FR2486528A1 - DERIVATIVES OF THIADIAZOLE 1-OXIDE - Google Patents
DERIVATIVES OF THIADIAZOLE 1-OXIDE Download PDFInfo
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- FR2486528A1 FR2486528A1 FR8115119A FR8115119A FR2486528A1 FR 2486528 A1 FR2486528 A1 FR 2486528A1 FR 8115119 A FR8115119 A FR 8115119A FR 8115119 A FR8115119 A FR 8115119A FR 2486528 A1 FR2486528 A1 FR 2486528A1
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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
- C07D213/04—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
- 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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- C07D213/04—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
- 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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- C07D277/32—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
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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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Abstract
LA PRESENTE INVENTION A POUR OBJET, A TITRE DE PRODUITS INDUSTRIELS NOUVEAUX, DES COMPOSES DE FORMULE: (CF DESSIN DANS BOPI) R ET R POUVANT ETRE IDENTIQUES OU DIFFERENTS. CES COMPOSES PEUVENT SERVIR NOTAMMENT COMME PRODUITS DE DEPART DES PRODUITS SELON LA DEMANDE DE BREVET FRANCAIS N80 18670 DU 28AOUT 1980.THE SUBJECT OF THE PRESENT INVENTION, AS NEW INDUSTRIAL PRODUCTS, COMPOUNDS OF FORMULA: (CF DRAWING IN BOPI) R AND R WHICH MAY BE IDENTICAL OR DIFFERENT. THESE COMPOUNDS CAN BE USED IN PARTICULAR AS STARTING PRODUCTS FOR PRODUCTS ACCORDING TO FRENCH PATENT APPLICATION N80 18670 OF AUGUST 28, 1980.
Description
La présente invention a pour objet des composés nouveaux de formule (0)The present invention relates to novel compounds of formula (0)
7J 12,7J 12,
< II<II
R R12R R12
dans laquelle p est égal à 1 ou 2; R7 est un groupe partant tel qu'un halogène, un groupe alkoxy(inf) alkylthio(inf), phénoxy, phénylthio, phenoxy substitué et phénylthio substitué dont le noyau phényle peut comporter 1 ou 2 substituants tels qu'un halogène, alkyl(inf), alkoxy(inf) et nitro; et R12 est A(CH2)mZ(CH2)nNH-, R2R3N- ou HS(CH2)nNH- ou pour p=1 R12 peut être R7 o R2 et R3 sont indépendamment l'hydrogène, un groupe alkyl(inf) alkényl(inf), alkynyl(inf), cycloalkyl(inf), cycloalkyl(inf)alkyl(inf) hydroxyalkyl(inf),alkoxy(inf)alkyl(inf), alkylthio(inf)alkyl(inf), aminoalkyl(inf), alkyl(inf)aminoalkyl(inf), dialkyl(inf)aminoalkyl (inf), pyrrolidinoalkyl(inf), piperidinoalkyl(inf), morpholinoalkyl (inf), piperazinoalkyl(inf), pyridylalkyl(inf, amino, alkyl(inf)amino, dialkyl(inf)amino, 2,2,2-trifluoroéthyl, 2-fluoroéthyl, hydroxy, alkoxy(inf), 2,3-dihydroxypropyl, cyano, cyanoalkyl(inf), amidino, alkyl(inf)amidino, A'-(CH2)mZ'(CH2)n,-, phényle, phénylalkyl(inf) , phényle substitué ou phénylalkyl(inf) substitué dont le cycle phényle peut comporter un ou deux substituants choisis indépendamment parmi alkyl(inf), hydroxy, alkoxy(inf) et halogène, ou un substituant choisi parmi méthylénedioxy, trifluorométhyle et dialkyl(inf)amino; entendu que R2 et R3 ne sont pas en même temps cycloalkyl(inf), phényle, phényle substitué, amino, alkyl(inf)amino, dialkyl(inf)amino, hydroxy, alkoxy(inf) , cyano, amidino, alkyl(inf)amidino ou A'-(CH2)mZ'(CH2)n,-, ou bien, R2 et R3, forment ensemble -CH2CH2X(CH2)r-; r est un nombre entier égal à 1, 2 ou 3, X est le méthylène, le soufre, l'oxygène ou N-R4; étant entendu que si p=2 et R7 est un méthoxy, R2 et R3 pris ensemble avec l'atomnie d'azote auquel ils sont liés ne forment pas un groupe morpholino, et que si r=1, X est un méthylène; R4 est l'hydrogène, alkyl(inf), alkenyl(inf), alkynyl(inf) alkanoyl(inf) ou benzoyle ni et mni' sont indépendamment un nombre entier égal à 0,1 ou 2 l n et n' sont indépendamment des nombres entiers égaux à 2, 3 ou 4, in which p is 1 or 2; R7 is a leaving group such as halogen, alkoxy (inf) alkylthio (inf), phenoxy, phenylthio, substituted phenoxy and substituted phenylthio wherein the phenyl ring may have 1 or 2 substituents such as halogen, alkyl (lower alkyl), ), alkoxy (inf) and nitro; and R12 is A (CH2) mZ (CH2) nNH-, R2R3N- or HS (CH2) nNH- or for p = 1 R12 may be R7o R2 and R3 are independently hydrogen, alkyl (inf) alkenyl ( inf), alkynyl (inf), cycloalkyl (inf), cycloalkyl (inf) alkyl (inf) hydroxyalkyl (inf), alkoxy (inf) alkyl (inf), alkylthio (inf) alkyl (inf), aminoalkyl (inf), alkyl (inf) aminoalkyl (inf), dialkyl (inf) aminoalkyl (inf), pyrrolidinoalkyl (inf), piperidinoalkyl (inf), morpholinoalkyl (inf), piperazinoalkyl (inf), pyridylalkyl (inf, amino, alkyl (inf) amino, dialkyl) (inf) amino, 2,2,2-trifluoroethyl, 2-fluoroethyl, hydroxy, alkoxy (inf), 2,3-dihydroxypropyl, cyano, cyanoalkyl (inf), amidino, alkyl (inf) amidino, A '- (CH 2 mZ '(CH 2) n, -, phenyl, phenylalkyl (inf), substituted phenyl or substituted phenylalkyl, the phenyl ring of which may have one or two substituents independently selected from alkyl (inf), hydroxy, alkoxy (inf) and halogen, or a substituent selected from methylenedioxy, trifluoromethyl and dialkyl (inf) amino, wherein R2 and R3 are e are not at the same time cycloalkyl (inf), phenyl, substituted phenyl, amino, alkyl (inf) amino, dialkyl (inf) amino, hydroxy, alkoxy (inf), cyano, amidino, alkyl (inf) amidino or A'- (CH2) mZ '(CH2) n, - or R2 and R3 together form -CH2CH2X (CH2) r-; r is an integer of 1, 2 or 3, X is methylene, sulfur, oxygen or N-R4; it being understood that if p = 2 and R7 is methoxy, R2 and R3 taken together with the nitrogen atom to which they are bonded do not form a morpholino group, and that if r = 1, X is methylene; R4 is hydrogen, alkyl (inf), alkenyl (inf), alkynyl (inf) alkanoyl (inf) or benzoyl ni and mni 'are independently an integer equal to 0.1 or 2 ln and n' are independently numbers integers equal to 2, 3 or 4,
Z et Z' sont indépendamment S, 0 ou -CH2- Z and Z 'are independently S, O or -CH2-
A et A' indépendamment, sont des groupes phényle, imida- A and A 'independently are phenyl, imidazole,
zolyle, thiazolyle, isothiazolyle, oxazolyle, isoxazolyle, triazolyle, thiadiazolyle, oxadiazolyle, furyle, thiényle ou pyridyle et A et A' peuvent comporter indépendamment un ou deux substituants, le premier substituant étant un groupe alkyl(inf), hydroxy, trifluorométhyle, halogène, amino, hydroxyméthyle, alkoxy(inf) NHR -(CH2)qN = C< et -(CH2) qNR5R6 NHR4 et le second substituant étant un groupe alkyl(inf), hydroxy, trifluorométhyle, halogène, amino, hydroxyméthyle zolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl and A and A 'may independently comprise one or two substituents, the first substituent being an alkyl (inf), hydroxy, trifluoromethyl, halogen group; amino, hydroxymethyl, alkoxy (inf) NHR - (CH2) qN = C <and - (CH2) qNR5R6 NHR4 and the second substituent being alkyl (inf), hydroxy, trifluoromethyl, halogen, amino, hydroxymethyl
et alkoxy(inf).and alkoxy (inf).
q est un nombre entier compris entre 0 et 6 bornes comprises R4 indépendammentsont comme ci-dessus ou les deux groupes R4sont reliés entre eux pour former un groupe éthylène; et Rs et R6 sont indépendamment l'hydrogène, un radical alkyl(inf), alkényl{-inf),alkynyl(inf), cycloalkyl(inf), ou phényle étant entendu que R5 et R6 ne sont pas en même temps des groupes cycloalkyl(inf) ou phényle, ou bien R5 et R6 pris ensemble avec l'atome d'azote auquel ils sont liés, forment un cycle pyrrolidino, morpholino, piperidino, méthylpipéridino, N-méthylpipérazino ou homopipéridino; et consistent en ce composé, ou un de ses sels,non toxique pharmaceutiquement q is an integer from 0 to 6 inclusive R4 independently as above or both R4 groups are joined together to form an ethylene group; and Rs and R6 are independently hydrogen, alkyl (inf), alkenyl (-inf), alkynyl (inf), cycloalkyl (inf), or phenyl with the proviso that R5 and R6 are not at the same time cycloalkyl groups (inf) or phenyl, or R5 and R6 taken together with the nitrogen atom to which they are attached form a pyrrolidino, morpholino, piperidino, methylpiperidino, N-methylpiperazino or homopiperidino ring; and consisting of this compound, or a salt thereof, which is nontoxic
acceptable, hydrate, solvate ou N-oxyde. acceptable, hydrate, solvate or N-oxide.
Selon un mode de réalisation plus particulièrement préféré des composés de formule II, R2est A(CH2)mZ(CH2)nNH avec A est un groupe phényle, imidazolyle, thiazolyle, furyle, thiényle ou il3 24865Z8 pyridyle, chacun d'eux peut comporter un ou deux substituants, le premier substituant étant un radical alkyl(inf) NHR4 -N=C et -CH2NRsR6 -NHR4 et le second substituant étant un radical alkyl(inf) Z est le soufre, l'oxygène ou le méthylène; m est égal à 0 ou 1; n est égal à 2 ou 3; les groupes R4 indépendamment sont l'hydrogène, ou des alkyl(inf) ou bien les deux groupes R4 sont liés entre eux pour former un groupes éthylène; R5 et R6 pris indépendamment, sont l'hydrogène ou un radical alkyl(inf) ou bien R5 et R6 pris ensemble avec l'atome d'azote auquel ils sont liés, forment un groupe pyrrolidino, morpholino, piperidino, méthylpipéridino, Nméthylpipérazino ou homopipéridino; et R7 est un alkoxy(inf) Selon un autre mode de réalisation plus particulièrement préféré des composés de formule II According to a more particularly preferred embodiment of the compounds of formula II, R 2 is A (CH 2) m Z (CH 2) n NH with A is a phenyl, imidazolyl, thiazolyl, furyl, thienyl or pyridyl group, each of them may comprise a or two substituents, the first substituent being an alkyl (inf) NHR4 -N = C and -CH2NRsR6 -NHR4 radical and the second substituent being an alkyl (inf) radical Z is sulfur, oxygen or methylene; m is 0 or 1; n is 2 or 3; the groups R4 independently are hydrogen, or alkyl (inf) or the two R4 groups are linked together to form an ethylene group; R5 and R6 taken independently are hydrogen or an alkyl radical (inf) or R5 and R6 taken together with the nitrogen atom to which they are attached form a pyrrolidino, morpholino, piperidino, methylpiperidino, N-methylpiperazino or homopiperidino group ; and R7 is alkoxy (inf) According to another more particularly preferred embodiment of the compounds of formula II
R'2 est R2R3N-R'2 is R2R3N-
avecwith
R2et R3 sont indépendamment l'hydrogène, un radical alkyl(inf), alkenyl(inf). R2 and R3 are independently hydrogen, alkyl (inf), alkenyl (inf).
alkynyl(inf), cycloalkyl(inf)alkyl(inf), pyridylalkyl(inf), A'-(CH2)m, Z'(CH2)n,-, phénylalkyl(inf) ou 3,4-méthylénédioxybenzyle étant entendu que R2 et R3 ne peuvent pas être en même temps A'-(CH2)mnZ' (CH2)n,-; m' est égal à 0 ou 1; n' est égal à 2 ou 3; Z' est le soufre, l'oxygène ou le méthylène; A' est un groupe phényle, imidazolyle, thiazolyle, furyle, thiényle ou pyridyle, chacun de ces groupes pouvant comporter un ou deux substituants le premier substituant étant choisi parmi les alkyl(inf), alkynyl (inf), cycloalkyl (inf) alkyl (inf), pyridylalkyl (inf), A '- (CH2) m, Z' (CH2) n, -, phenylalkyl (inf) or 3,4-methylenedioxybenzyl with the proviso that R2 and R3 can not be at the same time A '- (CH2) mnZ' (CH2) n, -; m 'is 0 or 1; n 'is 2 or 3; Z 'is sulfur, oxygen or methylene; A 'is a phenyl, imidazolyl, thiazolyl, furyl, thienyl or pyridyl group, each of these groups may comprise one or two substituents, the first substituent being chosen from alkyl (inf),
C-NHR4C-NHR 4
-NHR=C " 4 et CH2NRSR6 -N=CR-NHR = C "4 and CH2NRSR6 -N = CR
1 24865281 2486528
les groupes R" sont indépendamment l'hydrogène ou des groupes alkyl(inf) ou bien les deux groupes R4 forment ensemble un groupe éthylène; Rs et R6sont indépendamment l'hydrogène ou un radical alkyl(inf) ou bien R5 et R6 pris ensemble avec l'atome d'azote auquel ils sont liés forment un groupe pyrrolidino, morpholino, piperidino, méthylpipéridino, N-méthylpipérazino, ou homopiperidino et, et R7 est un groupe alkoxy(inf) Selon un autre mode de réalisation des composés de formule II the groups R "are independently hydrogen or alkyl (inf) groups or both R4 groups together form an ethylene group; Rs and R6 are independently hydrogen or an alkyl (inf) radical or R5 and R6 taken together with the nitrogen atom to which they are attached form a pyrrolidino, morpholino, piperidino, methylpiperidino, N-methylpiperazino, or homopiperidino group and, and R7 is an alkoxy (inf) group. According to another embodiment of the compounds of formula II
R12 est HS(CH2)nNH-R12 is HS (CH2) nNH-
n avec n est un nombre entier compris entre 2 et 4 et R7 est un groupe alkoxy(inf) Selon un autre mode tout particulièrement préféré des composés de formule II R'2 est RI3 n with n is an integer between 2 and 4 and R7 is an alkoxy group (inf) According to another very particularly preferred mode of the compounds of formula II R'2 is RI3
>"NCH2- CH2ZCH2CH2NH-> "NCH2-CH2ZCH2CH2NH-
H3H3
avec Z est le soufre ou le groupe méthylène et R13est l'hydrogène ou le groupe méthyle -: et R7 est un groupe alkoxy(inf) Selon un autre mode de réalisation particulièrement préféré des composés de formule II H R12 est with Z is sulfur or methylene group and R13 is hydrogen or methyl group; and R7 is alkoxy (inf). According to another particularly preferred embodiment of compounds of formula II, R12 is
R4N' SR4N 'S
//
HH
CH2 ZCH2 C!42 NH-CH2 ZCH2 C42 NH-
avec Z est un atome de soufre ou le groupe méthylène les groupes R4sont indépendamment l'hydrogène ou le méthyle ou bien les deux groupes R" pris ensemble, forment un groupe éthylène et R7 est un groupe alkoxy (inf) Selon un autre mode de réalisation particulièrement préféré des composés de formule II, R1'2est R13 r with Z is a sulfur atom or the methylene group R4 groups are independently hydrogen or methyl or both R "groups taken together form an ethylene group and R7 is an alkoxy (inf) group According to another embodiment particularly preferred compounds of formula II, R1'2is R13 r
>CNCH2> CNCH2
CH2ZCH2CH2NH-CH2ZCH2CH2NH-
avec Rl'est l'hydrogène ou le méthyle; Z est le soufre ou un groupe méthylène et R7 est un groupe alkoxy(inf) Selon un autre mode de réalisation particulièrement préféré des composés de formule II R12est with R1 is hydrogen or methyl; Z is sulfur or a methylene group and R7 is an alkoxy (inf) group. According to another particularly preferred embodiment of the compounds of formula II, R12 is
R- NCH2 CH2ZCH2CH2NH-R-NCH2 CH2ZCH2CH2NH-
H-IC/NCH-IC / NC
avec R13est l'hydrogène ou le méthyle Z est le soufre ou un groupe méthylène et R7 est un groupe alkoxy(inf) Selon un autre mode de réalisation particulièrement préféré des composés de formule II R12est with R13is hydrogen or methyl Z is sulfur or methylene and R7 is alkoxy (inf) According to another particularly preferred embodiment of compounds of formula II R12is
2-NCH2 CH2ZCH2CH2NH-2-NCH2 CH2ZCH2CH2NH-
R6/ R6 avec R5 et R6 sont indépendamment l'hydrogène ou un groupe alkyl(inf) Z est le soufre ou le groupe méthylène et R7 est un groupe alkoxy(inf) Selon un autre mode de réalisation particulièrement préféré des composés de formule II R12est R6 / R6 with R5 and R6 are independently hydrogen or alkyl (inf) Z is sulfur or methylene and R7 is alkoxy (inf) According to another particularly preferred embodiment of the compounds of formula II R12is
i NCH2 OCH2CH2CH2NH-i NCH2 OCH2CH2CH2NH-
La présente invention se rapporte également à des composés nouveaux de formule s The present invention also relates to novel compounds of formula
II
R7 R7R7 R7
dans laquelle R7 est un groupe partant tel qu'un halogène, alkoxy(inf), alkylthio (inf) et phénoxy ou phénylthio éventuellement porteurs d'l ou 2 substituants choisis parmi les halogènes, les groupes alkyl(inf) alkoxy(inf) et nitro Selon un mode préféré de réalisation des composés de formule I, R7 est un groupe alkoxy(inf), phénoxy, phénoxy substitué; wherein R7 is a leaving group such as halogen, alkoxy (inf), alkylthio (inf) and phenoxy or phenylthio optionally carrying 1 or 2 substituents selected from halogens, alkyl (inf) alkoxy (inf) and nitro According to a preferred embodiment of the compounds of formula I, R7 is alkoxy (inf), phenoxy, substituted phenoxy;
de préférence, R7 est un groupe méthoxy. preferably, R7 is a methoxy group.
Dans la présente description, on entend par l'expression "sel non In the present description, the expression "salt not
toxique pharmaceutiquement acceptable", un sel de composé de formule I avec pharmaceutically acceptable toxicant ", a salt of a compound of formula I with
un acide organique ou minéral non toxique pharmaceutiquement acceptable. a non-toxic organic or inorganic acid pharmaceutically acceptable.
- Ces acides sont bien connus: ce sont les acides chlohydrique, brom- These acids are well known: they are hydrochloric acids, bromide
hydrique, sulfurique, sulfamique, phosphorique, nitrique, maléique, fumarique, succinique, oxalique, benzoique, méthanesulfonique, éthanedisulfonique, water, sulfuric, sulfamic, phosphoric, nitric, maleic, fumaric, succinic, oxalic, benzoic, methanesulfonic, ethanedisulfonic,
benzenesulfonique, acétique, propionique, tartrique, citrique, camphosulfoni- benzenesulfonic, acetic, propionic, tartaric, citric, camphorsulfonitrile
que, et similaires.that, and the like.
On prépare les sels selon les méthodes bien connues. On peut remarquer que certains des composés de formule I et les intermédiaires II décrits dans The salts are prepared according to well known methods. It may be noted that some of the compounds of formula I and the intermediates II described in
la présente description peuvent former des sels doubles ou triples, etc... this description may form double or triple salts, etc.
Il est bien entendu que les sels des intermédiaires ne sont pas limités aux sels avec les acides non toxiques pharmaceutiquement acceptables lorsque It is understood that the salts of the intermediates are not limited to the salts with the pharmaceutically acceptable non-toxic acids when
lesdits intermédiaires ne sont pas utilisés eux-mêmes en tant que médicaments. said intermediates are not used themselves as drugs.
On a constaté que le nombre de composés de formule I, de la présente invention, retiennent fortement les solvants à partir desquels on les a recristallisé. Dans certains cas, il semble que les produits sont de vrais solvates alors que dans d'autres cas les produits peuvent retenir surtout du solvant adventice ou bien, constituer un mélange de solvat avec du It has been found that the number of compounds of formula I of the present invention strongly retain the solvents from which they have been recrystallized. In some cases, it appears that the products are true solvates, while in other cases the products can retain mostly adventitious solvent or, to form a mixture of solvate with
solvant adventice.adventitious solvent.
Bien qu'il soit possible d'éliminer le solvant par séchage à température élevée, ceci a souvent pour effet de transformer un produit bien cristallisé en un solide caoutchouteux. Comme les produits solvatés ont en général des points de fusion fort nets, la pratique courante consiste à sécher les produits à température ambiante. S'il reste du solvant retenu, même après un séchage prolongé, on dose la teneur en solvant à l'aide d'une méthode convenable comme la RMN. Dans les exemples ci- dessous, on donne la teneur en solvant (le cas échéant); l'analyse et le point de fusion correspondent aux produits Although it is possible to remove the solvent by drying at elevated temperature, this often results in a well-crystallized product becoming a rubbery solid. Since solvated products generally have sharp melting points, it is common practice to dry the products at room temperature. If retained solvent remains, even after prolonged drying, the solvent content is measured using a suitable method such as NMR. In the examples below, the solvent content (where applicable) is given; the analysis and the melting point correspond to the products
solvatés, sauf indication contraire. solvated, unless otherwise indicated.
Les composés selon l'invention sont des composés nouveaux pouvant être notamment employés pour l'obtention des composés selon la première The compounds according to the invention are novel compounds that can be used in particular for obtaining the compounds according to the first
demande divisionnaire.divisional application.
EXEMPLE 1.EXAMPLE 1
Préparation de 3,4-diméthoxy-1,2,5-thiadiazole 1-oxyde On ajoute une solution de 3,4-diméthoxy-1,2,5-thiadiazole (35,2 g; 24,1mmoles) [préparé selon le procédé décrit dans J. Org. Chem., Preparation of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide A solution of 3,4-dimethoxy-1,2,5-thiadiazole (35.2 g, 24.1 mmol) (prepared according to method described in J. Org. Chem.
, 2749 (1975)] dans 100 ml de chloroforme en 3 minutes, à une so- , 2749 (1975)] in 100 ml of chloroform in 3 minutes at a
lution d'acide m-chloroperbenzoique (50,7 g; 25,0mioles;pur à 85%) dans 900 ml de chloroforme, à 20 C, sous agitation, en utilisant solution of m-chloroperbenzoic acid (50.7 g, 25.0 mol, 85% pure) in 900 ml of chloroform, at 20 ° C., with stirring, using
un bain réfrigérant pour empêcher que la réaction exothermique dépas- a cooling bath to prevent the exothermic reaction from exceeding
se une température de 32 C. Après 3 heures d'agitation à la température a temperature of 32 C. After 3 hours of agitation at room temperature
ambiante, on fait réagir l'excès de péracide avec 2,0 g supplémentai- room temperature, the excess peracid is reacted with an additional 2.0 g.
res de 3,4-dimnéthoxy-1,2,5-thiadiazole et on poursuit l'agitation 3,4-dimethoxy-1,2,5-thiadiazole and stirring continued
pendant 1 heure.for 1 hour.
On extrait la solution organique à l'aide de 2portions de 300 ml The organic solution is extracted using 300 ml portions
de solution à 1% de NaHCO3, lave par 250 ml d'eau, sèche, puis, éva- of 1% NaHCO3 solution, washed with 250 ml of water, dried, and then
pore sous pression réduite pour obtenir 47,0 g de produit. Par recris- pore under reduced pressure to obtain 47.0 g of product. By recreating
tallisation dans l'alcool isopropylique on obtient le composé en ru- in isopropyl alcohol, the compound is obtained
brique (34,0 g). Une recristallisation supplémentaire dans l'alcool brick (34.0 g). Additional recrystallization in alcohol
isopropylique permet d'obtenir un échantillon analytique (PF: 135- isopropyl gives an analytical sample (PF: 135-
137 C).137 C).
Le composé obtenu présente la formule brute The compound obtained has the formula
C4H6N203SC4H6N203S
et son analyse élémentaire conduit aux résultats suivants and his basic analysis leads to the following results
C H N SC H N S
calculé: 29,63 3,72 17,27 19,77 trouvé: 29,53 3,75 17,26 19,83 calculated: 29.63 3.72 17.27 19.77 found: 29.53 3.75 17.26 19.83
EXEMPLE I BisEXAMPLE I Bis
____________________________________
Autre exemple de préparationAnother example of preparation
On ajoute, goutte à qoutte, une solution de oxaldiimidate de dimé- A solution of dimeric oxaldiimidate is added drop by drop.
thyle (4,0g; 34,5mmole) et de pyridine (5,71ml, 5,58g, 70,6mmole) dans 8ml de CH2Cl2 à une solution refroidie de chlorure de thionyle (2,61ml, 4, 25g, 34,7mmole) dans 18ml de CH2C12, sous balayage de l'azote, à un thyl (4.0g, 34.5mmol) and pyridine (5.71ml, 5.58g, 70.6mmol) in 8ml CH2Cl2 to a cooled solution of thionyl chloride (2.61ml, 4.25g, 34.7mmol) ) in 18 ml of CH2Cl2, under a nitrogen sweep, at a
rythme tel que la température de réaction demeure comprise entre O et 15 C. such that the reaction temperature remains between 0 and 15 C.
Apres 20 minutes d'agitation à température ambiante, on lave le mélange réactionnel à l'aide de deux portions de 11ml de HCl aqueux 0,055 N. On extrait la phase aqueuse à l'aide de 2 portions de 20ml de CH2Cl2 et on sèche les phases organiques combinées et les évapore à sec sous pression réduite. On recristallise le résidu, solide dans l'alcool isopropylique After stirring for 20 minutes at room temperature, the reaction mixture is washed with two portions of 11 ml of 0.055N aqueous HCl. The aqueous phase is extracted with 2 portions of 20 ml of CH 2 Cl 2 and the extracts are dried. combined organic phases and evaporated to dryness under reduced pressure. The residue is recrystallized, solid in isopropyl alcohol
et on obtient 3,0g du composé en rubrique, F: 137-139 C. and 3.0 g of the title compound, mp 137-139 ° C.
On peut préparer les composés de formuleII à partir des composés de formule I selon d'autres schémas réactionnels en passant par plusieurs familles de nouveaux intermédiaires The compounds of formula II can be prepared from the compounds of formula I according to other reaction schemes through several families of new intermediates.
SCHEMA REACTIONNEL 1REACTION SCHEME 1
(O)p (O)p(O) p (O) p
S SS S
/N N A(CH2)mZ(CH2)nNH2 > N- II/ N N A (CH 2) m Z (CH 2) n NH 2> N-II
N N I ' -N N I '-
A(CH2)mZ(CH2)n RnA (CH2) mZ (CH2) n Rn
R7 R7R7 R7
EXEMPLE 2EXAMPLE 2
Le composé ainsi obtenu est utilisé pour l'obtention de 3-{2-[(5- The compound thus obtained is used to obtain 3- {2 - [(5-
méthyl-1H-imidazol-4-yl)méthylthio)-éthylamino}-4-méthylamino-1,2,5- methyl-1H-imidazol-4-yl) methylthio) ethylamino} -4-methylamino-1,2,5
thiadiazole 1-oxyde.thiadiazole 1-oxide.
On fait réagir une solution de 3,4-diméthoxy-1,2,5-thiadiazole 1-oxyde A solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide is reacted
obtenue selon l'Exemple 1 avec une quantité équimolaire de 2-E(5-méthyl- obtained according to Example 1 with an equimolar amount of 2-E (5-methyl)
1H-imidazol-4-yl)méthylthio]éthylamine, on traite le 3-{2-[(5-méthyl- 1H-Imidazol-4-yl) methylthio] ethylamine, the 3- {2 - [(5-methyl)
1H-imidazol-4-yl)méthylthiolèthylamino}-4-méthoxy-1,2,5-thiadiazole 1- 1H-imidazol-4-yl) methylthiolethylamino} -4-methoxy-1,2,5-thiadiazole
oxyde obtenu par un excès de méthylamine, ce qui permet d'obtenir le oxide obtained by an excess of methylamine, which makes it possible to obtain the
composé en rubrique.composed in section.
EXEMPLE 3EXAMPLE 3
3-{2-[(5-méthyt-lH-imidazot-4-yLt)méthytthio]-éthyltamino}-4- 3- {2 - [(5-methyl-lH-imidazot-4-YLT) méthytthio] -éthyltamino} -4
methoxy-1,2,5-thiadiazote 1,1-dioxyde methoxy-1,2,5-thiadiazole 1,1-dioxide
A une suspension de 3,4-diméthoxy-1,2,5-thiadiazole 1,1-dio- To a suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-diol
xyde (2,Og; 11,2 mnmloles) [préparé selon le procédé décrit dans J. Org. Chem., 40, 2743 (1975)] dans 200ml de méthanol xyd (2, Og, 11.2 minol) (prepared according to the method described in J. Org. Chem., 40, 2743 (1975)] in 200 ml of methanol
à température ambiante on ajoute une solution de 2-[(5-méthyl- at room temperature a solution of 2 - [(5-methyl)
1H-imidazol-4-yl)-méthylthio]éthylamine (à partir du dichlorhy- 1H-imidazol-4-yl) -methylthio] ethylamine (from dichlorhydrin)
drate, 2,73g; 11,2mmoles) [préparé selon le brevet belge 779 7751 dans 25ml de méthanol. Apres 30 minutes d'agitation, on obtient drate, 2.73 g; 11.2 mmol) [prepared according to Belgian Patent 779 7751 in 25 ml of methanol. After 30 minutes of stirring, we obtain
une solution méthanolique du composé en rubrique. a methanolic solution of the title compound.
La chromatographie en couche mince (Silice/CH2Cl2:CH30H(90/10) donne Rf = 0,44 Thin layer chromatography (Silica / CH 2 Cl 2: CH 3 OH (90/10) gives Rf = 0.44
EXEMPLE 4EXAMPLE 4
3-{2-[(5-diméthytariinoethyl-2-fur),l)méthyLthio] thytamino}-4- 3- {2 - [(5-dimethylaminoethyl-2-fur), 1-methylthio] thytamino} -4-
méthoxy-1,2,5-thiadiazote 1,1-dioxyde Methoxy-1,2,5-thiadiazole 1,1-dioxide
On ajoute une solution de 2-[(5-diméthylaminoniéthyl-2-furyl)-niéthyl- A solution of 2 - [(5-dimethylaminoniethyl-2-furyl) -nethyl)
thio]éthylamine (2,41 g; 11,2 muoles) [préparée selon le procédé uu brevet de Belgique 857,388J dans 20 mil de méthanol anhydre,en une foi! à une suspension de 3,4-diméthoxy-1,2,5-thiadiazole 1,1-dioxyde (2,0 g; 11, 2 miloles) dans 200 mil de méthanol à 8 C sous agitation énergique. Après 15 minutes d'agitation à 8-10 C, on obtient une thio] ethylamine (2.41 g; 11.2 mol) [prepared according to the method of the Belgian patent 857,388] in 20 mil of anhydrous methanol, in one faith! to a suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide (2.0 g; 11.2 miloles) in 200 ml of methanol at 8 C with vigorous stirring. After 15 minutes stirring at 8-10 C, a
solution méthanolique du composé en rubrique. methanol solution of the title compound.
Bien entendu, la présente invention n'est nullement limitée aux Of course, the present invention is not limited to
modes de réalisation décrits et représentés; elle est susceptible de nom- embodiments described and shown; it is likely to
breuses variantes accessibles à l'homme de l'art, sans que l'on ne many variants accessible to those skilled in the art, without
s'écarte pour cela de l'esprit de l'invention. deviate for that from the spirit of the invention.
2 24865282 2486528
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7251779A | 1979-09-04 | 1979-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2486528A1 true FR2486528A1 (en) | 1982-01-15 |
| FR2486528B1 FR2486528B1 (en) | 1984-12-21 |
Family
ID=22108102
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018670A Granted FR2476081A1 (en) | 1979-09-04 | 1980-08-28 | 1,2,5-Thiadiazole 1-oxide and 1,1-di:oxide derivs. - useful as anti-ulcer agents |
| FR8115119A Granted FR2486528A1 (en) | 1979-09-04 | 1981-08-04 | DERIVATIVES OF THIADIAZOLE 1-OXIDE |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8018670A Granted FR2476081A1 (en) | 1979-09-04 | 1980-08-28 | 1,2,5-Thiadiazole 1-oxide and 1,1-di:oxide derivs. - useful as anti-ulcer agents |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS63211272A (en) |
| KR (1) | KR850000759B1 (en) |
| AT (1) | AT380019B (en) |
| AU (2) | AU541849B2 (en) |
| BE (1) | BE885089A (en) |
| CS (2) | CS221977B2 (en) |
| FR (2) | FR2476081A1 (en) |
| GR (1) | GR70020B (en) |
| HU (2) | HU205753B (en) |
| YU (2) | YU41941B (en) |
| ZA (1) | ZA805250B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3175201D1 (en) * | 1980-04-30 | 1986-10-02 | Merck & Co Inc | Aminothiadiazoles as gastric secretion inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040696A2 (en) * | 1980-04-30 | 1981-12-02 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL22850A (en) * | 1964-03-18 | 1968-12-26 | Merck & Co Inc | 3-chloro-1,2,5-thiazdiazole-4-carboxylic acid being an intermediate in the preparation of sulfa drugs |
| CH482712A (en) * | 1964-10-01 | 1969-12-15 | Merck & Co Inc | Process for the preparation of 3-amino-1,2,5-thiadiazoles |
| DE1770152A1 (en) * | 1968-04-08 | 1971-09-30 | Lentia Gmbh | Process for the preparation of 3-amino-4-bromo-1,2,5-thiadiazole |
| US3657237A (en) * | 1968-05-22 | 1972-04-18 | Frosst & Co Charles E | Process for making 1 2 5-thiadiazoles in the sinister configuration |
| AT348517B (en) * | 1977-01-19 | 1979-02-26 | Chemie Linz Ag | PROCESS FOR THE PREPARATION OF PURE 3-METHOXY-4- (4'-AMINOBENZOLSULFONAMIDO) -1,2,5-THIADIAZOLE |
-
1980
- 1980-08-25 ZA ZA00805250A patent/ZA805250B/en unknown
- 1980-08-26 GR GR62755A patent/GR70020B/el unknown
- 1980-08-26 YU YU2132/80A patent/YU41941B/en unknown
- 1980-08-28 FR FR8018670A patent/FR2476081A1/en active Granted
- 1980-09-01 AU AU61942/80A patent/AU541849B2/en not_active Ceased
- 1980-09-03 HU HU893724A patent/HU205753B/en not_active IP Right Cessation
- 1980-09-03 HU HU85912A patent/HU201539B/en not_active IP Right Cessation
- 1980-09-04 CS CS806023A patent/CS221977B2/en unknown
- 1980-09-04 KR KR1019800003492A patent/KR850000759B1/en active
- 1980-09-04 BE BE0/201991A patent/BE885089A/en not_active IP Right Cessation
-
1981
- 1981-08-04 FR FR8115119A patent/FR2486528A1/en active Granted
- 1981-09-22 CS CS816980A patent/CS246052B2/en unknown
-
1983
- 1983-01-18 YU YU00094/83A patent/YU9483A/en unknown
-
1984
- 1984-02-27 AT AT0064684A patent/AT380019B/en not_active IP Right Cessation
- 1984-11-13 AU AU35396/84A patent/AU563856B2/en not_active Ceased
-
1988
- 1988-01-27 JP JP63014800A patent/JPS63211272A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0040696A2 (en) * | 1980-04-30 | 1981-12-02 | Merck & Co. Inc. | Aminothiadiazoles as gastric secretion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| CS246052B2 (en) | 1986-10-16 |
| BE885089A (en) | 1981-03-04 |
| KR830003434A (en) | 1983-06-20 |
| AU6194280A (en) | 1981-03-12 |
| YU213280A (en) | 1983-06-30 |
| KR850000759B1 (en) | 1985-05-25 |
| HU205753B (en) | 1992-06-29 |
| AU3539684A (en) | 1985-03-14 |
| YU9483A (en) | 1983-06-30 |
| HUT57755A (en) | 1991-12-30 |
| HU201539B (en) | 1990-11-28 |
| FR2476081A1 (en) | 1981-08-21 |
| JPS63211272A (en) | 1988-09-02 |
| AT380019B (en) | 1986-03-25 |
| ZA805250B (en) | 1981-09-30 |
| AU563856B2 (en) | 1987-07-23 |
| FR2476081B1 (en) | 1985-04-12 |
| AU541849B2 (en) | 1985-01-24 |
| GR70020B (en) | 1982-07-23 |
| CS221977B2 (en) | 1983-04-29 |
| ATA64684A (en) | 1985-08-15 |
| FR2486528B1 (en) | 1984-12-21 |
| YU41941B (en) | 1988-02-29 |
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