HRP20211583T1 - Tienopiridini i benzotiofeni korisni kao irak4 inhibitori - Google Patents
Tienopiridini i benzotiofeni korisni kao irak4 inhibitori Download PDFInfo
- Publication number
- HRP20211583T1 HRP20211583T1 HRP20211583TT HRP20211583T HRP20211583T1 HR P20211583 T1 HRP20211583 T1 HR P20211583T1 HR P20211583T T HRP20211583T T HR P20211583TT HR P20211583 T HRP20211583 T HR P20211583T HR P20211583 T1 HRP20211583 T1 HR P20211583T1
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- HR
- Croatia
- Prior art keywords
- methoxy
- carboxamide
- pyridine
- oxopyrrolidin
- ethyl
- Prior art date
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title 1
- 229940127590 IRAK4 inhibitor Drugs 0.000 title 1
- 229940125670 thienopyridine Drugs 0.000 title 1
- 239000002175 thienopyridine Substances 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- CXAVMJMSOVJRGN-GKAPJAKFSA-N 3-[[(2S)-4-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)C1C[C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC CXAVMJMSOVJRGN-GKAPJAKFSA-N 0.000 claims 2
- KYAUGNGWRPHIKM-HTRCEHHLSA-N 3-[[(2S,3R)-3-(difluoromethyl)-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound FC([C@H]1[C@H](NC(C1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)F KYAUGNGWRPHIKM-HTRCEHHLSA-N 0.000 claims 2
- MZIDQIJKMGDYNV-WDEREUQCSA-N 3-[[(2S,3R)-3-ethyl-4,4-dimethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1(C)C)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC MZIDQIJKMGDYNV-WDEREUQCSA-N 0.000 claims 2
- GRIFYPOVVPFKDP-MWLCHTKSSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-2-methylthieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC1=C(SC=2C1=NC(=C(C=2)C(=O)N)OC)C GRIFYPOVVPFKDP-MWLCHTKSSA-N 0.000 claims 2
- JOURHXMSIVDFOM-PSASIEDQSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC JOURHXMSIVDFOM-PSASIEDQSA-N 0.000 claims 2
- SGUQRVCNSLWDBQ-DTWKUNHWSA-N 3-[[(2S,3S)-3-ethyl-4,4-difluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1(F)F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC SGUQRVCNSLWDBQ-DTWKUNHWSA-N 0.000 claims 2
- UCMNRCASMUCEBF-POYBYMJQSA-N 3-[[(2S,3S)-4,4-difluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound FC1([C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C)F UCMNRCASMUCEBF-POYBYMJQSA-N 0.000 claims 2
- IDKCWTVRKJKDGD-JIMOISOXSA-N 3-[[(2S,3S,4R)-3-cyclopropyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C1(CC1)[C@H]1[C@H](NC([C@@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC IDKCWTVRKJKDGD-JIMOISOXSA-N 0.000 claims 2
- VCFPCGNQQWIFHX-LPBBDHJYSA-N 3-[[(2S,3S,4R)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC VCFPCGNQQWIFHX-LPBBDHJYSA-N 0.000 claims 2
- OMGRBHVIMQPNQG-FMTFEUNWSA-N 3-[[(2S,3S,4R)-4-fluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@@H]1[C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C OMGRBHVIMQPNQG-FMTFEUNWSA-N 0.000 claims 2
- VWWOWLQWHHFXGW-AVZKPZGTSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-1-benzothiophene-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC=1C2=C(SC=1)C=C(C(=C2)OC)C(=O)N VWWOWLQWHHFXGW-AVZKPZGTSA-N 0.000 claims 2
- LSDQOYGTTSEFJM-XRNSZHNASA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-2-methylthieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=C(SC=2C1=NC(=C(C=2)C(=O)N)OC)C LSDQOYGTTSEFJM-XRNSZHNASA-N 0.000 claims 2
- VCFPCGNQQWIFHX-VMAXQDLPSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC VCFPCGNQQWIFHX-VMAXQDLPSA-N 0.000 claims 2
- GEWAWLWMBOMUII-PXWWUCIGSA-N 3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-propan-2-yloxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC([C@H]1F)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC(C)C GEWAWLWMBOMUII-PXWWUCIGSA-N 0.000 claims 2
- OMGRBHVIMQPNQG-QXHCQDJKSA-N 3-[[(2S,3S,4S)-4-fluoro-3-methyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC)C OMGRBHVIMQPNQG-QXHCQDJKSA-N 0.000 claims 2
- GSTVNFHWOCHAQX-POYBYMJQSA-N 3-[[(2S,4R)-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound F[C@@H]1C[C@H](NC1=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC GSTVNFHWOCHAQX-POYBYMJQSA-N 0.000 claims 2
- SPFSJWXYGLXROC-BXKDBHETSA-N 5-cyclopropyloxy-3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound C1(CC1)OC1=C(C=C2C(=N1)C(=CS2)OC[C@H]1NC(C[C@H]1CC)=O)C(=O)N SPFSJWXYGLXROC-BXKDBHETSA-N 0.000 claims 2
- ZQBJYNDCQLGOLV-PXWWUCIGSA-N 5-cyclopropyloxy-3-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound C1(CC1)OC1=C(C=C2C(=N1)C(=CS2)OC[C@H]1NC([C@H]([C@H]1CC)F)=O)C(=O)N ZQBJYNDCQLGOLV-PXWWUCIGSA-N 0.000 claims 2
- HQHAVRFAHGXRBN-QMMMGPOBSA-N 5-methoxy-2-methyl-3-[[(2S)-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound COC1=C(C=C2C(=N1)C(=C(S2)C)OC[C@H]1NC(CC1)=O)C(=O)N HQHAVRFAHGXRBN-QMMMGPOBSA-N 0.000 claims 2
- JYJGHNLOJYOLJR-UHFFFAOYSA-N 5-methoxy-3-[(5-oxomorpholin-3-yl)methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound COC1=C(C=C2C(=N1)C(=CS2)OCC1NC(COC1)=O)C(=O)N JYJGHNLOJYOLJR-UHFFFAOYSA-N 0.000 claims 2
- DZTUQDCVTMYNMR-MQWKRIRWSA-N 5-methoxy-3-[[(2S)-4-methyl-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound COC1=C(C=C2C(=N1)C(=CS2)OC[C@H]1NC(C(C1)C)=O)C(=O)N DZTUQDCVTMYNMR-MQWKRIRWSA-N 0.000 claims 2
- KLPGJVRWLHHRRD-ZETCQYMHSA-N 5-methoxy-3-[[(2S)-5-oxopyrrolidin-2-yl]methoxy]thieno[2,3-b]pyridine-6-carboxamide Chemical compound COC=1C=C2C(=NC=1C(=O)N)SC=C2OC[C@H]1NC(CC1)=O KLPGJVRWLHHRRD-ZETCQYMHSA-N 0.000 claims 2
- GOGGJRZWBBJZNU-ZETCQYMHSA-N 5-methoxy-3-[[(2S)-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound COC1=C(C=C2C(=N1)C(=CS2)OC[C@H]1NC(CC1)=O)C(=O)N GOGGJRZWBBJZNU-ZETCQYMHSA-N 0.000 claims 2
- WBCQOZFYNQGZOW-VXNVDRBHSA-N 5-methoxy-3-[[(2S,3R)-3-methyl-5-oxopyrrolidin-2-yl]methoxy]thieno[3,2-b]pyridine-6-carboxamide Chemical compound COC1=C(C=C2C(=N1)C(=CS2)OC[C@H]1NC(C[C@H]1C)=O)C(=O)N WBCQOZFYNQGZOW-VXNVDRBHSA-N 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- IJVLTWIHDJTMLR-BXKDBHETSA-N 3-[[(2S,3R)-3-ethyl-5-oxopyrrolidin-2-yl]methoxy]-5-methoxy-1-benzothiophene-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C1)=O)COC=1C2=C(SC=1)C=C(C(=C2)OC)C(=O)N IJVLTWIHDJTMLR-BXKDBHETSA-N 0.000 claims 1
- DFEJEHBGWWIOHJ-WDEREUQCSA-N 3-[[(6S,7R)-7-ethyl-4-oxo-5-azaspiro[2.4]heptan-6-yl]methoxy]-5-methoxythieno[3,2-b]pyridine-6-carboxamide Chemical compound C(C)[C@H]1[C@H](NC(C11CC1)=O)COC1=CSC=2C1=NC(=C(C=2)C(=O)N)OC DFEJEHBGWWIOHJ-WDEREUQCSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 claims 1
- 101710126825 NACHT, LRR and PYD domains-containing protein 3 Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61K31/4025—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 not condensed and containing further heterocyclic rings, e.g. cromakalim
-
- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (13)
1. Spoj Formule (I)
[image]
ili njegova sol ili solvat, pri čemu:
X je CR4 ili N;
Y je CR5 ili N; pod uvjetom da samo jedan od X i Y je N;
R1 je:
[image]
svaki R1a je nezavisno H, -OH, F, C1-3 alkil, C1-3 fluoroalkil, C1-3 alkoksi, C1-3 fluoroalkoksi, ili C3-6 cikloalkil; ili dva R1a zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
svaki R1b je nezavisno H, -OH, F, C1-3 alkil, C1-3 fluoroalkil, C1-3 alkoksi, C1-3 fluoroalkoksi, ili C3-6 cikloalkil; ili dva R1b zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
svaki R1c je nezavisno H, -OH, F, C1-3 alkil, C1-3 fluoroalkil, C1-3 alkoksi, C1-3 fluoroalkoksi, ili C3-6 cikloalkil; ili dva R1c zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
Ria i R1b zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani cikloalkilni prsten;
R1b i R1c zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani cikloalkilni prsten;
R2 je H, halo, C1-3 alkil, ili C3-6 cikloalkil;
R3 je C1-4 alkoksi, C1-4 fluoroalkoksi, ili C3-6 cikloalkoksi;
R4 je H, halo, C1-4 alkil, C1-4 fluoroalkil, ili C3-6 cikloalkil; i
R5 je H, halo, C1-4 alkil, C1-4 fluoroalkil, ili C3-6 cikloalkil.
2. Spoj prema patentnom zahtjevu 1 ili njegova sol ili solvat, pri čemu:
svaki R1a je nezavisno H, -OH, F, C1-3 alkil, C1-2 fluoroalkil, C1-2 alkoksi, C1-2 fluoroalkoksi, ili C3-6 cikloalkil; ili dva R1a zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
svaki R1b je nezavisno H, -OH, F, C1-2 alkil, C1-2 fluoroalkil, C1-2 alkoksi, C1-2 fluoroalkoksi, ili C3-6 cikloalkil; ili dva R1b zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
svaki R1c je nezavisno H, F, C1-2 alkil, C1-2 fluoroalkil, ili C3-6 cikloalkil; ili dva R1c zajedno sa atomom ugljika za koji su vezani, mogu formirati 3- do 4-člani spirocikloalkilni prsten;
R2 je H, F, Cl, C1-2 alkil, ili C3-6 cikloalkil;
R3 je C1-3 alkoksi, C1-2 fluoroalkoksi, ili C3-6 cikloalkoksi;
R4 je H, halo, C1-4 alkil, C1-4 fluoroalkil, ili C3-6 cikloalkil; i
R5 je H, halo, C1-4 alkil, C1-4 fluoroalkil, ili C3-6 cikloalkil.
3. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2 ili njegova sol ili solvat, pri čemu:
svaki R1a je nezavisno H ili C1-2 alkil;
svaki R1b je nezavisno H, F, -CH3, -CHF2, ili ciklopropil; ili dva R1b zajedno sa atomom ugljika za koji su vezani, mogu formirati 3-člani spirocikloalkilni prsten;
svaki R1c je H;
R2 je H ili -CH3;
R3 je -OCH3, -OCH(CH3)2, ili -O(ciklopropil);
R4 je H; i
Rs je H.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3 ili njegova sol ili solvat, pri čemu:
[image]
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 2 i 4 ili njegova sol ili solvat, pri čemu:
svaki Ria je nezavisno H ili C1-2 alkil; i
svaki R1b je nezavisno H, F, -CH3, -CHF2, ili ciklopropil; ili dva R1b zajedno sa atomom ugljika za koji su vezani, formiraju 3-člani spirocikloalkilni prsten.
6. Spoj prema patentnom zahtjevu 1 ili njegova sol ili solvat, pri čemu: R1 je
[image]
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6 ili njegova sol ili solvat, pri čemu:
svaki Ria je nezavisno H ili C1-2 alkil;
svaki R1b je nezavisno H, F, -CH3, -CHF2, ili ciklopropil; i
svaki R1c je H.
8. Spoj prema patentnom zahtjevu 1 ili njegova sol ili solvat, pri čemu navedeni spoj je odabran od: 3-(((2S,3S)-3-etil-4,4-difluoro-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b] piridin-6-karboksamida (1); 3-(((2S,3S,4S)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b] piridin-6-karboksamida (2); (S)-5-metoksi-3-((5-oksopirolidin-2-il)metoksi)tieno[2,3-b]piridin-6-karboksamida (3); 3-(((2S,3S,4S)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksibenzo[b] tiofen-6-karboksamida (4); (S)-5-metoksi-3-((5-oksopirolidin-2-il)metoksi)tieno [3,2-b]piridin-6-karboksamida (5); 3-(((2S,3R)-3-etil-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (6); 5-metoksi-3-((5-oksomorfolin-3-il)metoksi)tieno[3,2-b]piridin-6-karboksamida (7); 3-(((2S,3S,4R)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (8); 3-(((6S,7R)-7-etil-4-okso-5-azaspiro[2.4]heptan-6-il)metoksi)-5-metoksitieno[3,2-b] piridin-6-karboksamida (9); 3-(((2S,3R)-3-etil-4,4-dimetil-5-oksopirolidin-2-il) metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (10); 3-(((2S,4R)-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (11); 3-(((2S,3R)-3-(difluorometil)-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b] piridin-6-karboksamida (12); 5-metoksi-3-(((2S)-4-metil-5-oksopirolidin-2-il) metoksi)tieno[3,2-b]piridin-6-karboksamida (13-14); 3-(((2S)-4-etil-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (15-16); 5-metoksi-3-(((2S,3R)-3-metil-5-oksopirolidin-2-il)metoksi)tieno[3,2-b]piridin-6-karboksamida (17); 3-(((2S,3S,4R)-3-ciklopropil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (18); 3-(((2S,3R)-3-etil-5-oksopirolidin-2-il)metoksi)-5-metoksi-2-metiltieno[3,2-b]piridin-6-karboksamida (19); 5-ciklopropoksi-3-(((2S,3R)-3-etil-5-oksopirolidin-2-il)metoksi)tieno[3,2-b]piridin-6-karboksamida (20); 3-(((2S,3S)-4,4-difluoro-3-metil-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (21); 3-(((2S,3S,4S)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-metoksi-2-metiltieno[3,2-b]piridin-6-karboksamida (22); 3-(((2S,3S,4S)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)-5-izopropoksitieno [3,2-b]piridin-6-karboksamida (23); 5-ciklopropoksi-3-(((2S,3S,4S)-3-etil-4-fluoro-5-oksopirolidin-2-il)metoksi)tieno[3,2-b]piridin-6-karboksamida (24); (S)-5-metoksi-2-metil-3-((5-oksopirolidin-2-il)metoksi)tieno[3,2-b]piridin-6-karboksamida (25); 3-(((4R,5S)-5-etil-2-oksooksazolidin-4-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (26); 3-(((2S,3S,4R)-4-fluoro-3-metil-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (27); 3-(((2S,3S,4S)-4-fluoro-3-metil-5-oksopirolidin-2-il)metoksi)-5-metoksitieno[3,2-b]piridin-6-karboksamida (28); i 3-(((2S,3R)-3-etil-5-oksopirolidin-2-il)metoksi)-5-metoksibenzo[b]tiofen-6-karboksamida (29).
9. Spoj prema patentnom zahtjevu 1 ili njegova sol ili solvat, pri čemu navedeni spoj je
[image]
10. Farmaceutska kompozicija koja sadrži jedno ili više spojeva prema bilo kojem od patentnih zahtjeva 1-9 i farmaceutski prihvatljiv nosač ili razblaživač.
11. Spoj prema bilo kojem od patentnih zahtjeva 1-9 ili njegova sol ili solvat ili kompozicija prema patentnom zahtjevu 10 za primjenu u terapiji.
12. Spoj prema bilo kojem od patentnih zahtjeva 1-9 ili njegova sol ili solvat ili kompozicija prema patentnom zahtjevu 10 za primjenu u liječenju inflamatorne bolesti, autoimune bolesti, ili raka.
13. Spoj ili njegova sol ili solvat za primjenu prema patentnom zahtjevu 12, pri čemu bolest je odabrana od Kronove bolesti, ulceroznog kolitisa, astme, bolesti "transplantata protiv domaćina", odbacivanja alografta, kronične opstruktivne plućne bolesti, Gravesove bolesti, reumatoidnog artritisa, sustavnog eritematoznog lupusa, lupusa nefritis, kožnog lupusa, psorijaze, periodičnog sindroma koji je povezan sa kriopirinom, periodičnog sindroma koji je povezan sa receptorima TNF, obiteljske mediteranske groznice, Stilove bolesti kod odraslih, sustavnog početka juvenilnog idiopatskog artritisa, multiple skleroze, neuropatske boli, gihta, i gihtnog artritisa.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762504956P | 2017-05-11 | 2017-05-11 | |
| PCT/US2018/031945 WO2018209012A1 (en) | 2017-05-11 | 2018-05-10 | Thienopyridines and benzothiophenes useful as irak4 inhibitors |
| EP18727589.6A EP3621960B1 (en) | 2017-05-11 | 2018-05-10 | Thienopyridines and benzothiophenes useful as irak4 inhibitors |
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| HRP20211583T1 true HRP20211583T1 (hr) | 2022-01-07 |
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| HRP20211583TT HRP20211583T1 (hr) | 2017-05-11 | 2018-05-10 | Tienopiridini i benzotiofeni korisni kao irak4 inhibitori |
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| AU (1) | AU2018265130B2 (hr) |
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| AU2018338314A1 (en) | 2017-09-22 | 2020-04-09 | Kymera Therapeutics, Inc | Protein degraders and uses thereof |
| EP3684366A4 (en) | 2017-09-22 | 2021-09-08 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES OF THE LATEST |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| JP2021508703A (ja) | 2017-12-26 | 2021-03-11 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| EP3737675A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND THEIR USES |
| EP3817748A4 (en) | 2018-07-06 | 2022-08-24 | Kymera Therapeutics, Inc. | TRICYCLIC CRBN LIGANDS AND USES THEREOF |
| SG11202105424PA (en) | 2018-11-30 | 2021-06-29 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| TW202115086A (zh) | 2019-06-28 | 2021-04-16 | 美商輝瑞大藥廠 | Bckdk抑制劑 |
| JP2022541819A (ja) * | 2019-07-23 | 2022-09-27 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用なチエノピリジニルおよびチアゾロピリジニル化合物 |
| IL293917A (en) | 2019-12-17 | 2022-08-01 | Kymera Therapeutics Inc | Iraq joints and their uses |
| EP4076524A4 (en) | 2019-12-17 | 2023-11-29 | Kymera Therapeutics, Inc. | IRAQ DEGRADERS AND USES THEREOF |
| CN111285844B (zh) * | 2020-02-24 | 2022-08-12 | 河南师范大学 | 具有生物活性的苯并噻吩取代酰胺类化合物及其合成方法和应用 |
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-
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| US20200062777A1 (en) | 2020-02-27 |
| CY1124552T1 (el) | 2022-07-22 |
| ES2889926T3 (es) | 2022-01-14 |
| IL270494B (en) | 2022-04-01 |
| KR20200004871A (ko) | 2020-01-14 |
| HUE056493T2 (hu) | 2022-02-28 |
| BR112019023290A2 (pt) | 2020-06-16 |
| KR102604900B1 (ko) | 2023-11-21 |
| PT3621960T (pt) | 2021-09-16 |
| US10829496B2 (en) | 2020-11-10 |
| PE20191817A1 (es) | 2019-12-27 |
| CL2019003198A1 (es) | 2020-03-20 |
| AU2018265130A1 (en) | 2020-01-02 |
| DK3621960T3 (da) | 2021-09-27 |
| EA201992674A1 (ru) | 2020-04-06 |
| WO2018209012A1 (en) | 2018-11-15 |
| EA039189B1 (ru) | 2021-12-15 |
| RS62430B1 (sr) | 2021-11-30 |
| EP3621960A1 (en) | 2020-03-18 |
| LT3621960T (lt) | 2021-10-11 |
| JP7154229B2 (ja) | 2022-10-17 |
| SI3621960T1 (sl) | 2021-11-30 |
| AU2018265130B2 (en) | 2022-03-24 |
| CN110612298B (zh) | 2023-05-05 |
| JP2020519596A (ja) | 2020-07-02 |
| AR111689A1 (es) | 2019-08-07 |
| CA3062602A1 (en) | 2018-11-15 |
| PL3621960T3 (pl) | 2021-11-08 |
| CN110612298A (zh) | 2019-12-24 |
| EP3621960B1 (en) | 2021-08-04 |
| TW201900640A (zh) | 2019-01-01 |
| CO2019012494A2 (es) | 2020-01-17 |
| MX2019012929A (es) | 2020-01-14 |
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