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HRP20200141T1 - Derivati piperidina kao gpr119 agonisti - Google Patents

Derivati piperidina kao gpr119 agonisti Download PDF

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Publication number
HRP20200141T1
HRP20200141T1 HRP20200141TT HRP20200141T HRP20200141T1 HR P20200141 T1 HRP20200141 T1 HR P20200141T1 HR P20200141T T HRP20200141T T HR P20200141TT HR P20200141 T HRP20200141 T HR P20200141T HR P20200141 T1 HRP20200141 T1 HR P20200141T1
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Croatia
Prior art keywords
fluoro
carboxamide
methoxy
piperidin
methylpropyl
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HRP20200141TT
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English (en)
Inventor
Changsik LEE
Taegsu JANG
DaeKyu CHOI
Moosung Ko
Dohoon Kim
Soyoung Kim
Jaeki Min
Woosik Kim
Youngtae Lim
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Chong Kun Dang Pharmaceutical Corp.
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Publication of HRP20200141T1 publication Critical patent/HRP20200141T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/452—Piperidinium derivatives
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • 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
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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/02—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
    • 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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    • C07D—HETEROCYCLIC COMPOUNDS
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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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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D487/04—Ortho-condensed systems

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Claims (7)

1. Derivati piperidina iz formule 1 izložene u nastavku, njihovi stereoizomeri ili njihove farmaceutski prihvatljive soli: pri čemu W je O; Ra i Rb su svaki neovisno H; Rc je -F ili -CF3; Rd i Re su svaki neovisno odabrani iz skupine koja obuhvaća -CH3 i -CH2CH3; je skupine koja obuhvaća: pri čemu su Rf1 i Rf2 svaki neovisno H, -F ili -CN; je odabrano iz skupine koja obuhvaća:
pri čemu su Rk1 i Rk2 svaki neovisno H, -F ili -CN; je Q je odabrano iz skupine koja obuhvaća: pri čemu Rx1 jeste -C(O)NH2; i Rx2 je H, OH, -F, -CN, -CF3, -CH2OH ili -C(O)NH2.
2. Derivati piperidina, njegovi stereoizomeri, njihove farmaceutski prihvatljive soli sukladno patentnom zahtjevu 1, pri čemu se derivat piperidina odabire skupine koja koja obuhvaća: (S)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(2-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (R)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(3-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (2S)-1-(2,2’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2’,3-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; 1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; 1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4- il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metlpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(5-(3-fluoro-4-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)fenil)pikolinoil)pirolidin-2-karboksamid; 1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(3’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(3,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(2’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(2’,3-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(2,2’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; 1-(4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-4-karboksamid; 1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-4-karboksamid; (R)-1-(3’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(3’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; 1-(3-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-4-karboksamid; 1-(4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-3-fluorobifenilkarbonil)piperidin-4-karboksamid; (R)-1-(3,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(3,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4- il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; 1-(2,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenikarbonil)piperidin-4-karboksamid; (R)-1-(2,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2,3’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-2-karboksamid; (R)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-2-karboksamid; (R)-1-(2’,3-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)piperidin-2-karboksamid; (2R)-1-(2,2’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(4-(6-((1-(3,3,3-trifluoro-2,2-dimetilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2- karboksamid; (R)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(2-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-2-karboksamid; (S)-1-(2-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-2-karboksamid; 1-(2-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-4-karboksamid; (2S)-1-(2,6’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(3,6’-difluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(3-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3- il)benzoil)piperidin-2-karboksamid; (S)-1-(3-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-2-karboksamid; 1-(3-fluoro-4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-4-karboksamid; (S)-1-(4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-3-fluorobifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(2’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (S)-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (R)-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (R)-1-(2’-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (S)-1-(4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-2-fluorobifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4-(5-((1-(2-etil-2-fluorobutIl)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)piridin-2-il)-2-fluorobenzoil)pirolidin-2-karboksamid; (2S,4R)-1-(4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)-4-hidroksipirolidin-2-karboksamid; (S)-1-(5-(2-fluoro-4-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)fenil)pikolinoil)pirolidin-2-karboksamid; (S)-1-(4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-2,3’-difluorobifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-2-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-3-fluorobifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(3’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(2’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2’-cijano-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2-ffuoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)pirimidin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(5-(3-cijano-4-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)fenil)pikolinoil)pirolidin-2-karboksamid; (R)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)pirimidin-2-il)benzoil)piperidin-2-karboksamid; (S)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)pirimidin-2-il)benzoil)pirolidin-2-karboksamid; (R)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)pirimidin-2-il)benzoil)piperidin-2-karboksamid; (S)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)pirimidin-2-il)-2-fluorobenzoil)pirolidine-2-karboksamid; (R)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)pirimidin-2-il)-2-fluorobenzoil)piperidin-2-karboksamid; (R)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)pirimidin-2-il)-3-fluorobenzoil)piperidin-2-karboksamid; (2S,4R)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)-4-hidroksipirolidin-2-karboksamid; (R)-1-(4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-2-karboksamid; (S)-1-(4-(6-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-3-il)benzoil)piperidin-2-karboksamid; (S)-1-(5-(2-fluoro-4-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)fenil)pirazin-2-karbonil)pirolidin-2-karboksamid; (2S,4S)-4-fluoro-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (2S,4R)-1-(3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)-4-hidroksipirolidin-2-karboksamid; (S)-1-(3’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-2-fluorobifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(3’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)-2-fluorobifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; i (R)-1-(2’-cijano-4’-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid.
3. Derivat piperidina, njegovi stereoizomeri ili njihove farmaceutski prihvatljive soli sukladno patentnim zahtjevima 2, pri čemu je derivat piperidina skupine koja obuhvaća: (S)-1-(2-fluoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4-(5-((1-(2-etil-2-fluorobutil)piperidin-4-il)metoksi)piridin-2-il)benzoil)pirolidin-2-karboksamid; (S)-1-(3’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2’-cijano-3-fluoro-4’-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; i (S)-1-(2-ffuoro-4-(5-((1-(2-fluoro-2-metilpropil)piperidin-4-il)metoksi)pirimidin-2-il)benzoil)pirolidin-2-karboksamid.
4. Derivati piperidina, njegovi stereoizomeri ili njihove farmaceutski prihvatljive soli, pri čemu se derivat piperidina odabire iz skupine koja obuhvaća: (S)-1-(4-(6-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4-(6-((1-((1-(trifluorometil)ciklopropil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin- 2-karboksamid; (S)-1-(4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(4-(6-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(3-fluoro-4-(6-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(2-fluoro-4-(6-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4’-((1-((1-fluorocikloheksil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4-(6-((1-((1-(trifluorometil)ciklopentil)metil)piperidin-4-il)metoksi)piridine-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4-(6-((1-((1 -(trifluorometil)cikloheksil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2- karboksamid; 1-(4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-4-karboksamid; (S)-1-(2’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(3-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2,3’-difluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (R)-1-(2’-fluoro-4’-((1-((1-(trifluorometi)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(2’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (R)-1-(2’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (S)-1-(3’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (R)-1-(3’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-3-karboksamid; (R)-1-(3’-fluoro-4’-((1-((1-(trifluorometi)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(3’-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)piperidin-2-karboksamid; (S)-1-(3,3’-difluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(5-(3-fluoro-4-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)fenil)pikolinoil)pirolidin-2-karboksamid; (2S)-1-(2,2’-difluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2’,3-difluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(2-fluoro-4’-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (S)-1-(4’-((1-((1-fluorociklobutil)metil)piperidin-4-il)metoksi)bifenilkarbonil)pirolidin-2-karboksamid; (2S,4R)-4-hidroksi-1-(4-(6-((1-((1-(trifuorometil)ciklobutil)metil)piperidin-4-il)metoksi)piridin-3-il)benzoil)pirolidin-2-karboksamid; (S)-1-(4-(2-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)pirimidin-5-il)benzoil)pirolidin- 2-karboksamid; (S)-1-(3-fluoro-4-(2-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)pirimidin-5-il)benzoil)pirolidin-2-karboksamid; (S)-1-(2-fluoro-4-(2-((1-((1-(trifluorometil)ciklobutil)metil)piperidin-4-il)metoksi)pirimidin-5-il)benzoil)pirolidin-2-karboksamid;
5. Farmaceutska tvar koja obuhvaća derivat piperidina, njegove stereoizomere ili njegove farmaceutski prihvatljive soli u sukladno bilo kojim od patentnih zahtjeva 1 do 4 i farmaceutski prihvatljivim nosačima.
6. Farmaceutska tvar sukladno patentnom zahtjevu 5 za uporabu u liječenju bolesti povezane s GPR119 agonistom.
7. Farmaceutska tvar za uporabu sukladno patentnom zahtjevu 6, pri čemu je navedena bolest povezana s GPR119 agonistom dijabetes melitus.
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