DK2969000T3 - Nye forbindelser - Google Patents
Nye forbindelser Download PDFInfo
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- DK2969000T3 DK2969000T3 DK14711577.8T DK14711577T DK2969000T3 DK 2969000 T3 DK2969000 T3 DK 2969000T3 DK 14711577 T DK14711577 T DK 14711577T DK 2969000 T3 DK2969000 T3 DK 2969000T3
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- alkyl
- pyridin
- alkoxy
- nr4ar4b
- pyrrolo
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- 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
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Claims (12)
1. Forbindelse af formel (I) eller et farmaceutisk acceptabelt salt, eller N-oxid deraf:
Hvor Y er valgt fra hydrogen, hydroxyl, -NH2, -NH-Ci-4-alkyl, -NH-halo-Ci-4-alkyl eller Ci-4-alkoxy; Z er valgt fra hydrogen, halogen, hydroxyl, cyano, Ci-4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy halo-Ci-4-alkoxy, CONH2, SO2NH2, -NH2, -NH-Ci-4-alkyl, -NH-halo-Ci-4-alkyl; R1 er en phenyl-ring, eller en 5- eller 6-leddet heteroaryl-ring, hvor hver ring eventuelt er substitueret med en eller flere substituenter valgt fra halogen, cyano, C1 4-alkyl, halo-Ci-4-alkyl, cyano-Ci-4-alkyl, Ci-4-alkoxy, halo-Ci-4-alkoxy, -NR4AR4B,-NR6C(0)0R5, -NR6C(0)R5, -NR6C(0)NR4AR4B, -C(O)NR4AR4B, -C(O)R5, -C(0)0R5, og -NR6S(0)2R5; W er en phenyl-ring eller en 5- eller 6-leddet heteroaryl-ring, hvor hver ring eventuelt er substitueret med en eller flere substituenter valgt fra halogen, cyano, C1 4-alkyl, halo-Ci-4-alkyl, cyano-Ci-4-alkyl, Ci-4-alkoxy, halo-Ci-4-alkoxy, -NR4AR4B,-NR6C(0)0R5, -NR6C(0)R5, -NR6C(0)NR4AR4B, -C(O)NR4AR4B, -C(O)R5, -C(0)0R5,-S02R5, -S02NR4AR4B og -NR6S(0)2R5; R2 er -B-Q-[R3]n eller -B-R3; hvor n = 1,2,3, eller 4 B er en binding, -O-, -NR5-, -C(O)- eller Ci-3-alkylen; Q er en mættet eller delvist umættet 3-7-leddet heterocyklisk eller C3-7-cy kloalky I-ring; når R2 er -B-0-[R3]n, R3 er valgt fra hydrogen, halogen, cyano, amino, hydroxyl, oxo, Ci-4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy, Ci-4alkoxy-Ci-4alkyl, hydroxy-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, Ci-4-alkylamino-Ci-4-alkyl, di(Ci-4-alkyl)amino-Ci-4-alkyl, -NR4AR4B, -NR6C(0)0R5, -NR6C(0)R5, -NR6C(0)NR4AR4B,-C(O)NR4AR4B, -C(0)R5, -C(0)0R5, -NR6S(0)2R5, -S(0)2R5, Ci-4-alkyl-NR6C(0)0R5,-Ci-4-alkyl-NR6C(0)NR4AR4B, amino-Ci-4-alkoxy-Ci-4-alkyl-, (amino-Ci-4-alkyl)-amino-Ci-4-alkyl-, -Ci-4-alkyl-C(0) R5, -0C(0)R5, -Ci-4-alkyl-C(0)0R5, -Ci-4-alkyl-C(0)NR4AR4B, -Ci-4-alkyl-NR6C(0)NR4AR4B, 3-7-leddet heterocyklyl, C3-7-cykloalkyl, 3-7-leddet heterocyklyI-C1 -4-alkyl-, (3-7-leddet heterocyklyl-Ci-4-alkyl)-amino-Ci-4-alkyl-, phenyl-Ci-4-alkyl og 5- eller 6-leddet heteroaryl-Ci-4-alkyl, og hvor en hvilken som helst phenyl-eller heteroaryl-rest eventuelt er substitueret med en eller flere substituenter valgt fra halogen, cyano, C1 4-alkyl, halo-Ci-4-alkyl, C1-4-alkoxy, Ci-4alkoxy-Ci-4alkyl, hydroxy-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, Ci-4-alkylamino-Ci-4-alkyl, di(Ci-4-alkyl)amino-Ci-4-alkyl, -NR4AR4B, -NR6C(0)0R5,-NR6C(O)R5, -NR6C(0)NR4AR4B, -C(0)NR4AR4B, -C(0)R5, -C(0)0R5, -NR6S(0)2R5; når R2 er -B-R3, R3 er valgt fra -NH2, Ci-4-alkoxy, Ci-4alkoxy-Ci-4alkyl, hydroxy-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, Ci-4-alkylamino-Ci-4-alkyl, di( C1-4-alky I) am ino-C1-4-alky I, -NR4AR4B, -NR6C(0)0R5, -NR6C(0)R5,-NR6C(0)NR4AR4B, -C(O)NR4A1R4B, -C(0)R5, -NR6S(0)2R5, 3-7-leddet heterocyklyl-C1-4-alky I-, phenyl-Ci-4-alkyl og heteroaryl-Ci-4-alkyl, og hvor en hvilken som helst phenyl- eller heteroaryl-rest eventuelt er substitueret med en eller flere substituenter valgt fra halogen, cyano, C1-4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy, Ci-4alkoxy-Ci-4alkyl, hydroxy-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, Ci-4-alkylamino-Ci-4-alkyl, di(Ci-4-alkyl)amino-Ci-4-alkyl, -NR4AR4B, -NR6C(0)0R5, -NR6C(0)R5,-NR6C(0)NR4AR4B, -C(O)NR4AR4B, -C(0)R5, -C(0)0R5, -NR6S(0)2R5, givet at når R2 er -B-R3, og B er en binding og R3 er -C(0)R5, så er R5 ikke hydrogen; R4A, R4B og R5 er hver uafhængigt valgt fra hydrogen, C1 4-alkyl, hydroxy-C1 4-alkyl, halo-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, C1-4- alkylam ino-Ci 4-alky I, di(Ci-4-alkyl)amino-Ci-4-alkyl eller Ci-4alkoxy-Ci-4alkyl, 3-7-leddet heterocyklyl-, 3-7-leddet heterocyklyl-Ci-4-alkyl-, C1-4-alkyl-NR6C(0)0R5, Ci-4-alkyl-NR6C(0)R5, (3-7-leddet heterocyklyl-Ci-4-alkyl)-amino-Ci 4-alkyl-, C3-7-cykloalkyl eller 5- eller 6-leddet heteroaryl-Ci-4-alkyl hvor alkyldelen af den 5- eller 6-leddede heteroaryl-Ci-4-alkylgruppe eventuelt er substitueret på et eller flere kulstofatomer med gruppe valgt fra halogen, Ci-4alkyl, eller C3-7-cykloalkyl, eller et af kulstofatomerne af den samme alkyldel er substitueret med to Ci-4alkyl-substituenter, der sammen med kulstofatomet til hvilket de er fastgjort danner en C3-7-cykloalkyI-ring, eller R4A og R4B sammen med nitrogenet til hvilket de er fastgjort danner en 4-7 leddet cyklisk aminogruppe eventuelt substitueret med en eller flere substituenter valgt fra: oxo, halogen, hydroxyl, cyano, C1 4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy, Ci-4alkoxy-Ci-4alkyl-, halo-Ci-4-alkoxy, -C(0)NR4AR4B, -CONH2, -SO2NH2, -NH2,-NHCi-4-alkyl, -NHhalo-Ci-4-alkyl, -C(0)R5, -C(0)0R5 eller -SO2R5, eller C3-7-cykloalkyl; medmindre på anden vis specificeret er den 3-7-leddede heterocyklyl, eller heterocyklyl-delen af den 3-7-leddede heterocyklyl-Ci 4-alkyl-, (3-7-leddet heterocyklyl-Ci-4-alkyl)-amino-Ci-4-alkyl-, eller (3-7-leddet heterocyklyl-Ci-4-alkyl)-C(O)- gruppe eventuelt substitueret med en eller flere substituenter valgt fra Ci-4-alkyl-,-C(0)0R5, -C(0)R5, -C(0)NR4AR4B, -NR4AR4B, - C1 -4- alky I- C(O) NR4AR4B, eller Ci-4alkoxy-Ci-4alkyl; og R4A1 er valgt fra C1 4-alkyl, hydroxy-Ci-4-alkyl, halo-Ci-4-alkyl, cyano-Ci-4-alkyl, amino-Ci-4-alkyl, Ci-4-alkylamino-Ci-4-alkyl, di(Ci-4-alkyl)amino-Ci-4-alkyl eller Ci-4alkoxy-Ci-4alkyl; eller R4A1 og R4B sammen med nitrogenet til hvilket de er fastgjort danner en 4-7 leddet cyklisk aminogruppe eventuelt substitueret med en eller flere substituenter valgt fra: oxo, halogen, hydroxyl, cyano, C1 4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy, Ci-4alkoxy-Ci-4alkyl-, halo-Ci-4-alkoxy, -CONH2, -SO2NH2, -NH2,-NHCi-4-alkyl, -NHhalo-Ci-4-alkyl, -C(0)R5, -C(0)0R5 eller -SO2R5, eller Cs-7-cykloalkyl. R6 er hydrogen eller C1 4-alkyl.
2. Forbindelse ifølge krav 1, hvor Yeller Z er H.
3. Forbindelse ifølge krav 1 eller krav 2, hvor R1 er en phenyl-ring eller en 6-leddet heteroaryl-ring, hvor hver ring eventuelt er substitueret med en eller flere substituenter valgt fra halogen, Ci 4-alkyl eller halo-Ci-4-alkyl.
4. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, hvor W er en 5- eller 6-leddet heteroaryl-ring eventuelt substitueret med en eller flere substituenter valgt fra halogen, Ci 4-alkyl, halo-Ci-4-alkyl, Ci-4-alkoxy, halo-Ci-4-alkoxy eller -NR4AR4B.
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor R2 er -Q-[R3]n
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor Q er en 7-leddet mættet eller delvist umættet 7-leddet heterocyklisk eller cykloalkyl-ring.
7. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, hvor Q er en 5- eller 6-leddet mættet eller delvist umættet 5- eller 6-leddet heterocyklisk eller cykloalkyl-ring.
8. Forbindelse ifølge et hvilket som helst af kravene 1 til 7, hvor R3 er valgt fra hydrogen, C1-4-alkyl, Ci-4-alkoxy, halo-Ci 4-alkoxy, 3-7-leddet heterocyklyl, 3-7-leddet heterocyklyl-Ci-4-alkyl- eller -C(0)NR4AR4B.
9. Forbindelse ifølge et hvilket som helst af kravene 1 til 8, hvor Q er piperidinyl og R3 er -CONH2.
10. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, hvor R2 er -B-R3, B er -Ci-3-alkylen-, og -R3 er -NR4AR4B, og R4A og R4B er hver uafhængigt valgt fra hydrogen og Ci-4-alkyl.
11. Forbindelse ifølge krav 1 valgt fra: 4-[2-(6-Aminopyridin-3-yl)-1-(4-chlorphenyl)-l H-pyrrolo[2,3-c]pyridin-3-yl] piperidin-1 -carboxamid; 4-[1-(4-Chlorphenyl)-2-(pyridin-3-yl)-1 H-pyrrolo[2,3-c] pyridin-3-y I] piperidin-1 -carboxamid; 4-[1-(4-Chlorphenyl)-2-(6-methoxypyridin-3-yl)-1 H-py r rolo[ 2,3-c] pyridin- 3- y I] piperidin-1 -carboxamid; 4- [1-(4-Chlorphenyl)-2-(2-methoxypyridin-4-yl)-l H-pyrrolo[2,3-c]pyridin- 3- y I] piperidin-1 -carboxamid; 4- [1 -(4-Chlorphenyl)-2-[2-(4-methylpiperazin-1 -y I) pyridin-4-y I] -1H-pyrrolo[2,3-c] pyridin-3-yl] piperidin-1 -carboxamid; 4-[1-(4-Chlorphenyl)-2-[6-(morpholin-4-yl)pyridin-3-yl]-1 H-pyrrolo[2,3- c] py ridin-3-y I] piperidin-1 -carboxamid; 4-[1 -(4-Chlorphenyl)-2-(pyrimidin-5-yl)-1 H-pyrrolo[2,3-c]pyridin-3-y I] piperidin-1 -carboxamid; 4-[1 - (4-Chlorpheny 1)-2-(1 H-pyrazol-3-yl)-1 H-pyrrolo[2,3-c] pyridin-3-y I] piperidin-1 -carboxamid; 4-[ 1 - (4-Chlorpheny 1)-2-(1 H-pyrazol-4-yl)-1 H-pyrrolo[2,3-c] py rid in-3-y I] piperidin-1 -carboxamid; 4-[1 -(4-Chlorpheny 1)-2-(1 - met hyl-1 H-pyrazol-4-yl)-1 H-pyrrolo[2,3-c] py ridin-3-y I] piperid in-1 - carboxamid; 4-[1 - (4-Chlorpheny 1)-2-(1 - methyl-1 H-pyrazol-5-yl)-1 H-pyrrolo[2,3-c] py ridin-3-y I] piperid in-1 - carboxamid; 4-[1 - (4-Chlorpheny 1)-2-(1 - methyl-1 H-imidazol-5-yl)-1 H-pyrrolo[2,3-c] py ridin-3-y I] piperid in-1 - carboxamid; 4-[1 - (4-Chlorpheny 1)-2-(1 H-pyrazol-1 - y I) -1 H-pyrrolo[2,3-c] pyridin-3-y I] piperidin-1 -carboxamid; 4-[1 - (4-Chlorpheny 1)-2-(1 H-imidazol-1 - y I) -1 H-pyrrolo[2,3-c] py rid in-3-y I] piperidin-1 -carboxamid; 4-[1 - (4-Chlorpheny I)-2-(1 H-1,2,3-triazol-1 -yl) -1 H-pyrrolo[2,3-c] pyridin-3-y I] piperidin-1 -carboxamid; 4-[1 - (4-Chlorpheny I)-2-(1 H-1,2,4-triazol-1 -y I) -1 H-pyrrolo[2,3-c] pyridin-3-y I] piperidin-1 -carboxamid; 4- [1 - (4-Chlorpheny l)-3-(piperidin-4-y 1)-1 H-pyrrolo[2,3-c] py ridin-2-y I] py ridin; 5- [1 - (4-Chlorpheny I)-3-(piperidin-4-y 1)-1 H-pyrrolo[2,3-c] py ridin-2-yl]pyridin-2-amin; {[1 - (4-Chlorpheny I) - 2-(pyridin-4-y 1)-1 H-pyrrolo[2,3-c]pyridin-3-yI] methyl} dimethylamin; {[1 -(4-Chlorphenyl)-2-(pyridin-3-yl)-1 H-pyrrolo[2,3-c]pyridin-3-yl] methyl} dimethylamin; og 4-[ 1 -(4-Chlorpheny I)-2-(2 H-1,2,3,4-tetrazol-5-yl)-1 H-pyrrolo[2,3-c]pyridin-3-yl]piperidin; og farmaceutisk acceptable salte deraf.
2. Farmaceutisk sammensætning omfattende en forbindelse ifølge et hvilket som helst af kravene 1 til 11, og en eller flere egnede excipienser.
3. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 til anvendelse i behandlingen af inflammation, en inflammatorisk sygdom, en immun- eller en autoimmun-lidelse, eller inhibition af tumorvækst.
4. Forbindelse til anvendelse ifølge krav 13, hvor inflammationen eller den inflammatoriske sygdom eller immun- eller autoimmunlidelsen er arthritis inklusiv rheumatoid arthritis, juvenil rheumatoid arthritis, osteoarthritis og psoriasisgigt, synovitis, vaskulitis, Sjogrens sygdom, en tilstand associeret med inflammation af tarmene inklusiv Crohns sygdom, ulcerativ colitis, inflammatorisk tarmsygdom og irritabel tyktarmssyndrom, aterosklerose, multipel sklerose, Alzheimers sygdom, vaskulær demens, Parkinsons sygdom, cerebral amyloid angiopati, cerebral autosomal dominant arteriopati med subkortikal infarkt og leukoencefalopati , en lungeinflammatorisk sygdom inklusiv astma, kronisk obstruktiv lungesygdom og akut lungesvigt-syndrom, en fibrotisk sygdom inklusiv idiopatisk lungefibrose, hjertefibrose, leverfibrose og systemisk sklerose også kendt som scleroderma, en inflammatorisk sygdom i huden inklusiv kontakteksem, atopisk eksem og psoriasis, en inflammatorisk sygdom i øjet inklusiv aldersrelateret makulær degeneration, uveitis og diabetisk retinopati, systemisk inflammatorisk responssyndrom, sepsis, en inflammatorisk og/eller autoimmun tilstand af leveren inklusiv autoimmun hepatitis, primær biliser cirrose, alkoholisk leversygdom, skleroserende cholangit, og autoimmun cholangit, type I- eller ll-diabetes og/eller komplikationerne deraf, kronisk hjertesvigt, hjertesvigt, en iskæmisk sygdom inklusiv slagtilfælde og iskæmi-reperfusionsskade eller myokardieinfarkt og/eller komplikationerne deraf, eller epilepsi.
15. Forbindelse til anvendelse ifølge krav 13 til behandling af en sygdom valgt fra rheumatoid arthritis, osteoarthritis, leverfibrose, kronisk obstruktiv lungesygdom, multipel sklerose, Sjogrens sygdom, Alzheimers sygdom, Parkinsons sygdom, inflammatorisk tarmsygdom og vaskulær demens.
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PCT/GB2014/050764 WO2014140591A1 (en) | 2013-03-13 | 2014-03-13 | New compounds |
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TW201630907A (zh) * | 2014-12-22 | 2016-09-01 | 必治妥美雅史谷比公司 | TGFβR拮抗劑 |
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US6982286B2 (en) | 2001-07-12 | 2006-01-03 | Biotie Therapies Corp. | Carbocyclic hydrazino inhibitors of copper-containing amine oxidases |
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US9580415B2 (en) | 2017-02-28 |
WO2014140591A1 (en) | 2014-09-18 |
HK1219071A1 (zh) | 2017-03-24 |
GB201304527D0 (en) | 2013-04-24 |
AU2014229762A1 (en) | 2015-09-10 |
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