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SI2855449T1 - Derivati sulfonil piperidina in njihova uporaba pri zdravljenju bolezni, povezanih s prokineticinom - Google Patents

Derivati sulfonil piperidina in njihova uporaba pri zdravljenju bolezni, povezanih s prokineticinom Download PDF

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SI2855449T1
SI2855449T1 SI201331026T SI201331026T SI2855449T1 SI 2855449 T1 SI2855449 T1 SI 2855449T1 SI 201331026 T SI201331026 T SI 201331026T SI 201331026 T SI201331026 T SI 201331026T SI 2855449 T1 SI2855449 T1 SI 2855449T1
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sulfonyl
pyrazol
piperidine
dimethyl
trimethyl
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Colm Carroll
Anne Goldby
Martin Teall
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Takeda Pharmaceutical Company Limited
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    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/96—Sulfur atom
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    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

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Claims (25)

  1. DERIVATI SULFONIL PIPERIDINA IN NJIHOVA UPORABA PRI ZDRAVLJENJU BOLEZNI, POVEZANIH S PROKINETICINOM Patentni zahtevki
    1. Spojina s formulo (la) ali njena farmacevtsko sprejemljiva sol,
    pri čemer velja naslednje: W1, X , Y1 in Z1 vsi neodvisno predstavljajo N, NH ali CH, pri čemer vsaj dva od W1, X1, Y1 in Z1 predstavljata N ali NH; pis 0, 1, 2 ali 3; vsak R11 neodvisno predstavlja halogen, ciano, C1-C6 alkoksi, C1-C6 haloalkil, Ci-Ce haloalkoksi , Ci-Ce alkiltio, CrC6alkilkarbonil ali Ci-Ce alkil, poljubno nadomeščenim s karboksilom ali C1-C6 alkoksikarbonilom; q je 0, 1, 2, 3 ali 4; vsak R12 neodvisno predstavlja halogen, ciano, karboksil, hidroksil, Ci-Ce alkil, CrC6 haloalkil, C1-C6 alkoksi, Ci-Cehidroksialkil, Ci-Ce alkoksikarbonil, C1-C6 alkoksiCi-C6 alkil ali 5- do 9-členski heterociklični obroč; R13 predstavlja atom kisika ali skupino C=O, NR15 ali CR16R17, pod pogojem, da (i) ko R13 predstavlja CO ali NH in obroč A predstavlja pirazol-4-il ali imidazol-4-il, mora biti p 3 in R14 predstavlja nadomeščen fenilni, piridinilni ali naftilni obroč, in (ii) ko R13 predstavlja CH2 in obroč A predstavlja pirazol-4-il ali imidazol-4-il, je p 3 ali p je 2 in q je najmanj 1; R15 predstavlja atom vodika ali skupino C1-C6 alkila; R16 in R17 vsak neodvisno predstavljata atom vodika ali halogena ali ciano, karboksil, hidroksil, C1-C6 alkil, C1-C6 haloalkil, C1-C6 alkoksi, Ci-Ce hidroksialkil, Ci-C6 alkoksikarbonil, Ci-C6alkoksiCi-C6 alkil ali 5- do 9-členski heterociklični obroč; R14 predstavlja fenilni, piridinilni ali naftilni obroč, pri čemer se sam obroč lahko poljubno nadomesti z vsaj enim substituentom, izbranim iz skupine, ki zajema halogen, hidroksil, ciano, okso, Ci-Cealkil, C2-C6 alkenil, C2-C6 alkinil, Ci-C6 haloalkil, Ci-C6hidroksialkil, Ci-C6 alkoksi, Ci-C6 haloalkoksi, Ci-Ce alkiltio, C1-C6 alkilsulfonil, C1-C6 alkilsulfonil, C1-C6 alkilkarbonil, Ci-Ce alkilkarboniloksi, Ci-C6 alkoksikarbonil, amino, -CON(R18)2, Ci-Ce alkilamino, di-(Ci-C6 alkil)amino, C3-C6 cikloalkil, C3-Cecikloalkoksi ali C3-C6 cikloalkilmetil; in vsak R18 neodvisno predstavlja atom vodika ali skupino C1-C6 alkila; vendar so izključene naslednje spojine: 1) 1-[(3,5-dimetil-1/-/-pirazol-4-il)sulfonil]-4-(4-metilfenoksi)piperidin,
    2) 1-[(3,5-dimetil-1/-/-pirazol-4-il)sulfonil]-4-(4-fluorofenoksi)piperidin, 3) 1-[(3,5-dimetil-1H-pirazol-4-il)sulfonil]-4-(4-metoksifenoksi)piperidin, 4) 1 -[(3,5-d imetil-1 H-pirazol-4-il)sulfonilj-4-fenoksipiperidin, 5) 1-[(3,5-dimetil-1 H-pirazol-4-il)sulfonil]-4-(3-etilfenoksi)piperidin, 6) 4-fenoksi-1-(1H-pirazol-4-ilsulfonil)piperidin, 7) 4-(3-klorofenoksi)-1-[(3,5-dimetil-1H-pirazol-4-il)sulfonil]piperidin, 8) [1 -[(5-kloro-1,3-d imeti I-1 /-/-p irazol-4-i l)su Ifon il]-4-piperid in i l](4-metoksifenil)metanon, 9) 1-[(3,5-dimetil-1H-pirazol-4-il)sulfonil]-4-(2-metilfenoksi)piperidin, 10) 1-[(3,5-dimetil-1/-/-pirazol-4-il)sulfonil]-4-[[2-(trifluorometil)fenil]metil]-4-piperidinmetanol, 11) 1 -[(3,5-d imeti I-1 /-/-pirazol-4-il)sulfonil]-4-[(4-metoksifenil)metil]-4-piperidinkarboksilna kislina, etil ester, 12) 4-[[1-[(1-metil-1 H-pirazol-4-il)sulfonil]-4-piperidinil]oksi]benzonitril, 13) /V-(2-metilfenil)-1-[(1,3,5-trimetil-1W-pirazol-4-il)sulfonil]-4-piperidinamin, 14) 1 -[[1-(difluorometil)-3-metil-1/7-pirazol-4-il]sulfonil]-4-(4-fluorofenoksi)piperidin, 15) 4-(3-fluorofenoksi)-1-[(3-metil-1-propil-1/-/-pirazol-4-il)sulfonil]piperidin, 16) 1-[[1-(difluorometil)-3,5-dimetil-1H-pirazol-4-il]sulfonil]-4-(2-fluorofenoksi)piperidin, 17) 1 -[(5-kloro-1,3-dimetil-1 /-/-pirazol-4-il)sulfon il]-4-(fen ilmetil)piperidi n, 18) 1 -[[1 -(difluorometil)-3,5-dimetil-1 H-pirazol-4-il]su Ifon il]-4-(fenilmetil)piperidin, 19) 1-[(1-etil-3,5-dimetil-1H-pirazol-4-il)sulfonil]-4-(fenilmetil)piperidin, 20) (4-(4-metoksibenzil)-1 -(1,3,5-trimetil-1 H-pirazol-4-il)sulfonil)piperidin-4-il)metanol, 21) (4-(4-klorobenzil)-1-(1,3,5-trimetil-1/7-pirazol-4-il)sulfonil)piperidin-4-il)metanol, 22) 1 -[(5-kloro-1,3-dimetil-1 /-/-pirazol-4-il)sulfonil]-4-[(4-metoksifenil)metil]-4-piperidinmetanol, 23) 4-(fenilmetil)-1 -[(1,3,5-trimetil-1 H-pirazol-4-il)suIfoniljpiperidin, 24) [1-[(5-kloro-1,3-dimetil-1/-/-pirazol-4-il)sulfonil]-4-piperidinil](4-fluorofenil)metanon, 25) 1-[(1-metil-1H-imidazol-4-i)sulfonil]-4-(2-naftaleniloksi)piperidin, 26) 4-((fenil)(metoksi)metil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin, in 27) 4-(fenilmetil)-1-(1H-imidazol-5-ilsulfonil)piperidin.
  2. 2. Spojina v skladu s patentnim zahtevkom 1, pri čemer je p 2 ali 3.
  3. 3. Spojina v skladu s patentnim zahtevkom 1 ali 2, pri čemer vsak R11 neodvisno predstavlja halogen, C1-C6 haloalkil ali Ci-C6 alkil.
  4. 4. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 3, pri čemer je q 0 ali 1.
  5. 5. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 4, pri čemer vsak R12 neodvisno predstavlja halogen, ciano, hidroksil, C1-C6 alkil, CrCealkoksi, Cr C6 alkoksikarbonil ali Ci-Ce alkoksiCi-C6 alkil.
  6. 6. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 5, pri čemer R13 predstavlja atom kisika.
  7. 7. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 5, pri čemer R13 predstavlja NR15.
  8. 8. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 5, pri čemer R13 predstavlja CR16R17.
  9. 9. Spojina v skladu s patentnim zahtevkom 8, pri čemer R16 in R17 vsak neodvisno predstavljata atom vodika ali skupino Ci-C6 alkila.
  10. 10. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 9, pri čemer R14 predstavlja fenilni, piridinilni ali naftilni obroč, pri čemer se sam obroč lahko poljubno nadomesti z vsaj enim substituentom, izbranim iz skupine, ki zajema halogen, ciano, Ci-C6 alkil, C1-C6 haloalkil, CrC6 alkoksi in CrC6 haloalkoksi.
  11. 11. Spojina v skladu s patentnim zahtevkom 1, izbrana med naslednjimi možnostmi: 4-(3,4-diklorofenoksi)-1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin, 4-(3,4-diklorofenoksi)-1-[(3,5-dimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-[4-(trifluorometoksi)fenoksi]-1-[(1,3,5-trimetil-1 H-pirazol-4-il)sulfonil]piperidin, 4-(4-metilfenoksi)-1 -[(1,3,5-trimetil-1 /7-pirazol-4-il)sulfonil]piperid in, 4-(4-klorofenoksi)-1-[(1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(3-klorofenoksi)-1-[(1,3,5-trimetil-1 /-/-pirazol-4-il)sulfonil]piperidin, 4-({1 -[(1,3,5-trimetil-1 /7-pirazol-4-il)sulfonil]piperid in-4-il}oksi)benzon itril, 4-(4-klorofenoksi)-1-[(3,5-dimetil-1 /-/-pirazol-4-il)sulfonil]piperidin, 1-[(1-etil-3,5-dimetil-1H-pirazol-4-il)sulfonil]-4-(4-metilfenoksi)piperidin, 1 -{[1,5-dimetil-3-(trifluorometil)-1 H-pirazol-4-il]sulfon il}-4-(4-metilfenoksi)piperidin, 1-[(5-kloro-1,3-dimetil-1/-/-pirazol-4-il)sulfonil]-4-(4-metilfenoksi)piperidin, 4-[4-(trifluorometil)fenoksi]-1-[(1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(2,4-diklorofenoksi)-1-[(1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(4-bromo-2-fluorofenoksi)-1-[(1,3,5-trimetil-1/7-pirazol-4-il)sulfonil]piperidin, 1-[(5-kloro-1,3-dimetil-1/-/-pirazol-4-il)sulfonil]-4-(4-klorofenoksi)piperidin, 4-(4-klorofenoksi)-1-{[1,5-dimetil-3-(trifluorometil)-1/7-pirazol-4- il]sulfonil}piperidin, 4-(3-metoksifenoksi)-1-[(1,3,5-trimetil-1H-pirazol-4-il)sulfonil]piperidin, 4-(4-metoksifenoksi)-1 -[(1,3,5-trimetil-1 H-pirazol-4-i l)sulfon iljpiperid in, 4-fenoksi-1-[(1,3,5-trimetil-1H-pirazol-4-il)sulfonil]piperidin, 4-(4-fluorofenoksi)-1-[(1,3,5-trimetil-1H-pirazol-4-il)sulfonil]piperidin, 4-(4-klorofenoksi)-3-metil-1-[(1,3,5-trimetil-1/7-pirazol-4-il)sulfonil]piperidin, 4-(2,4-diklorofenoksi)-1-[(3,5-dimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(naftalen-2-iloksi)-1 -[(1,3,5-trimetil-1 /-/-pirazol-4-il)sulfon il jpiperid in, 4-(4-klorofenoksi)-2-metil-1-[(1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 1-[(5-kloro-1,3-dimetil-1H-pirazol-4-il)sulfonil]-4-(2,4-diklorofenoksi)piperidin, 4-(2,4-diklorofenoksi)-1-{1,3-dimetil-5-(trifluorometil)-1/-/-pirazol-4- iljsulfoniljpiperidin, 4-(2,4-diklorofenoksi)-1-[(1,3-dimetil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(2,4-diklorofenoksi)-1-[(3,5-dietil-1-metil-1/-/-pirazol-4-il)sulfonil]piperidin, 4-(2,4-diklorofenoksi)-1-{[1-(difluorometil)-3,5-dimetil-1H-pirazol-4-il]sulfonil}piperidin, 4- (4-kloro-2-fluorofenoksi)-1-(trimetil-1 B-pirazol-4-sulfonil)piperidin, 5- kloro-2-{[1-(trimetil-1H-pirazol-4-sulfonil)piperidin-4-il]oksi}benzonitril, 1-[(3,5-dimetil-1B-pirazol-4-il)sulfonil]-4-[4-(trifluorometoksi)fenoksi]piperidin, 1-[(3,5-dimetil-1H-pirazol-4-il)sulfonil]-4-(naftalen-2-iloksi)piperidin, 5-kloro-2-{[1-(3,5-dimetil-1/-/-pirazol-4-sulfonil)piperidin-4-il]oksi}benzonitril, 4-(4-kloro-2-fluorofenoksi)-1-(3,5-dimetil-1B-pirazol-4-sulfonil)piperidin, 4-(2,4-diklorofenoksi)-1 -(1,4-d imetil-1 B-pirazol-5-sulfonil)piperidin, 4-(4-klorofenoksi)-1-(1,4-dimetil-1/-/-pirazol-5-sulfonil)piperidin, 1-(3,5-dimetil-1B-pirazol-4-sulfonil)-4-(2,6-dimetilfenoksi)piperidin, 4-[4-kloro-2-(trifluorometil)fenoksi]-1-(trimetil-1B-pirazol-4-sulfonil)piperidin, 4-[4-kloro-2-(trifluorometil)fenoksi]-1-(3,5-dimetil-1B-pirazol-4-sulfonil)piperidin, 1-(3,5-dimetil-1B-pirazol-4-sulfonil)-4-(3-fluoro-4-metoksifenoksi)piperidin, 4-(3,5-difluoro-4-metoksifenoksi)-1-(3,5-dimetil-1/-/-pirazol-4-sulfonil)piperidin, 4-(3-fluoro-4-metoksifenoksi)-1-(trimetil-1/-/-pirazol-4-sulfonil)piperidin, 4-(3,5-difluoro-4-metoksifenoksi)-1-(trimetil-1 B-pirazol-4-sulfonil)piperidin, 4-(4-kloro-3-fluorofenoksi)-1-(trimetil-1/-/-pirazol-4-sulfonil)piperidin, 4-(4-kloro-2,6-difluorofenoksi)-1-(trimetil-1H-pirazol-4-sulfonil)piperidin, 4- (4-kloro-3-fluorofenoksi)-1-(3,5-dimetil-1B-pirazol-4-sulfonil)piperidin, 5- kloro-2-((1 -((1,3,5-trimetil-1 B-pirazol-4-i l)su lfonil)piperid in-4-il)oksi)pi rid in, (4-klorofenil)(1 -((1,3,5-trimetil-1 B-pirazol-4-il)sulfonil)piperidin-4-il)metanon, (3,4-diklorofenil)(1-((1,3,5-trimetil-1B-pirazol-4-il)sulfonil)piperidin-4-il)metanon, N-(4-klorofenil)-1-((1,3,5-trimetil-1B-pirazol-4-il)sulfonil)piperidin-4-amin, N-(3,4-diklorofenil)-1 -((1,3,5-trimetil-1 /7-pirazol-4-il)sulfonil)piperidin-4-amin, 4-kloro-A/-{[1 -(trimetil-1 B-pirazol-4-sulfonil)piperidin-4-il]metil}anilin, 3,4-dikloro-A/-{[1 -(trimetil-1 B-pirazol-4-sulfonil)piperidin-4-il]metil}anilin, 4-(4-klorobenzil)-1-((1,3,5-trimetil-1H-pirazol-4-il)sulfonil)piperidin, 4-(3,4-diklorobenzil)-1-((1,3,5-trimetil-1H-pirazol-4-il)sulfonil)piperidin, 4-(4-klorobenzil)-1-((1,3,5-trimetil-1B-pirazol-4-il)sulfonil)piperidin-4-ol, 4-(4-klorobenzil)-4-metoksi-1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin, 4-(2,4-diklorobenzil)-1 -((1,3,5-trimetil-1 H-pirazol-4-il)sulfonil)piperidin-4-ol, 4-(4-klorobenzil)-4-(metoksimetil)-1 -((1,3,5-trimetil-1 /-/-pirazol-4-il)sulfonil)piperidin, etil 4-(4-klorobenzil)-1-((1,3,5-trimetil-1B-pirazol-4-il)sulfonil)piperidin-4-karboksilat, etil 4-(4-bromobenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4- karboksilat, etil 4-(4-bromobenzil)-1-((1,3,5-trimetil-1B-pirazol-4-il)sulfonil)piperidin-4- karboksilat, 4-(4-klorobenzil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-karbonitril, 4-(2,4-diklorobenzil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4- karbonitril, 1 -((5-kloro-1,3-d imetil-1 H-pirazol-4-il)sulfonil)-4-(4klorobenzil)piperidin, 4-(3,4-diklorobenzil)-1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-ol, 4-(3,4-diklorobenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4-ol, 4-(4-kloro-3-fluorobenzil)-1-((1,3,5-trimetil-1H-pirazol-4-il)sulfonil)piperidin, 4-(4-kloro-2-metoksifenoksi)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin, 4-(4-kloro-2-metoksifenoksi)-1-((1,3,5-trimetil-1H-pirazol-4-il)sulfonil)piperidin, 4- (4-kloro-2-fluorobenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4-ol, 1- ((3,5-dimetil-1H-pirazol-4-il)sulfonil)-4-(2-fluorofenoksi)piperidin, 5- kloro-3-fluoro-2-((1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)oksi)piridin, 4-(4-kloro-2-metoksibenzil)-1 -((1,3,5-trimetil-1 H-pirazol-4-il)su Ifon il)piperidin, 4-(4-kloro-2-fluorobenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)-4- fluoropiperidin, 4-(4-kloro-2-fluorobenzil)-4-fluoro-1 -((1,3,5-trimeti I-1 H-pirazol-4-il)sulfonil)piperidin, 4- (4-kloro-2-fluorobenzil)-1-((1,3,5-trimetil-1H-pirazol-4-il)sulfonil)piperidin, 5- kloro-3-metoksi-2-((1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)oksi)piridin, 5-kloro-2-((1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)oksi)-3- metoksipiridin, 4-(4-kloro-2-metoksibenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)-4- metoksipiperidin, 4-(4-kloro-2-metoksibenzil)-4-metoksi-1-((1,3,5-trimetil-1/-/-pirazol-4- il)sulfonil)piperidin, 4-(4-kloro-2-metoksibenzil)-1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin- 4-ol, 4-(4-kloro-2-metoksibenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4- ol, 4-(4-kloro-2-metoksibenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)-4- fluoropiperidin, 4-(4-kloro-2-metoksibenzil)-4-fluoro-1 -((1,3,5-trimetil-1 H-pirazol-4-il)sulfonil)piperidin, 2- (4-kloro-2-fluorofenil)-2-(1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4-il)acetonitril, 2-(4-klorofenil)-2-(1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4- il)acetonitril, (4-klorofenil)(1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4-il)metanol, (4-klorofenil)(1-((1,3,5-trimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)metanol, 4-((4-klorofenil)(metoksi)metil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin, 4-((4-klorofenil)(metoksi)metil)-1 -((1,3,5-trimeti I-1 H-pirazol-4-il)sulfonil)piperidin, 2-(4-klorofenil)-2-(1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)etanol, 1-(4-klorofenil)-1-(1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin-4-il)etanol, 4-(1-(4-klorofenil)etil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidin, 4-((4-klorofenil)(etoksi)metil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin, 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1A7-pirazol-4-il)sulfonil)piperidin, 4-(4-klorobenzil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidin-4-ol, 4-(1-(4-klorofenil)-2-metoksietil)-1-((3,5-dimetil-1H-pirazol-4- il)sulfonil)piperidin, 4-(1-(4-klorofenil)-2,2-difluoroetil)-1-((3,5-dimetil-1A7-pirazol-4- il)sulfonil)piperidin, in njihovih farmacevtsko sprejemljivih soli.
  12. 12. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina racemna mešanica enatiomera R in S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidina ali njena farmacevtsko sprejemljiva sol.
  13. 13. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina mešanica enatiomera R in S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidina ali njena farmacevtsko sprejemljiva sol.
  14. 14. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina enatiomer R 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidina ali njena farmacevtsko sprejemljiva sol.
  15. 15. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina enatiomer S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidina ali njena farmacevtsko sprejemljiva sol.
  16. 16. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina racemna mešanica enatiomera R in S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidina.
  17. 17. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina mešanica enatiomera R in S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidina.
  18. 18. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina enatiomer R 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1H-pirazol-4-il)sulfonil)piperidina.
  19. 19. Spojina v skladu s patentnim zahtevkom 1, pri čemer je spojina enatiomer S 4-((4-klorofenil)fluorometil)-1-((3,5-dimetil-1/-/-pirazol-4-il)sulfonil)piperidina.
  20. 20. Postopek za pripravljanje spojine formule (la), kot je opredeljena v patentnem zahtevku 1, ali njene farmacevtsko sprejemljive soli, ki zajema: (i) reagiranje spojine sjormulo
    pri čemer L1 predstavlja zapuščajočo skupino, p, W1, X1, Y1, Z1 in R11 pa so opredeljeni, kot je določeno v formuli (la), s spojino s formulo
    ali njeno ustrezno soljo, pri čemer so q, R12, R13 in R opredeljeni, kot je določeno v formuli (la); ali
    (ii) reagiranje spojine s formulo
    pri čemer L predstavlja zapuščajočo skupino, p, q, W1, X1, Y1, Z1,R11 in R12 pa so opredeljeni, kot je določeno v formuli (la), s spojino s formulo L3-R13-R14 (Va), pri čemer L3 predstavlja zapuščajočo skupino, R13 in R14 pa sta opredeljena, kot je določeno v formuli (la); in poljubno nadaljnje izvajanje enega ali več naslednjih postopkov: • pretvorba spojine s formulo (la) v drugo spojino s formulo (la) • odstranitev morebitnih zaščitnih skupin • tvorba farmacevtsko sprejemljive soli.
  21. 21. Farmacevtska sestava, ki zajema spojino v skladu s katerim koli od patentnih zahtevkov od 1 do 19 v zvezi s farmacevtsko sprejemljivim adjuvansom, razredčilom ali prenašalcem in poljubno z eno ali več drugimi zdravilnimi učinkovinami.
  22. 22. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 19 za uporabo pri zdravljenju bolezni ali stanja, povezanega s prokineticinom.
  23. 23. Spojina v skladu s katerim koli od patentnih zahtevkov od 1 do 19 za uporabo pri zdravljenju shizofrenije, shizofreniformne motnje, shizoafektivne motnje, kognitivnih motenj ali bolečine.
  24. 24. Spojina v skladu s patentnim zahtevkom 23 za uporabo pri zdravljenju bolečine.
  25. 25. Komplet, ki zajema pripravo prve aktivne sestavine, ki je spojina v skladu z katerim koli od patentnih zahtevkov od 1 do 19, in pripravo druge aktivne sestavine, ki je karbamazepin, olanzapin, kvetiapin, verapamil, lamotrigin, okskarbazepin, risperidon, aripiprazol, ziprazidon ali litij, ter navodila za hkratno, zaporedno ali ločeno dovajanje pripravkov bolniku, ki to potrebuje.
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