SI20690B - Novi derivati 2-(N-cianoimino)tiazolidin-4-ona - Google Patents

Novi derivati 2-(N-cianoimino)tiazolidin-4-ona Download PDF

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Publication number
SI20690B
SI20690B SI9920104A SI9920104A SI20690B SI 20690 B SI20690 B SI 20690B SI 9920104 A SI9920104 A SI 9920104A SI 9920104 A SI9920104 A SI 9920104A SI 20690 B SI20690 B SI 20690B
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cyanoimino
thiazolidin
benzylidene
alkyl group
ring
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SI9920104A
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SI20690A (sl
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Fumio Yoneda
Hironori Ohde
Mayumi Watanabe
Takashi Ando
Takuya Yasusa
Yuko Uegaki
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Fujimoto Brothers Co Ltd
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Priority claimed from PCT/JP1999/006352 external-priority patent/WO2001036402A1/ja
Publication of SI20690A publication Critical patent/SI20690A/sl
Publication of SI20690B publication Critical patent/SI20690B/sl

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/54Nitrogen and either oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/64Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/68Benzothiazoles 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 in position 2
    • C07D277/70Sulfur atoms
    • C07D277/74Sulfur atoms substituted by carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/12Heterocyclic 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 chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Novi derivati 2-(N-cianoimino)tiazolidin-4-ona s splosno formulo I, ki kazejo odlicne ucinke pri znizevanju holesterola in znizevanju triglicerida inso uporabni pri preprecevanju ali zdravljenju hiperlipidemije in bolezni, ki iz nje izvirajo.

Claims (9)

1 Patentni zahtevki 1. Derivati 2-(N-cianoimino)tiazolidin-4-ona, prikazani s formulo I, ali njihova farmacevtsko sprejemljiva sol ali solvat:
benzotiazol, fluorenski obroč, indanski obroč, indolinski obroč ali piridinski obroč, pri čemer je lahko vsak substituiran z enim ali več substituenti, izbranimi izmed ravno verižne ali razvejene Ci-Czralkilne skupine, Ci-C4-haloalkilne skupine, atoma halogena in -OR5, R1 pomeni enojno vez, atom kisika, atom žvepla, metinsko skupino, ravnoverižno ali razvejeno CrC4-alkilensko ali alkenilensko skupino, po izbiri substituirano s fenilno skupino, R6-X, X-R6, X-R6-X, R6-X-R6, -C(=0)-NR7- ali -NR7-C(=0)-, R in R sta enaka ali različna in vsak pomeni atom vodika, CrC4-alkilno skupino, o -OR ali atom halogena, R1 2 3 pomeni atom vodika ali Ci-C4-alkilno skupino, R5 pomeni atom vodika ali Ci-C4-alkilno skupino, R6 pomeni ravnoverižno ali razvejeno CrC4-alkilensko ali alkenilensko skupino, ”7 . R pomeni atom vodika ali Ci-C4-alkilno skupino, o R pomeni atom vodika, Ci-C4-alkilno skupino ali fenil(Ci-C4)alkilno skupino, X pomeni atom kisika ali atom žvepla. 1 Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da obroč A pomeni benzenski obroč, ki je 2 lahko substituiran z enim ali več substituenti, izbranimi izmed ravnoverižne ali 3 razvejene Ci-C4-alkilne skupine, C]-C4-haloalkilne skupine, atoma halogena in -OR5; R5 pomeni atom vodika ali Ci-C4-alkilno skupino. 2
3. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da R1 pomeni metinsko skupino ali ravnoverižno ali razvejeno Ci-C4-alkilensko ali alkenilensko skupino, po izbiri substituirano s fenilno skupino.
4. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da R1 pomeni atom kisika ali atom žvepla.
5. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da R1 pomeni enojno vez.
6. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da R1 pomeni R6- X, X-R6, X-R6-X ali R6-X-R6; R6 pomeni ravnoverižno ali razvejeno Ci-C4-alkilensko ali alkenilensko skupino; X pomeni atom kisika ali atom žvepla.
7. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, da R1 pomeni -C(=0)-NR7- ali -NR7-C(=0)-; R7 pomeni atom vodika ali CrC4-alkilno skupino.
8. Derivati 2-(N-cianoimino)tiazolidin-4-ona ali njihova farmacevtsko sprejemljiva sol ali solvat po zahtevku 1, označeni s tem, daje spojina s formulo I katerakoli izmed naslednjih: 2-(N-cianoimino)-5-[(E)-4-stirilbenziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[(E)-4-(a-metilstiril)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[-4-(benziloksimetil)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[(E)-4-(b-metilstiril)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(3-fenilpropoksi)benziliden]tiazolidin-4-on 3 2-(N-cianoimino)-5-[4-(4-klorofenoksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(4-feniltiobenziliden)tiazolidin-4-on 2-(N-cianoimino)-5-[(E)-4-(2-fluorostiril)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(2,5-dimetilfenoksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(4-fenetiloksibenziliden)tiazolidin-4-on 2-(N-cianoimino)-5-[4-(2-fenilpropoksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(3-fenetiloksibenziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(4-benziloksibenziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(5-klorobenzofuran-2-il)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[(E)-4-(4-metoksistiril)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(3-fenoksibenziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(l,3-benzodioksol-5-ilmetoksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(4-metilbenziloksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(4-klorobenziloksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[3-metoksi-(E)-4-stirilbenziliden]tiazolidin-4-on 2-(N-cianoimino)-5-(2-fenetiloksibenziliden)tiazolidin-4-on 2-(N-cianoimino)-5-(4-fenoksibenziliden)tiazolidin-4-on 2-(N-cianoimino)-5-[3-(benziloksi)benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[4-(benziltio)benziliden]tiazolidin-4-on 2 - (N- cianoimino)- 5 - (4- fenetilbenziliden)tiazolidin-4-on 2-(N-cianoimino)-5-[4-[2-(4-klorofenil)etoksi]benziliden]tiazolidin-4-on 2-(N-cianoimino)-5-[l-[(E)-4-(4-metoksistiril)fenil]etiliden]tiazolidin-4-on 2-(N-cianoimino)-5-(4-benziloksi-2,5-dimetilbenziliden]tiazolidin-4-on ali 2-(N-cianoimino)-5-[(E)-3-stirilbenziliden]tiazolidin-4-on.
9. Postopek za pripravo derivata 2-(N-cianoimino)tiazolidin-4-ona ali njegove farmacevtsko sprejemljive soli ali solvata po zahtevku 1, označen s tem, da obsega reakcijo spojine, prikazane s formulo II, ali njenih soli z aldehidom ali ketonom, prikazanim s formulo III: 4
kjer obroč A pomeni benzenski obroč, benzodioksolni obroč, benzofuranski obroč, benzotiazol, fluorenski obroč, indanski obroč, indolinski obroč ali piridinski obroč, pri čemer je lahko vsak substituiran z enim ali več substituenti, izbranimi izmed ravnoverižne ali razvejene Cj-C^alkilne skupine, Ci-Czphaloalkilne skupine, atoma halogena in -OR5, R1 pomeni enojno vez, atom kisika, atom žvepla, metinsko skupino, ravnoverižno ali razvejeno CpC^alkilensko ali alkenilensko skupino, po izbiri substituirano s fenilno skupino, R6-X, X-R6, X-R6-X, R6-X-R6, -C(=0)-NR7- ali -NR7-C(=0)-, R in R sta enaka ali različna in vsak pomeni atom vodika, Ci-C4-alkilno skupino, o -OR ali atom halogena, R4 pomeni atom vodika ali Ci-C4-alkilno skupino, R5 pomeni atom vodika ali Ci-C4-alkilno skupino, R6 pomeni ravnoverižno ali razvejeno C]-C4-alkilensko ali alkenilensko skupino, R7 pomeni atom vodika ali Ci-C4-alkilno skupino, a R pomeni atom vodika, CrC4-alkilno skupino ali fenil(Ci-C4)alkilno skupino, X pomeni atom kisika ali atom žvepla.
10. Farmacevtski sestavek za zdravljenje hiperlipidemije, označen s tem, da obsega nove derivate 2-(N-cianoimino)tiazolidin-4-ona in/ali njihovo farmacevtsko sprejemljivo sol in/ali sol vat po kateremkoli od zahtevkov 1-8 kot aktivno sestavino in farmacevtsko sprejemljiv nosilec.
SI9920104A 1998-07-14 1999-11-12 Novi derivati 2-(N-cianoimino)tiazolidin-4-ona SI20690B (sl)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10232216A JP2000026438A (ja) 1998-07-14 1998-07-14 新規な2−(n−シアノイミノ)チアゾリジン−4− オン誘導体
PCT/JP1999/006352 WO2001036402A1 (fr) 1998-07-14 1999-11-12 Nouveaux derives de 2-(n-cyano-imino)thiazolidin-4-one

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SI20690B true SI20690B (sl) 2008-02-29

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DE69934027T2 (de) * 1999-11-12 2007-06-21 Fujimoto Brothers Co., Ltd., Matubara 2-(n-cyanimino)thiazolidin-4-on derivate
JP2001199888A (ja) * 2000-01-24 2001-07-24 Fujimoto Brothers:Kk 糖尿病治療剤
ES2601856T3 (es) 2007-06-08 2017-02-16 Mannkind Corporation Inhibidores de la IRE-1A
EP2543729B1 (en) * 2010-03-04 2017-11-01 Masaru Okabe Model animal for pregnancy-induced hypertension syndrome, and treatment method therefor

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