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HRP20200280T1 - Derivati 1,3,4-oksadiazolsulfamida kao inhibitor histonske deacetilaze 6 i farmaceutski pripravak koji ih sadrži - Google Patents

Derivati 1,3,4-oksadiazolsulfamida kao inhibitor histonske deacetilaze 6 i farmaceutski pripravak koji ih sadrži Download PDF

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HRP20200280T1
HRP20200280T1 HRP20200280TT HRP20200280T HRP20200280T1 HR P20200280 T1 HRP20200280 T1 HR P20200280T1 HR P20200280T T HRP20200280T T HR P20200280TT HR P20200280 T HRP20200280 T HR P20200280T HR P20200280 T1 HRP20200280 T1 HR P20200280T1
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Jaekwang Lee
Younghue HAN
Yuntae Kim
Jaeki Min
Miseon BAE
Dohoon Kim
Seokmin JIN
Jangbeen KYUNG
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Chong Kun Dang Pharmaceutical Corp.
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4245—Oxadiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
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    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
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    • A61P19/00—Drugs for skeletal disorders
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems

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Claims (11)

1. Spoj derivata 1,3,4-oksadiazolsulfamida, naznačen time, da je predstavljen sljedećom formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol: [image] gdje je svaki od L1, L2 ili L3 neovisno jedna veza ili –(C1-C2-alkilen)-; svaki od Z1 do Z4 je neovisno N ili CRZ, gdje RZ je -H ili -X; R1 je -CX2H ili -CX3; R2 je [image] [image] ili -NR8R9, pri čemu Y je -N-, -O- ili -S(=O)2-, svaki od a do d je neovisno cijeli broj 1, 2 ili 3, svaki od Ra do Rd je neovisno -H ili –(C1-C4-alkil), crtkana linija je jednostruka veza ili dvostruka veza, svaki od R4 i R5 je neovisno -H, -X, –(C1-C4-alkil), -aril ili -NReRf, uz uvjet da je crtkana linija dvostruka veza, R5 je nula, svaki od Re i Rf je neovisno -H ili –(C1-C4-alkil), kada Y je -N-, svaki od R6 i R7 je neovisno -H, –(C1-C4-alkil), –(C1-C4-alkil)-O-(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -C(=O)-O(C1-C4-alkil), -C(=O)-CF3, -(C1-C4-alkil)-C(=O)-O(C1-C4-alkil), -S(=O)2-(C1-C4-alkil), -(C3-C7-cikloalkil), -(C2-C6-heterocikloalkil), -aril, -(C1-C4-alkil)-aril, -heteroaril ili amino-zaštitna skupina, pri čemu najmanje jedan H iz -(C1-C4-alkila) može biti supstituiran s -X ili -OH, najmanje jedan H iz -arila, -(C1-C4-alkil)-arila ili -heteroarila, može biti supstituiran s -X, -OH ili CF3, i -(C2-C6-heterocikloalkil) može sadržavati atome N, O ili S u prstenu, te time, da ako Y je -O- ili -S(=O)2-, tada su R6 i R7 nula, svaki od R8 i R9 je neovisno -H, –(C1-C4-alkil), -(C3-C7-cikloalkil), -(C2-C6-heterocikloalkil), -(C1-C4-alkil)-(C2-C6-heterocikloalkil), -aril, -heteroaril ili –(C1-C4-alkil)-aril, pri čemu najmanje jedan H iz -(C3-C7-cikloalkila), -(C2-C6-heterocikloalkila), -(C1-C4-alkil)-(C2-C6-heterocikloalkila), -arila, -heteroarila ili –(C1-C4-alkil)-arila, može biti supstituiran sa sljedećima: –(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -S(=O)2-(C1-C4-alkil) ili -(C2-C6-heterocikloalkil); i R3 je -H, –(C1-C4-alkil), –(C1-C4-alkil)-O(C1-C4-alkil), –(C1-C4-alkil)-C(=O)-O(C1-C4-alkil), -(C3-C7-cikloalkil), -aril, -heteroaril ili [image] gdje najmanje jedan H iz -(C3-C7-cikloalkila), -arila ili -heteroarila, može biti supstituiran sa sljedećima: -X, -OH, –(C1-C4-alkil), CF3, –(C1-C4-alkil)-(C2-C6-heterocikloalkil)–(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -C(=O)-O(C1-C4-alkil), -O(C1-C4-alkil), -OCF3, -S(=O)2-(C1-C4-alkil), -aril, -heteroaril ili NR11R12, svaki od R11 i R12 je neovisno -H ili –(C1-C4-alkil), R1, L1, Z1, Z2, Z3 i Z4 su isti kao što su prethodno definirani; i X je F, Cl, Br ili I.
2. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 1, naznačen time, da je svaki od L1 ili L3 neovisno jedna veza; L2 je –(C1-alkilen)-; svaki od Z1 do Z4 je neovisno N ili CRZ, gdje RZ je -H ili -X; R1 je -CX2H ili -CX3; R2 je [image] ili -NR8R9, pri čemu Y je -N-, -O- ili -S(=O)2-, svaki od a do d je neovisno cijeli broj 1 ili 2, svaki od Ra do Rd je neovisno -H ili –(C1-C4-alkil), kada Y je -N-, svaki od R6 i R7 je neovisno -H, –(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -S(=O)2-(C1-C4-alkil), -(C3-C7-cikloalkil) ili -(C2-C6-heterocikloalkil), pri čemu najmanje jedan H iz -(C1-C4-alkila) može biti supstituiran s -X ili -OH, i -(C2-C6-heterocikloalkil) može sadržavati jedan od atoma N, O ili S, te time, da ako Y je -O- ili -S(=O)2-, tada su R6 i R7 nula, svaki od R8 i R9 je neovisno -H, –(C1-C4-alkil) ili -(C1-C4-alkil)-(C2-C6-heterocikloalkil), pri čemu najmanje jedan H iz -(C1-C4-alkil)-(C2-C6-heterocikloalkila), može biti supstituiran sa sljedećima: –(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -S(=O)2-(C1-C4-alkil) ili -(C2-C6-heterocikloalkil); R3 je -aril ili -heteroaril, pri čemu najmanje jedan H iz -arila ili -heteroarila, može biti supstituiran s -X; i X je F, Cl, Br ili I.
3. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 2, naznačen time, da je svaki od L1 ili L3 neovisno jedna veza; L2 je –(C1-alkilen)-; svaki od Z1 do Z4 je neovisno N ili CRZ, gdje RZ je -H ili -X; R1 je -CF2H ili -CF3; R2 je [image] ili [image] pri čemu Y je -N- ili -S(=O)2-, svaki od a do d je neovisno cijeli broj 1 ili 2, svaki od Ra do Rd je neovisno -H ili –(C1-C4-alkil), kada Y je -N-, svaki od R6 i R7 je neovisno -H, –(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -S(=O)2-(C1-C4-alkil), -(C3-C7-cikloalkil) ili -(C2-C6-heterocikloalkil), pri čemu najmanje jedan H iz -(C1-C4-alkila) može biti supstituiran s -X ili -OH, i -(C2-C6-heterocikloalkil) može sadržavati jedan od atoma N, O ili S, te time, da ako Y je -S(=O)2-, tada su R6 i R7 nula; R3 je -aril ili -heteroaril, pri čemu najmanje jedan H iz -arila ili -heteroarila, može biti supstituiran s -X; i X je F, Cl, Br ili I.
4. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 3, naznačen time, da je svaki od L1 ili L3 neovisno jedna veza; L2 je –(C1-alkilen)-; svaki od Z1 do Z4 je neovisno N ili CRZ, gdje RZ je -H ili -X; R1 je -CF2H ili -CF3; R2 je [image] ili [image] pri čemu Y je -N- ili -S(=O)2-, a i b su 2, dok c i d su 1, svaki od Ra do Rd je neovisno -H ili –(C1-C4-alkil), kada Y je -N-, svaki od R6 i R7 je neovisno -H, –(C1-C4-alkil), -C(=O)-(C1-C4-alkil), -S(=O)2-(C1-C4-alkil), -(C3-C7-cikloalkil) ili -(C2-C6-heterocikloalkil), pri čemu najmanje jedan H iz -(C1-C4-alkila) može biti supstituiran s -X ili -OH, i -(C2-C6-heterocikloalkil) može sadržavati jedan od atoma N, O ili S, te time, da ako Y je -S(=O)2-, tada su R6 i R7 nula; R3 je -aril ili -heteroaril, pri čemu najmanje jedan H iz -arila ili -heteroarila, može biti supstituiran s -F; i X je F ili Cl.
5. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 1, naznačen time, da je spoj koji je predstavljen formulom I, odabran iz skupine koja se sastoji od spojeva opisanih u sljedećoj tablici: [image] (nastavak) [image] (nastavak) [image] (nastavak) [image] (nastavak) [image] (nastavak) [image] (nastavak) [image]
6. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 5, naznačen time, da je spoj koji je predstavljen formulom I, odabran iz skupine koja se sastoji od spojeva opisanih u sljedećoj tablici: [image] (nastavak) [image] (nastavak) [image] (nastavak) [image]
7. Spoj derivata 1,3,4-oksadiazolsulfamida, koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s patentnim zahtjevom 6, naznačen time, da je spoj koji je predstavljen formulom I, odabran iz skupine koja se sastoji od spojeva opisanih u sljedećoj tablici: [image] (nastavak) [image] (nastavak) [image]
8. Farmaceutski pripravak za preventivu ili liječenje bolesti posredovane histonskom deacetilazom, naznačen time, da kao djelatni sastojak, obuhvaća spoj predstavljen formulom I, kao i njegov stereoizomer ili njegovu farmaceutski prihvatljivu sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 7.
9. Farmaceutski pripravak u skladu s patentnim zahtjevom 8, naznačen time, da je bolest posredovana histonskom deacetilazom odabrana između infektivnih bolesti; neoplazmi; endokrinih, nutritivnih i metaboličkih bolesti; mentalnih poremećaja i poremećaja ponašanja; neuroloških bolesti; bolesti oka i njegovih adneksa; kardiovaskularnih bolesti; respiratornih bolesti; digestivnih bolesti; bolesti kože i potkožnog tkiva; bolesti muskuloskeletnog sustava i njegovog vezivnog tkiva; ili kongenitalnih abnormalnosti, deformacija i kromosomskih abnormalnosti.
10. Spoj koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time, da se upotrebljava u postupku liječenja bolesti posredovane histonskom deacetilazom.
11. Spoj koji je predstavljen formulom I, kao i njegov stereoizomer ili njegova farmaceutski prihvatljiva sol za uporabu u skladu s patentnim zahtjevom 10, naznačen time, da je bolest posredovana histonskom deacetilazom odabrana iz skupine koja se sastoji od sljedećih: prionska bolest, mijelodisplastični sindrom, multipli mijelom, limfom, leukemija, rak pluća, rektalni rak, rak debelog crijeva, rak prostate, urotelijalni karcinom, rak dojke, melanom, rak kože, rak jetre, rak mozga, rak želuca, rak jajnika, rak gušterače, rak glave i vrata, rak usne šupljine, gliom, Wilsonova bolest, amiloidoza, dijabetes, depresija, Rettov sindrom, Huntingtonova bolest, spinalna mišićna atrofija (SMA), spinocerebralna ataksija (SCA), Alzheimerova bolest, Parkinsonova bolest, nasljedna neuropatija (Charcot-Marie-Tooth-bolest), sporadična neuropatija, upalna neuropatija, neuropatija izazvana supstancama, amiotrofna lateralna skleroza (ALS), multipla skleroza (MS), uveitis, atrijska fibrilacija, moždani udar, astma, alkoholna bolest jetre, upalna bolest crijeva, Crohnova bolest, ulcerativna bolest crijeva, psorijaza, reumatoidni artritis, osteoartritis, sustavna lupus eritematoza (SLE), i autosomalna dominantna policistična bolest bubrega.
HRP20200280TT 2015-07-27 2020-02-18 Derivati 1,3,4-oksadiazolsulfamida kao inhibitor histonske deacetilaze 6 i farmaceutski pripravak koji ih sadrži HRP20200280T1 (hr)

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KR20150106177 2015-07-27
PCT/KR2016/008218 WO2017018805A1 (en) 2015-07-27 2016-07-27 1,3,4-oxadiazole sulfamide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same
EP16830838.5A EP3328844B1 (en) 2015-07-27 2016-07-27 1,3,4-oxadiazole sulfamide derivatives as histone deacetylase 6 inhibitor and pharmaceutical composition comprising the same

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