups. Examples of such groups are acetaminophenyl or benzoylaminophenyl. A diacylimidophenyl group is, for example, the phthalimidophenyl group.
The compounds of general formula I obtainable according to the invention are distinguished by an exceptional blood sugar-lowering activity when administered orally. The compounds have a short residence time in the organism and are excreted largely unchanged. They can therefore be used as medicaments in the form of pharmaceutical preparations which they contain as a mixture with a suitable pharmaceutical, organic or inorganic inert carrier material.
example
10 g of 1 - (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) -ham material are dissolved in 120 ml of sodium hydroxide solution (1.4 g of NaOH), 3 g of sodium borohydride (about 70%) are added and the mixture is carried out for 15 hours stirred at 200. The reaction solution is carefully acidified with dilute acetic acid. The precipitate is filtered off and recrystallized from ethanol / water. 1 - (p-Toluenesulfonyl) -3- (2'-hydroxycyclohexyl) urea is obtained.
PATENT CLAIM
Process for the preparation of sulfonylurea derivatives of the formula
T
EMI1.2
in which R is phenyl, which can be substituted by halogen, lower alkyl, lower alkoxy, lower alkylthio, acetyl, amino, acylamino or diacylimido groups, and n is the number 3 or 4, characterized in that a corresponding o-oxo -cyclopentyl- or. -cyclohexyl derivative reduced.
SUBCLAIMS
1. The method according to claim, characterized in that 1- (p-toluenesulfonyl) -3- (2'-oxocyclohexyl) urea is reduced.
2. The method according to claim and dependent claim 1, characterized in that one reduces by means of sodium borohydride.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH787169A CH510647A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
CH787569A CH509992A (en) | 1966-08-08 | 1966-08-08 | Process for the preparation of sulfonamides |
CH787269A CH510648A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
CH787469A CH509991A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
CH787369A CH509990A (en) | 1966-08-08 | 1967-07-07 | Sulphonamides and process for the manufacture thereof |
SE10481/67A SE334354B (en) | 1966-08-08 | 1967-07-12 | |
IL28401A IL28401A (en) | 1966-08-08 | 1967-07-26 | Arylsulfonyl ureas,their manufacture and pharmaceutical compositions containing them |
DE1967H0063446 DE1668199B2 (en) | 1966-08-08 | 1967-07-29 | BENZOLSULFONYL-3- (2-HYDROXYCYCLOHEXYL) UREA |
NL6710676A NL6710676A (en) | 1966-08-08 | 1967-08-02 | |
GB50520/68A GB1147404A (en) | 1966-08-08 | 1967-08-04 | Novel sulphonamide derivatives |
GB50521/68A GB1147405A (en) | 1966-08-08 | 1967-08-04 | Novel oxazolidinone derivatives |
BE702280D BE702280A (en) | 1966-08-08 | 1967-08-04 | |
GB35845/67A GB1147403A (en) | 1966-08-08 | 1967-08-04 | Sulphonamides |
DK401867AA DK122761B (en) | 1966-08-08 | 1967-08-07 | Analogous process for the preparation of arylsulfonylurea derivatives. |
ES343910A ES343910A1 (en) | 1966-08-08 | 1967-08-07 | Sulphonamides |
FR117194A FR1546595A (en) | 1966-08-08 | 1967-08-08 | Process for the preparation of sulfonamides |
JP5054967A JPS5516575B1 (en) | 1966-08-08 | 1967-08-08 | |
FR117192A FR7148M (en) | 1966-08-08 | 1967-08-08 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH787469A CH509991A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
CH787569A CH509992A (en) | 1966-08-08 | 1966-08-08 | Process for the preparation of sulfonamides |
CH1136566A CH500176A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CH509991A true CH509991A (en) | 1971-07-15 |
Family
ID=27175874
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH787469A CH509991A (en) | 1966-08-08 | 1966-08-08 | Sulphonamides and process for the manufacture thereof |
CH787569A CH509992A (en) | 1966-08-08 | 1966-08-08 | Process for the preparation of sulfonamides |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH787569A CH509992A (en) | 1966-08-08 | 1966-08-08 | Process for the preparation of sulfonamides |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS5516575B1 (en) |
BE (1) | BE702280A (en) |
CH (2) | CH509991A (en) |
DE (1) | DE1668199B2 (en) |
DK (1) | DK122761B (en) |
ES (1) | ES343910A1 (en) |
FR (1) | FR7148M (en) |
GB (3) | GB1147404A (en) |
IL (1) | IL28401A (en) |
NL (1) | NL6710676A (en) |
SE (1) | SE334354B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MD3259253T2 (en) | 2015-02-16 | 2020-06-30 | Univ Queensland | Sulfonylureas and related compounds and use of same |
US11840543B2 (en) | 2017-05-24 | 2023-12-12 | The University Of Queensland | Compounds and uses |
ES2906280T3 (en) | 2017-07-07 | 2022-04-18 | Inflazome Ltd | Novel Carboxamide Sulfonamide Compounds |
-
1966
- 1966-08-08 CH CH787469A patent/CH509991A/en not_active IP Right Cessation
- 1966-08-08 CH CH787569A patent/CH509992A/en not_active IP Right Cessation
-
1967
- 1967-07-12 SE SE10481/67A patent/SE334354B/xx unknown
- 1967-07-26 IL IL28401A patent/IL28401A/en unknown
- 1967-07-29 DE DE1967H0063446 patent/DE1668199B2/en active Granted
- 1967-08-02 NL NL6710676A patent/NL6710676A/xx unknown
- 1967-08-04 GB GB50520/68A patent/GB1147404A/en not_active Expired
- 1967-08-04 GB GB50521/68A patent/GB1147405A/en not_active Expired
- 1967-08-04 BE BE702280D patent/BE702280A/xx unknown
- 1967-08-04 GB GB35845/67A patent/GB1147403A/en not_active Expired
- 1967-08-07 ES ES343910A patent/ES343910A1/en not_active Expired
- 1967-08-07 DK DK401867AA patent/DK122761B/en unknown
- 1967-08-08 FR FR117192A patent/FR7148M/fr not_active Expired
- 1967-08-08 JP JP5054967A patent/JPS5516575B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
GB1147404A (en) | 1969-04-02 |
DE1668199A1 (en) | 1971-09-02 |
SE334354B (en) | 1971-04-26 |
FR7148M (en) | 1969-08-04 |
DE1668199B2 (en) | 1976-06-24 |
CH509992A (en) | 1971-07-15 |
DK122761B (en) | 1972-04-10 |
BE702280A (en) | 1968-02-05 |
GB1147403A (en) | 1969-04-02 |
IL28401A (en) | 1971-04-28 |
ES343910A1 (en) | 1968-10-01 |
GB1147405A (en) | 1969-04-02 |
JPS5516575B1 (en) | 1980-05-02 |
NL6710676A (en) | 1968-02-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |