HRP20201402T1 - Spojevi inhibitora acetilkolinsteraze i agonisti serotonergičkih receptora 5ht4, s promnezijskim učinkom, postupci za njihovu pripremu i farmaceutski pripravci koji ih sadržavaju - Google Patents
Spojevi inhibitora acetilkolinsteraze i agonisti serotonergičkih receptora 5ht4, s promnezijskim učinkom, postupci za njihovu pripremu i farmaceutski pripravci koji ih sadržavaju Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims 21
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title claims 3
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 title 1
- 239000000544 cholinesterase inhibitor Substances 0.000 title 1
- 230000000694 effects Effects 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 230000000862 serotonergic effect Effects 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims 8
- 239000004480 active ingredient Substances 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- BBHZRGFJDRKUNV-UHFFFAOYSA-N 1-(4-amino-5-chloro-2-methoxyphenyl)-2-(1-butylpiperidin-4-yl)propan-1-one Chemical compound C1CN(CCCC)CCC1C(C)C(=O)C1=CC(Cl)=C(N)C=C1OC BBHZRGFJDRKUNV-UHFFFAOYSA-N 0.000 claims 1
- DRWBHZSJKUMHGN-UHFFFAOYSA-N 5,6-dimethoxy-2-methyl-2,3-dihydroinden-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)C(C)C2 DRWBHZSJKUMHGN-UHFFFAOYSA-N 0.000 claims 1
- 108091005482 5-HT4 receptors Proteins 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 102000012440 Acetylcholinesterase Human genes 0.000 claims 1
- 108010022752 Acetylcholinesterase Proteins 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAKCOJKXWMIQSX-ROMGYVFFSA-N CO\N=C(\CCC1CCN(CC2CCCCC2)CC1)c1cc(Cl)c(N)cc1OC Chemical compound CO\N=C(\CCC1CCN(CC2CCCCC2)CC1)c1cc(Cl)c(N)cc1OC ZAKCOJKXWMIQSX-ROMGYVFFSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000004097 EU approved flavor enhancer Substances 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 229940022698 acetylcholinesterase Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 235000019264 food flavour enhancer Nutrition 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003544 oxime group Chemical class 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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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
- C07D211/34—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
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- 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
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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
-
- 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
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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
- C07D211/26—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 nitrogen atoms
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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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (19)
1. Spoj opće formule (I):
[image]
naznačen time, da:
X predstavlja
atom vodika ili
atom halogena (Hal), pri čemu je (Hal) fluor, klor, brom ili jod,
ili Cp(Hal)2p+1 polihaloalkilna skupina s ravnim ili razgrananim lancem, pri čemu p = 1, 2, 3 ili 4, (Hal) imaju isto značenje kao što je gore navedeno;
Y predstavlja
atom kisika, ili
atom sumpora, ili N-R" radikal pri čemu R" predstavlja atom vodika, -OH radikal, CqH2q+1 alkilni radikal ravnog ili razgrananog lanca, pri čemu je q = 1, 2, 3 ili 4;
()m predstavlja broj m metilenske skupine, čija vrijednost je 1, 2 ili 3
()n predstavlja broj n metilenskih skupina, čija vrijednost je 0, 1, 2 ili 3
()r i (s) predstavljaju broj r i s metilenskih skupina, čije su vrijednosti: r = s = 0;
ili r = s = 1; ili r = s = 2; ili r = 0 i s = 1; ili na kraju r = 0 i s = 2;
R predstavlja
atom vodika ili
C1-C5 alkilnu skupinu ravnog ili razgrananog lanca koja može nositi jedan ili više F atoma
R' predstavlja
C3-C10 cikloalkil koji može nositi jednu ili više R skupina i posjedovati atom kisika ili dušikov atom koji može biti supstituiran s R,
kao i njihove enantiomere ili dijastereoizomere i njihove racemate, njihove kisele soli, njihove hidrate ili proizvode otapanja.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da X u svojoj formuli (I) predstavlja atom halogena.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da Y u svojoj formuli (I) predstavlja atom kisika.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da u svojoj formuli (I) svi koeficijenti m, n, r i s imaju vrijednost 1.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da R u svojoj formuli (I) predstavlja H, CH3, CH2CH3 ili CH2-CH2F.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time, da R' u svojoj formuli (I) predstavlja radikal preuzet iz skupine koju čine radikali ciklopropil, ciklobutil, ciklopentil, cikloheksil, cikloheptil i 4-piperidin.
7. Spoj prema zahtjevima 2 do 6, naznačen time, da R u svojoj formuli (I) predstavlja metilni radikal i R', C4-C7 cikloalkilni radikal.
8. Spoj naznačen time, da navedeni spoj je 2-kloro-4-[[2-[1-(cikloheksilmetil)-4-piperidil]etil]-N-metoksikarbonimidoil]-5-metoksianilin.
9. Postupak dobivanja spojeva u skladu s patentnim zahtjevom 1, u formuli (I), pri čemu R = H i X, Y, m, n, r, s i R' imaju značenja u skladu s patentnim zahtjevom 1, naznačen time, da spoj u skladu s patentnim zahtjevom 1, u formuli (I), pri čemu R predstavlja metilnu skupinu, reagira s aluminijevim kloridom u prisutnosti natrijevog jodida u acetonitrilu, kako bi dobio željeni spoj formule (I).
10. Postupak dobivanja spojeva u skladu s patentnim zahtjevom 1, formule (I), pri čemu R predstavlja ravni ili razgranani C1-C3 alkilni radikal koji može nositi jedan ili više atoma fluora, X, Y, Z, m, n , r, s i R' imaju značenja u skladu s patentnim zahtjevom 1, naznačen time, da spoj u skladu s patentnim zahtjevom 1, pri čemu je R = H i X, Y, m, n, r, s i R' imaju značenja u skladu s patentnim zahtjevom 1, reagira s halogenidom ili C1-C3 alkil tozilatom ravnog ili razgrananog lanca koji je sposoban nositi jedan ili više atoma fluora, u prisutnosti kalijevog karbonata, u odgovarajućem otapalu.
11. Postupak pripreme spojeva formule (I) kako je naznačeno u skladu s patentnim zahtjevom 1, pri čemu je Y moguća O-supstituirana oksim skupina, a X, m, n i R' su kako je naznačeno u skladu s patentnim zahtjevom 1, naznačen time, da spoj u skladu s patentnim zahtjevom 1, formule (I), od kojih X, m, n i R' imaju gore navedena značenja, a Y = O, reagira sa O-supstituiranom hidroksilaminom soli u prisutnosti kalcijevog karbonata u smjesi etanol / voda, za dobivanje željenog spoja formule (I).
12. Farmaceutski sastav, naznačen time, da sadržava kao aktivni sastojak barem jedan spoj u skladu s jednim od patentnih zahtjeva 1 do 8.
13. Farmaceutski pripravak u skladu s patentnim zahtjevom 12, naznačen time, da sadržava farmaceutski prihvatljiv ekscipijent.
14. Farmaceutski pripravak u skladu s jednim od patentnih zahtjeva 12 ili 13, naznačen time, da je spoj formule (I) koji pripravak sadržava farmaceutski prihvatljiv.
15. Farmaceutski pripravak u skladu s jednim od patentnih zahtjeva 12 do 14, naznačen time, da sadržava barem jedan aktivni sastojak koji ima inhibirajuće djelovanje acetilkolinesteraze i izabran je iz skupine koju tvore:
a) 1, 2, 3, 4-tetrahidroakridin-9-amin
b) (RS)-2-[(1-benzil-4-piperidil) metil-5, 6-dimetoksi-2, 3-dihidroinden-1- on
c) (S)-N-etil-N-metil-3-[(l-dimetilamino)etil]-fenilkarbamata i
d) 4aS, 6R, 8aS)-5, 6, 9, 10, 11, 12-heksahidro-3-metoksi-11-metil-4aH- [1]benzofuro [3a,3,2-ef][2]benzazepin-6-ol
16. Farmaceutski sastav u skladu s jednim od patentnih zahtjeva 12 do 15, naznačen time, da sadržava barem jedan djelomični agonist 5-HT4 receptora odabran iz skupine koju tvore:
a) 1-(4-amino-5-kloro-2-metoksifenil)-2-[l-butil-4-piperidil]propan-1on,
b) N-(2-(4-(3-(4-amino-5-kloro-3-metoksifenil)-3-oksipropil) piperidin-1-il) etil)metansulfonamid,
pri čemu je navedeni agonist u omjeru između 10/90 i 90/10 u odnosu na aktivni sastojak formiran iz najmanje jednog spoja u skladu s jednim od patentnih zahtjeva 1 do 8.
17. Farmaceutski sastav u skladu s jednim od patentnih zahtjeva 12 do 16, naznačen time, da se upotrebljava u liječenju neuroloških bolesti s amnestičkim deficitom kod sisavaca.
18. Farmaceutski sastav u skladu s patentnim zahtjevom 17, naznačen time, da se upotrebljava u liječenju Alzheimerove bolesti kod ljudskog subjekta.
19. Farmaceutski pripravak u skladu s jednim od patentnih zahtjeva 12 do 16, naznačen time, da je aktivni sastojak pakiran u obliku smjese s disperzivnim sredstvima, omekšivačima, suspenzijama, zaslađivačima ili pojačivačima ukusa.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1355155A FR3006686A1 (fr) | 2013-06-05 | 2013-06-05 | Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant |
| EP14806879.4A EP3004058B1 (fr) | 2013-06-05 | 2014-05-19 | Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant |
| PCT/FR2014/051149 WO2014195593A2 (fr) | 2013-06-05 | 2014-05-19 | Composes inhibiteurs de l'acetylcholinesterase et agonistes des recepteurs serotoninergiques 5ht4, a effet promnesiant, leurs procedes de preparation et compositions pharmaceutiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201402T1 true HRP20201402T1 (hr) | 2020-11-27 |
Family
ID=49546495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201402TT HRP20201402T1 (hr) | 2013-06-05 | 2020-09-03 | Spojevi inhibitora acetilkolinsteraze i agonisti serotonergičkih receptora 5ht4, s promnezijskim učinkom, postupci za njihovu pripremu i farmaceutski pripravci koji ih sadržavaju |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9663465B2 (hr) |
| EP (1) | EP3004058B1 (hr) |
| JP (1) | JP6386541B2 (hr) |
| CN (1) | CN105705488B (hr) |
| DK (1) | DK3004058T3 (hr) |
| ES (1) | ES2808669T3 (hr) |
| FR (1) | FR3006686A1 (hr) |
| HK (1) | HK1225381A1 (hr) |
| HR (1) | HRP20201402T1 (hr) |
| HU (1) | HUE050953T2 (hr) |
| PL (1) | PL3004058T3 (hr) |
| PT (1) | PT3004058T (hr) |
| WO (1) | WO2014195593A2 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3628660A1 (en) | 2018-09-28 | 2020-04-01 | Université de Caen Normandie | Donecopride and flucopride as neuroprotective agents in the treatment of neurodegenerative diseases |
| CA3136360A1 (en) * | 2019-04-12 | 2020-10-15 | Loma Linda University | Methods for treatment of niemann-pick disease type c |
| WO2023116915A1 (zh) * | 2021-12-24 | 2023-06-29 | 珠海市藤栢医药有限公司 | AChE/SERT双靶点抑制剂及其制备方法和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ243993A (en) * | 1991-08-20 | 1994-10-26 | Smithkline Beecham Plc | Pharmaceutical compositions having 5-ht4 receptor antagonist activity and selected compounds having such activity |
| IL109776A (en) * | 1993-05-26 | 1998-03-10 | Syntex Inc | 1- (5-alo-4-aminophil) (C6-2) alkane-1-one, history of preparation and pharmaceuticals containing it |
| KR970702247A (ko) * | 1994-03-30 | 1997-05-13 | 고야 마사시 | 벤조산 화합물 및 이들의 약제로서의 용도(benzoic acid compound and use thereof as medicine) |
| JPH111472A (ja) * | 1996-04-30 | 1999-01-06 | Dainippon Pharmaceut Co Ltd | ベンズアミド誘導体及びそれを含有する医薬組成物 |
| WO1998002432A1 (en) * | 1996-07-16 | 1998-01-22 | Takeda Chemical Industries, Ltd. | Bicyclic compounds for controlling micturition |
| IL150982A (en) | 2002-07-30 | 2007-02-11 | Ori Lerman | Process for making Donafzil |
| US7459460B2 (en) * | 2003-05-28 | 2008-12-02 | Bristol-Myers Squibb Company | Trisubstituted heteroaromatic compounds as calcium sensing receptor modulators |
| GB0525661D0 (en) * | 2005-12-16 | 2006-01-25 | Glaxo Group Ltd | Novel compounds |
| MX343165B (es) * | 2010-02-12 | 2016-10-26 | Raqualia Pharma Inc | Agonistas del receptor 5-ht4 para el tratamiento de demencia. |
-
2013
- 2013-06-05 FR FR1355155A patent/FR3006686A1/fr not_active Withdrawn
-
2014
- 2014-05-19 EP EP14806879.4A patent/EP3004058B1/fr active Active
- 2014-05-19 DK DK14806879.4T patent/DK3004058T3/da active
- 2014-05-19 ES ES14806879T patent/ES2808669T3/es active Active
- 2014-05-19 HU HUE14806879A patent/HUE050953T2/hu unknown
- 2014-05-19 PT PT148068794T patent/PT3004058T/pt unknown
- 2014-05-19 JP JP2016517648A patent/JP6386541B2/ja active Active
- 2014-05-19 CN CN201480032241.2A patent/CN105705488B/zh active Active
- 2014-05-19 PL PL14806879T patent/PL3004058T3/pl unknown
- 2014-05-19 US US14/895,731 patent/US9663465B2/en active Active
- 2014-05-19 WO PCT/FR2014/051149 patent/WO2014195593A2/fr active Application Filing
-
2016
- 2016-12-01 HK HK16113674A patent/HK1225381A1/zh unknown
-
2020
- 2020-09-03 HR HRP20201402TT patent/HRP20201402T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2014195593A2 (fr) | 2014-12-11 |
| DK3004058T3 (da) | 2020-08-31 |
| JP2016522215A (ja) | 2016-07-28 |
| HUE050953T2 (hu) | 2021-01-28 |
| ES2808669T3 (es) | 2021-03-01 |
| PL3004058T3 (pl) | 2020-11-16 |
| CN105705488B (zh) | 2020-03-24 |
| JP6386541B2 (ja) | 2018-09-05 |
| HK1225381A1 (zh) | 2017-09-08 |
| EP3004058A2 (fr) | 2016-04-13 |
| WO2014195593A3 (fr) | 2015-12-30 |
| EP3004058B1 (fr) | 2020-06-10 |
| PT3004058T (pt) | 2020-09-03 |
| US9663465B2 (en) | 2017-05-30 |
| FR3006686A1 (fr) | 2014-12-12 |
| CN105705488A (zh) | 2016-06-22 |
| US20160122300A1 (en) | 2016-05-05 |
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