HRP20180160T1 - Spiro-oksazoloni - Google Patents

Spiro-oksazoloni Download PDF

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HRP20180160T1
HRP20180160T1 HRP20180160TT HRP20180160T HRP20180160T1 HR P20180160 T1 HRP20180160 T1 HR P20180160T1 HR P20180160T T HRP20180160T T HR P20180160TT HR P20180160 T HRP20180160 T HR P20180160T HR P20180160 T1 HRP20180160 T1 HR P20180160T1
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Croatia
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spiro
oxazol
piperidin
dihydro
inden
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HRP20180160TT
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Valerie Runtz-Schmitt
Patrick Schnider
Cosimo Dolente
Bernhard FASCHING
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F. Hoffmann - La Roche Ag
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
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    • A61P25/22—Anxiolytics
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/10—Spiro-condensed systems
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    • C07D—HETEROCYCLIC COMPOUNDS
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (15)

1. Spoj, naznačen time, da ima formulu I [image] u kojoj X1 je C-R1 ili N; X2 je C-R1 ili N; X3 je C-R1 ili N; X4 je C-R1 ili N; pri čemu samo jedan od X1, X2, X3 i X4 je N; svaki R1 zasebno je odabran iz skupine koju čine vodik, halogen, hidroksi, C1-6-alkil i C1-6-alkoksi; R2 odabran je iz skupine koju čine H i C1-6-alkil; R3 odabran je iz skupine koju čine H i C1-6-alkil; ili R2 i R3 zajedno su =O; Y1 je C-R4 ili N; Y2 je C-R4 ili N; Y3 je C-R4 ili N; Y4 je C-R4 ili N; pri čemu samo jedan od Y1, Y2, Y3 i Y4 je N; svaki R4 zasebno je odabran iz skupine koju čine vodik, halogen, halogen-C1-6-alkil, hidroksi, C1-6-alkil, C1-6-alkoksi i Si(C1-6,-alkil)3; m je 1, 2 ili 3; i n je 0 ili 1; ili njihove farmaceutski prihvatljive soli.
2. Spoj prema patentnom zahtjevu 1, naznačen time, da X1 je C-H ili N; X2 je C-R1 ili N; X3 je C-R1; X4 je C-H ili N; pri čemu samo jedan od X1, X2, X3 i X4 je N; svaki R1 zasebno je odabran iz skupine koju čine vodik, halogen, hidroksi i C1-6-alkil; R2 odabran je iz skupine koju čine H i C1-6-alkil; R3 odabran je iz skupine koju čine H i C1-6-alkil; ili R2 i R3 zajedno su =O; Y1 je C-H ili N; Y2 je C-R4 ili N; Y3 je C-R4 ili N; Y4 je C-H ili N; pri čemu samo jedan od Y1, Y2, Y3 i Y4 je N; svaki R4 zasebno je odabran iz skupine koju čine vodik, halogen, hidroksi i C1-6-alkil; m je 1; i n je 1.
3. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da svaki od X1, X2, X3 i X4 je CH; svaki od R2 i R3 je H; svaki od m i n je 1; svaki od Y1 i Y4 je CH; i svaki od Y2 i Y3 je CF.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2, naznačen time, da svaki od X1, X2 i X3 je CH i X4 je N; svaki od R2 i R3 jeC1-6-alkil; svaki od m i n je 1; i svaki od Y1, Y2, Y3 i Y4 je CH.
5. Intermedijer spoja formule I prema patentnom zahtjevu 1, naznačen time, da X1 je C-R1; X2 je C-R1; X3 je C-R1; X4 je NO; svaki R1 zasebno je odabran iz skupine koju čine vodik, halogen, hidroksi, C1-6-alkil i C1-6-alkoksi; R2 odabran je iz skupine koju čine H i C1-6-alkil; R3 odabran je iz skupine koju čine H i C1-6-alkil; ili R2 i R3 zajedno su =O; Y1 je C-R4 ili N; Y2 je C-R4 ili N; Y3je C-R4 ili N; Y4je C-R4 ili N; pri čemu samo jedan od Y1, Y2, Y3 i Y4 je N; svaki R4 zasebno je odabran iz skupine koju čine vodik, halogen, halogen-C1-6-alkil, hidroksi, C1-6-alkil, C1-6-alkoksi i Si(C1-6,-alkil)3; m je 1, 2 ili 3; i n je 0 ili 1; ili njihove farmaceutski prihvatljive soli. m je 1, 2 ili 3; i n je 0 ili 1; ili njihove farmaceutski prihvatljive soli.
6. Intermedijer spoja formule I prema patentnom zahtjevu 5, naznačen time, da svaki od X1, X2 i X3 je CH i X4 je NO; svaki od R2 i R3 je C1-6-alkil; svaki od m i n je 1; i svaki od Y1, Y2, Y3 i Y4 je CH.
7. Intermedijer spoja formule I prema patentnom zahtjevu 5, naznačen time, da svaki od X1, X2 i X3 je CH i X4 je NO; svaki od R2 i R3 je H; svaki od m i n je 1; i svaki od Y1, Y2, Y3 i Y4 je CH.
8. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da je odabran iz skupine koju čine: (1R)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-2,3-dihidro-4’H-spiro[inden-1,5’-[1,3]oksazol] -4'-on, (1S)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-2,3-dihidro-4’H-spiro[inden-1,5’-[1,3]oksazol] -4'-on, 1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(4’-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2'-il)-1’H,3H spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(4’-okso-3,4-dihidro-2H,4’H-spiro[naftalen-1,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-difluoro-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-dihidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-dimetoksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5,6-dimetil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5-hidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5-metoksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5-metil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-[(2R)-4'-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2'-il]-1’-H,3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-[(2R)-5-metil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-[(2S)-4'-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2'-il]-1’-H,3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-[(2S)-5-metil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4'-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1'-il)-3-(trifluorometil)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5'-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-3,4-dihidro-2H,4’H-spiro[naftalen-1,5'-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-3,4-dihidro-1H,4’H-spiro[naftalen-2,5'-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5-(trimetilsilil)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[b]piridin-6,5’-[1,3]oksazol]-4’-on, 2’-(2-hidroksi-7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(2-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(2-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3,3-dimetil-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-hidroksi-7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(4-metil-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(5,5-dimetil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(6-metil-1H,1’H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(6-metil-1’H,3H-spiro[furo[3,4-c]piridin-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-5-metoksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-5-hidroksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-4-metoksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-4-hidroksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1-oksido-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-5-on, 2-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-7-on, 2’-spiro[5H-furo[3,4-b]piridin-7,4’-piperidin]-1’-ilspiro[indan-2,5’-oksazol]-4’-on, 2’-spiro[7H-furo[3,4-b]piridin-5,4’-piperidin]-1’-ilspiro[indan-2,5’-oksazol]-4’-on, 3-(klorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-(difluorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-(fluorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-5-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-7-on, 3-metil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 4-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 4-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 4-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-difluoro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5,6-dihidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-dimetoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-dimetil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-bromo-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-kloro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-fluoro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 6-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 6-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[furo[3,4-c]piridin-1,4’-piperidin]-3-on, i 7-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on.
9. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da je odabran iz skupine koju čine: (+)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-2,3-dihidro-4’H-spiro[inden-1,5’-[1,3]oksazol]-4’-on, (-)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-2,3-dihidro-4’H-spiro[inden-1,5’-[1,3]oksazol]-4’-on, 1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(4’-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2’-il)-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(4’-okso-3,4-dihidro-2H,4’H-spiro[naftalen-1,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-difluoro-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-dihidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-dimetoksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5,6-dimetil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5-hidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-(5-metoksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 1’-[5-metil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il]-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-[4’-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2’-il]-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-3-on enantiomer A, 1’-[4’-okso-3,4-dihidro-1H,4’H-spiro[naftalen-2,5’-[1,3]oksazol]-2’-il]-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-3-on enantiomer B, (-)-1'-[5-metil-4'-okso-1,3-dihidro-4'H-spiro[inden-2,5'-[1,3]oksazol]-2'-il]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, (+)-1'-[5-metil-4'-okso-1,3-dihidro-4'H-spiro[inden-2,5'-[1,3]oksazol]-2'-il]-3H-spiro[2-benzofuran-1,4'-piperidin]-3-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2'-(1'H,3H-spiro[2-benzofuran-1,4'-piperidin]-1'-il)-3-(trifluorometil)-5,7-dihidro-4'H-spiro[ciklopenta[c]piridin-6,5'-[1,3]oksazol]-4’-on, 2'-(1'H,3H-spiro[2-benzofuran-1,4'-piperidin]-1'-il)-3,4-dihidro-2H,4'H-spiro[naftalen-1,5'-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-3,4-dihidro-1H,4'H-spiro[naftalen-2,5'-[1,3]oksazol]-4’-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5-(trimetilsilil)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(1H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[b]piridin-6,5’-[1,3]oksazol]-4’-on, 2’-(2-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(2-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3,3-dimetil-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(4-metil-1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(5,5-dimetil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(6-metil-1H,1’H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(6-metil-1’H,3H-spiro[furo[3,4-c]piridin-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5'-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5'-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-5-metoksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-5-hidroksi-1,3-dihidro-4’H-spiro[inden-2,5'-[1,3]]oksazol]-4’-on, 2-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-5-on, 2-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-7-on, 2’-(1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 3-(klorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-(difluorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-(fluorometil)-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-5-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-7-on, 3-metil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-5,7-dihidro-4’H-spiro[ciklopenta[c]piridin-6,5’-[1,3]oksazol]-4’-on, 4-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 4-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 4-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-difluoro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5,6-dihidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-dimetoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5,6-dimetil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-bromo-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-kloro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-fluoro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-metil-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 6-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-kloro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’,-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 6-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metoksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1-on, 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[furo[3,4-c]piridin-1,4’-piperidin]-3-on, i 7-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on.
10. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 9, naznačen time, da je odabran iz skupine koju čine: 1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-difluoro-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5,6-dihidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-(5-hidroksi-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 1’-[(2R)-5-metil-4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il]-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(5,5-dimetil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(6-metil-1’H,1’H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-5-hidroksi-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-5-on, 3-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-7-on, 5,6-difluoro-2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 5,6-dihidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-fluoro-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 5-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 6-hidroksi-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, i 6-metil-1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2’-il)-1H-spiro[furo[3,4-b]piridin-3,4’-piperidin]-1-on.
11. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da je odabran iz skupine koju čine: 2’-(1’H,3H-spiro[2-benzofuran-1,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 1’-(4’-okso-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-2'-il)-3H-spiro[2-benzofuran-1,4’-piperidin]-3-on, 2’-(6-metil-1H,1’H-spiro[furo[3,4-c]piridin-3,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, 2’-(3-metil-1’H,5H-spiro[furo[3,4-b]piridin-7,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on, i 2’-(3-metil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on.
12. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da je to 2’-(7,7-dimetil-1’H,7H-spiro[furo[3,4-b]piridin-5,4’-piperidin]-1’-il)-1,3-dihidro-4’H-spiro[inden-2,5’-[1,3]oksazol]-4’-on.
13. Spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 12 , naznačen time, da se upotrebljava kao terapeutski djelatna tvar.
14. Spoj formule I prema patentnim zahtjevima 1 do 12, naznačen time, da se upotrebljava kao terapeutski djelatna tvar koja djeluje periferno i centralno u uvjetima nepravilnog lučenja vazopresina, anksioznosti, depresivnih poremećaja, opsesivno kompulzivnog poremećaja, poremećaja autističnog spektra, shizofrenije, agresivnog ponašanja i poremećaja spavanja uslijed faznog pomaka, posebno kod promjene vremenske zone.
15. Farmaceutski pripravak, naznačen time, da sadrži spoj formule I prema bilo kojem od patentnih zahtjeva 1 do 12 i farmaceutski prihvatljiv nosač i/ili farmaceutski prihvatljivu pomoćnu tvar.
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