SI20690B - Novi derivati 2-(N-cianoimino)tiazolidin-4-ona - Google Patents
Novi derivati 2-(N-cianoimino)tiazolidin-4-ona Download PDFInfo
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- 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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- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical class O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 title claims 25
- PFSHNSJERVOFEU-UHFFFAOYSA-N (4-oxo-1,3-thiazol-2-yl)cyanamide Chemical class O=C1CSC(=NC#N)N1 PFSHNSJERVOFEU-UHFFFAOYSA-N 0.000 claims abstract 11
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract 2
- -1 N-cyanoimino Chemical group 0.000 claims 41
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004450 alkenylene group Chemical group 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 1
- 125000005977 3-phenylpropyloxy group Chemical group 0.000 claims 1
- WDXULVFWZQBIBC-RVOJJYEQSA-N C(#N)N=C1S/C(/C(N1)=O)=C/C1=CC(=C(C=C1)C=CC1=CC=CC=C1)OC Chemical compound C(#N)N=C1S/C(/C(N1)=O)=C/C1=CC(=C(C=C1)C=CC1=CC=CC=C1)OC WDXULVFWZQBIBC-RVOJJYEQSA-N 0.000 claims 1
- HRTFPUCBELFSAY-PGFAXQRZSA-N C(#N)N=C1S/C(/C(N1)=O)=C/C1=CC(=CC=C1)C=CC1=CC=CC=C1 Chemical compound C(#N)N=C1S/C(/C(N1)=O)=C/C1=CC(=CC=C1)C=CC1=CC=CC=C1 HRTFPUCBELFSAY-PGFAXQRZSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
Landscapes
- 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.
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 (en) | 1998-07-14 | 1999-11-12 | Novel 2-(n-cyanoimino)thiazolidin-4-one derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI20690A SI20690A (sl) | 2002-04-30 |
| SI20690B true SI20690B (sl) | 2008-02-29 |
Family
ID=26440209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9920104A SI20690B (sl) | 1998-07-14 | 1999-11-12 | Novi derivati 2-(N-cianoimino)tiazolidin-4-ona |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2000026438A (sl) |
| SI (1) | SI20690B (sl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001036402A1 (en) * | 1998-07-14 | 2001-05-25 | Fujimoto Brothers Co., Ltd. | Novel 2-(n-cyanoimino)thiazolidin-4-one derivatives |
| JP2001199888A (ja) | 2000-01-24 | 2001-07-24 | Fujimoto Brothers:Kk | 糖尿病治療剤 |
| MX2009013332A (es) | 2007-06-08 | 2010-01-25 | Mannkind Corp | Inhibidores de ire-1 alfa. |
| JP5885657B2 (ja) * | 2010-03-04 | 2016-03-15 | 勝 岡部 | 妊娠高血圧症候群モデル動物とその治療方法 |
-
1998
- 1998-07-14 JP JP10232216A patent/JP2000026438A/ja not_active Withdrawn
-
1999
- 1999-11-12 SI SI9920104A patent/SI20690B/sl not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000026438A (ja) | 2000-01-25 |
| SI20690A (sl) | 2002-04-30 |
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| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the prs date | ||
| OU02 | Decision according to article 73(2) ipa 1992, publication of decision on partial fulfilment of the invention and change of patent claims |
Effective date: 20080104 |
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| SP73 | Change of data on owner |
Owner name: FUJIMOTO CO., LTD.; JP Effective date: 20101020 |
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| KO00 | Lapse of patent |
Effective date: 20150717 |