PE20200446A1 - Nuevos inhibidores de hdac6 selectivos - Google Patents
Nuevos inhibidores de hdac6 selectivosInfo
- Publication number
- PE20200446A1 PE20200446A1 PE2019001995A PE2019001995A PE20200446A1 PE 20200446 A1 PE20200446 A1 PE 20200446A1 PE 2019001995 A PE2019001995 A PE 2019001995A PE 2019001995 A PE2019001995 A PE 2019001995A PE 20200446 A1 PE20200446 A1 PE 20200446A1
- Authority
- PE
- Peru
- Prior art keywords
- absent
- new selective
- hdac6
- hdac6 inhibitors
- selective hdac6
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 102100022537 Histone deacetylase 6 Human genes 0.000 title 1
- 101000899330 Homo sapiens Histone deacetylase 6 Proteins 0.000 title 1
- WWGBHDIHIVGYLZ-UHFFFAOYSA-N N-[4-[3-[[[7-(hydroxyamino)-7-oxoheptyl]amino]-oxomethyl]-5-isoxazolyl]phenyl]carbamic acid tert-butyl ester Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC(C(=O)NCCCCCCC(=O)NO)=NO1 WWGBHDIHIVGYLZ-UHFFFAOYSA-N 0.000 title 1
- 102000011427 Histone Deacetylase 6 Human genes 0.000 abstract 3
- 108010023925 Histone Deacetylase 6 Proteins 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 206010052779 Transplant rejections Diseases 0.000 abstract 1
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- 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
- C07D417/02—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 two hetero rings
- C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- A61K31/41—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
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- 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
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- A61K31/33—Heterocyclic compounds
- 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
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- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- 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
- A61K31/433—Thidiazoles
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- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
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- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- 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
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
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Abstract
Referido a un compuesto de formula (I) y (II); A es N, O, S en (I), y N en (II); B es C, N; C es N, O en (I), y N en (II); X es CH2, S, NH, O, CD2; n es 0, 1; R4 =R5 = H, F; R1 esta ausente o es H, -NH2, entre otros; R2 esta ausente o es H, alquilo, cicloalquilo, entre otros; R3 esta ausente o es H, alcoxiarilo, entre otros; R6 es un residuo mono o policiclico sustituido o no sustituido, entre otros; a sus sales, estereoisomeros y profarmacos farmaceuticamente aceptables. Estos compuestos son inhibidores benzohidroxamicos selectivos de la enzima histona desacetilasa 6 (HDAC6). Un compuesto seleccionado es: -(S)-N-(1-(3-(4-(hidroxicarbamoil)bencil)-1,2,4-oxadiazol-5-il)-2-(tiazol-4-il)etil)-3,4-dimetoxibenzamida (comp. 1). Tambien se refiere a su uso en el tratamiento de enfermedades asociadas con actividad HDAC6, tales como rechazo de injertos, miositosis, entre otros.
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IT102017000041723A IT201700041723A1 (it) | 2017-04-14 | 2017-04-14 | Nuovi inibitori selettivi di HDAC6 |
PCT/EP2018/059468 WO2018189340A1 (en) | 2017-04-14 | 2018-04-12 | Selective hdac6 inhibitors |
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WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
CN109942564A (zh) * | 2019-04-16 | 2019-06-28 | 四川大学华西医院 | 一种组蛋白去乙酰化酶抑制剂及其制备方法和用途 |
WO2021013163A1 (en) * | 2019-07-23 | 2021-01-28 | Taipei Medical University | Histone deacetylase 6 inhibitors and method for treating neuropathic pain |
CN116157398A (zh) | 2020-08-07 | 2023-05-23 | 意大发马克股份公司 | 作为组蛋白去乙酰化酶6(HDAC6)的选择性抑制剂用于治疗例如周围神经病变的2-(4-((5-(苯并[b]噻吩-3-基)-1H-四唑-1-基)甲基)苯基)-5-(二氟甲基)-1,3,4-噁二唑衍生物和类似化合物 |
CN112250638B (zh) * | 2020-11-13 | 2022-05-03 | 郑州大学 | 一种1,3-二芳基-1,2,4-三氮唑类化合物及其制备方法和应用 |
IT202100009926A1 (it) | 2021-04-20 | 2022-10-20 | Italfarmaco Spa | Una combinazione comprendente un inibitore di hdac6 specifico e almeno un inibitore del checkpoint ctla4 |
TW202340480A (zh) | 2021-11-23 | 2023-10-16 | 義大利商義大利藥品股份有限公司 | 檢測rna生物標記之方法 |
WO2023219456A1 (ko) * | 2022-05-12 | 2023-11-16 | 숙명여자대학교 산학협력단 | 퀴놀린 계열 히스톤디아세틸화 효소 저해활성물질, 이의 제조방법 및 이를 유효성분으로 포함하는 약학적 조성물 |
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AU2015274334B2 (en) | 2014-06-12 | 2020-12-17 | Cedars-Sinai Medical Center | Compositions and methods for treating cancers |
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