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ME03754B - Derivaтi karbazola - Google Patents

Derivaтi karbazola

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Publication number
ME03754B
ME03754B MEP-2019-363A MEP2019363A ME03754B ME 03754 B ME03754 B ME 03754B ME P2019363 A MEP2019363 A ME P2019363A ME 03754 B ME03754 B ME 03754B
Authority
ME
Montenegro
Prior art keywords
carboxamide
carbazole
fluoro
tetrahydro
hydroxypropan
Prior art date
Application number
MEP-2019-363A
Other languages
German (de)
English (en)
French (fr)
Inventor
Saleem Ahmad
Douglas G Batt
Qingjie Liu
John E Macor
Joseph A Tino
Scott Hunter Watterson
Satheesh Kesavan Nair
Tarun Kumar Maishal
Original Assignee
Bristol Myers Squibb Co
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=54427879&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ME03754(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co
Publication of ME03754B publication Critical patent/ME03754B/me

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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
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    • 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]
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
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    • A61P37/00—Drugs for immunological or allergic disorders
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    • 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
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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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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    • 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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    • C07D471/02—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
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    • 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
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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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  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • 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. Jedinjenje formule (I) ili njegova so, gde:dve isprekidane linije predstavljaju ili dve jednostruke ili dve dvostruke veze; i R1b i R2b su prisutni samo ako su dve isprekidane linije dve jednostruke veze;Q je:(i) (ii) (iii) ili(iv) 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) R1b, kada je prisutan, je H ili -CH3, pod uslovom da ako R1a je H onda R1b je takođe H;R2a je H, F, ili Cl, pod uslovom 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 supstituisan 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; iR13 je H, C1-4 alkil, ili ciklopropil;pod uslovima da:(a) ako Q je i R7d je -CN ili -C(O)CH=CH2, onda R3 je H; i(b) ako isprekidane linije predstavljaju dve jednostruke veze, onda:(i) Q nije (ii) R11, ako je prisutan, je H; i(iii) jedinjenje formule (I) nije:
2. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde:Q jeR1a je:(i) H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b; ili(ii)R1b, kada je prisutan, je H ili -CH3, pod uslovom da ako R1a je H onda R1b je takođe H;R2a je H ili F, pod uslovom 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; iR13 je H, C1-4 alkil, ili ciklopropil;pod uslovom da ako isprekidane linije predstavljaju dve jednostruke veze, onda:(i) Q nije(ii) R11, ako je prisutan, je H; i(iii) jedinjenje formule (I) nije:
3. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde:R1a je H, -CN, -CF3, -CH3, -CR8aR8bOH, -CH(OH)CH2OH, -NHR9, ili -C(O)NR10aR10b.
4. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde:R6a je H ili -CH3;R6c je H ili -CH3;R7a je -C(O)CH=CH(R11) ili -S(O)2CH=CH2; iR13 je H.
5. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, koje ima strukturu formule (Ia):
6. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, koje ima strukturu formule (Ib):
7. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde:Q je
8. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde: Q je
9. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde 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. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde R3 je F ili Cl.
11. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde R3 je F.
12. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde je navedeno jedinjenje: (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-hloro-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-hloro-2-(hidroksimetil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smeša dijastereomera (8); 5-(3-akrilamido-2-metilfenil)-6-hloro-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, smeša 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-hloro-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, smeša dijastereomera (22); (2R)-6-hloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(N-metilvinilsulfonamido) fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smeša 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-hloro-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-hloro-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-hloro-2-(2-hidroksipropan-2-il)-5-(2-metil-3-(vinilsulfonamido)fenil)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, smeša 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-hloro-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, smeša 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-hloro-2-(hidroksimetil)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemski dijastereomeri (55 i 56); 5-(3-akrilamido-2-metilfenil)-6-hloro-N2,N2-dimetil-2,3,4,9-tetrahidro-1H-karbazol-2,8-dikarboksamid, pojedinačni racemski dijastereomeri (57 i 58); 5-(3-akrilamido-2-metilfenil)-6-hloro-2-(2-hidroksipropan-2-il)-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemski dijastereomeri (59 i 60); 5-(3-akrilamido-2-metilfenil)-6-hloro-2-(2-hidroksipropan-2-il)-2-metil-2,3,4,9-tetrahidro-1H-karbazol-8-karboksamid, pojedinačni racemski 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, smeša 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, smeša 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-akriloilizoindolin-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-hloro-9H-karbazol-1-karboksamid (126); 4-((4aS,7aS)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-hloro-9H-karbazol-1-karboksamid i 4-((4aR,7aR)-1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-3-hloro-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-hloro-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-hloro-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-hloro-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-hloro-3-fluoro-9H-karbazol-1-karboksamid (182); 4-(1-(but-2-inoil)oktahidro-6H-pirolo[3,4-b]piridin-6-il)-6-hloro-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. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde je navedeno jedinjenje: (S)-4-(3-(but-2-inamido)piperidin-1-il)-3-fluoro-9H-karbazol-1-karboksamid.
14. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde je navedeno jedinjenje: 3-fluoro-4-((2-vinilpiridin-4-il)metil)-9H-karbazol-1-karboksamid.
15. Jedinjenje u skladu sa patentnim zahtevom 1 ili njegova so, gde je navedeno jedinjenje: 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 jedinjenje u skladu sa bilo kojim od patentnih zahteva 2-9 ili 13-15 i farmaceutski prihvatljiv nosač.
17. Jedinjenje u skladu sa bilo kojim od patentnih zahteva 9 ili 13-15, za primenu u terapiji.
18. Jedinjenje u skladu sa bilo kojim od patentnih zahteva 2-9 ili 13-15 za primenu u terapiji u lečenju autoimune bolesti ili hronične inflamatorne bolesti.
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