SI8711857B - Oxadiazole-alkyl-purine derivatives - Google Patents

Oxadiazole-alkyl-purine derivatives Download PDF

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SI8711857B
SI8711857B SI8711857A SI8711857A SI8711857B SI 8711857 B SI8711857 B SI 8711857B SI 8711857 A SI8711857 A SI 8711857A SI 8711857 A SI8711857 A SI 8711857A SI 8711857 B SI8711857 B SI 8711857B
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Slovenia
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methyl
purine
oxadiazol
dione
dihydro
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SI8711857A
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Slovenian (sl)
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SI8711857A (en
Inventor
Dezso Korbonits
Emil Minker
Zoltan Vargai
Gergely Heja
Gabor Kovacs
Agnes Gottsegen
Sandor Antus
Sandor Virag
Andrea Bolehovszky
Jeno Marton
Katalin Marmarosi-Kellner
Lorand Debreczeni
Laszlo Tardos
Peter Koermoeczy
Vera Gergely
Gabor Horvath
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Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.
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Priority claimed from HU864230A external-priority patent/HU197574B/en
Application filed by Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. filed Critical Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt.
Publication of SI8711857A publication Critical patent/SI8711857A/en
Publication of SI8711857B publication Critical patent/SI8711857B/en

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Claims (8)

Patentni zahtevki 1. Oksadiazolil-alkilpurinski derivati s splošno formulo IOxadiazolyl-alkylpurine derivatives of general formula I (I) , kjer A označuje Cj 4alkilen in R1 predstavlja C1_6alkil, hidroksialkil, haloalkil, karboksialkil, C5 6cikloalkil, aminoalkil s splošno formulo -(CH2)n-NR2R3, kjer je n celo število 1-3; R2 in R3 vsak predstavlja vodik ali CMalkil, ali skupaj z atomom dušika, na katerega sta vezana, tvorita 5- ali 6-členski obroč, ki vsebuje heterociklični obroč, ki lahko v danem primeru obsega še nadaljnji atom dušika ali atom kisika kot heteroatom; ali R1 predstavlja fenil, hidroksifenil, karboksifenil, benzil ali dimetoksibenzil, in njihove fiziološko sprejemljive kislinske adicijske soli tvorjene z anorganskimi bazami.(I) wherein A denotes C1-4alkylene and R1 represents C1-6alkyl, hydroxyalkyl, haloalkyl, carboxyalkyl, C5-6cycloalkyl, aminoalkyl of the general formula - (CH2) n-NR2R3, wherein n is an integer 1-3; R 2 and R 3 each represent hydrogen or C 1-4 alkyl, or together with the nitrogen atom to which they are attached form a 5- or 6-membered ring containing a heterocyclic ring which may optionally comprise a further nitrogen atom or an oxygen atom as a heteroatom; or R 1 represents phenyl, hydroxyphenyl, carboxyphenyl, benzyl or dimethoxybenzyl, and their physiologically acceptable acid addition salts formed with inorganic bases. 2. Naslednje spojine po zahtevku 1: 3.7- dihidro-3-metil-7-[(5-metil-l,2,4-oksadiazol-3-il)metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-(propan-l-il)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-(butan-l-il)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-(pentan-l-il)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2,6-dion; 2 3,7-dihidro-3-metil-7-[(5-(propan-2-il)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-cikloheksil-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-klorometil-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-(2-hidroksietan-l-il)-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-dietilaminometil-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6,-dion; 3.7- dihidro-3-metil-7-[(5-piperidinometil-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-morfolinometil-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-benzil-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-dimetoksibenzil)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[(5-(3-karboksipropan-l-il)-l,2,4-oksadiazol-3-il)-metil)-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-fenil-l,2,4-oksadiazol-3-il)-metil]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[(5-(2-hidroksifenil)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion in 3.7- dihidro-3-metil-7-[(5-(2-karboksifenil)-l,2,4-oksadiazol-3-il)-metil]-lH-purin- 2.6- dion.The following compounds according to claim 1: 3.7-dihydro-3-methyl-7 - [(5-methyl-1,2,4-oxadiazol-3-yl) methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (propan-1-yl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (butan-1-yl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (pentan-1-yl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 2 3,7-Dihydro-3-methyl-7 - [(5- (propan-2-yl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-cyclohexyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-chloromethyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (2-hydroxyethan-1-yl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-diethylaminomethyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6,1-dione; 3.7-Dihydro-3-methyl-7 - [(5-piperidinomethyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-morpholinomethyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-benzyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-dimethoxybenzyl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (3-carboxypropan-1-yl) -1,2,4-oxadiazol-3-yl) -methyl) -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5-phenyl-1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7 - [(5- (2-hydroxyphenyl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione and 3,7-dihydro-3- methyl-7 - [(5- (2-carboxyphenyl) -1,2,4-oxadiazol-3-yl) -methyl] -1H-purine-2,6-dione. 3. Naslednje spojine po zahtevku 1: 3.7- dihidro-3-metil-7-[2-(5-metil-l,2,4-oksadiazol-3-il)-etan-l-il]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[2-(5-dietilaminometil-l,2,4-oksadiazol-3-il)-etan-l-il]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[2-(5-piperidinometil-l,2,4-oksadiazol-3-il)-etan-l-il]-lH-purin-2,6-dion; 3.7- dihidro-3-metil-7-[2-(5-(2-piperidinoetan-l-il)-l,2,4-oksadiazol-3-il)-etan-l-il]— lH-purin-2,6-dion in 3.7- dihidro-3-metil-7-[2-(5-(2-dietilaminoetan-l-il)-l,2,4-oksadiazol-3-il)-etan-l-il]--lH-purin-2,6-dion. 3The following compounds according to claim 1: 3.7-dihydro-3-methyl-7- [2- (5-methyl-1,2,4-oxadiazol-3-yl) -ethan-1-yl] -1H-purine- 2,6-dione; 3.7-Dihydro-3-methyl-7- [2- (5-diethylaminomethyl-1,2,4-oxadiazol-3-yl) -ethan-1-yl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7- [2- (5-piperidinomethyl-1,2,4-oxadiazol-3-yl) -ethan-1-yl] -1H-purine-2,6-dione; 3.7-Dihydro-3-methyl-7- [2- (5- (2-piperidinoethan-1-yl) -1,2,4-oxadiazol-3-yl) -ethan-1-yl] -1H-purine 2,6-dione and 3.7-dihydro-3-methyl-7- [2- (5- (2-diethylaminoethan-1-yl) -1,2,4-oxadiazol-3-yl) -ethan-1-yl ] - 1H-purine-2,6-dione. 3 4. Naslednje spojine po zahtevku 1: 3,7-dihidro-3-metil-7-[3-(5-metil-l,2,4-oksadiazol-3-il)-propan-l-il]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[3-(5-(2-dietilaminoetan-l-il)-l,2,4-oksadiazol-3-il)-propan-l-il]-lH-purm-2,6-dion in 3.7- dihidro-3-metil-7-[3-(5-(2-piperidinoetan-l-il)-l,2,4-oksadiazol-3-il)-propan-l-il]-lH-purin-2,6-dion.The following compounds according to claim 1: 3,7-dihydro-3-methyl-7- [3- (5-methyl-1,2,4-oxadiazol-3-yl) -propan-1-yl] -1H- purine- 2.6- dione; 3.7-Dihydro-3-methyl-7- [3- (5- (2-diethylaminoethan-1-yl) -1,2,4-oxadiazol-3-yl) -propan-1-yl] -1H-purine- 2,6-dione and 3.7-dihydro-3-methyl-7- [3- (5- (2-piperidinoethan-1-yl) -1,2,4-oxadiazol-3-yl) -propan-1-yl ] -1H-purine-2,6-dione. 5. Naslednje spojine po zahtevku 1: 3.7- dihidro-3-metil-7-[4-(5-metil-l,2,4-oksadiazol-3-il)-butan-l-il]-lH-purin- 2.6- dion; 3.7- dihidro-3-metil-7-[4-(5-(2-dietilaminoetan-l-il)-l,2,4-oksadiazo!-3-il)-butan-l-il]-lH-purin-2,6-dion in 3.7- dihidro-3-metil-7-[4-(5-(2-piperidinoetan-l-il)-l,2,4-oksadiazol-3-il)-butil]-lH--purin-2,6-dion.The following compounds according to claim 1: 3.7-dihydro-3-methyl-7- [4- (5-methyl-1,2,4-oxadiazol-3-yl) -butan-1-yl] -1H-purine- 2.6- dione; 3.7-Dihydro-3-methyl-7- [4- (5- (2-diethylaminoethan-1-yl) -1,2,4-oxadiazol-3-yl) -butan-1-yl] -1H-purine -2,6-dione and 3.7-dihydro-3-methyl-7- [4- (5- (2-piperidinoethan-1-yl) -1,2,4-oxadiazol-3-yl) -butyl] -1H --purine-2,6-dione. 6. Postopek za pripravo oksadiazolil-alkilpurinskih derivatov s splošno formulo I po zahtevkih 1 do 5 H-A process for the preparation of oxadiazolyl-alkylpurine derivatives of the general formula I as claimed in claims 1 to 5. CH 3 (I) kjer imata A in R1 enake pomene, kot je podano v zahtevku 1, in njihovih farmacevtsko sprejemljivih soli, označen s tem, da a) amidoksim s splošno formulo II . NOH OCH 3 (I) wherein A and R 1 have the same meanings as given in claim 1 and their pharmaceutically acceptable salts, characterized in that a) is an amidoxime of general formula II. NOH O CH Cii), 3 2 4 kjer je A, kot je podano zgoraj, presnovimo s karboksilno kislino s splošno formulo III R4-COOH (III), kjer ima R4 pomen R1 ali označuje skupino, ki jo lahko pretvorimo v skupino R1, ali z njenim reaktivnim derivatom in, če je želeno, skupino R4 pretvorimo v skupino R1, ali b) amidoksim s splošno formulo II, kjer ima A gornji pomen, presnovimo s karboksilno kislino s splošno formulo III, kjer ima R4 gornji pomen, ali njenim reaktivnim derivatom, spojino s splošno formulo IV, ki se tvori,CH Cii), 3 2 4 wherein A, as given above, is reacted with a carboxylic acid of general formula III R4-COOH (III) wherein R4 is R1 or denotes a group which can be converted to the R1 group, or by its reactive derivative and, if desired, the R4 group is converted to the R1 group, or b) the amidoxime of general formula II, wherein A is as defined above, is reacted with a carboxylic acid of general formula III, wherein R4 is as defined above, or a reactive derivative thereof , a compound of general formula IV which is formed, kjer imata A in R4 gornji pomen, cikliziramo po ali brez izolacije s cepljenjem vode, in, če je želeno, skupino R4 pretvorimo v skupino R1, ali (IV), c) oksadiazolni derivat s splošno formulo V Χ-Α-wherein A and R4 have the above meaning, are cyclized after or without isolation by water grafting, and, if desired, the group R4 is converted to the group R1, or (IV), c) an oxadiazole derivative of general formula V Χ-Α- (V) , kjer imata R4 in A gornji pomen in X označuje halogensko ali sulfonatno skupino, presnovimo s 3-metilksantinom s formulo VI(V), where R4 and A have the above meaning and X represents a halogen or sulphonate group, are reacted with 3-methylxanthine of formula VI ali njegovo natrijevo ali kalijevo soljo v prisotnosti bazičnega katalizatorja in, če je želeno, skupino R4 pretvorimo v skupino R1. 5or a sodium or potassium salt thereof in the presence of a basic catalyst and, if desired, converting the group R4 to the group R1. 5 7. Postopek za pripravo spojin s splošno formulo I po zahtevku 1, kjer A označuje skupino -(CH2)2- in ima Rl gornji pomen, označen s tem, da olefin s splošno formulo VIIA process for the preparation of compounds of general formula I according to claim 1, wherein A denotes the group - (CH 2) 2 - and R 1 has the above meaning, characterized in that the olefin of general formula VII (VII), kjer ima R4 gornji pomen, presnovimo s 3-metilksantinom s formulo VI v prisotnosti bazičnega katalizatorja, in če je želeno, skupino R4 pretvorimo v skupino R1 in, če je želeno, tako dobljeno spojino s formulo I pretvorimo v terapevtsko primerno sol.(VII), wherein R4 has the above meaning, is reacted with 3-methylxanthine of formula VI in the presence of a basic catalyst, and if desired, the group R4 is converted into a group R1 and, if desired, the compound of formula I thus obtained is converted into a therapeutically suitable sol. 8. Farmacevtsko sredstvo, označeno s tem, da vsebuje spojino s splošno formulo I po zahtevku 1 ali 2 ali njeno terapevtsko primerno sol. Za / CHINOIN GYOGYSZER ES VEGYESZETI / /Pharmaceutical agent, characterized in that it contains a compound of general formula I according to Claim 1 or 2, or a therapeutically suitable salt thereof. For / CHINOIN GYOGYSZER ES VEGYESZETI / / TERMEKEK GYARA RT.: MHATERMEKEK GYARA RT .: MHA
SI8711857A 1986-10-09 1987-10-08 Oxadiazole-alkyl-purine derivatives SI8711857B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU864230A HU197574B (en) 1986-10-09 1986-10-09 Process for production of derivatives of 3,7-dihydro-3-methil-7-//1,2,4-oxadiasole/-3-il/alkylenil/-1h-purin-2,6-dion and medical compositions containing these substances
YU185787A YU47545B (en) 1986-10-09 1987-10-08 NEW OXADIAZOL-ALKYL-PURINE DERIVATIVES AND PROCEDURE FOR THEIR PRODUCTION

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SI8711857A SI8711857A (en) 1996-10-31
SI8711857B true SI8711857B (en) 1998-06-30

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