DE1445006B2 - - Google Patents
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- Publication number
- DE1445006B2 DE1445006B2 DE1445006A DE1445006A DE1445006B2 DE 1445006 B2 DE1445006 B2 DE 1445006B2 DE 1445006 A DE1445006 A DE 1445006A DE 1445006 A DE1445006 A DE 1445006A DE 1445006 B2 DE1445006 B2 DE 1445006B2
- Authority
- DE
- Germany
- Prior art keywords
- sulfamyl
- methyl
- chloro
- dioxide
- benzothiadiazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
- C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
- C07D285/30—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with hydrocarbon radicals, substituted by hetero atoms, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Gegenstand des Patentes 11 12 079 ist ein Verfahren zur Herstellung von 3,4-Dihydro-l,2,4-benzothiadiazin-l,l-dioxyden der allgemeinen FormelThe subject of patent 11 12 079 is a method for the preparation of 3,4-dihydro-l, 2,4-benzothiadiazine-l, l-dioxydes of the general formula
R5 — HNO2SR 5 - HNO 2 S
CH-R2 CH-R 2
(D(D
3535
4040
worin R1, R3 und R5 Wasserstoffatome, Alkyl- oder Acylreste bedeuten, R2 für ein Wasserstoffatom, eine Alkyl-, Vinyl-, Aryl- oder Aralkylgruppe oder einen heterocyclischen Rest, der auch über einen Alkylrest an den Thiadiazinring gebunden sein kann, steht, wobei die Alkylgruppe eine Hydroxy-, Alkoxy- oder Dialkylaminogruppe oder ein Halogenatom tragen kann und Arylgruppen und heterocyclische Reste durch Alkyl-, Hydroxy-, Alkoxy-, Mercapto- oder Alkylmercapto-, Dialkylamino- oder Sulfamylgruppen oder Halogenatome substituiert sein können, und R4. ein Halogenatom, einen Alkylrest oder eine verätherte Hydroxygruppe darstellt, und Salzen dieser Verbindüngen, ausgenommen 6-Chlor-7-sulfamyl-3,4-dihydro-l,2,4-benzothiadiazin-l,l-dioxyd; sie werden erhalten, wenn man entweder a) eine 2-SuIfamyl-anilinverbindung der allgemeinen Formelwherein R 1 , R 3 and R 5 represent hydrogen atoms, alkyl or acyl radicals, R 2 represents a hydrogen atom, an alkyl, vinyl, aryl or aralkyl group or a heterocyclic radical which can also be bonded to the thiadiazine ring via an alkyl radical , where the alkyl group can carry a hydroxy, alkoxy or dialkylamino group or a halogen atom and aryl groups and heterocyclic radicals can be substituted by alkyl, hydroxy, alkoxy, mercapto or alkylmercapto, dialkylamino or sulfamyl groups or halogen atoms, and R 4 . represents a halogen atom, an alkyl radical or an etherified hydroxyl group, and salts of these compounds, with the exception of 6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide; they are obtained when either a) a 2-sulfamylaniline compound of the general formula
R5 — HNO2SR 5 - HNO 2 S
NH-R3 NH-R 3
SO2NH-R1,SO 2 NH-R 1 ,
(H)(H)
65 reste stehen, oder deren Salze mit einem Aldehy der Formel R2—CHO umsetzt oder b) ein 1,2,4-Benzc thiadiazin-1,1-dioxyd der allgemeinen Formel 65 radicals, or the salts thereof with an aldehyde of the formula R 2 —CHO, or b) a 1,2,4-benzothiadiazine-1,1-dioxide of the general formula
R5 — HNO2SR 5 - HNO 2 S
C-R2 CR 2
N-R1 NR 1
(III a)(III a)
O OO O
R3 R 3
R4.R4.
R5 — HNO2SR 5 - HNO 2 S
C-R,C-R,
S
O* ^OS.
O * ^ O
(III b)(III b)
worin R1, und R3, für Wasserstoffatome oder Alkylmit einem Alkalimetallborhydrid hydriert oder elektrolytisch reduziert und gegebenenfalls anschließend erhaltene Verbindungen, in denen R1, R3 und/oder R5 Wasserstoffatome darstellen, in an sich bekannter Weise alkyliert oder acyliert und/oder erhaltene Salze in die freien Verbindungen oder erhaltene freie Verbindungen in ihre Salze überführt.wherein R 1 and R 3 , hydrogen atoms or alkyl with an alkali metal borohydride, hydrogenated or electrolytically reduced and optionally then obtained compounds in which R 1 , R 3 and / or R 5 represent hydrogen atoms, alkylated or acylated and / or in a manner known per se obtained salts converted into the free compounds or obtained free compounds converted into their salts.
Es wurde nun gefunden, daß Verbindungen der allgemeinen Formel I, worin R1 für eine Methylgruppe steht, R5 ein Wasserstoffatom bedeutet, R4 ein Chloratom darstellt, R5 für ein Wasserstoffatom und R2 für eine Methyl- oder Butylgruppe steht, und ihre Salze wertvolle diuretische und natriuretische Wirksamkeit besitzen. So zeigen sie im Vergleich zur Verbindung der Formel I, worin R1, R2, R3 und R5 Wasserstoffatome und R4 ein Chloratom bedeutet (Hydrochlorothiazid; Experientia, Bd. 14, S. 463 [1958]) verstärkte diuretische und natriuretische Ausscheidung bei gleichbleibender Kaliumausscheidung und verringerter Toxizität. It has now been found that compounds of the general formula I in which R 1 is a methyl group, R 5 is a hydrogen atom, R 4 is a chlorine atom, R 5 is a hydrogen atom and R 2 is a methyl or butyl group, and their Salts have valuable diuretic and natriuretic properties. Compared to the compound of the formula I in which R 1 , R 2 , R 3 and R 5 are hydrogen atoms and R 4 is a chlorine atom (hydrochlorothiazide; Experientia, Vol. 14, p. 463 [1958]), they show increased diuretic and natriuretic Elimination with constant potassium excretion and reduced toxicity.
Die Erfindung betrifft somit die Herstellung von 2 - Methyl - 3 - R2 - 6 - chlor - 7 - sulfamyl - 3,4 - dihydro-1,2,4-benzothiadiazin-1,1-dioxyden, worin R2 eine Methyl- oder Butylgruppe bedeutet, und Salzen dieser Verbindungen gemäß Patent 11 12 079, dadurch gekennzeichnet, daß man entweder (a) 2-(N-Methylsulfamyl)-4-sulfamyl-5-chIor-anilin oder ein Salz davon mit einem Aldehyd der allgemeinen Formel R2—CHO, worin R2 die oben angegebene Bedeutung hat, umsetzt, oder (b) ein gemäß Hauptpatent hergestelItes3-R2-6-Chlor-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazin-1,1 -dioxyd, worin R2 die oben angegebene Bedeutung hat, in an sich bekannter Weise mit einem reaktionsfähigen Ester des Methylalkohols umsetzt, oder (c) ein 2-Methyl-3-R2-6-chlor-7-sulfamyl-1,2,4-benzothiadiazin-1,1-dioxyd, worin R2 die oben angegebene Bedeutung hat, mittels Alkalimetallborhydriden oder elektrolytisch reduziert und die erhaltene Verbindung gewünschtenfalls in an sich bekannter Weise in ein Metallsalz überführt.The invention thus relates to the preparation of 2 - methyl - 3 - R 2 - 6 - chloro - 7 - sulfamyl - 3,4 - dihydro-1,2,4-benzothiadiazine-1,1-dioxyden, in which R 2 is a methyl or butyl group, and salts of these compounds according to Patent 11 12 079, characterized in that either (a) 2- (N-methylsulfamyl) -4-sulfamyl-5-chloroaniline or a salt thereof with an aldehyde of the general formula R 2 —CHO, in which R 2 has the meaning given above, converts, or (b) a 3 -R 2 -6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine prepared according to the main patent 1,1 -dioxide, in which R 2 has the meaning given above, is reacted in a manner known per se with a reactive ester of methyl alcohol, or (c) a 2-methyl-3-R 2 -6-chloro-7-sulfamyl- 1,2,4-benzothiadiazine-1,1-dioxide, in which R 2 has the meaning given above, is reduced by means of alkali metal borohydrides or electrolytically and the compound obtained, if desired, is converted into a metal salt in a manner known per se convicted.
Die Erfindung wird in den nachfolgenden Beispielen näher beschrieben. Die Temperaturen sind in Celsiusgraden angegeben.The invention is described in more detail in the following examples. The temperatures are in Degrees Celsius.
9,4 g S-Methyl-o-chlor^-sulfamyl^-dihydrol,2,4-benzothiadiazin-l,l-dioxyd werden in einer Mischung von 33 cm3 einer normalen wäßrigen Natriumhydroxydlösung und 120 cm3 Wasser gelöst. Vom Unlöslichen wird abfiltriert, und dann auf 10° gekühlt, 2,4 g Dimethylsulfat zugegeben und bei dieser Temperatur 1 Stunde stehengelassen. Man hält eine weitere Stunde bei Raumtemperatur, filtriert die Reaktionsmischung und kristallisiert den Rückstand 2mal aus einer 1:1-Mischung aus Äthanol und Wasser um. Man erhält so 0,9 g 2,3-Dimethyl-6-chlor-7-sulfamyl-3,4-dihydro- 1,2,4-benzothiadiazin-1,1 -dioxyd vom F. 274 bis 276°.9.4 g of S-methyl-o-chloro ^ -sulfamyl ^ -dihydrol, 2,4-benzothiadiazine-l, l-dioxide are dissolved in a mixture of 33 cm 3 of normal aqueous sodium hydroxide solution and 120 cm 3 of water. The insolubles are filtered off and then cooled to 10 °, 2.4 g of dimethyl sulfate are added and the mixture is left to stand at this temperature for 1 hour. It is kept at room temperature for a further hour, the reaction mixture is filtered and the residue is recrystallized twice from a 1: 1 mixture of ethanol and water. This gives 0.9 g of 2,3-dimethyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide with a melting point of 274 ° to 276 °.
Die Umkristallisationsmutterlaugen werden eingeengt, wobei der Rückstand fest wird und sich aus Methanol kristallisieren läßt. Man kristallisiert aus wäßrigem Äthanol um. Das 2,3-Dimethyl-6-chlor-7 - (N - methyl - sulfamyl) - 3,4 - dihydro -1,2,4 - benzothiadiazin-1,1-dioxyd schmilzt bei 248 bis 25Γ; Ausbeute 0,2 g.The recrystallization mother liquors are concentrated, the residue solidifying and separating Can crystallize methanol. It is recrystallized from aqueous ethanol. 2,3-Dimethyl-6-chloro-7 - (N-methyl-sulfamyl) -3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide melts at 248 to 25Γ; Yield 0.2g.
Das Ausgangsmaterial läßt sich wie folgt erhalten: Eine Mischung von 2,9 g 5-Chlor-2,4-disulfamylanilin, 20 cm3 wasserfreiem Diäthylenglykol-dimethyläther, 0,44 g Acetaldehyd und 0,5 cm3 einer Salzsäurelösung in Essigsäureäthylester (109,5 g Chlorwasserstoffsäure pro Liter) wird auf 80 bis 90° erhitzt und 1 Stunde bei dieser Temperatur gehalten. Die Reaktionsmischung wird unter vermindertem Druck eingeengt, dann Wasser zugefügt und das auskristallisierte Produkt abfiltriert. Das so erhaltene 3-Methyl-6-chlor-7-sulfamyl - 3,4 - dihydro - 1,2,4 - benzothiadiazin -1,1 - dioxyd vom F. 258 bis 260° läßt sich aus wäßrigem Äthanol Umkristallisieren.The starting material can be obtained as follows: A mixture of 2.9 g of 5-chloro-2,4-disulfamylaniline, 20 cm 3 of anhydrous diethylene glycol dimethyl ether, 0.44 g of acetaldehyde and 0.5 cm 3 of a hydrochloric acid solution in ethyl acetate (109 , 5 g of hydrochloric acid per liter) is heated to 80 to 90 ° and held at this temperature for 1 hour. The reaction mixture is concentrated under reduced pressure, then water is added and the product which has crystallized out is filtered off. The 3-methyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide with a melting point of 258 ° to 260 ° can be recrystallized from aqueous ethanol.
Eine Lösung von 10,6 g 3-n-Butyl-6-chlor-7-sulfamyl - 3,4 - dihydro - 1,2,4 - benzothiadiazin - 1,1 - dioxyd in 66 cm3 einer 1-normalen wäßrigen Natriumhydroxydlösung und 120 cm3 Wasser wird auf 20° abgekühlt und 4,2 g Dimethylsulfat langsam zugegeben. Dann rührt man die ReaktionsmischungA solution of 10.6 g of 3-n-butyl-6-chloro-7-sulfamyl - 3,4 - dihydro - 1,2,4 - benzothiadiazine - 1,1 - dioxide in 66 cm 3 of a 1 normal aqueous sodium hydroxide solution and 120 cm 3 of water is cooled to 20 ° and 4.2 g of dimethyl sulfate are slowly added. The reaction mixture is then stirred
1 Stunde bei dieser Temperatur, eine weitere Stunde bei Raumtemperatur und extrahiert 3mal mit Essigsäureäthylester. Die organische Schicht wird über Natriumsulfat getrocknet, das Lösungsmittel eingedampft, worauf man eine amorphe Mischung von1 hour at this temperature, a further hour at room temperature and extracted 3 times with ethyl acetate. The organic layer is dried over sodium sulfate, the solvent evaporated, whereupon you get an amorphous mixture of
2 - Methyl - 3 - η - butyl - 6 - chlor - 7 - sulfamyl - 3,4-dihydro-1,2,4-benzothiadiazin-1,1-dioxyd und 2-Methyl-2 - methyl - 3 - η - butyl - 6 - chloro - 7 - sulfamyl - 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide and 2-methyl-
3 - η - butyl - 6 - chlor - 7 - (N - methylsulfamyl) - 3,4 - dihydro-1,2,4-benzothiadiazin-1,1-dioxyd erhält. Sie schmilzt bei 90 bis 95° (unter Zersetzung und Schäumen); Ausbeute 3,9 g.3 - η - butyl - 6 - chloro - 7 - (N - methylsulfamyl) - 3,4 - dihydro-1,2,4-benzothiadiazine-1,1-dioxide receives. It melts at 90 to 95 ° (with decomposition and foaming); Yield 3.9g.
Claims (1)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71845258A | 1958-03-03 | 1958-03-03 | |
| US72724258A | 1958-04-09 | 1958-04-09 | |
| US74058258A | 1958-06-09 | 1958-06-09 | |
| US75162058A | 1958-07-29 | 1958-07-29 | |
| US76448258A | 1958-09-29 | 1958-09-29 | |
| DEC0028409 | 1959-02-27 | ||
| DEC0024178 | 1959-02-27 | ||
| DEC0024177 | 1959-02-27 | ||
| DEC0024176 | 1959-02-27 | ||
| DEC0024176 | 1959-02-27 | ||
| DEC0028408 | 1959-02-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445006A1 DE1445006A1 (en) | 1968-10-24 |
| DE1445006B2 true DE1445006B2 (en) | 1975-05-07 |
| DE1445006C3 DE1445006C3 (en) | 1976-01-22 |
Family
ID=
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445574A1 (en) | 1969-01-16 |
| CH371454A (en) | 1963-08-31 |
| FR1217929A (en) | 1960-05-06 |
| DE1112079B (en) | 1961-08-03 |
| FR1264468A (en) | 1961-06-23 |
| CH376514A (en) | 1964-04-15 |
| DE1445007A1 (en) | 1968-10-24 |
| OA03826A (en) | 1971-12-24 |
| DE1445008A1 (en) | 1968-10-24 |
| OA01178A (en) | 1969-01-25 |
| CH377365A (en) | 1964-05-15 |
| GB861367A (en) | 1961-02-22 |
| MY6200051A (en) | 1962-12-31 |
| CH387642A (en) | 1965-02-15 |
| DE1445005A1 (en) | 1968-10-24 |
| DE1445006A1 (en) | 1968-10-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) |