DK3097086T3 - (2s)-n-[(1s)-1-cyan-2-phenylethyl]-1,4-oxazepan-2-carboxamider som dipeptidyl-peptidase i-hæmmere - Google Patents

(2s)-n-[(1s)-1-cyan-2-phenylethyl]-1,4-oxazepan-2-carboxamider som dipeptidyl-peptidase i-hæmmere Download PDF

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DK3097086T3
DK3097086T3 DK15701577.7T DK15701577T DK3097086T3 DK 3097086 T3 DK3097086 T3 DK 3097086T3 DK 15701577 T DK15701577 T DK 15701577T DK 3097086 T3 DK3097086 T3 DK 3097086T3
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carboxamide
ethyl
phenyl
oxazepan
oxo
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Hans Roland Loenn
Stephen Connolly
Steven Swallow
Staffan Po Karlsson
Carl Johan Aurell
John Fritiof Ponten
Kevin James Doyle
Graham Peter Jones
David Wyn Watson
Jaqueline Anne Macritchie
Nicholas John Palmer
De Poël Amanda Jane Van
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Astrazeneca Ab
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Claims (11)

1. Forbindelse med formlen (I) hvor
R1 e
R2 er udvalgt fra hydrogen, F, Cl, Br, OSO2C1-3-alkyl, eller Ci-3-alkyl; R3 er udvalgt fra hydrogen, F, Cl, Br, CN, CF3, SC>2Ci-3-alkyl, CONH2 eller S02NR4R5, hvor R4 og R5 sammen med det nitrogenatom, hvortil de er bundet, danner en azetidin-, pyrrolidin- eller piperidinring; eller R1 er udvalgt fra
X er udvalgt fra O, S eller CF2; Y er udvalgt fra O eller S; Q er udvalgt fra CH eller N; R6 er udvalgt fra Ci-3-alkyl, hvor Ci-3-alkyl eventuelt er substitueret med 1, 2 eller 3 F og eventuelt med én substituent udvalgt fra OH, OCi-3-alkyl, N(Ci-3-alkyl)2, cyclopropyl eller tetrahydropyran; R7 er udvalgt fra hydrogen, F, Cl eller CH3; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor R1 er
eller et farmaceutisk acceptabelt salt deraf.
3. Forbindelse ifølge enten krav 1 eller krav 2, hvor X er O; R6 er C i-3-alkyl; og R7 er hydrogen; eller et farmaceutisk acceptabelt salt deraf.
4. Forbindelse med formlen (I) ifølge krav, der er udvalgt fra: (25)-/Y-[(15)-1 -cyan-2-(4'-cyanobiphcnyl-4-yl)cthyl]-l,4-oxazepan-2-carboxamid; (2S)-N- j( 15)-1-cyan-2-[4-(3-methyl-2-oxo-2,3-dihydro-l ,3-bcnzoxazol-5-yl)phcnyl Jethyl}-1,4 -oxazepan-2-carboxamid; (25)-iV-{( 15)-1-cyan-2-[4-(3,7-dimcthyl-2-oxo-2,3-dihydro-1 ,3-benzoxazol-5-yl)phcnyl]ethyl} -1,4-oxazepan-2-carboxamid; 4'-[(25)-2-cyan-2-{[(25)-l,4-oxazepan-2-ylcarbonyl]amino}ethyl]biphenyl-3-yl methansulfonat; (2S)-N- {(15)-1 -cyan-2-[4-(3-methyl-l ,2-benzoxazol-5-yl)phenyl]ethyl} -1,4-oxazepan-2-carbo xamid; (:2S)-N- {(1 S)-1 -cyan-2-[4'-(trifluormethyl)biphenyl-4-yl]ethyl} -1,4-oxazepan-2-carboxamid; (25)-/V-[(15)-l-cyan-2-(3',4'-difluorbiphenyl-4-yl)ethyl]-l,4-oxazepan-2-carboxamid; (2 S)-N- {(15)-1 -cyan-2-[4-(6-cyanopyridin-3-yl)phenyl]ethyl} -1,4-oxazepan-2-carboxamid; (25)-/V-{(15)-l-cyan-2-[4-(4-mcthyl-3-oxo-3,4-dihydro-2//-l,4-benzothiazin-6-yl)phenyl]ethyl } -1,4-oxazepan-2-carboxamid; (25)-/V-{(15)-l-cyan-2-[4-(3-cthyl-7-mcthyl-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl)phenyl]et hyl} -1,4-oxazepan-2-carboxamid; (25)-A'-[(15)-1 -cyan-2- (4-[3-(2-hydroxy-2-methylpropyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-5 -yljphenyl} ethyl]-1,4-oxazepan-2-carboxamid; (25)-jV-[(15)-l-cyan-2-{4-[3-(2,2-difluorethyl)-7-fluor-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl] phenyl} ethyl]-l ,4-oxazepan-2-carboxamid; (25)-/Y-[( 1 5)-1 -cyan-2-(4- {3-[2-(dimethylamino)ethyl]-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl }phenyl)ethyl]-1,4-oxazepan-2-carboxamid; (2 S)-N- {(15)-1 -cyan-2-[4-(3,3-difluor-1 -methyl-2-oxo-2,3-dihydro-1 /7-indol-6-yl)phcnyl]cthyl } -1,4-oxazepan-2-carboxamid; (2S)-N- {(1 S)-1 -cyan-2-[4-(7-fluor-3-methyl-2-oxo-2,3-dihydro-l ,3-bcnzoxazol-5-yl)phcnyl]ct hyl} -1,4-oxazepan-2-carboxamid; (25)-iV-{(15)-l-cyan-2-[4-(3-ethyl-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl)phenyl]ethyl}-l,4-o xazepan-2-carboxamid; (25)-iV-[(15)-l-cyan-2-{4-[3-(cyclopropylmethyl)-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl]phe nyl} ethyl] -1,4-oxazepan-2-carboxamid; (25)-7V-[(15)-1 -cyan-2- {4-[3-(2-methoxyethyl)-2-oxo-2,3-dihydro-1,3-benzothiazol-5-yl]pheny 1} ethyl] -1,4-oxazepan-2-carboxamid; (25)-iV-[(15)-1-cyan-2-{4-[2-oxo-3-(propan-2-yl)-2,3-dihydro-1,3-benzoxazol-5-yl]phenyl} eth yl]-1,4-oxazepan-2-carboxamid; (25)-.V-{( 15)-1-cyan-2-[4-(4-methyl-3-oxo-3,4-dihydro-2//-l,4-benzoxazin-6-yl)phenyl]ethyl} -1,4-oxazepan-2-carboxamid; (25)-7V-[(l 5)-1 -cyan-2-{4-[3-(2-mcthoxycthyl)-2-oxo-2,3-dihydro-l ,3-benzoxazol-5-yl]phcnyl } ethyl] -1,4-oxazepan-2-carboxamid; (25)-77- i (1 S)-1 -cyan-2-[4-(5-cyanothiophcn-2-yl)phcnyl]cthyl} -1,4-oxazepan-2-carboxamid; (25)-7V-[(15)-2-(4'-carbamoyl-3'-fluorbiphcnyl-4-yl)-l -cyanocthyl]-l,4-oxazepan-2-carboxami d; (2 S)-N- {(15)-1 -cyan-2-[4-(l -methyl-2-oxo-1,2-dihydroquinolin-7-yl)phenyl] ethyl} -1,4-oxazep an-2-carboxamid; (25)-7V-[(15)-1 -cyan-2- {4-[2-oxo-3-(tctrahydro-2//-pyran-4-ylmcthyl)-2,3-dihydro-1,3-benzox azol-5-yl]phenyl}ethyl]-l,4-oxazepan-2-carboxamid; (25)-.V-{(15)-2-[4-(7-chlor-3-methyl-2-oxo-2,3-dihydro-l ,3-bcnzoxazol-5-yl)phcnyl]-l-cyanoc thyl} -1,4-oxazepan-2-carboxamid; (25)-.V-[( 15)-1 -cyan-2- {4-[3-(2,2-difluorethyl)-2-oxo-2,3-dihydro-1,3-benzoxazol-5-yl]phenyl } ethyl] -1,4-oxazepan-2-carboxamid; (25)-.V-[( 15)-1 -cyan-2- {4-[2-oxo-3-(2,2,2-trifluorethyl)-2,3-dihydro-1,3-benzoxazol-5-yl]phen yl} ethyl] -1,4-oxazepan-2-carboxamid; (25)-/V-{( 15)-l-cyan-2-[4-(3-methyl-2-oxo-2,3-dihydro-l ,3-bcnzothiazol-5-yl)phcnyl]cthyl}-l, 4-oxazepan-2-carboxamid; (25)-A-{(15)-1 -cyan-2-[4'-(mcthylsulfonyl)bi phenyl-4-yl]ethyl}-l,4-oxazcpan-2-carboxam id; (2S)-N-{( 15)-2-[4'-(azetidin-1 -ylsulfonyl)biphcnyl-4-yl]-1 -cyanoethyl } -1,4-oxazcpan-2-carbox amid; (25)-7V-[( 1 S)-1 -cyan-2-(4'-fluorbiphcnyl-4-yl)cthyl]- l,4-oxazepan-2-carboxamid; (25)-./V-{(15)-2-[4-(l,3-benzothiazol-5-yl)phenyl]-l-cyanoethyl}-l,4-oxazepan-2-carboxamid; (25)-/V-[( 1 S)-1 -cyan-2-(4'-cyanbiphcnyl-4-yl)cthyl]-1,4-oxazcpan-2-carboxamid og farmaceutisk acceptable salte deraf.
5. Forbindelse ifølge krav 1, der er (25)-vV-{(15)-l-cyan-2-[4-(3-methyl-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl)phenyl]ethyl}-l,4 -oxazepan-2-carboxamid
eller et farmaceutisk acceptabelt salt deraf.
6. Forbindelse ifølge krav 1, der er (25)-/V-{(15)-l-cyan-2-[4-(3-mcthyl-2-oxo-2,3-dihydro-l,3-benzoxazol-5-yl)phenyl]ethyl}-l,4 -oxazepan-2-carboxamid
7. Farmaceutisk sammensætning, der omfatter en forbindelse med formlen (I) ifølge et hvilket som helst af kravene 1 til 6 og et farmaceutisk acceptabelt adjuvans, fortyndingsmiddel eller bærestof.
8. Forbindelse med formlen (I) ifølge et hvilket som helst af kravene 1 til 6 til anvendelse i terapi.
9. Forbindelse med formlen (I) ifølge et hvilket som helst af kravene 1 til 6, til anvendelse i behandling af obstruktive luftvejssygdomme: herunder en hvilken som helst af astma, der indbefatter bronkial, allergisk, intrinsisk, ekstrinsisk, anstrengelsesinduceret, lægemiddelinduceret (herunder aspirin- og NSAID-induceret) og støvinduceret astma, begge intermitterende og vedvarende og af enhver alvorsgrad, og andre årsager til luftvejs hyperresponsivitet; kronisk obstruktiv lungesygdom (COPD); bronkitis, herunder infektiøs og eosinofil bronkitis; emfysem; bronkiektasi; cystisk fibrose; sarkoidose; alpha-l-antitrypsindeficiens; tærskerlunge og beslægtede sygdomme; hypersensibilitetspneumonitis; lungefibrose, herunder kryptogen fibrøs alveolitis, idiopatiske interstitielle pneumonier, fibrose, der komplicerer antineoplastisk terapi og kronisk infektion, herunder tuberkulose og aspergillose og andre svampeinfektioner; komplikationer ved lungetransplantation; vaskulitiske og trombotiske forstyrrelser i lungevaskulatur, og pulmonal hypertension; hostestillende aktivitet, der indbefatter behandling af kronisk hoste forbundet med inflammatoriske og sekretoriske luftvejstilstande, og iatrogen hoste; akut og kronisk rhinitis, herunder rhinitis medicamentosa, og vasomotor rhinitis; stadig tilbagevendende og sæsonbetinget allergisk rhinitis, herunder rhinitis nervosa (høfeber); næsepolypose; akut virusinfektion, herunder almindelig forkølelse, og infektion på grund af respiratorisk syncytialvirus, influenza, coronavirus (herunder SARS) og adenovirus, akut lungelæsion, ARDS (adult respiratory distress syndrome), såvel som exacerbationer af hver af de foregående luftvejssygdomstilstande, navnlig exacerbationer af samtlige typer af astma eller COPD.
10. Forbindelse med formlen (I) til anvendelse ifølge krav 9 til anvendelse i behandling af astma eller kronisk obstruktiv lungesygdom.
11. Kombination af en forbindelse med formlen (I) ifølge et hvilket som helst af kravene 1 til 6 og ét eller flere midler, der er uafhængigt udvalgt fra: • en ikke-steroid glucocorticoidreceptoragonist; • en selektiv P2-adrenoceptoragonist; • en phosphodiesterasehæmmer; • en proteasehæmmer; • et glucocorticoid; • et anticholinergt middel; • en modulator af kemokinreceptorfunktion og • en hæmmer af kinasefunktion.
DK15701577.7T 2014-01-24 2015-01-23 (2s)-n-[(1s)-1-cyan-2-phenylethyl]-1,4-oxazepan-2-carboxamider som dipeptidyl-peptidase i-hæmmere DK3097086T3 (da)

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PCT/GB2015/050155 WO2015110826A1 (en) 2014-01-24 2015-01-23 (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides as dipeptidyl peptidase i inhibitors

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DK17195612.1T DK3323814T3 (da) 2014-01-24 2015-01-23 (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepan-2-carboxamider som dipeptidylpeptidase i-hæmmere

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NO2699580T3 (da) 2014-01-24 2018-02-24
US20180028541A1 (en) * 2016-07-29 2018-02-01 Astrazeneca Ab Certain (2s)-n-[(1s)-1-cyano-2-phenylethyl]-1,4-oxazepane-2-carboxamides as dipeptidyl peptidase 1 inhibitors for treating bronchiectasis
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