CH434233A - Process for the production of new, orally active, blood sugar lowering sulfonylureas - Google Patents
Process for the production of new, orally active, blood sugar lowering sulfonylureasInfo
- Publication number
- CH434233A CH434233A CH911064A CH911064A CH434233A CH 434233 A CH434233 A CH 434233A CH 911064 A CH911064 A CH 911064A CH 911064 A CH911064 A CH 911064A CH 434233 A CH434233 A CH 434233A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonylureas
- blood sugar
- new
- formula
- orally active
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 12
- 239000008280 blood Substances 0.000 title claims description 7
- 210000004369 blood Anatomy 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- -1 alkylcycloalkyl radical Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OEOOQMSPHMFXJL-UHFFFAOYSA-N 4-chlorobutan-1-amine Chemical compound NCCCCCl OEOOQMSPHMFXJL-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003672 ureas Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung neuer, oral wirksamer blutzuckersenkender Sulfonylharnstoffe
Die Darstellung von Arylsulfonylharnstoffen und der an beiden N-Atomen substituierten Verbindungen ist in zahlreichen Veröffentlichungen und Patenten beschrieben, da diese Verbindungen eine gute bakteriostatische Wirkung besitzen. Die blutzuckersenkende Wirkung der Sulfonylharnstoffe ist erst in der letzten Zeit bekanntgeworden.
Die Darstellung der Sulfonylharnstoffe ist in der USA-PatentscJhrift Nr. 2390253, der franz¯sischen Pabentschrift Nr. 993 405 umddenÖsterreichischen Pa tentschriften Nrn. 195436 und 196413 beschrieben.
Die in den vorstehend genannten Patentschriften angegebenen Verbindungen besitzen zum Teil eine f r den Dafuergebrauch als orales Diabetesmittel uner wünschte chemotherapeutische Wirkung, zum Teil besitzen sie keine bzw. eine den vonliegenden Verfahrens- produkten im Hinblick auf die Dauer der Wirkung eine unterlegene blutzuckersenkende Wirksamkeit.
Gegenstand der Erfindung ist die Herstellung von neuen Sulfonylharnstoffen der Formel R-SO2-NH-CO-NH-R, worin R einen Alkyl-, Cycloalkyl- oder Alkylcycloalkylrest oder einen durch Alkyl substituierten Phenylrest bedeutet, wobei mindestens einer der Reste R ein- oder mehrfach durch Halogen oder Rhodanid substi- tuiert sein muss und der dem Rest R zugrunde liegende Kohlenwasserstoff 3 bis 8 C-Atome aufweisen muss, und deren Salzen. Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, da¯ man Verbindungen der Formel R-SO2-X2, worin X2 die Reste-NCO,-NH-COOR,-NH-COHal oder-NH-CONH2 bedeutet, mit Aminen der Formel
R-NH2 umsetzt.
Zu Bildung der Salze können alkalische MitteS, beispielsweise Alkali- oder Erdalkalihydroxyde, Alkali carbonate oder organische B'asen mit den erhaltenen Sulfonylharnstoffen zur Reaktion gebracht werden.
Die im Rahmen der Erfindung angewendete Her- stellungsmethode ist an sich bekannt und zur Ge winnung von anderen Sulfonylhamstorfen bereits benützt worden.
Nach einer besonderen Ausf hrungsform des erfindungsgemässen Verfahrens können die gewünschten Sulfonylharnstoffe erhalten werden, indem man entsprechend substituierte Alkyl-, Cycloalkyl-, Alkylcycloalkyl- oder Alkylphenylsulfonylisocyanate mit Butyl- amin bzw. substituierten primären Aminen zur Umsetzung bringt.
Eine weitare Ausf hrungsform des erfindungsgemässen Verfahrens besteht darin, da¯ man Urethane mit den primären Aminen zur Reaktion bringt, indem man beispielsweise Halogen-oder Rhodanid-substituierte Alkyl-, Cycloalkyl-, Alkylcycloalkyl- oder Alkylphenyl sutfonylurethane mit den primären Aminen umsetzt.
Anstelle von Urethanen kann man auch von ent- sprechenden einfach substituierten Harnstoffen ausgehen und diese mit den primÏren Aminen umsetzen.
Die Rdaktionsbediinjgungen können beim Verfahren gemäss der Erfindung weitgehend variiert werden. Dabei ist vor allem die Verwendung von Lösungsmitteln und die Wahl der Reaktionstemperatur hervorzuheben, die einen massgeblichen Einflu¯ auf die Ausbeute besitzen.
Die nach dem erfindungsgemϯen Verfahren er- hältlichen Verbindungen sind kristallisierte Stoffe von gro¯er BestÏndigkeit, die physiologische Bedeutung besitzen. Sie haben eine starke blutzuckersenkende Wirkung von langer Dauer und weisen eine Ïu¯erst geringe ToxizitÏt auf. Wesentlich ist, da¯ keine der Verbindungen eine bakteriostatische Wirkung besitzt, die bei den Sulfonylharnstoffen als unangenehme Begleiterscheinung bei der oralen Diabetestherapie auftritt.
Die Bestimmung der blutzuckersenkenden Wirkung wurde an verschiedenen Versuchstieren, vorwiegend Ratez, Kaninchen, Hunden, durch orale Verabreichung der Substanz, oder durch i. v. Applikation des Natrumsalzes der Verbindungen durchgeführt. Als Beispie2 sei die Wirkung von 50 mg N1-4-Chlor-butylsulfonyl-N2butylharnstoff, der in Form des Natriumsalzes i. v. ver abreicht wurde, erwähnt. Der Blutzucker des gesunden hungernden Kaninchens fiel innerhalb von 10 Minuten von 120 mg % auf 52 mg%undbliebaufdiesem Wert durchschnittlich 12 bis 16 Stunden.
Bei gesunden nüchternen Versuchspersonen betrug die Senkung des Blutzuckers, bei einer Dosis von 0, 5g,durchschnittiMi 25 bis 30 mg%. Bei langdauernder Verabreichung an Versuchstieren (0, 5 g durch 4 Wochen) konnten keine Veränderungen ah der Leber, Niere, Milz gefunden werden. Die Granulation der Zelten des Pankreas war durchaus normal.
Beispiel 1
N1-Cyclohexansulfonyl-N2-4'-chlorobutylharnstoff
Zu einer Lösung von 100 g Cyclohexansulfoniso- cyanat (Kp. : 78-81¯C/O, 05 mm) in 150 cm3 absolutem Benzol lässt man 55 g 1-Chlor-4-aminobutan langsam zutropfen. Anschliessend wird 2 Stunden unter Rückfluss gekocht und dann das Benzol abdestilliert. Der Rückstand wird zur Reinigung in verdünntem Ammoniak aufgenommen, filtriert, mit Tierkohle geklärt und in der Kälte mit Essigsäure auf pH 3 bis 4 gebracht. Der so erhaltene N1-Cyclohexansulfonyl-N2-4'-chlorbutylharnstoff wird aus Essigester umkristallisiert. Fp. : 118 bis 120 C. Ausbeute 86%.
Beispiel 2
N1-Chlorbutylsulfonyl-N2-propylharnstoff
120 g Chlorbutylsulfonylcarbaminsäureäthylester (aus dem entsprechenden Sulfoinsäureamid und Chlorameisensäureester dargestelit) werden in 100 cm3 Dioxan gelöst ; zu der Mischung l'ässt man 35 g Propylamin zutropfen und kocht 12 Stunden unter R ckflu¯k hlung.
Das Lösungsmittel wird abdestilliert, der Rückstand mit Wasser angerieben. Die weitere Reinigung erfolgt auf dem üblichen Wege. Fp. : 82-83¯ C). Ausbeute 87 %.
In analoger Weise erhält man bei Verwendung von Rhodanid-substituierten Ausgangsstoffen die erfindungsgemϯen neuen Sulfonylharnstoffe.
Process for the production of new, orally active, blood-sugar-lowering sulfonylureas
The preparation of arylsulfonylureas and the compounds substituted on both N atoms is described in numerous publications and patents, since these compounds have a good bacteriostatic effect. The blood sugar lowering effect of sulfonylureas has only recently become known.
The representation of the sulfonylureas is described in the USA patent publication No. 2390253, the French patent specification No. 993 405 and the Austrian patent specification No. 195436 and 196413.
Some of the compounds specified in the above-mentioned patents have a chemotherapeutic effect which is undesirable for use as an oral diabetic agent, and some have no or one of the underlying process products with regard to the duration of the effect an inferior blood sugar-lowering effectiveness.
The invention relates to the preparation of new sulfonylureas of the formula R-SO2-NH-CO-NH-R, in which R is an alkyl, cycloalkyl or alkylcycloalkyl radical or a phenyl radical substituted by alkyl, where at least one of the radicals R is one or must be substituted several times by halogen or rhodanide and the hydrocarbon on which the radical R is based must have 3 to 8 carbon atoms, and their salts. The process according to the invention is characterized in that compounds of the formula R-SO2-X2, in which X2 denotes the radicals -NCO, -NH-COOR, -NH-COHal or -NH-CONH2, with amines of the formula
R-NH2 converts.
To form the salts, alkaline agents, for example alkali metal or alkaline earth metal hydroxides, alkali carbonates or organic bases, can be reacted with the sulfonylureas obtained.
The production method used in the context of the invention is known per se and has already been used for the extraction of other sulfonyl hamsters.
According to a particular embodiment of the process according to the invention, the desired sulfonylureas can be obtained by reacting appropriately substituted alkyl, cycloalkyl, alkylcycloalkyl or alkylphenylsulfonyl isocyanates with butyl amine or substituted primary amines.
A further embodiment of the process according to the invention consists in reacting urethanes with the primary amines by reacting, for example, halogen- or rhodanide-substituted alkyl, cycloalkyl, alkylcycloalkyl or alkylphenylsutfonylurethane with the primary amines.
Instead of urethanes, one can also start from corresponding monosubstituted ureas and react these with the primary amines.
The reaction conditions can largely be varied in the method according to the invention. In particular, the use of solvents and the choice of reaction temperature should be emphasized, which have a decisive influence on the yield.
The compounds obtainable by the process according to the invention are crystallized substances of great stability which have physiological significance. They have a strong hypoglycemic effect over a long period of time and are extremely low in toxicity. It is essential that none of the compounds has a bacteriostatic effect, which occurs with the sulfonylureas as an unpleasant side effect in oral diabetes therapy.
The blood sugar-lowering effect was determined on various test animals, mainly Ratez, rabbits, dogs, by oral administration of the substance, or by i. v. Application of the sodium salt of the compounds carried out. As an example, the effect of 50 mg N1-4-chloro-butylsulfonyl-N2butylurea, which in the form of the sodium salt i. v. was administered, mentioned. The blood sugar of the healthy starving rabbit fell from 120 mg% to 52 mg% in 10 minutes and remained there for an average of 12 to 16 hours.
In healthy, fasted test subjects, the reduction in blood sugar was, at a dose of 0.5 g, an average of 25 to 30 mg%. After long-term administration to test animals (0.5 g for 4 weeks), no changes in the liver, kidneys or spleen could be found. The granulation of the cells of the pancreas was quite normal.
example 1
N1-Cyclohexanesulfonyl-N2-4'-chlorobutylurea
55 g of 1-chloro-4-aminobutane are slowly added dropwise to a solution of 100 g of cyclohexanesulphonic isocyanate (bp: 78-81¯C / 0.05 mm) in 150 cm3 of absolute benzene. The mixture is then refluxed for 2 hours and the benzene is then distilled off. The residue is taken up in dilute ammonia for cleaning, filtered, clarified with animal charcoal and brought to pH 3 to 4 in the cold with acetic acid. The N1-cyclohexanesulfonyl-N2-4'-chlorobutylurea obtained in this way is recrystallized from ethyl acetate. M.p .: 118 to 120 C. Yield 86%.
Example 2
N1-chlorobutylsulfonyl-N2-propylurea
120 g of ethyl chlorobutylsulfonylcarbamic acid (prepared from the corresponding sulfoic acid amide and chloroformic acid ester) are dissolved in 100 cm3 of dioxane; 35 g of propylamine are added dropwise to the mixture and it is reflushed for 12 hours.
The solvent is distilled off and the residue is rubbed with water. Further purification takes place in the usual way. M.p .: 82-83¯ C). Yield 87%.
The novel sulfonylureas according to the invention are obtained in an analogous manner when using rhodanide-substituted starting materials.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT249158A AT204563B (en) | 1958-04-05 | 1958-04-05 | Process for the production of new sulfonylureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH434233A true CH434233A (en) | 1967-04-30 |
Family
ID=3535237
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7147859A CH407978A (en) | 1958-04-05 | 1959-04-02 | Process for the production of new, orally active, blood-sugar-lowering sulfonylureas |
| CH911064A CH434233A (en) | 1958-04-05 | 1959-04-02 | Process for the production of new, orally active, blood sugar lowering sulfonylureas |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7147859A CH407978A (en) | 1958-04-05 | 1959-04-02 | Process for the production of new, orally active, blood-sugar-lowering sulfonylureas |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT204563B (en) |
| CH (2) | CH407978A (en) |
| ES (1) | ES248449A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3069466A (en) * | 1959-04-21 | 1962-12-18 | Anton Von Waldheim | New n1-halogenoalkyl-phenyl-sulfonyl-n2-substituted ureas, and the corresponding cyclohexyl compounds |
| US5254589A (en) * | 1991-10-15 | 1993-10-19 | Warner-Lambert Company | Sulfonyl urea and carbamate ACAT inhibitors |
-
1958
- 1958-04-05 AT AT249158A patent/AT204563B/en active
-
1959
- 1959-04-02 CH CH7147859A patent/CH407978A/en unknown
- 1959-04-02 CH CH911064A patent/CH434233A/en unknown
- 1959-04-04 ES ES0248449A patent/ES248449A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH407978A (en) | 1966-02-28 |
| AT204563B (en) | 1959-07-25 |
| ES248449A1 (en) | 1960-01-01 |
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