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HRP20192197T2 - Derivati karbazola - Google Patents

Derivati karbazola Download PDF

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Publication number
HRP20192197T2
HRP20192197T2 HRP20192197TT HRP20192197T HRP20192197T2 HR P20192197 T2 HRP20192197 T2 HR P20192197T2 HR P20192197T T HRP20192197T T HR P20192197TT HR P20192197 T HRP20192197 T HR P20192197T HR P20192197 T2 HRP20192197 T2 HR P20192197T2
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Croatia
Prior art keywords
carbazole
carboxamide
fluoro
tetrahydro
hydroxypropan
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HRP20192197TT
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English (en)
Inventor
Saleem Ahmad
Douglas G Batt
Qingjie Liu
John E. Macor
Joseph A. Tino
Scott Hunter Watterson
Satheesh Kesavan NAIR
Tarun Kumar MAISHAL
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Bristol-Myers Squibb Company
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Application filed by Bristol-Myers Squibb Company filed Critical Bristol-Myers Squibb Company
Publication of HRP20192197T1 publication Critical patent/HRP20192197T1/hr
Publication of HRP20192197T8 publication Critical patent/HRP20192197T8/hr
Publication of HRP20192197T2 publication Critical patent/HRP20192197T2/hr

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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
    • A61K31/435—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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • 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
    • C07D471/04—Ortho-condensed systems
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    • C07D471/00—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
    • 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
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • General Chemical & Material Sciences (AREA)
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  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Claims (18)

1. Spoj formule (I) [image] ili njegova sol, gdje: dvije isprekidane linije predstavljaju ili dvije jednostruke ili dvije dvostruke veze; i R1b i R2b su prisutni samo ako su dvije isprekidane linije dvije jednostruke veze; Q je: (i) [image] (ii) [image] [image] (iii) [image] [image] [image] ili (iv) [image] [image] [image] R1a je: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morfolinil), -C(O)(piperazinil), ili -C(O)(metil piperazinil); ili (ii) [image] R1b, kada je prisutan, je H ili -CH3, pod uvjetom da ako R1a je H onda R1b je također H; R2a je H, F, ili Cl, pod uvjetom da ako R1a je drugačije od H onda R2a je H; R2b, kada je prisutan, je isti kao R2a; R3 je H, F, ili Cl; R4 je H, F, Cl, ili -CH3; R5a je H, F, Cl, -OCH3, ili -OCF3; R5b je H, F, Cl, -OCH3, ili -OCF3; R6a je H, -CH3 ili ciklopropil; R6c je H, -CH3 ili ciklopropil; R7a je -C(O)CH=CH(R11), -C(O)C≡CR12, ili -S(O)2CH=CH2; R7b je -C(O)CH=CH2; R7c je -C(O)CH=CH2 ili -C(O)C≡CR12; R7d je -CN, -C(O)CH=CH2, ili -C(O)C≡CR13; R7e je -CH=CH2 ili -C≡CR13; R7f je pirolidinil supstituiran sa R7c, -CH=CHC(O)(morfolinil), ili -CH=CHC(O)(pirolidinil); R8a je H ili -CH3; R8b je H ili -CH3; R9 je C1-4 alkil; R10a i R10b su nezavisno H ili -CH3; R11 je H ili -CH3; R12 je H, C1-4 alkil, ili ciklopropil; i R13 je H, C1-4 alkil, ili ciklopropil; pod uvjetima da: (a) ako Q je [image] i R7d je -CN ili -C(O)CH=CH2, onda R3 je H; i (b) ako isprekidane linije predstavljaju dvije jednostruke veze, onda: (i) Q nije [image] (ii) R11, ako je prisutan, je H; i (iii) spoj formule (I) nije: [image]
2. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image] [image] [image] R1a je: (i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b; ili (ii) [image] R1b, kada je prisutan, je H ili -CH3, pod uvjetom da ako R1a je H onda R1b je također H; R2a je H ili F, pod uvjetom da ako R1a je drugačije od H onda R2a je H; R2b, kada je prisutan, je isti kao R2a; R3 je H, F, ili Cl; R4 je H, F, Cl, ili -CH3; R5a je H, F, Cl, -OCH3, ili -OCF3; R5b je H, F, Cl, -OCH3, ili -OCF3; R6a je H, -CH3 ili ciklopropil; R6c je H, -CH3 ili ciklopropil; R7a je -C(O)CH=CH(R11), -C(O)C≡CR12, ili -S(O)2CH=CH2; R7b je -C(O)CH=CH2; R7c je -C(O)CH=CH2 ili -C(O)C≡CR12; R7d je -C(O)CH=CH2 ili -C(O)C≡CR13; R8a je H ili -CH3; R8b je H ili -CH3; R9 je C1-4 alkil; R10a i R10b su nezavisno H ili -CH3; R11 je H ili -CH3; R12 je H, C1-4 alkil, ili ciklopropil; i R13 je H, C1-4 alkil, ili ciklopropil; pod uvjetom da ako isprekidane linije predstavljaju dvije jednostruke veze, onda: (i) Q nije [image] (ii) R11, ako je prisutan, je H; i (iii) spoj formule (I) nije: [image]
3. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: R1a je H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b.
4. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: R6a je H ili -CH3; R6c je H ili -CH3; R7a je -C(O)CH=CH(R11) ili -S(O)2CH=CH2; i R13 je H.
5. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, koje ima strukturu formule (Ia): [image]
6. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, koje ima strukturu formule (Ib): [image]
7. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image]
8. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje: Q je [image]
9. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R1a je H, -CN, -CF3, -CH3, -CR8aR8bOH, -CR8aR8bCR8aR8bOH, -CH(OH)CH2OH, -NHR9, -C(O)NR10aR10b, -C(O)(morfolinil), -C(O)(piperazinil), ili -C(O)(metil piperazinil)
10. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R3 je F ili Cl.
11. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje R3 je F.
12. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: (RS)-5-(3-akrilamidofenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (1); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (2); 5-(3-akrilamido-2-metilfenil)-2,2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (3); 4-(3-akrilamido-2-metilfenil)-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (4); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (5); (RS)-4-(3-akrilamido-2-metilfenil)-3-kloro-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (6); 5-(3-akrilamido-2-metilfenil)-2-(hidroksimetil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (7); (RS)-5-(3-akrilamido-2-metilfenil)-6-kloro-2-(hidroksimetil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (8); 5-(3-akrilamido-2-metilfenil)-6-kloro-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, smjesa dijastereomera (9); (RS)-5-(3-akrilamido-2-metilfenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (10); (RS)-(E)-4-(3-(but-2-enamido)-2-metilfenil)-3-kloro-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (11); 5-(3-akrilamido-2-metilfenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (12); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (13); (RS)-5-(3-akrilamido-2-metilfenil)-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (14); 4-(3-akrilamido-2-metilfenil)-7-cijano-9H-karbazol-1-karboksamid (15); (RS)-4-(3-akrilamido-2-metilfenil)-7-(1,2-dihidroksietil)-9H karbazol-1-karboksamid (16); 4-(3-akrilamido-2-metilfenil)-7-(izopropilamino)-9H-karbazol-1-karboksamid (17); (RS)-5-(3-akrilamido-2-metilfenil)-N2,N2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (18); (RS)-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (19); (RS)-2-(hidroksimetil)-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (20); (RS)-N2,N2-dimetil-5-(2-metil-3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid (21); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (22); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (23); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, jedan enantiomer (24); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, jedan enantiomer (25); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(N-metilvinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (26); 7-(2-hidroksipropan-2-il)-4-(2-metil-3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (27); 7-(2-hidroksipropan-2-il)-4-(3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (28); (RS)-3-fluoro-7-(2-hidroksipropan-2-il)-4-(2-metil-3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (29); (RS)-3-fluoro-7-(2-hidroksipropan-2-il)-4-(2-metil-3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (30); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(N-metilvinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (31); 7-(2-hidroksipropan-2-il)-4-(2-metil-3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (32); 7-(2-hidroksipropan-2-il)-4-(3-(vinilsulfonamido) fenil)-9H-karbazol-1-karboksamid (33); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(vinilsulfonamido)fenil)-9H-karbazol-1-karboksamid (34); (RS)-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (35); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (36); 7-(2-hidroksipropan-2-il)-4-(3-(N-metilakrilamido)fenil)-9H-karbazol-1-karboksamid (37); 3-fluoro-7-(2-hidroksipropan-2-il)-4-(3-(N-metilakrilamido)fenil)-9H-karbazol-1-karboksamid (38); (R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(3-(N-metilakrilamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (39); (S)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (40); (R)-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (41); (RS)-5-(2-fluoro-3-(N-metilakrilamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (42); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (43); (2R)-6-kloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (44); (RS)-5-(2-fluoro-3-(N-metilvinilsulfonamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (45); (RS)-5-(2-kloro-3-(N-metilvinilsulfonamido)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (46); (2R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (47); 5-(3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (48); 5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (49); (RS)-5-(3-akrilamido-4-metoksifenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (50); (RS)-5-(3-akrilamido-4-(trifluorometoksi)fenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (51); (RS)-5-(3-akrilamido-4-fluorofenil)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (52); (RS)-5-(3-akrilamido-2-metilfenil)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (53); (RS)-5-(3-akrilamido-2-metilfenil)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (54); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(hidroksimetil)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (55 i 56); 5-(3-akrilamido-2-metilfenil)-6-kloro-N2,N2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, pojedinačni racemični dijastereomeri (57 i 58); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (59 i 60); 5-(3-akrilamido-2-metilfenil)-6-kloro-2-(2-hidroksipropan-2-il)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemični dijastereomeri (61 i 62); (S)-5-((1-akriloilpirolidin-3-il)amino)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (63); (E)-4-(3-(but-2-enamido)-2-metilfenil)-7-(2-hidroksipropan-2-il)-9H-karbazol-1-karboksamid (64); 5-(((S)-1-akriloilpirolidin-3-il)amino)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (65); (S)-5-(3-akrilamidopiperidin-1-il)-3,3,6-trifluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (66); (S)-4-(3-akrilamidopiperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (69); 5-(((S)-1-propioloilpirolidin-3-il)amino)-2-(RS)-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smjesa dijastereomera (72); (S)-5-(3-(but-2-inamido) piperidin-1-il)-3,3,6-trifluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (73); (S)-3-fluoro-4-(3-(N-metilbut-2-inamido)piperidin-1-il)-9H-karbazol-1-karboksamid (74); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (75); (S)-4-(3-(3-ciklopropilpropiolamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (76); 5-(((S)-1-akriloilpirolidin-3-il)amino)-2-(trifluorometil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni dijastereomeri (77 i 78); 3-fluoro-4-((6-vinilpiridin-3-il)metil)-9H-karbazol-1-karboksamid (87); (RS)-4-(2-akriloilisoindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (89); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-7-il)-3-fluoro-9H-karbazol-1-karboksamid (90); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (91); 4-(1-akriloilindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (92); 4-(1-akriloilindolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (95); 4-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (96); (RS)-4-(1-akriloilpiperidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (97); 4-(1-akriloilpiperidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid, pojedinačni enantiomeri (98 i 99); 3-fluoro-4-((2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (100); 4-(1-akriloilpirolidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (112); 4-(1-akriloilpirolidin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (113 i 114); cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (115); cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (116 i 117); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (118); cis-4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (119); cis-4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (120 i 121); 3-fluoro-4-((2-vinilpirimidin-5-il)metil)-9H-karbazol-1-karboksamid (122); cis-4-(1-akriloilheksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (123); cis-4-(1-akriloilheksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (124 i 125); 4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (126); 4-((4aS,7aS)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid i 4-((4aR,7aR)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (127 i 128); 3-fluoro-4-((2-(prop-1-in-1-il)piridin-4-il)metil)-9H-karbazol-1-karboksamid (129); 5-((S)-3-(but-2-inamido) piperidin-1-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (130, 131, i 132); 4-(2-akriloilizoindolin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (133); 4-(1-akriloil-2,5-dihidro-1H-pirol-3-il)-3-fluoro-9H-karbazol-1-karboksamid (134); 5-(1-akriloilpirolidin-3-il)-6-fluoro-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (135); (R)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid (136); 4-(1-(but-2-inoil)heksahidropirolo[3,4-b]pirol-5(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (137); 4-(1-akriloil-1,4,5,6-tetrahidropiridin-3-il)-3-fluoro-9H-karbazol-1-karboksamid (138); 4-(7-(but-2-inoil)-2,7-diazaspiro[4.4] nonan-2-il)-3-fluoro-9H-karbazol-1-karboksamid (139); 4-(7-akriloil-2,7-diazaspiro [4.4]nonan-2-il)-3-fluoro-9H-karbazol-1-karboksamid (140); 4-(1-akriloiloktahidro-5H-pirolo[3,2-c]piridin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (141); 4-(1-(but-2-inoil)oktahidro-5H-pirolo[3,2-c]piridin-5-il)-3-fluoro-9H-karbazol-1-karboksamid (142); 4-(6-akriloil-3,6-diazabiciklo[3.2.0]heptan-3-il)-3-fluoro-9H-karbazol-1-karboksamid (143); 4-(6-(but-2-inoil)-3,6-diazabiciklo[3.2.0] heptan-3-il)-3-fluoro-9H-karbazol-1-karboksamid (144); 4-(7-akriloiloktahidro-2,7-naftiridin-2(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (145); 4-(1-akriloiloktahidro-6H-pirolo[3,4-b] piridin-6-il)-3-kloro-9H-karbazol-1-karboksamid (146); 4-(1-(but-2-inoil)indolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (147); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-7-il)-3-fluoro-9H-karbazol-1-karboksamid (148); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (149); 4-(2-(but-2-inoil)izoindolin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (150); 4-(1-(but-2-inoil)indolin-6-il)-3-fluoro-9H-karbazol-1-karboksamid (151); 3-fluoro-4-((6-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (152); 3-kloro-4-((6-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (153); 4-((6-etinilpiridin-3-il)metil)-3-fluoro-9H-karbazol-1-karboksamid (154); 3-kloro-4-((6-vinilpiridin-3-il)metil)-9H-karbazol-1-karboksamid (155); 4-((2-etinilpiridin-4-il)metil)-3-fluoro-9H-karbazol-1-karboksamid (156); 3-fluoro-4-((2-viniltiazol-5-il)metil)-9H-karbazol-1-karboksamid (157); 3-fluoro-4-((6-(prop-1-in-1-il)piridin-3-il)metil)-9H-karbazol-1-karboksamid (158); 3-fluoro-4-((5-vinilpirazin-2-il)metil)-9H-karbazol-1-karboksamid (159); 4-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (160); 4-(1-akriloilpiperidin-3-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (161 i 162); (S)-4-(3-akrilamidopiperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (163); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (164); (R)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (165); (S)-4-(3-(3-ciklopropilpropiolamido)piperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (166); (S)-4-(3-cijanamidopiperidin-1-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (167); 4-(2-akriloilizoindolin-4-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (168); 4-(1-akriloilindolin-4-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (169); 4-(1-akriloilindolin-6-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (170); 4-(1-akriloil-1-azaspiro[4.4]nonan-7-il)-3-fluoro-7-(trifluorometil)-9H-karbazol-1-karboksamid (171); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-7-(4-metilpiperazin-1-karbonil)-9H-karbazol-1-karboksamid (172); (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-N7,N7-dimetil-9H-karbazol-1,7-dikarboksamid (173); 3-fluoro-N7,N7-dimetil-4-(2-vinilpiridin-4-il)-9H-karbazol-1,7-dikarboksamid (174); (S)-4-((1-cijanopirolidin-3-il)amino)-3-fluoro-N7,N7-dimetil-9H-karbazol-1,7-dikarboksamid (175); (S)-4-((1-cijanopirolidin-3-il)amino)-3-fluoro-7-(4-metilpiperazin-1-karbonil)-9H-karbazol-1-karboksamid (176); 4-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (177); 4-(2-(but-2-inoil)-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (178); 4-(2-cijano-1,2,3,4-tetrahidroizohinolin-5-il)-7-(morfolin-4-karbonil)-9H-karbazol-1-karboksamid (179); 4-(1-akriloilindolin-6-il)-3-fluoro-7-(2-hidroksietil)-9H-karbazol-1-karboksamid (180); 4-(1-cijanoindolin-6-il)-3-fluoro-7-(2-hidroksietil)-9H-karbazol-1-karboksamid (181); 4-(1-akriloiloktahidro-6H-pirolo[3,4-b]piridin-6-il)-6-kloro-3-fluoro-9H-karbazol-1-karboksamid (182); 4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-6-kloro-3-fluoro-9H-karbazol-1-karboksamid (183); 5-(1-akriloil-1,2,5,6-tetrahidropiridin-3-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (184); (R)-6-fluoro-2-(2-hidroksipropan-2-il)-5-((6-vinilpiridin-3-il)metil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (185); 5-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-6-fluoro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (186 i 187); 6-fluoro-2-(2-hidroksipropan-2-il)-5-((6-(prop-1-in-1-il)piridin-3-il)metil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (188); 3-fluoro-4-(2-vinilpiridin-4-il)-9H-karbazol-1-karboksamid (189); 4-(7-(but-2-inoil)oktahidro-2,7-naftiridin-2(1H)-il)-3-fluoro-9H-karbazol-1-karboksamid (190); 4-(1-akriloil-1,2,3,6-tetrahidropiridin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (191); 4-(1-(but-2-inoil)-1,2,3,6-tetrahidropiridin-4-il)-3-fluoro-9H-karbazol-1-karboksamid (192); 3-fluoro-4-(5-(N-metilakrilamido)piridin-2-il)-9H-karbazol-1-karboksamid (193); 4-((1S,4S)-2-akriloil-2-azabiciklo[2.2.1]heptan-5-il)-3-fluoro-9H-karbazol-1-karboksamid (194); 3-fluoro-4-((2-metil-6-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (195); 3-fluoro-4-((2-metil-6-vinilpirimidin-4-il)metil)-9H-karbazol-1-karboksamid (196); 3-fluoro-4-((4-metil-6-vinilpirimidin-2-il)metil)-9H-karbazol-1-karboksamid (197); 3-fluoro-4-((3-fluoro-2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid (198); 4-(3-(1-akriloilpirolidin-2-il)fenil)-3-fluoro-9H-karbazol-1-karboksamid (199); 4-(3-(1-(but-2-inoil)pirolidin-2-il)fenil)-3-fluoro-9H-karbazol-1-karboksamid (200); (E)-3-fluoro-4-(3-(3-morfolino-3-oksoprop-1-en-1-il)fenil)-9H-karbazol-1-karboksamid (201); (E)-3-fluoro-4-(3-(3-okso-3-(pirolidin-1-il)prop-1-en-1-il)fenil)-9H-karbazol-1-karboksamid (202); ili 5-(2-akriloil-1,2,3,4-tetrahidroizohinolin-5-il)-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid (203 i 204).
13. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid.
14. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: 3-fluoro-4-((2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid.
15. Spoj u skladu sa patentnim zahtjevom 1 ili njegova sol, gdje je navedeno spoj: cis-4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-fluoro-9H-karbazol-1-karboksamid.
16. Farmaceutska kompozicija koja sadrži spoj u skladu sa bilo kojim od patentnih zahtjeva 2-9 ili 13-15 i farmaceutski prihvatljiv nosač.
17. Spoj u skladu sa bilo kojim od patentnih zahtjeva 9 ili 13-15, za primjenu u terapiji.
18. Spoj u skladu sa bilo kojim od patentnih zahtjeva 2-9 ili 13-15 za primjenu u terapiji u liječenju autoimune bolesti ili kronične inflamatorne bolesti.
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