HRP20231347T1 - Derivati 4-(1,3,4-oksadiazol-2-il)piridin-2(1h)-ona kao inhibitori histon deacetilaze 6 (hdac6) za liječenje npr. infekcije - Google Patents
Derivati 4-(1,3,4-oksadiazol-2-il)piridin-2(1h)-ona kao inhibitori histon deacetilaze 6 (hdac6) za liječenje npr. infekcije Download PDFInfo
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- HRP20231347T1 HRP20231347T1 HRP20231347TT HRP20231347T HRP20231347T1 HR P20231347 T1 HRP20231347 T1 HR P20231347T1 HR P20231347T T HRP20231347T T HR P20231347TT HR P20231347 T HRP20231347 T HR P20231347T HR P20231347 T1 HRP20231347 T1 HR P20231347T1
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- -1 4-(1,3,4-oxadiazole-2-yl)pyridine-2(1h)-one derivatives Chemical class 0.000 title claims 11
- 102000011427 Histone Deacetylase 6 Human genes 0.000 title claims 4
- 108010023925 Histone Deacetylase 6 Proteins 0.000 title claims 4
- 208000015181 infectious disease Diseases 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 201000010099 disease Diseases 0.000 claims 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 230000003287 optical effect Effects 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 230000000694 effects Effects 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 208000031404 Chromosome Aberrations Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 230000003542 behavioural effect Effects 0.000 claims 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims 2
- 231100000005 chromosome aberration Toxicity 0.000 claims 2
- 210000002808 connective tissue Anatomy 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 230000003340 mental effect Effects 0.000 claims 2
- 230000004060 metabolic process Effects 0.000 claims 2
- 210000002346 musculoskeletal system Anatomy 0.000 claims 2
- 230000035764 nutrition Effects 0.000 claims 2
- 235000016709 nutrition Nutrition 0.000 claims 2
- 206010033675 panniculitis Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 210000002345 respiratory system Anatomy 0.000 claims 2
- 230000028327 secretion Effects 0.000 claims 2
- 210000004304 subcutaneous tissue Anatomy 0.000 claims 2
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 claims 1
- 108010033040 Histones Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D413/04—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
-
- 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
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Claims (8)
1. Spojevi derivati 1,3,4-oksadiazola predstavljeni sljedećom formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli:
[image]
naznačeni time što,
X, Y i Z su svaki neovisno CR3 ili N;
L je -(C1-C6 alkilen)-, -(C2-C6 alkenilen)-, -(C=O)-(C1-C4 alkilen)-, -(C=O)O-(C1-C4 alkilen)-, -(C=O)NH-(C1-C4 alkilen)-, -O(C=O)-(C1-C4 alkilen)- ili jednostruka veza, pri čemu najmanje jedan H od -(C1-C6 alkilen)-, -(C2-C6 alkenilen)-, -(C=O)-(C1-C4 alkilen)-, -(C=O)O-(C1-C4 alkilen)-, -(C=O)NH-(C1-C4 alkilen)- i -O(C=O)-(C1-C4 alkilen)- mogu biti supstituirani s arilom ili heteroarilom;
R1 je vodik, -C1-C6 alkil, -C2-C6 alkenil, -C3-C8 cikloalkil, heterocikloalkil, benzil, aril, heteroaril ili -NR4R5, pri čemu najmanje jedan H od arila ili heteroarila može biti supstituiran s -C1-C6 alkilom, -C2-C6 alkenilom, -C1-C6 haloalkilom, -C1-C6 aminoalkilom, -C1-C6 hidroksialkilom, -C1-C6 alkoksi, hidroksi, cijano, halo, nitro, -CF2H, -CF3, -NR6R7, - C(=O)-Rs ili -S(=O)2-R9;
R2 je -CF2H ili -CF3;
R3 je vodik, halo ili -C1-C6 alkil;
R4 do R7 su svaki neovisno H ili -C1-C6 alkil; i
R8 i R9 su svaki neovisno H, OH ili -C1-C6 alkil.
2. Spojevi derivati 1,3,4-oksadiazola predstavljeni formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema zahtjevu 1, naznačeni time što:
X, Y i Z su svaki neovisno CR3 ili N;
L je -(C1-C6 alkilen)-, -(C2-C6 alkenilen)-, -(C=O)-(C1-C4 alkilen)-, -(C=O)O-(C1-C4 alkilen)-, -(C=O)NH-(C1-C4 alkilen)-, -O(C=O)-(C1-C4 alkilen)- ili jednostruka veza, pri čemu najmanje jedan H od -(C1-C6 alkilen)-, -(C2-C6 alkenilen)-, -(C=O)-(C1-C4 alkilen)-, -(C=O)O-(C1-C4 alkilen)-, -(C=O) NH-(C1-C4 alkilen)- i -O(C=O)-(C1-C4 alkilen)- mogu biti supstituirani s arilom;
R1 je vodik, -C1-C6 alkil, -C2-C6 alkenil, heterocikloalkil, benzil, aril, heteroaril ili -NR4R5, pri čemu najmanje jedan H od arila ili heteroarila može biti supstituiran s -C1-C6 alkilom, -C1-C6 alkoksi, halo, nitro, -CF3 ili -S(=O)2-R9;
R2 je -CF2H ili -CF3;
R3 je vodik ili halo;
R4 do R5 su svaki neovisno -C1-C6 alkil; i
R9 je svaki neovisno -C1-C6 alkil.
3. Spojevi derivati 1,3,4-oksadiazola predstavljeni formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema zahtjevu 1, naznačeni time što:
X, Y i Z su svaki neovisno CR3;
L je -(C1-C4 alkilen)-, -(C2-C4 alkenilen)-, -(C=O)-(C1-C2 alkilen)-, -(C=O)O-(C1-C2 alkilen)-, -(C=O)NH-(C1-C2 alkilen)-, -O(C=O)-(C1-C2 alkilen)- ili jednostruka veza, pri čemu najmanje jedan H od -(C1-C4 alkilen)-, -(C2-C4 alkenilen)-, -(C=O)-(C1-C2 alkilen)-, -(C=O)O-(C1-C2 alkilen)-, -(C=O)NH-(C1-C2 alkilen)- i -O(C=O)-(C1-C2 alkilen)- mogu biti supstituirani s arilom;
R1 je -C1-C6 alkil, -C2-C6 alkenil,
[image]
benzil, fenil, naftil,
[image]
ili -NR4R5, pri čemu najmanje jedan H predstavlja fenil, naftil,
[image]
[image]
može biti supstituiran s -C1-C6 alkilom, -C1-C6 alkoksi, halo, nitro, -CF3 ili -S(=O)2-R9;
R2 je -CF2H ili -CF3;
R3 je vodik;
R4 do R5 su svaki neovisno -C1-C4 alkil; i
R9 je svaki neovisno -C1-C4 alkil.
4. Spojevi derivati 1,3,4-oksadiazola predstavljeni formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema zahtjevu 1, naznačeni time što:
X, Y i Z su svaki neovisno CR3;
L je -(C1-C4 alkilen)-, -(C2-C4 alkenilen)-, -(C=O)-(C1-C2 alkilen)-, -(C=O)NH-(C1-C2 alkilen)-, -O(C=O)-(C1-C2 alkilen)- ili jednostruka veza, pri čemu najmanje jedan H od -(C1-C4 alkilen)-, -(C2-C4 alkenilen)-, -(C=O)-(C1-C2 alkilen)-, -(C=O)NH-(C1-C2 alkilen)- ili -O(C=O)-(C1-C2 alkilen)- može biti supstituiran s arilom;
R1 je -C1-C6 alkil, -C2-C6 alkenil,
[image]
fenil, naftil,
[image]
pri čemu najmanje jedan H predstavlja fenil, naftil,
[image]
[image]
može biti supstituiran s -C1-C6 alkoksi, halo, nitro ili -CF3;
R2 je -CF2H; i
R3 je vodik.
5. Spojevi derivati 1,3,4-oksadiazola predstavljeni formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema zahtjevu 1, naznačeni time što su spojevi predstavljeni gornjom formulom I spojevi kako je opisano u sljedećoj tablici.
[image]
[image]
[image]
[image]
[image]
[image]
[image]
6. Spojevi derivati 1,3,4-oksadiazola predstavljeni formulom I, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema zahtjevu 5,
pri čemu su spojevi predstavljeni gornjom formulom I spojevi odabrani iz skupine koju čine spojevi 1, 2, 3, 5, 7, 8, 9, 10, 13, 14, 15, 20, 21, 24, 25, 26, 28, 29, 43, 44, 45, 50, 51, 52, 53, 55, 56, 57 i 58.
7. Farmaceutski pripravak za uporabu u prevenciji ili liječenju bolesti povezanih s aktivnošću histon deacetilaze 6, sadrži spojeve derivate 1,3,4-oksadiazola predstavljene formulom I, njihove optičke izomere ili njihove farmaceutski prihvatljive soli prema bilo kojem od zahtjeva 1 do 6 kao aktivni sastojak,
pri čemu su bolesti povezane s aktivnošću histon deacetilaze 6 najmanje jedna odabrana iz skupine koja se sastoji od zaraznih bolesti; neoplazma; unutarnje izlučivanje; bolesti prehrane i metabolizma; mentalni poremećaji i poremećaji ponašanja; neurološke bolesti; bolesti oka i očnih adneksa; bolesti cirkulacije; bolesti dišnog sustava; probavne bolesti; bolesti kože i potkožnog tkiva; bolesti mišićno-koštanog sustava i vezivnog tkiva; i teratoze ili deformacije, i kromosomske aberacije.
8. Spojevi derivati 1,3,4-oksadiazola, njihovi optički izomeri ili njihove farmaceutski prihvatljive soli prema bilo kojem od zahtjeva 1 do 6 za uporabu u prevenciji ili liječenju bolesti povezanih s aktivnošću histon deacetilaze 6, pri čemu su bolesti povezane s aktivnošću histon deacetilaze 6 najmanje jedna odabrana iz skupine koja se sastoji od zaraznih bolesti; neoplazma; unutarnje izlučivanje; bolesti prehrane i metabolizma; mentalni poremećaji i poremećaji ponašanja; neurološke bolesti; bolesti oka i očnih adneksa; bolesti cirkulacije; bolesti dišnog sustava; probavne bolesti; bolesti kože i potkožnog tkiva; bolesti mišićno-koštanog sustava i vezivnog tkiva; i teratoze ili deformacije, i kromosomske aberacije.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020180087455A KR102316234B1 (ko) | 2018-07-26 | 2018-07-26 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| PCT/KR2019/009228 WO2020022794A1 (en) | 2018-07-26 | 2019-07-25 | 1,3,4-oxadiazole derivative compounds as histone deacetylase 6 inhibitor, and pharmaceutical composition comprising the same |
| EP19841767.7A EP3827004B1 (en) | 2018-07-26 | 2019-07-25 | 4-(1,3,4-oxadiazole-2-yl)pyridine-2(1h)-one derivatives as histone deacetylase 6 (hdac6) inhibitors for the treatment of e.g. infections |
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| Publication Number | Publication Date |
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| HRP20231347T1 true HRP20231347T1 (hr) | 2024-02-16 |
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| HRP20231347TT HRP20231347T1 (hr) | 2018-07-26 | 2019-07-25 | Derivati 4-(1,3,4-oksadiazol-2-il)piridin-2(1h)-ona kao inhibitori histon deacetilaze 6 (hdac6) za liječenje npr. infekcije |
Country Status (20)
| Country | Link |
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| US (1) | US11958844B2 (hr) |
| EP (1) | EP3827004B1 (hr) |
| JP (1) | JP7085686B2 (hr) |
| KR (1) | KR102316234B1 (hr) |
| CN (1) | CN112839942A (hr) |
| AU (1) | AU2019310508B2 (hr) |
| BR (1) | BR112021000953A2 (hr) |
| CA (1) | CA3105662C (hr) |
| DK (1) | DK3827004T3 (hr) |
| ES (1) | ES2963111T3 (hr) |
| FI (1) | FI3827004T3 (hr) |
| HR (1) | HRP20231347T1 (hr) |
| HU (1) | HUE063879T2 (hr) |
| MX (1) | MX2021000737A (hr) |
| PH (1) | PH12021550039A1 (hr) |
| PL (1) | PL3827004T3 (hr) |
| PT (1) | PT3827004T (hr) |
| RU (1) | RU2763936C1 (hr) |
| TW (1) | TWI729443B (hr) |
| WO (1) | WO2020022794A1 (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| KR102316234B1 (ko) | 2018-07-26 | 2021-10-22 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| AU2020284606B2 (en) * | 2019-05-31 | 2023-01-19 | Chong Kun Dang Pharmaceutical Corp. | 1,3,4-oxadiazole homophthalimide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same |
| TW202126643A (zh) | 2019-09-27 | 2021-07-16 | 日商武田藥品工業股份有限公司 | 雜環化合物 |
| US20230322747A1 (en) * | 2022-04-08 | 2023-10-12 | Eikonizo Therapeutics, Inc. | Oxadiazole hdac6 inhibitors and uses thereof |
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2018
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- 2019-07-25 CN CN201980049375.8A patent/CN112839942A/zh active Pending
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| MX2021000737A (es) | 2021-03-26 |
| CA3105662C (en) | 2023-08-01 |
| PH12021550039A1 (en) | 2021-09-20 |
| EP3827004B1 (en) | 2023-10-11 |
| RU2763936C1 (ru) | 2022-01-11 |
| CA3105662A1 (en) | 2020-01-30 |
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| CN112839942A (zh) | 2021-05-25 |
| WO2020022794A1 (en) | 2020-01-30 |
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| FI3827004T3 (fi) | 2023-11-02 |
| JP7085686B2 (ja) | 2022-06-16 |
| US11958844B2 (en) | 2024-04-16 |
| AU2019310508A1 (en) | 2021-02-04 |
| HUE063879T2 (hu) | 2024-02-28 |
| DK3827004T3 (da) | 2023-10-30 |
| BR112021000953A2 (pt) | 2021-04-20 |
| KR20200012316A (ko) | 2020-02-05 |
| TWI729443B (zh) | 2021-06-01 |
| EP3827004A4 (en) | 2022-06-08 |
| AU2019310508B2 (en) | 2021-12-23 |
| US20210188831A1 (en) | 2021-06-24 |
| PT3827004T (pt) | 2023-11-07 |
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