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HRP20220208T1 - Prolijekovi riluzola i njihova primjena - Google Patents

Prolijekovi riluzola i njihova primjena Download PDF

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Publication number
HRP20220208T1
HRP20220208T1 HRP20220208TT HRP20220208T HRP20220208T1 HR P20220208 T1 HRP20220208 T1 HR P20220208T1 HR P20220208T T HRP20220208T T HR P20220208TT HR P20220208 T HRP20220208 T HR P20220208T HR P20220208 T1 HRP20220208 T1 HR P20220208T1
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HR
Croatia
Prior art keywords
amino
methyl
thiazol
trifluoromethoxy
benzo
Prior art date
Application number
HRP20220208TT
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English (en)
Inventor
Jay Edward Wrobel
Allen B. Reitz
Jeffery Claude Pelletier
Garry Robert Smith
Haiyan Bian
Original Assignee
Biohaven Therapeutics Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Biohaven Therapeutics Ltd. filed Critical Biohaven Therapeutics Ltd.
Publication of HRP20220208T1 publication Critical patent/HRP20220208T1/hr

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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/425Thiazoles
    • A61K31/428Thiazoles condensed with carbocyclic rings
    • AHUMAN NECESSITIES
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • A61K9/006Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454Non 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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    • A61K31/33Heterocyclic compounds
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    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K31/33Heterocyclic compounds
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    • A61K31/535Heterocyclic 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
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • A61K31/53771,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • A61K31/54Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/541Non-condensed thiazines containing further heterocyclic rings
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    • A61K38/05Dipeptides
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/68Benzothiazoles 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 in position 2
    • C07D277/82Nitrogen atoms
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    • C07D417/12Heterocyclic 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 chain containing hetero atoms as chain links
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    • C07K5/06Dipeptides
    • C07K5/06008Dipeptides with the first amino acid being neutral
    • C07K5/06017Dipeptides with the first amino acid being neutral and aliphatic
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    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
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    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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    • A61K9/0056Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
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Claims (4)

1. Spoj koji ima formulu : [image] uključujući enantiomere, dijastereoizomere, hidrate, solvate i farmaceutski prihvatljive soli istih, pri čemu: R23 je odabrano iz grupe koja se sastoji H, CH3, CH2CH3, CH2CH2CH3, CH2CCH, CH(CH3)2, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2OH, CH2OCH2Ph, CH2CH2OCH2Ph, CH(OH)CH3, CH2Ph, CH2(cikloheksil), CH2(4-OH-Ph), (CH2)4NH2, (CH2)3NHC(NH2)NH, CH2(3-indol), CH2(5-imidazol), CH2CO2H, CH2CH2CO2H, CH2CONH2, i CH2CH2CONH2;
2. Spoj prema patentnom zahtjevu 1 odabran iz grupe koja se sastoji od: (S)-2-amino-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)propanamida; (R)-2-amino-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)propanamida; (S)-2-amino-3-metil-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)butanamida; (R)-2-amino-3-metil-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)butanamida; (S)-2-amino-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)-3-fenilpropanamida; (R)-2-amino-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)-3-fenilpropanamida; (S)-2-amino-4-metil-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)pentanamida; (R)-2-amino-4-metil-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)pentanamida; (S)-2-amino-3-hidroksi-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)propanamida; (R)-2-amino-3-hidroksi-N-(2-(metil(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)amino)-2-oksoetil)propanamida; 2-(2-aminoacetamido)-N-metil-N-(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)acetamida; ili farmaceutski prihvatljiva sol istog.
3. Spoj prema patentnom zahtjevu 1 pri čemu R23 je H.
4. Spoj prema patentnom zahtjevu 2 koje je 2-(2-aminoacetamido)-N-metil-N-(2-okso-2-((6-(trifluorometoksi)benzo[d]tiazol-2-il)amino)etil)acetamid.
HRP20220208TT 2015-03-03 2016-02-26 Prolijekovi riluzola i njihova primjena HRP20220208T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562127684P 2015-03-03 2015-03-03
EP16759303.7A EP3265448B1 (en) 2015-03-03 2016-02-26 Riluzole prodrugs and their use
PCT/US2016/019787 WO2016140879A1 (en) 2015-03-03 2016-02-26 Riluzole prodrugs and their use

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HRP20220208T1 true HRP20220208T1 (hr) 2022-04-29

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US (9) US10639298B2 (hr)
EP (2) EP4011870A1 (hr)
JP (2) JP6700293B2 (hr)
KR (2) KR20230147746A (hr)
CN (1) CN107567438B (hr)
AU (3) AU2016226463B2 (hr)
BR (1) BR112017018832B1 (hr)
CA (1) CA2978158C (hr)
CY (1) CY1125112T1 (hr)
DK (1) DK3265448T3 (hr)
EA (1) EA034759B1 (hr)
ES (1) ES2905318T3 (hr)
HR (1) HRP20220208T1 (hr)
HU (1) HUE058204T2 (hr)
IL (2) IL253989B (hr)
LT (1) LT3265448T (hr)
MX (1) MX380828B (hr)
PH (2) PH12021550250A1 (hr)
PL (1) PL3265448T3 (hr)
PT (1) PT3265448T (hr)
RS (1) RS62915B1 (hr)
SG (2) SG10201908354VA (hr)
SI (1) SI3265448T1 (hr)
WO (2) WO2016140878A2 (hr)

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WO2013138753A1 (en) 2012-03-16 2013-09-19 Fox Chase Chemical Diversity Center, Inc. Prodrugs of riluzole and their method of use
RS59490B1 (sr) * 2014-11-21 2019-12-31 Biohaven Therapeutics Ltd Sublingvalna formulacija riluzola
US12295942B2 (en) * 2015-03-03 2025-05-13 Biohaven Therapeutics Ltd. Riluzole prodrugs and their use
SG10201908354VA (en) 2015-03-03 2019-10-30 Biohaven Pharm Holding Co Ltd Riluzole prodrugs and their use
US11911369B2 (en) 2015-03-03 2024-02-27 Biohaven Therapeutics Ltd. Prodrugs of riluzole and their method of use
JP2017061430A (ja) * 2015-09-25 2017-03-30 芳男 ▲浜▼田 新規なプロドラッグ
RS65474B1 (sr) * 2016-05-20 2024-05-31 Biohaven Therapeutics Ltd Primena riluzola, prolekova riluzola ili analoga riluzola sa imunoterapijama za lečenje kancera
US12029731B2 (en) 2016-08-10 2024-07-09 Biohaven Therapeutics Ltd. Acyl benzo[d]thiazol-2-amine and their methods of use
AU2017363804B2 (en) * 2016-11-25 2021-12-23 Genuv Inc. Composition for promoting differentiation of and protecting neural stem cells and method for inducing neural regeneration using same
CN110291089B (zh) 2017-01-17 2022-05-27 海帕瑞吉尼克斯股份有限公司 用于促进肝再生或者减少或预防肝细胞死亡的蛋白激酶抑制剂
US12201618B2 (en) * 2017-01-18 2025-01-21 Biohaven Therapeutics Ltd. Use of riluzole prodrugs to treat Alzheimer's disease
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