HU201539B - Process for production of derivatives of 1,2,5-tiadiasole-1-oxid applicable as intermedier - Google Patents

Process for production of derivatives of 1,2,5-tiadiasole-1-oxid applicable as intermedier Download PDF

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HU201539B
HU201539B HU85912A HU91285A HU201539B HU 201539 B HU201539 B HU 201539B HU 85912 A HU85912 A HU 85912A HU 91285 A HU91285 A HU 91285A HU 201539 B HU201539 B HU 201539B
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thiadiazole
derivatives
tiadiasole
intermedier
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HU85912A
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Ronnie Ray Crenshaw
Aldo Antonio Algieri
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Bristol Myers Squibb Co
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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Abstract

The title compds. of formula (I) and their non-toxic salts or hydrates are prepd. by treating compds. of formula (II); in the presence of an inactive solvent, with compds. of formulas (A) and (B) , successively. In the formulas, P is 1 or 2; R1 is -NR2R3; R2 and R3 are H, (lower)alkyl, (lower) alkenyl, etc.; m is 0 or 1; n is 2 or 3; Z is S, O or methylene; A is phenyl, imidazolyl, pyridyl, etc; and R7 is halo, (lower)alkyl, (lower) alkylthio, phenoxy, etc. The prods. are useful as antiulcer agents.

Description

A leírás terjedelme: 4 oldal, 1 ábra (xxxviii)

Ft'

R‘ // \\ N N σ>

w m

HU 201539 Β

A találmány tárgya eljárás közbenső termékként alkalmazott új (XXXVIII) általános képletű 1,2,5-tiadiazol-1 -oxid-származékok előállítására.

E vegyületek hisztamin H2-antagonista hatású, (I) általános képletű 1,2,5-tiadioazol-származékok előnyös előállítására alkalmazhatók, (lásd a 2170/80 alalpszámú töizsbejelentésünket, T/29366 számon közzétéve.)

A (ΧΧΧνίΠ) álatlános képletben

R7 1-4 szénatomos alkoxicsoport, p értéke 1.

A találmány szerint úgy járunk el, hogy egy (X) általános képletű 3,4-di(l—4 szénatomos alkoxi)-1,2,5tiadiazolt - ahol

R7 a fenti oxidálunk.

A (XXXVni) általános képletű vegyületek előállításánál alkalmazott (X) általános képletű vegyületeket úgy állíthatjuk eló, hogy a (IX) általános képletű, megfelelően szubsztituált oxál-diimidát-észtert SCI2 vagy S2Cl2-vel reagáltatjuk nem-reakcióképes oldószerrel, például dimetil- formamiddal készült reakcióelegyben, amikor megkapjuk a 3,4- diszubsztituált-l,2,5-tiadiazolt [a (X) általános képletű vegyület], amit azután a megfelelő képletű 1-oxiddá oxidálunk.

A (IX) általános képletű oxál-diimidát-észterek, ahol az általános képletben R7 jelentése 1-4 szénatomos alkoxicsoport, ismert vegyületek, előállításukat az alábbi közleményben írják le: Chem. Bér., 107, 3121, 1974.

Azoknak a (X) általános képletű vegyületeknek a leírását, ahol az általános képletben R7 metoxi- vagy etoxicsoport, az alábbi közleményben találjuk meg: J. Org. Chem., 40, 2749, 1975.

Az irodalom szerint az 1,2,5-tiadiazol-mag oxidációra érzékeny, a tiadiazol oxidációját persavakkal általában gyűrűhasadás követi, és szulfátion-képződés; a perecetsavas oxidációval végrehajtott 1,2,5-tiadiazol-l,l-dioxid-előállítások gyűrűhasadást eredményeznek;

Úgy találtuk, hogy a (XXXVIII) általános képletű 3,4-di(l-4 szénatomos alkoxi)-1,2,5-tiadiazol-l-oxidokat jó kitermeléssel könnyen előállíthatjuk a megfelelő 3,4-di(l-4 szénatomos alkoxi)- 1,2,5-tiadiazolok [(X) általános képletű vegyületek] persavval, például m-klór-perbenzoesavval kivitelezett oxidációjával, nem reakcióképes oldószerben, például kloroformban.

A találmányt a továbbiakban - a találmány oltalmi körének szűkítése nélkül - az alábbi példával szemléltetjük.

Példa

A 3,4-dimetoxi-l,2,5-tiadiazol-l-oxid előállítása

100 ml kloroformban 35,2 g (24,1 mM), a J. Org. Chem., 40, 2749, 1975. közleményben megadottak szerint előállított 3,4-dimetoxi- 1,2,5-tiadiazolt oldunk, az oldatot 3 perc alatt 50,7 g (25,0 mM, 85 százalék) 900 ml, 20 °C hőmérsékletű kloroformban oldott m-klőr-perbenzoesavhoz adjuk keverés közben, miközben a reakcióedényt hűtőfürdőben tartjuk, hogy a hómérséklet ne emelkedjen 32 °C fölé az exoterm reakció következtében. 3 órán át szobahőmérsékleten keverjük a reakcióelegyet, a fölös persav reagáltatására további 2,0 g 3,4-dimetioxi-1,2,5-tiadiazolt adagolunk, majd 1 órán át folytatjuk a keverést.

2x300 ml 1 százalékos nátrium-hidrogén-karbonát-oldattal extraháljuk a szerves oldószeres oldatot, 250 ml vízzel mossuk, vízmentesítjük és csökkentett nyomáson desztilláljuk, amiután 74,0 g terméket kapunk. Ezt izopropanolból átkristályosítva 40,0 g 3,4dimetoxi-1,2,5-tiadiazol-1-oxidot kapunk. A terméket izopropil-alkoholból ismét kikristályosítjuk, amiután 135-137 °C hóméréskleten olvadó analitikai mintát kapunk.

Elemanalízis a C4H6N2O3S képlet alapján: számított: C: 29,63, H: 3,72, N: 17,27, S: 19,77 %;

talált: C: 29,53, H: 3,75, N: 17,26, S: 19,83 %.

Scope of the description: 4 pages, Figure 1 (xxxviii)

ft '

R '// NN σ>

wm

EN 201539

The present invention relates to a process for the preparation of a novel 1,2,5-thiadiazol-1-oxide derivative (XXXVIII) as an intermediate.

These compounds are useful in the preparation of histamine H2 antagonist compounds for the preferred preparation of 1,2,5-thiadiazole derivatives of formula (I) (see our disclosure of subclass 2170/80, published in T / 29366).

The (ΧΧΧνίΠ) general formula

R 7 is C 1-4 alkoxy, p is 1.

According to the present invention, a 3,4-di (C1-C4 alkoxy) -1,2,5thiadiazole of the general formula (X) wherein:

R 7 is oxidized above.

Compounds of formula (X) used in the preparation of compounds of formula (XXXVni) may be prepared by reacting a suitably substituted oxaldiimidate ester of formula (IX) with SCI2 or S2Cl2 with a non-reactive solvent such as dimethylformamide. in a reaction mixture to give 3,4-disubstituted-1,2,5-thiadiazole (compound of formula X) which is then oxidized to the corresponding oxide of formula (I).

The oxalidimidate esters of formula (IX) wherein R 7 is C 1-4 alkoxy are known compounds and are described in Chem. Bér., 107, 3121, 1974.

For compounds of formula (X), the description of which is found by the formula R 7 is methoxy or ethoxy, in general terms in J. Org. Chem., 40, 2749, 1975.

According to literature, 1,2,5-thiadiazole core is sensitive to oxidation, the oxidation of thiadiazole with peracid is generally followed by ring cleavage and sulfate ion formation; 1,2,5-thiadiazole-1,1-dioxide production by acetic acid oxidation results in ring cleavage ;

It has now been found that 3,4-di (1-4C) alkoxy-1,2,5-thiadiazole-1-oxides of formula XXXVIII can be readily prepared in good yield from the corresponding 3,4-di (C1-C4) alkoxy) 1,2,5-thiadiazoles (compounds of formula X) by oxidation with peracid such as m-chloroperbenzoic acid in a non-reactive solvent such as chloroform.

The invention will now be further illustrated by the following example, without limiting the scope of the invention.

Example

Preparation of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide

35.2 g (24.1 mM) of J. Org. Chem., 40, 2749, 3,475-dimethoxy-1,2,5-thiadiazole, prepared as described in 1975, was dissolved in 50.7 g (25.0 mM, 85%) over 3 minutes. To the m-chloroperbenzoic acid dissolved in chloroform at-° C was added with stirring while the reaction vessel was kept in a cooling bath to prevent the temperature from rising above 32 ° C as a result of the exothermic reaction. After stirring at room temperature for 3 hours, an additional 2.0 g of 3,4-dimethoxy-1,2,5-thiadiazole was added and the mixture was stirred for 1 hour.

Extract with 2 x 300 mL of 1% sodium bicarbonate solution, wash the organic solvent, wash with 250 mL of water, dry and distill under reduced pressure to give 74.0 g of product. Recrystallization from isopropanol gave 40.0 g of 3,4-dimethoxy-1,2,5-thiadiazole-1-oxide. The product was recrystallized from isopropyl alcohol to give an analytical sample melting at 135-137 ° C.

Calcd for C4 H6 N2 O3 S: C, 29.63; H, 3.72; N, 17.27; S, 19.77;

Found: C, 29.53; H, 3.75; N, 17.26; S, 19.83.

Claims (1)

SZABADALMI IGÉNYPONTPATIENT PERSONALITY 1. Eljárás a (XXXVIII) általános képletű vegyületek előállítására, aholA process for preparing compounds of formula (XXXVIII), wherein R7 jelentése 1-4 szénatomos alkoxicsoport, p jelentése 1, azzal jellemezve, hogy egy (X) általános képletű 3,4-di(l-4 szénatomos alkoxi)-l,2,5-tiadiazolt - ahol R7 a fenti -oxidálunk. R7 is 1-4C-alkoxy, p is 1, wherein (X) is reacted with 3,4-di (Cl-C4 alkoxy) -l, 2,5-thiadiazole - where R 7 as defined above - oxidized. -2HU 201539 Β-2 Apr 201539 Β R.R. FVFV R7 R7 R 7 R 7 HNHN NH (ix) (x) (xxxviii)NH (ix) (x) (xxxviii)
HU85912A 1979-09-04 1980-09-03 Process for production of derivatives of 1,2,5-tiadiasole-1-oxid applicable as intermedier HU201539B (en)

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BE885089A (en) 1981-03-04
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AU6194280A (en) 1981-03-12
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FR2476081A1 (en) 1981-08-21
JPS63211272A (en) 1988-09-02
AT380019B (en) 1986-03-25
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AU563856B2 (en) 1987-07-23
FR2476081B1 (en) 1985-04-12
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FR2486528A1 (en) 1982-01-15
GR70020B (en) 1982-07-23
CS221977B2 (en) 1983-04-29
ATA64684A (en) 1985-08-15
FR2486528B1 (en) 1984-12-21
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