HRP20150842T1 - Derivati ciklopentilakrilamida - Google Patents
Derivati ciklopentilakrilamida Download PDFInfo
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- HRP20150842T1 HRP20150842T1 HRP20150842TT HRP20150842T HRP20150842T1 HR P20150842 T1 HRP20150842 T1 HR P20150842T1 HR P20150842T T HRP20150842T T HR P20150842TT HR P20150842 T HRP20150842 T HR P20150842T HR P20150842 T1 HRP20150842 T1 HR P20150842T1
- Authority
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- Croatia
- Prior art keywords
- acrylamide
- phenyl
- difluorocyclopentyl
- cyclopropylsulfonyl
- methylsulfonyl
- Prior art date
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- VQHNAVNFDQCDFF-UHFFFAOYSA-N 2-cyclopentylprop-2-enamide Chemical class NC(=O)C(=C)C1CCCC1 VQHNAVNFDQCDFF-UHFFFAOYSA-N 0.000 title 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 105
- 150000001875 compounds Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 19
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 15
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- -1 hydroxylamino group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 101710185622 Pyrrolidone-carboxylate peptidase Proteins 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- YACKEPLHDIMKIO-UHFFFAOYSA-L methylphosphonate(2-) Chemical compound CP([O-])([O-])=O YACKEPLHDIMKIO-UHFFFAOYSA-L 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
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- 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/77—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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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
- C07D213/72—Nitrogen atoms
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
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- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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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- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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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- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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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Claims (22)
1. Spoj prikazan općom formulom (1) ili njegova farmaceutski prihvatljiva sol:
[image]
naznačen time da su R1 i R2 svaki neovisno vodikov atom, atom halogena, amino skupina, hidroksil skupina, hidroksilamino skupina, nitro skupina, cijano skupina, sulfamoil skupina, C1 do C6 alkil skupina, C1 do C6 alkoksi skupina, C1 do C6 alkilsulfanil skupina, C1 do C6 alkilsulfinil skupina, C1 do C6 alkilsulfonil skupina, C1 do C6 alkoksi-C1 do C6alkilsulfonil skupina i A je supstituirana ili nesupstituirana heteroaril skupina.
2. Spoj prema zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time da su R1 i R2 svaki neovisno atom vodika, ili C1 do C6 alkilsulfonil skupina.
3. Spoj prema zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time da je R1 atom vodika i R2 je C1 do C6 alkilsulfonil skupina.
4. Spoj prema zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time da R1 je atom vodika i R2 je ciklopropilsulfonil skupina.
5. Spoj prema zahtjevu 1 ili njegova farmaceutski prihvatljiva sol, naznačen time da je R1 atom vodika i R2 je metilsulfonil skupina.
6. Spoj prema bilo kojem od zahtjeva 1 do 5 ili njegova farmaceutski prihvatljiva sol, naznačen time da je spoj prikazan općom formulom (1a):
[image]
pri čemu su R1, R2 i A kao što je gore definirano.
7. Spoj prema bilo kojem od zahtjeva 1 do 5 ili njegova farmaceutski prihvatljiva sol, naznačen time da je spoj prikazan općom formulom (1b):
[image]
pri čemu su R1, R2 i A kao što je gore definirano.
8. Spoj prema bilo kojem od zahtjeva 1 do 7 ili njegova farmaceutski prihvatljiva sol, naznačen time da je A nesupstituirana heteroaril skupina ili heteroaril skupina koja je mono supstituirana sa atomom halogena, C1 do C6 alkil skupinom proizvoljno supstituiranom s atomom halogena ili hidroksil skupinom, C1 do C6 alkoksi skupina proizvoljno supstituirana s atomom halogena ili hidroksil skupinom, nitro skupinom, cijano skupinom, ili skupinom prikazanom formulom –(O)p(CH2)mC(O)OR3, pri čemu je R3 atom vodika ili C1 do C6 alkil skupina, m je cijeli broj od 0 do 2 i p je 0 ili 1.
9. Spoj prema bilo kojem od zahtjeva 1 do 7 ili njegova farmaceutski prihvatljiva sol, naznačen time da je A heteroaril skupina koja je mono supstituirana s C1 do C6alkilsulfanil skupinom koja je skupinom supstituirana s atomom halogena ili hidroksil skupinom.
10. Spoj prema zahtjevu 8 ili 9 ili njegova farmaceutski prihvatljiva sol, naznačen time da je A nesupstituiran ili monosupstituiran petero ili šesteročlani heteroaromatski prsten, heteroaromatski prsten sadrži 1 do 3 heteroatoma izabrana od atoma sumpora, atoma kisika i atoma dušika, od kojih je atom dušika susjedan atomu koji je vezan za prsten.
11. Spoj prema bilo kojem od zahtjeva 8 ili 9 ili njegova farmaceutski prihvatljiva sol, naznačen time da je A nesupstituiran ili monosupstituiran spojeni heterocikal koji ima petero ili šesteročlani heteroaromatski prsten, heteroaromatski prsten sadrži 1 do 3 heteroatoma izabrana od atoma sumpora, atoma kisika i atoma dušika, jedan od heteroatoma je atom dušika susjedan atomu koji je vezan za prsten.
12. Spoj prema bilo kojem od zahtjeva 8 ili 9 ili njegova farmaceutski prihvatljiva sol, naznačen time da je A nesupstituiran ili monosupstituiran heteroaromatski prsten odabran od slijedećih prstena:
[image]
[image]
[image]
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13. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time da je odabran iz skupine koju čine
(E)-3-[(1α,3α,4α)-3,4-difluorociklopentil]-2-[4-(metilsulfonil)fenil]-N-(tiazol-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-fluorotiazol-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-N-(5-klorotiazol-2-il)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(4-metiltiazol-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(5-metiltiazol-2-il)akrilamid, (+)-(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[4-(2,2-dimetil-1,3-dioksolan-4-il)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (-)-(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[4-(2,2-dimetil-1,3-dioksolan-4-il)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (+)-(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[4-(1,2-dihidroksietil)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (-)-(E)-3-[(1α, 3α, 4α)-3,4-difluorociklo pentil]-N-[4-(1,2-dihidroksietil)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-N-[4-terc-butiltiazol-2-il]-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-{4-[2-(tetrahidro-2H-piran-2-iloksi)etil]tiazol-2-il}akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorocikclopentil]-N-[4-(2-hidroksietil)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(N,N-dimetilsulfamoil) tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil)-N-[5-(4-metilpiperazin-1-ilsulfonil)tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(1,2,4-tiadiazol-5-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(3-metil-1,2,4-tiadiazol-5-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(3-etil-1,2,4-tiadiazol-5-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(3-metoksi-1,2,4-tiadiazol-5-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(piridin-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-fluoropiridin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-N-(5-kloropiridin-2-il)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-[5-(metiltio)piridin-2-il]akrilamid, (E)-N-(5-ciklopropilpiridin-2-il)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(hidroksimetil)piridin-2-il)-2-(4-(metilsulfonil) fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(N,N-dimetilsulfamoil) piridin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-(pirazin-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-metilpirazin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-etilpirazin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-metoksipirazin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metiletoksi)pirazin-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metoksietoksi)pirazin-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(3-metoksipropoksi)pirazin-2-il]-2-(4-(metilsulfonil)fenil) akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-etoksietoksi)pirazin-2-il-]-2-(4-(metilsulfonil) fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-{5-[2-(metiltio)etoksi]pirazin-2-il}akrilamid, (E)-2-(4-(metilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-hidroksietiltio)pirazin-2-il]akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-{5-[2-(tetrahidro-2H-piran-2-iloksi)etoksi]pirazin-2-il]akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-(hidroksietoksi)pirazin-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(4R)-2,2-dimetil-1,3-dioksolan-4-il]pirazin-2-il}-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-[(4S)-2,2-dimetil-1,3-dioksolan-4-ilpirazin-2-il)-2-(4-(metilsulfonil)fenil) akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(2R)-1,2-dihidroksietil]pirazin-2-il}-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(2S)-1,2-dihidroksietil]pirazin-2-il}-2-(4-(metilsulfonil)fenil)akrilamid, dietil 5-{(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil-2-(4-(metilsulfonil)fenil)]akrilamid)pirazin-2-il fosfonat, dietil (5-{(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil-2-(4-(metilsulfonil)fenil)]akrilamid}pirazin-2-il)metilfosfonat, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-metil-1H-pirazol-3-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-etil-1H-pirazol-3-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(difluorometil)-1H-pirazol-3-il]-2-(4-(metilsulfonil) fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(2-fluoroetil)-1H-pirazol-3-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-(4-(metilsulfonil)fenil)-N-[1-(2,2,2-trifluoroetil)-1H-pirazol-3-il]akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(2-hidroksietil)-1H-pirazol-3-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(2-hidroksi-2-metilpropil)-1H-pirazol-3-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-{[(4R)-2,2-dimetil-1,3-dioksolan-4-il]metil}-1H-pirazol-3-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-{[(4S)-2,2-dimetil-1,3-dioksolan-4-il]metil}-1H-pirazol-3-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{1-[(2R)-2,3-dihidroksipropil]-1H-pirazol-3-il)-2-(4-(metilsulfonil)fenil) akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{1-[(2S)-2,3-dihidroksipropil]-1H-pirazol-3-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(izoksazol-3-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(6-metoksibenzo[d]tiazol-2-il)-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[6-(difluorometoksi)benzo[d]tiazol-2-il]-2-(4-(metilsulfonil)fenil)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metoksietoksi)tiazolo[5,4-b]piridin-2-il]-2-(4-metilsulfonil)fenil)akrilamid, i etil (E)-2-(2-[(R)-2-(4-(metilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid] tiazolo[5,4-b]piridin-2-iloksi]acetat.
14. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, izabrano iz grupe koju čine
(E)-2-[4-(ciklopropilsulfonil)fenil]-3-[(1α,3α,4α)-3,4-difluorociklopentil)-N-(tiazol-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil)-N-(5-fluorotiazol-2-il)akrilamid, (E)-N-(5-bromotiazol-2-il)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil] akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(4-metiltiazol-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-metiltiazol-2-il)akrilamid, (+)-(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[4-(2,2-dimetil-1,3-dioksolan-4-il)tiazol-2-il]akrilamid, (-)-(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[4-(2,2-dimetil-1,3-dioksolan-4-il)tiazol-2-il]akrilamid, (E)-N-(4-terc-butiltiazol-2-il)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklo pentil]-N-[5-(4-metilpiperazin-1-ilsulfonil)tiazol-2-il]akrilamid, metil 3-{2-[(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid]tiazol-4-il] propionat, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1,2,4-tiadiazol-5-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(3-metil-1,2,4-tiadiazol-5-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(3-etil-1,2,4-tiadiazol-5-il) akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(3-fenil-1,2,4-tiadiazol-5-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(piridin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(metiltio)piridin-2-il]akrilamid, (E)-N-(5-ciklopropilpiridin-2-il)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(hidroksimetil)piridin-2-il] akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(N,N-dimetilsulfamoil)piridin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(pirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-metilpirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-etilpirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(5-metoksipirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(metiltio)pirazin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metiletoksi)pirazin-2-il ]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metoksietoksi)pirazin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(3-metoksipropoksi)pirazin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-etoksietoksi)pirazin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[2-(metiltio)etoksilpirazin-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[2-(tetrahidro-2H-piran-2-iloksi)etoksi]pirazin-2-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-(hidroksietoksi)pirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(4R)-2,2-dimetil-1,3-dioksolan-4-il]pirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(4S)-2,2-dimetil-1,3-dioksolan-4-il]pirazin-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(2R)-1,2-dihidroksietil]pirazin-2-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{5-[(2S)-1,2-dihidroksietil]pirazin-2-il)akrilamid, dietil 5-{(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid}pirazin-2-il fosfonat, dietil (5-{(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid}pirazin-2-ilmetilfosfonat, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-metil-1H-pirazol-3-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-etil-1H-pirazol-3-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(2-(2-fluoroetil)-1H-pirazol-3-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(2-hidroksietil)-1H-pirazol-3-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[1-(2-hidroksi-2-metilpropil)-1H-pirazol-3-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-{[(4R)-2,2-dimetil-1,3-dioksolan-4-il]metil}-1H-pirazol-3-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-{[(4S)-2,2-dimetil-1,3-dioksolan-4-il]metil}-1H-pirazol-3-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil) fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-{1-[(2R)-2,3-dihidroksipropil]-1H-pirazol-3-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α,3α,4α)-3,4-difluorociklopentil]-N-{1-[(2S)-2,3-dihidroksipropil]-1H-pirazol-3-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(1-{[(4S)-2,2-dimetil-1,3-dioksolan-4-il]metil)-1H-pirazol-3-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α,3α,4α)-3,4-difluorociklopentil]-N-{1-[(2S)-2,3-dihidroksipropyl]-1H-pirazol-3-il}akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N- (izoksazol-3-il)akrilamid, (E)-N-(benzo[d]tiazol-2-il)-2-(4-(ciklopropilsulfonil) fenil) -3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(6-metoksibenzo[d]tiazol-2-il)akrilamid, (E)-2-(4-(ciklopropilsulfonil) fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[6-difluorometoksi)benzo[d]tiazol-2-il]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α,3α,4α)-3,4-difluorociklopentil]-N-(6-fluorobenzo[d]tiazol-2-il)akrilamid, 1-metiletil 2-{(E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α,3α,4α)-3,4-difluorociklo pentil]akrilamid}benzo[d]tiazol-6-karboksilat, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-(tiazolo[5,4-b]piridin-2-il)akrilamid, (E)-N-(5-butoksitiazolo[5,4-b]piridin-2-il)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid, (E)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-N-[5-(2-metoksietoksi)tiazolo[5,4-b]piridin-2-il)akrilamid, i etil 2-{2-[(R)-2-(4-(ciklopropilsulfonil)fenil)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]akrilamid]tiazolo[5,4-b]piridin-5-iloksi)acetat.
15. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time da je odabran iz skupine koju čine
(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(etilsulfonil)fenil]-N-(tiazol-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(etilsulfonil)fenil]-N-(5-metilpirazin-2-il)akrilamid, i (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(etilsulfonil)fenil]-N-(1-metil-1H-pirazol-3-il)akrilamid.
16. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time da je odabran iz skupine koju čine
(E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(2-metoksietilsulfonil)fenil]-N-(tiazol-2-il)akrilamid, (E)-3-[(1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(2-metoksietilsulfonil)fenil]-N-(5-metilpirazin-2-il)akrilamid i (E)-3-[1α, 3α, 4α)-3,4-difluorociklopentil]-2-[4-(2-metoksietilsulfonil)fenil]-N-(1-metil-1H-pirazol-3-il)akrilamid.
17. Spoj prema bilo kojem zahtjevu od 1 do 16 ili njegova farmaceutski prihvatljiva sol naznačen time da je za uporabu za liječenje ili prevenciju dijabetesa.
18. Upotreba spoja prema bilo kojem zahtjevu od 1 do 16 ili njegove farmaceutski prihvatljive soli naznačena time da je za proizvodnju farmaceutika za liječenje ili prevenciju dijabetesa.
19. Farmaceutska kompozicija, naznačena time da sadrži spoj prema bilo kojem zahtjevu od 1 do 16 ili njegovu farmaceutski prihvatljivu sol i farmaceutski prihvatljiv nosač.
20. Spoj prikazan općom formulom (2):
[image]
naznačen time da su R1 i R2 svaki neovisno vodikov atom, atom halogena, amino skupina, hidroksil skupina, hidroksilamino skupina, nitro skupina, cijano skupina, sulfamoil skupina, C1 do C6 alkil skupina, C1 do C6 alkoksi skupina, C1 do C6 alkilsulfanil skupina, C1 do C6 alkilsulfinil, C1 do C6 alkilsulfonil, ili C1 do C6 alkoksi-C1 do C6alkilsulfonil skupina.
21. Spoj prema zahtjevu 20, naznačen time da je R1 atom vodika i R2 je ciklopropilsulfonil skupina.
22. Spoj prema zahtjevu 20, naznačen time da je R1 atom vodika i R2 je metilsulfonil skupina.
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