HRP20100714T1 - Derivati 5-(benz-(z)-iliden)-tiazolidin-4-ona kao imunosupresivna sredstva - Google Patents
Derivati 5-(benz-(z)-iliden)-tiazolidin-4-ona kao imunosupresivna sredstva Download PDFInfo
- Publication number
- HRP20100714T1 HRP20100714T1 HR20100714T HRP20100714T HRP20100714T1 HR P20100714 T1 HRP20100714 T1 HR P20100714T1 HR 20100714 T HR20100714 T HR 20100714T HR P20100714 T HRP20100714 T HR P20100714T HR P20100714 T1 HRP20100714 T1 HR P20100714T1
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- Croatia
- Prior art keywords
- thiazolidin
- benz
- ylidene
- hydroxy
- ethoxy
- Prior art date
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- 229960003444 immunosuppressant agent Drugs 0.000 title 1
- 239000003018 immunosuppressive agent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 43
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical class O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 claims abstract 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- -1 5,6,7,8-tetrahydronaphth-1-yl Chemical group 0.000 claims abstract 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract 15
- 150000002367 halogens Chemical class 0.000 claims abstract 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 9
- 239000000203 mixture Substances 0.000 claims abstract 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 230000000877 morphologic effect Effects 0.000 claims abstract 2
- 239000002904 solvent Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 210000000987 immune system Anatomy 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims 1
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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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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/426—1,3-Thiazoles
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Abstract
Farmaceutski sastav, naznacen time, da on obuhvaca barem jedan derivat tiazolidin-4-ona Opce formule (I) Opca formula (I) gdje: R1 predstavlja nizi alkil; nizi alkenil; cikloalkil; 5,6,7,8-tetrahidronaft-1-il; 5,6,7,8-tetrahidronaft-2-il; fenilna skupina; ili fenilna skupina neovisno mono-, di- ili tri-supstituirana nizim alkilom, halogenom, nizim alkoksi, ili -CF3;R2 predstavlja nizi alkil; alil; ciklopropil; ciklobutil; ciklopentil; ili mono- ili di-nizi alkilamino; R3 predstavlja -O-CR7R8-CR9R10-(CR11R12)n-O-R13; R4 predstavlja vodik; hidroksi; nizi alkoksi; nizi alkil; ili halogen; R5 i R6 svaki predstavlja neovisno nizi alkil; R7 predstavlja vodik, nizi alkil, ili hidroksimetil; R8, R9, R11 i R12 svaki predstavlja neovisno vodik ili metil; R10 predstavlja vodik ili nizi alkil; i u slucaju kada n predstavlja cijeli broj 1, tada R10 dodatno predstavlja nizi alkoksi, hidroksi, -NH2, -NHR5 ili -NR5R6;R13 predstavlja vodik; nizi alkil; hidroksikarbonil-nizi alkil; 1-gliceril; ili 2-gliceril; n predstavlja cijeli broj 0 ili 1; i konfiguracijske izomere, opticki ciste enantiomere, mjesavine enantiomera kao sto su racemati, diastereomeri, mjesavine diastereomera, diastereomerni racemati, mjesavine diastereomernih racemata i mezo-oblik, kao i farmaceutski prihvatljive soli, komplekse otapala, i morfoloske oblike, te inertne prijenosne materijale; pri cemu izrazi "nizi alkil", "nizi alkoksi", "mono- ili di-nizi alkilamino", i "nizi alkenil" imaju sljedeca znacenja:"nizi alkil", sam ili u kombinaciji s drugim skupinama, znaci zasicene, ravnolancane ili razgranate skupine lanaca s jednim do sedam atoma ugljika;"nizi alkoksi" znaci R-O skupina, gdje R je nizi alkil;"mono- ili di-nizi alkilamino" znaci R'-NH- ili R'-NR''- skupina, gdje su R' i R'' svaki neovisno nizi alkil; i"nizi alkenil", sam ili u kombinaciji s drugim skupinama, znaci ravnolancane ili razgranate skupine lanaca koje sadrze olefinsku vezu i tri do sedam atoma ugljika. Patent sadrzi jos 23 patentna zahtjeva.
Claims (24)
1. Farmaceutski sastav, naznačen time, da on obuhvaća barem jedan derivat tiazolidin-4-ona Opće formule (I)
[image]
Opća formula (I)
gdje:
R1 predstavlja niži alkil; niži alkenil; cikloalkil; 5,6,7,8-tetrahidronaft-1-il; 5,6,7,8-tetrahidronaft-2-il; fenilna skupina; ili fenilna skupina neovisno mono-, di- ili tri-supstituirana nižim alkilom, halogenom, nižim alkoksi, ili -CF3;
R2 predstavlja niži alkil; alil; ciklopropil; ciklobutil; ciklopentil; ili mono- ili di-niži alkilamino;
R3 predstavlja -O-CR7R8-CR9R10-(CR11R12)n-O-R13;
R4 predstavlja vodik; hidroksi; niži alkoksi; niži alkil; ili halogen;
R5 i R6 svaki predstavlja neovisno niži alkil;
R7 predstavlja vodik, niži alkil, ili hidroksimetil;
R8, R9, R11 i R12 svaki predstavlja neovisno vodik ili metil;
R10 predstavlja vodik ili niži alkil; i u slučaju kada n predstavlja cijeli broj 1, tada R10 dodatno predstavlja niži alkoksi, hidroksi, -NH2, -NHR5 ili -NR5R6;
R13 predstavlja vodik; niži alkil; hidroksikarbonil-niži alkil; 1-gliceril; ili 2-gliceril;
n predstavlja cijeli broj 0 ili 1;
i konfiguracijske izomere, optički čiste enantiomere, mješavine enantiomera kao što su racemati, diastereomeri, mješavine diastereomera, diastereomerni racemati, mješavine diastereomernih racemata i mezo-oblik, kao i farmaceutski prihvatljive soli, komplekse otapala, i morfološke oblike, te inertne prijenosne materijale;
pri čemu izrazi “niži alkil”, “niži alkoksi”, “mono- ili di-niži alkilamino”, i “niži alkenil” imaju sljedeća značenja:
“niži alkil”, sam ili u kombinaciji s drugim skupinama, znači zasićene, ravnolančane ili razgranate skupine lanaca s jednim do sedam atoma ugljika;
“niži alkoksi” znači R-O skupina, gdje R je niži alkil;
“mono- ili di-niži alkilamino” znači R'-NH- ili R'-NR''- skupina, gdje su R' i R'' svaki neovisno niži alkil; i
“niži alkenil”, sam ili u kombinaciji s drugim skupinama, znači ravnolančane ili razgranate skupine lanaca koje sadrže olefinsku vezu i tri do sedam atoma ugljika.
2. Farmaceutski sastav prema zahtjevu 1, naznačen time, da spomenuti derivati tiazolidin-4-ona su (Z,Z)-izomeri prema Općoj formuli (I) u zahtjevu 1.
3. Uporaba jednog ili više spojeva Opće formule (I) prema zahtjevu 1, naznačena time, da služi za proizvodnju lijeka za uporabu u prevenciji ili liječenju poremećaja povezanih s aktiviranim sustavom imuniteta.
4. Novi derivati tiazolidin-4-ona Opće formule (II)
[image]
Opća formula (II)
gdje:
R14 predstavlja niži alkil; niži alkenil; cikloalkil; 5,6,7,8-tetrahidronaft-1-il; 5,6,7,8-tetrahidronaft-2-il; fenilnu skupinu; ili fenilnu skupinu mono-, di- ili tri-supstituiranu neovisno sa nižim alkilom, halogenom, nižim alkoksi, ili -CF3;
R15 predstavlja niži alkil; alil; ciklopropil; ciklobutil; ciklopentil; ili mono- ili di-niži alkilamino;
R16 predstavlja vodik; hidroksi; niži alkoksi; niži alkil; ili halogen;
R17 predstavlja vodik, niži alkil, ili hidroksimetil;
R18, R19, R21 i R22 svaki predstavlja neovisno vodik ili metil;
R20 predstavlja vodik ili niži alkil; i u slučaju kada m predstavlja cijeli broj 1, tada R20 dodatno predstavlja niži alkoksi, hidroksi, -NH2, -NHR5 ili -NR5R6, pri čemu svaki R5 i R6 neovisno predstavlja niži alkil;
R23 predstavlja vodik; niži alkil; hidroksikarbonil-niži alkil; 1-gliceril; ili 2-gliceril;
m predstavlja cijeli broj 0 ili 1;
i konfiguracijski izomeri, optički čisti enantiomeri, mješavine enantiomera kao što su racemati, diastereomeri, mješavine diastereomera, diastereomerni racemati, mješavine diastereomernih racemata i mezo-oblik, kao i farmaceutski prihvatljive soli;
i pri čemu izrazi “niži alkil”, “niži alkoksi”, “mono- ili di-niži alkilamino”, i “niži alkenil” imaju sljedeća značenja:
“niži alkil”, sam ili u kombinaciji s drugim skupinama, znači zasićene, ravnolančane ili razgranate skupine lanaca s jednim do sedam atoma ugljika;
“niži alkoksi” znači R-O skupina, gdje R je niži alkil;
“mono- ili di-niži alkilamino” znači R'-NH- ili R'-NR''- skupina, gdje su R' i R'' svaki neovisno niži alkil; i
“niži alkenil”, sam ili u kombinaciji s drugim skupinama, znači ravnolančane ili razgranate skupine lanaca koje sadrže olefinsku vezu i tri do sedam atoma ugljika.
5. Derivati tiazolidin-4-ona prema zahtjevu 4, naznačeni time, da spomenuti derivati tiazolidin-4-ona prema formuli (II) su (Z,Z) izomeri.
6. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R14 predstavlja nesupstituiranu, ili mono- ili di-supstituiranu fenilnu skupinu.
7. Derivati tiazolidin-4-ona prema bilo kojem zahtjevu 4 do 6, naznačeni time, da R14 predstavlja nesupstituiranu, ili mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom.
8. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R15 predstavlja niži alkil.
9. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R16 predstavlja halogen ili metil.
10. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da m predstavlja cijeli broj 0, a R17, R18, R19 i R20 predstavljaju vodik.
11. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da m predstavlja cijeli broj 1, R17, R18, R19, R21 i R22 predstavljaju vodik, a R20 predstavlja hidroksi.
12. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R23 predstavlja vodik.
13. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da m predstavlja cijeli broj 0, a R17, R18, R19, R20 i R23 predstavljaju vodik.
14. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da m predstavlja cijeli broj 1, R17, R18, R19, R21, R22 i R23 predstavljaju vodik, a R20 predstavlja hidroksi.
15. Derivati tiazolidin-4-ona prema zahtjevima 4 do 9, naznačeni time, da R14 predstavlja nesupstituiranu, ili a mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom, a R15 predstavlja niži alkil.
16. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R14 predstavlja nesupstituiranu, ili a mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom, m predstavlja cijeli broj 0, a R17, R18, R19, R20 i R23 predstavljaju vodik.
17. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R14 predstavlja nesupstituiranu, ili a mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom, m predstavlja cijeli broj 1, R17, R18, R19, R21, R22 i R23 predstavljaju vodik, a R20 predstavlja hidroksi.
18. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R14 predstavlja nesupstituiranu, ili a mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom, R15 predstavlja niži alkil, R16 predstavlja metil ili halogen, m predstavlja cijeli broj 0, a R17, R18, R19, R20 i R23 svaki predstavljaju vodik.
19. Derivati tiazolidin-4-ona prema zahtjevima 4 i 5, naznačeni time, da R14 predstavlja nesupstituiranu, ili a mono- ili di-supstituiranu fenilnu skupinu, supstituiranu metilom ili halogenom, R15 predstavlja niži alkil, R16 predstavlja metil ili halogen, m predstavlja cijeli broj 1, R17, R18, R19, R21 R22, i R23 predstavljaju vodik, a R20 predstavlja hidroksi.
20. Derivat tiazolidin-4-ona prema bilo kojem zahtjevu 4 do 19, naznačen time, da je odabran iz skupine koja sadrži:
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 4
{2-[4-(2-([Z]-izopropilimino)-4-okso-3-fenil-tiazolidin-5-[Z]-ilidenmetil)-fenoksi]-etoksi}-osctena kiselina, 5
5-{4-[2-(2,3-dihidroksi-propoksi)-etoksi]-benz[Z]iliden}-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 6
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 7
5-[3-fluilio-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 8
5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 9
5-[4-(2-hidroksi-etoksi)-3-metoksi-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 10
5-[4-(3-hidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 11
5-[4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 12
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 13
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 18
5-{4-[2-(2,3-dihidroksi-propoksi)-etoksi]-benz[Z]iliden}-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 19
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 20
5-[4-(2-hidroksi-etoksi)-3-metoksi-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 22
5-[4-(3-hidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 23
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 24
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-m-tolil-tiazolidin-4-on, 29
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-m-tolil-tiazolidin-4-on, 30
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-m-tolil-tiazolidin-4-on, 31
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-p-tolil-tiazolidin-4-on, 34
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-p-tolil-tiazolidin-4-on, 35
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-p-tolil-tiazolidin-4-on, 36
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 40
5-{4-[2-(2,3-dihidroksi-propoksi)-etoksi]-benz[Z]iliden}-3-(2,3-dimetil-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 41
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 42
3-(2,3-dimetil-fenil)-5-[3-fluilio-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 43
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 44
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-3-metoksi-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 45
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 46
3-(2,4-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 49
3-(2,6-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 51
3-(2-kloro-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 55
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2-kloro-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 56
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2-kloro-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 57
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-(2-metoksi-fenil)-tiazolidin-4-on, 59
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-(2-metoksi-fenil)-tiazolidin-4-on, 60
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-(4-metoksi-fenil)-tiazolidin-4-on, 64
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-(4-metoksi-fenil)-tiazolidin-4-on, 65
3-alil-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 69
3-alil-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 70
3-alil-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 71
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 74
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 75
5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 76
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 77
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 80
5-[4-(3-hidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 81
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 82
5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 83
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 84
(R)-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 85
(S)-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 86
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-propilimino)-tiazolidin-4-on, 89
5-{4-[2-(2,3-dihidroksi-propoksi)-etoksi]-benz[Z]iliden}-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 90
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 91
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-2-([Z]-propilimino)-tiazolidin-4-on, 92
3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-3-metoksi-benz[Z]iliden]-2-([Z]-propilimino)-tiazolidin-4-on, 93
5-[4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 94
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 95
2-([Z]-tert-butilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 97
2-(dimetil-hidrazono)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 100
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-(dimetil-hidrazono)-3-fenil-tiazolidin-4-on, 101
2-([Z]-etilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 102
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-etilimino)-3-fenil-tiazolidin-4-on, 103
2-([Z]-etilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-o-tolil-tiazolidin-4-on, 107
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-etilimino)-3-o-tolil-tiazolidin-4-on, 108
3-(2,3-dimetil-fenil)-2-([Z]-etilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-tiazolidin-4-on, 109
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-etilimino)-tiazolidin-4-on, 110
2-([Z]-butilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 111
2-([Z]-butilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 112
2-([Z]-butilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-o-tolil-tiazolidin-4-on, 113
2-([Z]-butilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-o-tolil-tiazolidin-4-on, 114
2-([Z]-butilimino)-3-(2,3-dimetil-fenil)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-tiazolidin-4-on, 115
2-([Z]-butilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-tiazolidin-4-on, 116
2-([Z]-sec-butilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 120
2-([Z]-ciklopropilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 123
3-cikloheksil-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-tiazolidin-4-on, 124
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-cikloheksil-2-([Z]-izopropilimino)-tiazolidin-4-on, 125
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-izopropil-2-([Z]-izopropilimino)-tiazolidin-4-on, 129
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-izopropil-2-([Z]-izopropilimino)-tiazolidin-4-on, 130
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-izopropil-2-([Z]-izopropilimino)-tiazolidin-4-on, 131
2-([Z]-alilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 149
2-([Z]-alilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 150
3-alil-2-([Z]-alilimino)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-tiazolidin-4-on, 154
3-alil-2-([Z]-alilimino)-5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-tiazolidin-4-on, 155
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-metilimino)-3-fenil-tiazolidin-4-on, i 156
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-metilimino)-tiazolidin-4-on. 157
21. Derivat tiazolidin-4-ona prema bilo kojem zahtjevu 4 do 19, naznačen time, da je odabran iz skupine koja sadrži:
5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 4
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-fenil-tiazolidin-4-on, 7
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-izopropilimino)-3-o-tolil-tiazolidin-4-on, 24
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 42
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-izopropilimino)-tiazolidin-4-on, 46
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 75
5-[4-(2-hidroksi-etoksi)-3-metil-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 76
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-fenil-2-([Z]-propilimino)-tiazolidin-4-on, 77
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 84
(R)-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 85
(S)-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on, 86
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 91
5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-propilimino)-tiazolidin-4-on, 95
2-(dimetil-hidrazono)-5-[4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-fenil-tiazolidin-4-on, 100
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-2-([Z]-etilimino)-3-fenil-tiazolidin-4-on, 103
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-(2,3-dimetil-fenil)-2-([Z]-etilimino)-tiazolidin-4-on, i 110
5-[3-kloro-4-(2-hidroksi-etoksi)-benz[Z]iliden]-3-izopropil-2-([Z]-izopropilimino)-tiazolidin-4-on. 130
22. Derivat tiazolidin-4-ona prema bilo kojem zahtjevu 4 do 19, naznačen time, da je (R)-5-[3-kloro-4-(2,3-dihidroksi-propoksi)-benz[Z]iliden]-2-([Z]-propilimino)-3-o-tolil-tiazolidin-4-on.
23. Derivat tiazolidin-4-ona prema bilo kojem zahtjevu 4 do 22, naznačen time, da se upotrebljava kao lijek.
24. Spoj Opće formule (II) prema zahtjevu 4, naznačen time, da je njegova uporaba u prevenciji ili liječenju poremećaja povezanih s aktiviranim sustavom imuniteta.
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| EP0313072 | 2003-11-21 | ||
| PCT/EP2004/012953 WO2005054215A1 (en) | 2003-11-21 | 2004-11-16 | 5-(benz- (z) -ylidene) -thiazolidin-4-one derivatives as immunosuppressant agents |
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| AU2007323042B2 (en) | 2006-11-23 | 2012-12-20 | Actelion Pharmaceuticals Ltd | New process for the preparation of 2-imino-thiazolidin-4-one derivatives |
| LT2278960T (lt) | 2008-03-17 | 2017-02-10 | Actelion Pharmaceuticals Ltd. | S1p1 receptoriaus selektyvaus agonisto dozavimo režimas |
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