CA2537829A1 - Heteroaryl fused pyridines, pyrazines and pyrimidines as crf1 receptor ligands - Google Patents

Info

Publication number

CA2537829A1

CA2537829A1 CA002537829A CA2537829A CA2537829A1 CA 2537829 A1 CA2537829 A1 CA 2537829A1 CA 002537829 A CA002537829 A CA 002537829A CA 2537829 A CA2537829 A CA 2537829A CA 2537829 A1 CA2537829 A1 CA 2537829A1

Authority

CA

Canada

Prior art keywords

pyridin

pyrrolo

methoxy

ethyl

isopropyl

Prior art date

2003-09-05

Legal status (The legal status 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 status listed.)

Abandoned

Links

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• Global Dossier
• CIPO
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• 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 44
• 108091005471 CRHR1 Proteins 0.000 title claims abstract description 7
• 150000003230 pyrimidines Chemical class 0.000 title abstract description 6
• 239000003446 ligand Substances 0.000 title description 2
• 150000003216 pyrazines Chemical class 0.000 title 1
• 150000003222 pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 217
• 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims abstract description 53
• 238000000034 method Methods 0.000 claims abstract description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 230000027455 binding Effects 0.000 claims abstract description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 20
• 239000000523 sample Substances 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 11
• 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 9
• 208000030814 Eating disease Diseases 0.000 claims abstract description 7
• 235000014632 disordered eating Nutrition 0.000 claims abstract description 7
• -1 tri-substituted, 1- naphthyl Chemical group 0.000 claims description 236
• 239000000203 mixture Substances 0.000 claims description 211
• 125000000217 alkyl group Chemical group 0.000 claims description 167
• 229910052736 halogen Inorganic materials 0.000 claims description 140
• 150000002367 halogens Chemical class 0.000 claims description 139
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 126
• 125000005843 halogen group Chemical group 0.000 claims description 112
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 110
• 229910052739 hydrogen Inorganic materials 0.000 claims description 98
• 239000001257 hydrogen Substances 0.000 claims description 98
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 95
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 88
• 229910020008 S(O) Inorganic materials 0.000 claims description 86
• 150000002431 hydrogen Chemical class 0.000 claims description 76
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 229910052760 oxygen Inorganic materials 0.000 claims description 68
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 66
• 229910052757 nitrogen Inorganic materials 0.000 claims description 57
• 125000004432 carbon atom Chemical group C* 0.000 claims description 52
• 229910052799 carbon Inorganic materials 0.000 claims description 48
• 125000004043 oxo group Chemical group O=* 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 229910052717 sulfur Inorganic materials 0.000 claims description 43
• 125000003282 alkyl amino group Chemical group 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 239000001301 oxygen Substances 0.000 claims description 31
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 31
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 28
• 210000004027 cell Anatomy 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 28
• 125000004076 pyridyl group Chemical group 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 22
• 150000003462 sulfoxides Chemical class 0.000 claims description 21
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 230000000694 effects Effects 0.000 claims description 18
• 239000011593 sulfur Substances 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000001544 thienyl group Chemical group 0.000 claims description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 16
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 15
• 125000002541 furyl group Chemical group 0.000 claims description 15
• 238000000338 in vitro Methods 0.000 claims description 15
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 15
• 125000002971 oxazolyl group Chemical group 0.000 claims description 15
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
• 125000006165 cyclic alkyl group Chemical group 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 14
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000001425 triazolyl group Chemical group 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 10
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000005605 benzo group Chemical group 0.000 claims description 9
• 238000001525 receptor binding assay Methods 0.000 claims description 9
• 150000003457 sulfones Chemical class 0.000 claims description 9
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 239000013068 control sample Substances 0.000 claims description 8
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 8
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 7
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims description 7
• 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims description 7
• 238000012360 testing method Methods 0.000 claims description 7
• 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 6
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
• 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 6
• MTLCJOOCTPJNNV-ZDUSSCGKSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=CC2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC MTLCJOOCTPJNNV-ZDUSSCGKSA-N 0.000 claims description 5
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
• VKGAXMRRNWGUFM-HNNXBMFYSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] methanesulfonate Chemical compound CC=1C=C2N([C@H](COS(C)(=O)=O)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC VKGAXMRRNWGUFM-HNNXBMFYSA-N 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 238000005406 washing Methods 0.000 claims description 4
• PSDREHBPEVJWGI-AWEZNQCLSA-N 1-[(2s)-1-chlorobutan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](CCl)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC PSDREHBPEVJWGI-AWEZNQCLSA-N 0.000 claims description 3
• KPEVPNSVABOGHS-HNNXBMFYSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=CC2=NC=1C1=CC=C(C(C)C)N=C1OC KPEVPNSVABOGHS-HNNXBMFYSA-N 0.000 claims description 3
• SPRSJUDLZIKCAR-HNNXBMFYSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridine-3-carbonitrile Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C#N)C2=NC=1C1=CC=C(C(C)C)N=C1OC SPRSJUDLZIKCAR-HNNXBMFYSA-N 0.000 claims description 3
• GMLGLUVWTUJACE-YADHBBJMSA-N 1-[(3r,4s)-4-(2-fluoroethoxy)-1-methylpyrrolidin-3-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H]1[C@H](CN(C)C1)OCCF)C=C2C GMLGLUVWTUJACE-YADHBBJMSA-N 0.000 claims description 3
• NJOPGINYGSEGID-YADHBBJMSA-N 1-[(3r,4s)-4-(2-fluoroethoxy)-1-methylsulfonylpyrrolidin-3-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H]1[C@H](CN(C1)S(C)(=O)=O)OCCF)C=C2C NJOPGINYGSEGID-YADHBBJMSA-N 0.000 claims description 3
• AWGFEIBQECMDIC-ZDUSSCGKSA-N 1-[1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methylpyrrolo[3,2-b]pyridin-7-yl]pyrrolidine-2,5-dione Chemical compound C=12N([C@@H](C)COC)C=CC2=NC(C=2C(=CC(OC(F)(F)F)=CC=2)OC)=C(C)C=1N1C(=O)CCC1=O AWGFEIBQECMDIC-ZDUSSCGKSA-N 0.000 claims description 3
• BYVJZMGIFHMEFG-SXOMAYOGSA-N 2-morpholin-4-ylethyl (3s,4r)-3-(2-fluoroethoxy)-4-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]pyrrolidine-1-carboxylate Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H]1[C@H](CN(C1)C(=O)OCCN1CCOCC1)OCCF)C=C2C BYVJZMGIFHMEFG-SXOMAYOGSA-N 0.000 claims description 3
• GPCWPKOKMFSCRB-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC GPCWPKOKMFSCRB-UHFFFAOYSA-N 0.000 claims description 3
• SXPZIGSECPJBMG-LBPRGKRZSA-N 3-fluoro-1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(F)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC SXPZIGSECPJBMG-LBPRGKRZSA-N 0.000 claims description 3
• YMKMCFLUVMEVHP-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC YMKMCFLUVMEVHP-UHFFFAOYSA-N 0.000 claims description 3
• AIGNYRPZHNPUEC-HNNXBMFYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-[(2s)-1-methylsulfonylbutan-2-yl]pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](CS(C)(=O)=O)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC AIGNYRPZHNPUEC-HNNXBMFYSA-N 0.000 claims description 3
• 208000020925 Bipolar disease Diseases 0.000 claims description 3
• DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims description 3
• IMZUXKIHQMUHDC-HNNXBMFYSA-N 1-[(2s)-1-methoxybutan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC IMZUXKIHQMUHDC-HNNXBMFYSA-N 0.000 claims description 2
• QEKMJLXEUSWIMQ-HNNXBMFYSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6,7-trimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C(C)=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC QEKMJLXEUSWIMQ-HNNXBMFYSA-N 0.000 claims description 2
• FHYWMOVEPQZGFO-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridin-5-yl)-n-ethyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NCC FHYWMOVEPQZGFO-UHFFFAOYSA-N 0.000 claims description 2
• YUIDPRYRVCCYEO-LBPRGKRZSA-N 3-bromo-1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(Br)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC YUIDPRYRVCCYEO-LBPRGKRZSA-N 0.000 claims description 2
• BJSJUIAUEBQBJR-ZDUSSCGKSA-N 3-chloro-5-[(2s)-1-methoxypropan-2-yl]-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-7-methylpyrrolo[2,3-b]pyrazine Chemical compound ClC=1N=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC BJSJUIAUEBQBJR-ZDUSSCGKSA-N 0.000 claims description 2
• KHGNQABBBCRZKJ-HNNXBMFYSA-N 3-ethyl-5-[(2s)-1-methoxypropan-2-yl]-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-7-methylpyrrolo[2,3-b]pyrazine Chemical compound CCC1=NC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC KHGNQABBBCRZKJ-HNNXBMFYSA-N 0.000 claims description 2
• MQMPYVXRHMKMCD-LJQANCHMSA-N 4-[(2r)-2-[2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]butyl]morpholine Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCOCC1 MQMPYVXRHMKMCD-LJQANCHMSA-N 0.000 claims description 2
• JJBBAPZLAZRJMX-HNNXBMFYSA-N 5-(2-ethyl-6-methoxypyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OC)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C JJBBAPZLAZRJMX-HNNXBMFYSA-N 0.000 claims description 2
• UWWULBGQOSZTNU-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC UWWULBGQOSZTNU-UHFFFAOYSA-N 0.000 claims description 2
• GHAINVFSRSEKTM-UHFFFAOYSA-N 5-(3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridin-5-yl)-n,4-diethyl-n-methylpyridin-2-amine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)CC)C=C1CC GHAINVFSRSEKTM-UHFFFAOYSA-N 0.000 claims description 2
• FCCGIKZKBIBAQS-MRXNPFEDSA-N 5-[(2r)-1-methoxybutan-2-yl]-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC FCCGIKZKBIBAQS-MRXNPFEDSA-N 0.000 claims description 2
• VOUZMOZWFCOPDS-SFHVURJKSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-[(2s)-1-pyrrolidin-1-ylbutan-2-yl]pyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCCC1 VOUZMOZWFCOPDS-SFHVURJKSA-N 0.000 claims description 2
• OXUHZDRXXROIRN-UHFFFAOYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC OXUHZDRXXROIRN-UHFFFAOYSA-N 0.000 claims description 2
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 2
• 208000008589 Obesity Diseases 0.000 claims description 2
• VHOHEIRLXFSQPZ-IBGZPJMESA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] n-cyclopentylcarbamate Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)OC(=O)NC1CCCC1 VHOHEIRLXFSQPZ-IBGZPJMESA-N 0.000 claims description 2
• LQJFFSGDIXXQCZ-IBGZPJMESA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] piperidine-1-carboxylate Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)OC(=O)N1CCCCC1 LQJFFSGDIXXQCZ-IBGZPJMESA-N 0.000 claims description 2
• 210000001124 body fluid Anatomy 0.000 claims description 2
• 239000010839 body fluid Substances 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims description 2
• 238000001514 detection method Methods 0.000 claims description 2
• 238000002825 functional assay Methods 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 210000002569 neuron Anatomy 0.000 claims description 2
• 235000020824 obesity Nutrition 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 26
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 5
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 4
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 4
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 3
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
• GGHNFQROIOWAMJ-UHFFFAOYSA-N 6-[2-methoxy-4-(trifluoromethoxy)phenyl]-1,5-dimethyl-3-pentan-3-ylpyrrolo[2,3-b]pyridine Chemical compound CC=1C=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC GGHNFQROIOWAMJ-UHFFFAOYSA-N 0.000 claims 2
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
• XENRQXOMBBDKCZ-MRXNPFEDSA-N (2r)-1-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butan-2-ol Chemical compound CC=1C=C2N(C[C@H](O)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC XENRQXOMBBDKCZ-MRXNPFEDSA-N 0.000 claims 1
• LTHHZUSIRRDOAB-MRXNPFEDSA-N (2r)-2-[2-(2-chloro-4-methoxyphenyl)-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]-n-ethyl-n-methylbutan-1-amine Chemical compound CC=1N=C2N([C@@H](CN(C)CC)CC)C=C(C)C2=NC=1C1=CC=C(OC)C=C1Cl LTHHZUSIRRDOAB-MRXNPFEDSA-N 0.000 claims 1
• QMDJFXUCTKOXNJ-MRXNPFEDSA-N (2r)-2-[2-[4-(difluoromethoxy)-2-methoxyphenyl]-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]-n-ethyl-n-methylbutan-1-amine Chemical compound CC=1N=C2N([C@@H](CN(C)CC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)F)C=C1OC QMDJFXUCTKOXNJ-MRXNPFEDSA-N 0.000 claims 1
• QVZKLCPALQEGFL-CQSZACIVSA-N (2r)-2-[3-chloro-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)CC)C=C(Cl)C2=NC=1C1=CC=C(C(C)C)N=C1OC QVZKLCPALQEGFL-CQSZACIVSA-N 0.000 claims 1
• RRDIJFSPKQHODR-QGZVFWFLSA-N (2r)-2-[5-(2-ethoxy-6-ethyl-5-methylsulfonylpyridin-3-yl)-6-ethyl-3-methylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CCOC1=NC(CC)=C(S(C)(=O)=O)C=C1C(C(=C1)CC)=NC2=C1N([C@H](CC)CO)C=C2C RRDIJFSPKQHODR-QGZVFWFLSA-N 0.000 claims 1
• LVMCPHWRRJGGNR-OAHLLOKOSA-N (2r)-2-[5-(2-ethoxy-6-ethyl-5-methylsulfonylpyridin-3-yl)-6-ethyl-3-methylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound CCOC1=NC(CC)=C(S(C)(=O)=O)C=C1C(C(=C1)CC)=NC2=C1N([C@H](C)CO)C=C2C LVMCPHWRRJGGNR-OAHLLOKOSA-N 0.000 claims 1
• WKQQVKVMYRTUGO-OAHLLOKOSA-N (2r)-2-[5-(2-ethyl-6-methoxypyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(OC)N=C1CC WKQQVKVMYRTUGO-OAHLLOKOSA-N 0.000 claims 1
• KCETZOXRFCQSQT-MRXNPFEDSA-N (2r)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KCETZOXRFCQSQT-MRXNPFEDSA-N 0.000 claims 1
• UUKOISMWHKVYAV-QGZVFWFLSA-N (2r)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]pentan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC UUKOISMWHKVYAV-QGZVFWFLSA-N 0.000 claims 1
• RGTHSXIYRDMZFA-OAHLLOKOSA-N (2r)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](C)CO)C=C2C RGTHSXIYRDMZFA-OAHLLOKOSA-N 0.000 claims 1
• QKULNRKASLWVBK-OAHLLOKOSA-N (2r)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)CC)C=CC2=NC=1C1=CC=C(C(C)C)N=C1OC QKULNRKASLWVBK-OAHLLOKOSA-N 0.000 claims 1
• NLDWRHHOOXAXCG-QGZVFWFLSA-N (2r)-2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CCC=1C=C2N([C@@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NLDWRHHOOXAXCG-QGZVFWFLSA-N 0.000 claims 1
• BSUHHUKOJZLGBX-OAHLLOKOSA-N (2r)-2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound CCC1=CC=2N([C@H](C)CO)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC BSUHHUKOJZLGBX-OAHLLOKOSA-N 0.000 claims 1
• TWHTWEBOAZACAM-OAHLLOKOSA-N (2r)-3-methoxy-2-[2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]propan-1-ol Chemical compound CC=1N=C2N([C@H](CO)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC TWHTWEBOAZACAM-OAHLLOKOSA-N 0.000 claims 1
• DBVNLQXWPKYAFI-MRXNPFEDSA-N (2r)-3-methoxy-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound CC=1C=C2N([C@H](CO)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC DBVNLQXWPKYAFI-MRXNPFEDSA-N 0.000 claims 1
• CQPXGGBNSDNIJK-ZCNNSNEGSA-N (2r,6s)-4-[(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]-2,6-dimethylmorpholine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1C[C@H](C)O[C@H](C)C1 CQPXGGBNSDNIJK-ZCNNSNEGSA-N 0.000 claims 1
• KCETZOXRFCQSQT-INIZCTEOSA-N (2s)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KCETZOXRFCQSQT-INIZCTEOSA-N 0.000 claims 1
• ZKXORCRISXNHAF-INIZCTEOSA-N (2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]-n,n-dimethylbutan-1-amine Chemical compound CC=1C=C2N([C@H](CN(C)C)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC ZKXORCRISXNHAF-INIZCTEOSA-N 0.000 claims 1
• ZRNUFTUQKYCICK-AWEZNQCLSA-N (2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound CC=1C=C2N([C@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC ZRNUFTUQKYCICK-AWEZNQCLSA-N 0.000 claims 1
• SOQZGQJZMOXAEA-AWEZNQCLSA-N (2s)-2-[6-bromo-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]butan-1-ol Chemical compound BrC=1C=C2N([C@H](CO)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC SOQZGQJZMOXAEA-AWEZNQCLSA-N 0.000 claims 1
• BWULJCSBHUQEKU-KRWDZBQOSA-N (2s)-2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]-3-methoxypropan-1-ol Chemical compound CCC1=CC=2N([C@@H](CO)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC BWULJCSBHUQEKU-KRWDZBQOSA-N 0.000 claims 1
• BSUHHUKOJZLGBX-HNNXBMFYSA-N (2s)-2-[6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound CCC1=CC=2N([C@@H](C)CO)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC BSUHHUKOJZLGBX-HNNXBMFYSA-N 0.000 claims 1
• DBVNLQXWPKYAFI-INIZCTEOSA-N (2s)-3-methoxy-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]propan-1-ol Chemical compound CC=1C=C2N([C@@H](CO)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC DBVNLQXWPKYAFI-INIZCTEOSA-N 0.000 claims 1
• BYKPVWNNSGKMRL-KRWDZBQOSA-N (3s)-4-methoxy-3-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butanenitrile Chemical compound CC=1C=C2N([C@@H](CC#N)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC BYKPVWNNSGKMRL-KRWDZBQOSA-N 0.000 claims 1
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
• ZWCWGAPILYEVEV-UHFFFAOYSA-N 1-(1,3-dimethoxypropan-2-yl)-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(COC)COC)C=C2C ZWCWGAPILYEVEV-UHFFFAOYSA-N 0.000 claims 1
• QKUZAHVNLZHHPZ-UHFFFAOYSA-N 1-(1,3-dimethoxypropan-2-yl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(COC)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC QKUZAHVNLZHHPZ-UHFFFAOYSA-N 0.000 claims 1
• KMECCOHITUUDHO-UHFFFAOYSA-N 1-(1-methoxy-2-methylpropan-2-yl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)(C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KMECCOHITUUDHO-UHFFFAOYSA-N 0.000 claims 1
• YTGYNUMBKMOSRN-UHFFFAOYSA-N 1-(1-methoxypentan-2-yl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(COC)CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC YTGYNUMBKMOSRN-UHFFFAOYSA-N 0.000 claims 1
• OLUWAQSFFVASJK-UHFFFAOYSA-N 1-(1-methoxypropan-2-yl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OLUWAQSFFVASJK-UHFFFAOYSA-N 0.000 claims 1
• DGADZOHQRGXFOV-UHFFFAOYSA-N 1-(1-methoxypropan-2-yl)-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)COC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC DGADZOHQRGXFOV-UHFFFAOYSA-N 0.000 claims 1
• KTMHOFKROQUWFA-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCOCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KTMHOFKROQUWFA-UHFFFAOYSA-N 0.000 claims 1
• NTYHFENZSKYQAM-UHFFFAOYSA-N 1-(2-methoxyethyl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCOC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NTYHFENZSKYQAM-UHFFFAOYSA-N 0.000 claims 1
• BCIGRMIDQCDBIV-UHFFFAOYSA-N 1-(3-fluoropropyl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCCF)C=C2C BCIGRMIDQCDBIV-UHFFFAOYSA-N 0.000 claims 1
• ADVAXFRMJOTJCR-UHFFFAOYSA-N 1-(cyclopropylmethyl)-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC1CC1)C=C2C ADVAXFRMJOTJCR-UHFFFAOYSA-N 0.000 claims 1
• GGUAQRFGNURFHO-KRWDZBQOSA-N 1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](CF)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 GGUAQRFGNURFHO-KRWDZBQOSA-N 0.000 claims 1
• ITZDIINMLAOWGG-INIZCTEOSA-N 1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](CF)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ITZDIINMLAOWGG-INIZCTEOSA-N 0.000 claims 1
• OMUBYGTXDDCDAN-MRXNPFEDSA-N 1-[(2r)-1-fluorobutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](CF)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OMUBYGTXDDCDAN-MRXNPFEDSA-N 0.000 claims 1
• UPQDJTCMBXUFHT-QGZVFWFLSA-N 1-[(2r)-1-fluoropentan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](CF)CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC UPQDJTCMBXUFHT-QGZVFWFLSA-N 0.000 claims 1
• CFOKHRZCAAUIPV-OAHLLOKOSA-N 1-[(2r)-1-fluoropropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](C)CF)C=C2C CFOKHRZCAAUIPV-OAHLLOKOSA-N 0.000 claims 1
• WFSQCCAYGBJLFQ-GOSISDBHSA-N 1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 WFSQCCAYGBJLFQ-GOSISDBHSA-N 0.000 claims 1
• TVOGCLWMSRMISY-QGZVFWFLSA-N 1-[(2r)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC TVOGCLWMSRMISY-QGZVFWFLSA-N 0.000 claims 1
• BAGGKFDFSIBFFX-MRXNPFEDSA-N 1-[(2r)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=CC2=NC=1C1=CC=C(C(C)C)N=C1OC BAGGKFDFSIBFFX-MRXNPFEDSA-N 0.000 claims 1
• YTGYNUMBKMOSRN-GOSISDBHSA-N 1-[(2r)-1-methoxypentan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC YTGYNUMBKMOSRN-GOSISDBHSA-N 0.000 claims 1
• OLUWAQSFFVASJK-MRXNPFEDSA-N 1-[(2r)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OLUWAQSFFVASJK-MRXNPFEDSA-N 0.000 claims 1
• HJWVECYJKJHBMA-QGZVFWFLSA-N 1-[(2r)-2-methoxybutyl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C[C@@H](CC)OC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC HJWVECYJKJHBMA-QGZVFWFLSA-N 0.000 claims 1
• FISYNTJEQPADGC-FQEVSTJZSA-N 1-[(2s)-1-(3,3-dimethylpiperidin-1-yl)butan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCCC(C)(C)C1 FISYNTJEQPADGC-FQEVSTJZSA-N 0.000 claims 1
• VLZNQQPZYYRDRK-SFHVURJKSA-N 1-[(2s)-1-(4,4-difluoropiperidin-1-yl)butan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCC(F)(F)CC1 VLZNQQPZYYRDRK-SFHVURJKSA-N 0.000 claims 1
• SEDDFSZTUSQLNM-FQEVSTJZSA-N 1-[(2s)-1-(azepan-1-yl)butan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCCCCC1 SEDDFSZTUSQLNM-FQEVSTJZSA-N 0.000 claims 1
• ZJHDWEFHCBXFIC-SFHVURJKSA-N 1-[(2s)-1-ethoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](CC)COCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ZJHDWEFHCBXFIC-SFHVURJKSA-N 0.000 claims 1
• WNXIUJSYKGZMHR-KRWDZBQOSA-N 1-[(2s)-1-fluorobutan-2-yl]-3,6-dimethyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](CF)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 WNXIUJSYKGZMHR-KRWDZBQOSA-N 0.000 claims 1
• OMUBYGTXDDCDAN-INIZCTEOSA-N 1-[(2s)-1-fluorobutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](CF)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OMUBYGTXDDCDAN-INIZCTEOSA-N 0.000 claims 1
• TVOGCLWMSRMISY-KRWDZBQOSA-N 1-[(2s)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC TVOGCLWMSRMISY-KRWDZBQOSA-N 0.000 claims 1
• JGFHDUUWMAONLV-INIZCTEOSA-N 1-[(2s)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound C=1C=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC JGFHDUUWMAONLV-INIZCTEOSA-N 0.000 claims 1
• RCGLZSPGSCAEQI-INIZCTEOSA-N 1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethyl-5-(2-methyl-6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1C RCGLZSPGSCAEQI-INIZCTEOSA-N 0.000 claims 1
• OLUWAQSFFVASJK-INIZCTEOSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OLUWAQSFFVASJK-INIZCTEOSA-N 0.000 claims 1
• DGADZOHQRGXFOV-AWEZNQCLSA-N 1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC DGADZOHQRGXFOV-AWEZNQCLSA-N 0.000 claims 1
• DDEGIADHENMWRC-QGZVFWFLSA-N 1-[1-[(2r)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridin-7-yl]pyrrolidine-2,5-dione Chemical compound C=12N([C@@H](COC)CC)C=CC2=NC(C=2C(=NC(=CC=2)C(C)C)OC)=C(C)C=1N1C(=O)CCC1=O DDEGIADHENMWRC-QGZVFWFLSA-N 0.000 claims 1
• DYFGPACFQSXSOB-OAQYLSRUSA-N 1-[4-[(2r)-2-[2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]butyl]piperazin-1-yl]ethanone Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCN(C(C)=O)CC1 DYFGPACFQSXSOB-OAQYLSRUSA-N 0.000 claims 1
• SPGHAEGHQIZOPC-UHFFFAOYSA-N 1-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC(C)(C)O)C=C2C SPGHAEGHQIZOPC-UHFFFAOYSA-N 0.000 claims 1
• IFCJFYMYWXJSPI-UHFFFAOYSA-N 1-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]ethanone Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)=O)C=C2C IFCJFYMYWXJSPI-UHFFFAOYSA-N 0.000 claims 1
• DGXZGZWWHPKWRW-HNNXBMFYSA-N 1-[6-ethyl-2-methoxy-5-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]pyridin-3-yl]ethanone Chemical compound CCC1=NC(OC)=C(C(C)=O)C=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C DGXZGZWWHPKWRW-HNNXBMFYSA-N 0.000 claims 1
• VGBXSKDFSKSDNJ-UHFFFAOYSA-N 1-butan-2-yl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC VGBXSKDFSKSDNJ-UHFFFAOYSA-N 0.000 claims 1
• PEFFOKBTSSHVJK-UHFFFAOYSA-N 1-butan-2-yl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC PEFFOKBTSSHVJK-UHFFFAOYSA-N 0.000 claims 1
• HSERPNAIBJURQN-UHFFFAOYSA-N 1-butan-2-yl-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC HSERPNAIBJURQN-UHFFFAOYSA-N 0.000 claims 1
• LAGGGSMPRQYHHH-UHFFFAOYSA-N 1-butan-2-yl-6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC=1C=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC LAGGGSMPRQYHHH-UHFFFAOYSA-N 0.000 claims 1
• VQBIPUYAVBTHAK-UHFFFAOYSA-N 1-butyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC VQBIPUYAVBTHAK-UHFFFAOYSA-N 0.000 claims 1
• NYACDSKCBJAMAS-UHFFFAOYSA-N 1-butyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NYACDSKCBJAMAS-UHFFFAOYSA-N 0.000 claims 1
• AKRXYEMBTILPGJ-UHFFFAOYSA-N 1-ethyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC)C=C2C AKRXYEMBTILPGJ-UHFFFAOYSA-N 0.000 claims 1
• BASDOWQNVNYFOM-UHFFFAOYSA-N 1-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC BASDOWQNVNYFOM-UHFFFAOYSA-N 0.000 claims 1
• SFTUZPUXNQAOEU-LJQANCHMSA-N 2,6-diethyl-7-[1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-4-propan-2-ylpyrido[2,3-b]pyrazin-3-one Chemical compound N1=C(CC)C(=O)N(C(C)C)C(N=C2CC)=C1C=C2C1=C(C)C=C2N([C@@H](COC)CC)C=C(C)C2=N1 SFTUZPUXNQAOEU-LJQANCHMSA-N 0.000 claims 1
• HXNACWNITLCMHI-UHFFFAOYSA-N 2-(2-ethoxy-5-methylsulfonyl-6-pent-4-en-2-ylpyridin-3-yl)-3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCOC1=NC(C(C)CC=C)=C(S(C)(=O)=O)C=C1C(C(=N1)C)=NC2=C1N(C(CC)CC)C=C2C HXNACWNITLCMHI-UHFFFAOYSA-N 0.000 claims 1
• VPKUVCPWBCGHER-UHFFFAOYSA-N 2-(2-ethoxy-6-ethyl-5-methylsulfonylpyridin-3-yl)-3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCOC1=NC(CC)=C(S(C)(=O)=O)C=C1C(C(=N1)C)=NC2=C1N(C(CC)CC)C=C2C VPKUVCPWBCGHER-UHFFFAOYSA-N 0.000 claims 1
• GAVRLRCRNBKKNK-UHFFFAOYSA-N 2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC GAVRLRCRNBKKNK-UHFFFAOYSA-N 0.000 claims 1
• UCDGDYVDDIPKMD-UHFFFAOYSA-N 2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C UCDGDYVDDIPKMD-UHFFFAOYSA-N 0.000 claims 1
• FRXLBMQRBFUDAM-UHFFFAOYSA-N 2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-propylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC FRXLBMQRBFUDAM-UHFFFAOYSA-N 0.000 claims 1
• KKGMYPLWROEPBW-QGZVFWFLSA-N 2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC KKGMYPLWROEPBW-QGZVFWFLSA-N 0.000 claims 1
• KKGMYPLWROEPBW-KRWDZBQOSA-N 2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-5-[(2s)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC KKGMYPLWROEPBW-KRWDZBQOSA-N 0.000 claims 1
• USPILDXTYXDPNB-HXUWFJFHSA-N 2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-[(2r)-1-(4-methylpiperazin-1-yl)butan-2-yl]pyrrolo[2,3-b]pyrazine Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCN(C)CC1 USPILDXTYXDPNB-HXUWFJFHSA-N 0.000 claims 1
• ATSRJULUTDGNDC-LJQANCHMSA-N 2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-[(2r)-1-pyrrolidin-1-ylbutan-2-yl]pyrrolo[2,3-b]pyrazine Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCCC1 ATSRJULUTDGNDC-LJQANCHMSA-N 0.000 claims 1
• NZEHCAKUJVQXKG-UHFFFAOYSA-N 2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NZEHCAKUJVQXKG-UHFFFAOYSA-N 0.000 claims 1
• YIJSZEYGHDZUEE-UHFFFAOYSA-N 2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C YIJSZEYGHDZUEE-UHFFFAOYSA-N 0.000 claims 1
• YBUKMYGEETWPEW-UHFFFAOYSA-N 2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethyl-5-propylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC YBUKMYGEETWPEW-UHFFFAOYSA-N 0.000 claims 1
• RBOSKUKWORZETB-UHFFFAOYSA-N 2-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC RBOSKUKWORZETB-UHFFFAOYSA-N 0.000 claims 1
• YOUDFZJLFDOZQW-UHFFFAOYSA-N 2-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C YOUDFZJLFDOZQW-UHFFFAOYSA-N 0.000 claims 1
• HNGMEXFSROUIFJ-UHFFFAOYSA-N 2-[2-methoxy-4-(trifluoromethyl)phenyl]-3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound COC1=CC(C(F)(F)F)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C HNGMEXFSROUIFJ-UHFFFAOYSA-N 0.000 claims 1
• KKGVEWQCJFCLMC-UHFFFAOYSA-N 2-[3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]butan-1-ol Chemical compound CC=1N=C2C(C(CO)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KKGVEWQCJFCLMC-UHFFFAOYSA-N 0.000 claims 1
• GETVZSGZUADORZ-UHFFFAOYSA-N 2-[3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]butyl methanesulfonate Chemical compound CC=1N=C2C(C(COS(C)(=O)=O)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC GETVZSGZUADORZ-UHFFFAOYSA-N 0.000 claims 1
• UVKFCQSCZADXQG-UHFFFAOYSA-N 2-[3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]propan-1-ol Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)CO)=CN2C UVKFCQSCZADXQG-UHFFFAOYSA-N 0.000 claims 1
• ISWMKMGQHQKKJE-UHFFFAOYSA-N 2-[3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]propyl methanesulfonate Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)COS(C)(=O)=O)=CN2C ISWMKMGQHQKKJE-UHFFFAOYSA-N 0.000 claims 1
• FSHRMEDSESKGTE-UHFFFAOYSA-N 2-[3-[2-methoxy-4-(trifluoromethoxy)phenyl]-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]propan-1-ol Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)CO)=CN2C FSHRMEDSESKGTE-UHFFFAOYSA-N 0.000 claims 1
• NGPHUFKXMZDXAZ-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-2-methoxyphenyl]-3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound COC1=CC(OC(F)F)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C NGPHUFKXMZDXAZ-UHFFFAOYSA-N 0.000 claims 1
• RJTUUXBRSKLKPZ-UHFFFAOYSA-N 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]-2-methylpropan-1-ol Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)(C)CO)C=C2C RJTUUXBRSKLKPZ-UHFFFAOYSA-N 0.000 claims 1
• GGSMWJIVCUEOKV-UHFFFAOYSA-N 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]-n-methylpropanamide Chemical compound CC=1C=C2N(C(C)C(=O)NC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC GGSMWJIVCUEOKV-UHFFFAOYSA-N 0.000 claims 1
• XPDSGHSRZPMLEA-UHFFFAOYSA-N 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]ethanol Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCO)C=C2C XPDSGHSRZPMLEA-UHFFFAOYSA-N 0.000 claims 1
• BWFOTNIYRHBXDQ-YOFSQIOKSA-N 2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl (2r,6s)-2,6-dimethylmorpholine-4-carboxylate Chemical compound C1=C(C)C2=NC(C=3C(=CC(OC(F)(F)F)=CC=3)OC)=C(C)C=C2N1C(CC)COC(=O)N1C[C@H](C)O[C@H](C)C1 BWFOTNIYRHBXDQ-YOFSQIOKSA-N 0.000 claims 1
• BTXZUKOZCRVGOI-UHFFFAOYSA-N 2-[6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1,5-dimethylpyrrolo[2,3-b]pyridin-3-yl]butan-1-ol Chemical compound CC=1C=C2C(C(CO)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC BTXZUKOZCRVGOI-UHFFFAOYSA-N 0.000 claims 1
• YHKPZINUTBFNCL-UHFFFAOYSA-N 2-bromo-3-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound BrC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC YHKPZINUTBFNCL-UHFFFAOYSA-N 0.000 claims 1
• WADUPLMJFWFFOW-UHFFFAOYSA-N 2-ethyl-3-(2-ethyl-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazin-3-yl)-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C(C(=N1)CC)=NC2=C1C(C(CC)CC)=CN2C WADUPLMJFWFFOW-UHFFFAOYSA-N 0.000 claims 1
• MRKFLBGILHSEDF-UHFFFAOYSA-N 2-ethyl-3-(2-ethyl-6-propan-2-ylpyridin-3-yl)-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC MRKFLBGILHSEDF-UHFFFAOYSA-N 0.000 claims 1
• ZPZQWZLVKSMFSR-UHFFFAOYSA-N 2-ethyl-3-(2-ethyl-6-propan-2-ylpyridin-3-yl)-5-methyl-7-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=N1)CC)=NC2=C1C(C(C)C)=CN2C ZPZQWZLVKSMFSR-UHFFFAOYSA-N 0.000 claims 1
• YVBYQBFPVQPJNM-UHFFFAOYSA-N 2-ethyl-3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC YVBYQBFPVQPJNM-UHFFFAOYSA-N 0.000 claims 1
• HFGUWFKPPCDCOR-UHFFFAOYSA-N 2-ethyl-3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-5-methyl-7-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC1=NC=2C(C(C)C)=CN(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC HFGUWFKPPCDCOR-UHFFFAOYSA-N 0.000 claims 1
• LSWLMGGALRLYEL-UHFFFAOYSA-N 2-ethyl-3-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC LSWLMGGALRLYEL-UHFFFAOYSA-N 0.000 claims 1
• YFQCAVZGCZFBIL-UHFFFAOYSA-N 3,6-dimethyl-1-propan-2-yl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound C1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C YFQCAVZGCZFBIL-UHFFFAOYSA-N 0.000 claims 1
• NKSFFFHRLHNFDX-UHFFFAOYSA-N 3,6-dimethyl-5-(2-methyl-6-propan-2-ylpyridin-3-yl)-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C NKSFFFHRLHNFDX-UHFFFAOYSA-N 0.000 claims 1
• ZBNYKOJAOHEVQZ-UHFFFAOYSA-N 3,6-dimethyl-5-(6-propan-2-ylpyridin-3-yl)-1-propylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 ZBNYKOJAOHEVQZ-UHFFFAOYSA-N 0.000 claims 1
• JOEGXXVCRQULFO-UHFFFAOYSA-N 3,6-dimethyl-5-[2-(4-methylpiperazin-1-yl)-6-propan-2-ylpyridin-3-yl]-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound N=1C(C(C)C)=CC=C(C=2C(=CC=3N(C(C)C)C=C(C)C=3N=2)C)C=1N1CCN(C)CC1 JOEGXXVCRQULFO-UHFFFAOYSA-N 0.000 claims 1
• POQPZQSUZIKJCV-UHFFFAOYSA-N 3-(1-butan-2-yl-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC POQPZQSUZIKJCV-UHFFFAOYSA-N 0.000 claims 1
• OFAWQQBQGIGJIA-UHFFFAOYSA-N 3-(1-butyl-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CCCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC OFAWQQBQGIGJIA-UHFFFAOYSA-N 0.000 claims 1
• WHNQANIRXJKYCR-UHFFFAOYSA-N 3-(1-ethyl-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC WHNQANIRXJKYCR-UHFFFAOYSA-N 0.000 claims 1
• ZXZHAYSBRUBHFP-UHFFFAOYSA-N 3-(1-methoxybutan-2-yl)-6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1,5-dimethylpyrrolo[2,3-b]pyridine Chemical compound CC=1C=C2C(C(COC)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ZXZHAYSBRUBHFP-UHFFFAOYSA-N 0.000 claims 1
• CKBBHSOZNSGYPC-UHFFFAOYSA-N 3-(2-ethyl-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazin-3-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC CKBBHSOZNSGYPC-UHFFFAOYSA-N 0.000 claims 1
• JZOPVXJEIOKAJG-UHFFFAOYSA-N 3-(2-ethyl-5-methyl-7-propan-2-ylpyrrolo[2,3-b]pyrazin-3-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=NC=2C(C(C)C)=CN(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC JZOPVXJEIOKAJG-UHFFFAOYSA-N 0.000 claims 1
• AAGAILZTWJOHKM-UHFFFAOYSA-N 3-(2-ethyl-6-propan-2-ylpyridin-3-yl)-7-(1-methoxypropan-2-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)COC)=CN2C AAGAILZTWJOHKM-UHFFFAOYSA-N 0.000 claims 1
• UVGRJQCNFPCFOL-UHFFFAOYSA-N 3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethyl-7-propan-2-ylpyrrolo[2,3-b]pyrazine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)C)=CN2C UVGRJQCNFPCFOL-UHFFFAOYSA-N 0.000 claims 1
• IVIODJAGAFAHRB-UHFFFAOYSA-N 3-(3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC IVIODJAGAFAHRB-UHFFFAOYSA-N 0.000 claims 1
• DIHFDSVBFBZALV-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n,6-di(propan-2-yl)pyridin-2-amine Chemical compound CC(C)NC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C DIHFDSVBFBZALV-UHFFFAOYSA-N 0.000 claims 1
• XUSBBTHVAAIJMF-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CN(C)C1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C XUSBBTHVAAIJMF-UHFFFAOYSA-N 0.000 claims 1
• XZCONZUVSIZFKR-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n-ethyl-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C XZCONZUVSIZFKR-UHFFFAOYSA-N 0.000 claims 1
• KDSGDSOOIUSTDJ-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C KDSGDSOOIUSTDJ-UHFFFAOYSA-N 0.000 claims 1
• HPOCDELKVUWUTO-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridin-5-yl)-n,6-di(propan-2-yl)pyridin-2-amine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC(C)C HPOCDELKVUWUTO-UHFFFAOYSA-N 0.000 claims 1
• PCHCUXUJJRYZQO-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridin-5-yl)-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C PCHCUXUJJRYZQO-UHFFFAOYSA-N 0.000 claims 1
• IMUUBXMXCNCLHP-UHFFFAOYSA-N 3-(3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridin-5-yl)-n-(2-methoxyethyl)-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NCCOC IMUUBXMXCNCLHP-UHFFFAOYSA-N 0.000 claims 1
• FJSFPDRDFLAPGN-UHFFFAOYSA-N 3-(3,7-dimethyl-5-propan-2-ylpyrrolo[2,3-b]pyrazin-2-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N(C(C)C)C=C2C FJSFPDRDFLAPGN-UHFFFAOYSA-N 0.000 claims 1
• CEXQVAMBZOEYKI-UHFFFAOYSA-N 3-(3,7-dimethyl-5-propylpyrrolo[2,3-b]pyrazin-2-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1N=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC CEXQVAMBZOEYKI-UHFFFAOYSA-N 0.000 claims 1
• PXODGSQZNIVRIY-UHFFFAOYSA-N 3-(3-butan-2-yl-1,5-dimethylpyrrolo[2,3-b]pyridin-6-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2C(C(C)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC PXODGSQZNIVRIY-UHFFFAOYSA-N 0.000 claims 1
• GYYLZOISBUTECI-UHFFFAOYSA-N 3-(6-ethyl-3-methyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N(C(C)C)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC GYYLZOISBUTECI-UHFFFAOYSA-N 0.000 claims 1
• WPNKBDXSGPYICU-UHFFFAOYSA-N 3-[1-(1,3-dimethoxypropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(COC)COC)C=C2C WPNKBDXSGPYICU-UHFFFAOYSA-N 0.000 claims 1
• HXEWRJANHUWQGH-UHFFFAOYSA-N 3-[1-(1-methoxy-2-methylpropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)(C)COC)C=C2C HXEWRJANHUWQGH-UHFFFAOYSA-N 0.000 claims 1
• YOJWBDIZSSOPJW-UHFFFAOYSA-N 3-[1-(1-methoxypropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)COC)C=C2C YOJWBDIZSSOPJW-UHFFFAOYSA-N 0.000 claims 1
• FQQMUTWGBDWASM-UHFFFAOYSA-N 3-[1-(2-fluoroethyl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCF)C=C2C FQQMUTWGBDWASM-UHFFFAOYSA-N 0.000 claims 1
• XVAJIWRIRTXFBH-UHFFFAOYSA-N 3-[1-(3-fluoropropyl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCCF)C=C2C XVAJIWRIRTXFBH-UHFFFAOYSA-N 0.000 claims 1
• GHFPTCVANVGFRG-INIZCTEOSA-N 3-[1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](CF)COC)C=C2C GHFPTCVANVGFRG-INIZCTEOSA-N 0.000 claims 1
• XXASFCGNYSGFAY-QGZVFWFLSA-N 3-[1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC XXASFCGNYSGFAY-QGZVFWFLSA-N 0.000 claims 1
• YOJWBDIZSSOPJW-MRXNPFEDSA-N 3-[1-[(2r)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](C)COC)C=C2C YOJWBDIZSSOPJW-MRXNPFEDSA-N 0.000 claims 1
• GHFPTCVANVGFRG-MRXNPFEDSA-N 3-[1-[(2s)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](CF)COC)C=C2C GHFPTCVANVGFRG-MRXNPFEDSA-N 0.000 claims 1
• XIDPWFCKQOJIJD-INIZCTEOSA-N 3-[1-[(2s)-1-methoxypropan-2-yl]-3,6,7-trimethylpyrrolo[3,2-b]pyridin-5-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C(C)=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C XIDPWFCKQOJIJD-INIZCTEOSA-N 0.000 claims 1
• GYIAWRTWJIRRAL-HNNXBMFYSA-N 3-[1-[(2s)-1-methoxypropan-2-yl]-3,6,7-trimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1C)C)=NC2=C1N([C@@H](C)COC)C=C2C GYIAWRTWJIRRAL-HNNXBMFYSA-N 0.000 claims 1
• JSRKDQMOFOJRNV-SFHVURJKSA-N 3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n,6-di(propan-2-yl)pyridin-2-amine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC(C)C JSRKDQMOFOJRNV-SFHVURJKSA-N 0.000 claims 1
• XOFAFZFSOUPTKH-KRWDZBQOSA-N 3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C XOFAFZFSOUPTKH-KRWDZBQOSA-N 0.000 claims 1
• YOJWBDIZSSOPJW-INIZCTEOSA-N 3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C YOJWBDIZSSOPJW-INIZCTEOSA-N 0.000 claims 1
• OBBNXYXZIFULLR-UHFFFAOYSA-N 3-[2-ethyl-3-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methylpyrrolo[2,3-b]pyrazin-7-yl]propanenitrile Chemical compound CCC1=NC=2C(CCC#N)=CN(C)C=2N=C1C1=CC=C(OC(F)(F)F)C=C1OC OBBNXYXZIFULLR-UHFFFAOYSA-N 0.000 claims 1
• YBCJXSXCHGKIJQ-UHFFFAOYSA-N 3-[2-methoxy-4-(trifluoromethoxy)phenyl]-2,5-dimethyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC YBCJXSXCHGKIJQ-UHFFFAOYSA-N 0.000 claims 1
• JRGGNXONSYPLPT-UHFFFAOYSA-N 3-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazine Chemical compound C=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC JRGGNXONSYPLPT-UHFFFAOYSA-N 0.000 claims 1
• OAECMFPXHFSBGN-UHFFFAOYSA-N 3-[3,6-dimethyl-1-(2-methylpropyl)pyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC(C)C)C=C2C OAECMFPXHFSBGN-UHFFFAOYSA-N 0.000 claims 1
• OOFICFIVHPGPMH-FQEVSTJZSA-N 3-[3,6-dimethyl-1-[(2s)-1-morpholin-4-ylbutan-2-yl]pyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)NC)N1CCOCC1 OOFICFIVHPGPMH-FQEVSTJZSA-N 0.000 claims 1
• ICICWOCXGNDSID-LJQANCHMSA-N 3-[3,7-dimethyl-5-[(2r)-1-morpholin-4-ylbutan-2-yl]pyrrolo[2,3-b]pyrazin-2-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)NC)N1CCOCC1 ICICWOCXGNDSID-LJQANCHMSA-N 0.000 claims 1
• DRDATAVZNQSFBB-AWEZNQCLSA-N 3-[3-chloro-1-[(2s)-1-methoxypropan-2-yl]-6-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2Cl DRDATAVZNQSFBB-AWEZNQCLSA-N 0.000 claims 1
• MYZRMQNOCHQFMC-ZDUSSCGKSA-N 3-[3-chloro-5-[(2s)-1-methoxypropan-2-yl]-7-methylpyrrolo[2,3-b]pyrazin-2-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=N1)Cl)=NC2=C1N([C@@H](C)COC)C=C2C MYZRMQNOCHQFMC-ZDUSSCGKSA-N 0.000 claims 1
• QIEVDRTZANSVEK-HNNXBMFYSA-N 3-[3-ethyl-5-[(2s)-1-methoxypropan-2-yl]-7-methylpyrrolo[2,3-b]pyrazin-2-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=NC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC QIEVDRTZANSVEK-HNNXBMFYSA-N 0.000 claims 1
• HXHYWHCVQTUVRT-QGZVFWFLSA-N 3-[5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazin-2-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C HXHYWHCVQTUVRT-QGZVFWFLSA-N 0.000 claims 1
• NHABXPUWLQXKPT-MRXNPFEDSA-N 3-[5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazin-2-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC NHABXPUWLQXKPT-MRXNPFEDSA-N 0.000 claims 1
• NHABXPUWLQXKPT-INIZCTEOSA-N 3-[5-[(2s)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazin-2-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CC=1N=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC NHABXPUWLQXKPT-INIZCTEOSA-N 0.000 claims 1
• HNUBZKGVMGDBGZ-AWEZNQCLSA-N 3-[6-chloro-1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)Cl)=NC2=C1N([C@@H](CF)COC)C=C2C HNUBZKGVMGDBGZ-AWEZNQCLSA-N 0.000 claims 1
• NHYNMNXNYJOZMT-HNNXBMFYSA-N 3-[6-chloro-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound ClC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C NHYNMNXNYJOZMT-HNNXBMFYSA-N 0.000 claims 1
• PYBXAFRDABTGJM-HNNXBMFYSA-N 3-[6-chloro-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-ethyl-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC=C1C(C(=C1)Cl)=NC2=C1N([C@@H](C)COC)C=C2C PYBXAFRDABTGJM-HNNXBMFYSA-N 0.000 claims 1
• NIXUIZSVOAFJKY-AWEZNQCLSA-N 3-[6-chloro-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)Cl)=NC2=C1N([C@@H](C)COC)C=C2C NIXUIZSVOAFJKY-AWEZNQCLSA-N 0.000 claims 1
• YVYIZCXGEHJBLC-GOSISDBHSA-N 3-[6-ethyl-1-[(2r)-1-methoxybutan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC YVYIZCXGEHJBLC-GOSISDBHSA-N 0.000 claims 1
• GIGYPNKNFKBGCX-MRXNPFEDSA-N 3-[6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC GIGYPNKNFKBGCX-MRXNPFEDSA-N 0.000 claims 1
• GIGYPNKNFKBGCX-INIZCTEOSA-N 3-[6-ethyl-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1NC GIGYPNKNFKBGCX-INIZCTEOSA-N 0.000 claims 1
• HPRZXRYKBGRWEX-INIZCTEOSA-N 3-[6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n,n-dimethyl-6-propan-2-ylpyridin-2-amine Chemical compound COC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N(C)C HPRZXRYKBGRWEX-INIZCTEOSA-N 0.000 claims 1
• LWFGDGSQVGUYFD-HNNXBMFYSA-N 3-[6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)OC)=NC2=C1N([C@@H](C)COC)C=C2C LWFGDGSQVGUYFD-HNNXBMFYSA-N 0.000 claims 1
• DXQKTGMDMLTGDN-UHFFFAOYSA-N 3-[7-(1-methoxypropan-2-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-3-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)COC)=CN2C DXQKTGMDMLTGDN-UHFFFAOYSA-N 0.000 claims 1
• MIXOXSWKLMRXRF-UHFFFAOYSA-N 3-bromo-5-(3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-n,4-diethyl-n-methylpyridin-2-amine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)CC)C(Br)=C1CC MIXOXSWKLMRXRF-UHFFFAOYSA-N 0.000 claims 1
• AFECPAVMSVAGHD-UHFFFAOYSA-N 3-butan-2-yl-6-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1,5-dimethylpyrrolo[2,3-b]pyridine Chemical compound CC=1C=C2C(C(C)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC AFECPAVMSVAGHD-UHFFFAOYSA-N 0.000 claims 1
• STCOLTWHJYIWOS-UHFFFAOYSA-N 3-butan-2-yl-6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1,5-dimethylpyrrolo[2,3-b]pyridine Chemical compound CC=1C=C2C(C(C)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC STCOLTWHJYIWOS-UHFFFAOYSA-N 0.000 claims 1
• VOCOGJSWPFMTPN-AWEZNQCLSA-N 3-chloro-1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(Cl)C2=NC=1C1=CC=C(C(C)C)N=C1OC VOCOGJSWPFMTPN-AWEZNQCLSA-N 0.000 claims 1
• BIKBEZBEIWFJNS-LBPRGKRZSA-N 3-chloro-1-[(2s)-1-methoxypropan-2-yl]-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-6-methylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(Cl)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC BIKBEZBEIWFJNS-LBPRGKRZSA-N 0.000 claims 1
• DRAROCBRAGNJRJ-AWEZNQCLSA-N 3-chloro-1-[(2s)-1-methoxypropan-2-yl]-6-methyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(Cl)C2=NC=1C1=CC=C(C(C)C)N=C1 DRAROCBRAGNJRJ-AWEZNQCLSA-N 0.000 claims 1
• UWSAUVQYBOJDOI-UHFFFAOYSA-N 3-chloro-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2Cl UWSAUVQYBOJDOI-UHFFFAOYSA-N 0.000 claims 1
• MEWWRIMXKHBWTF-ZDUSSCGKSA-N 3-chloro-5-[(2s)-1-methoxypropan-2-yl]-7-methyl-2-(2-methyl-6-propan-2-ylpyridin-3-yl)pyrrolo[2,3-b]pyrazine Chemical compound ClC=1N=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1C MEWWRIMXKHBWTF-ZDUSSCGKSA-N 0.000 claims 1
• RGQVRHYNUADCLH-INIZCTEOSA-N 3-ethyl-1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-6-methylpyrrolo[3,2-b]pyridine Chemical compound N1=C2C(CC)=CN([C@@H](C)COC)C2=CC(C)=C1C1=CC=C(C(C)C)N=C1OC RGQVRHYNUADCLH-INIZCTEOSA-N 0.000 claims 1
• GRMTYDDSGLEKBP-HXUWFJFHSA-N 4-[(2r)-2-[2-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazin-5-yl]butyl]morpholine Chemical compound C([C@@H](CC)N1C2=NC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)CC)N1CCOCC1 GRMTYDDSGLEKBP-HXUWFJFHSA-N 0.000 claims 1
• HDKOESKTQUNERL-OAQYLSRUSA-N 4-[(2r)-2-[5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]morpholine Chemical compound C([C@@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)CC)N1CCOCC1 HDKOESKTQUNERL-OAQYLSRUSA-N 0.000 claims 1
• MVZDNXVMVUKYFE-HXUWFJFHSA-N 4-[(2r)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]morpholine Chemical compound C([C@@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCOCC1 MVZDNXVMVUKYFE-HXUWFJFHSA-N 0.000 claims 1
• HDKOESKTQUNERL-NRFANRHFSA-N 4-[(2s)-2-[5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]morpholine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)CC)N1CCOCC1 HDKOESKTQUNERL-NRFANRHFSA-N 0.000 claims 1
• MVZDNXVMVUKYFE-FQEVSTJZSA-N 4-[(2s)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]morpholine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=NC(=CC=1)C(C)C)OC)N1CCOCC1 MVZDNXVMVUKYFE-FQEVSTJZSA-N 0.000 claims 1
• CCIRNHGQHDBAST-SFHVURJKSA-N 4-[(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]morpholine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCOCC1 CCIRNHGQHDBAST-SFHVURJKSA-N 0.000 claims 1
• MJZMDIMPTONIJD-SFHVURJKSA-N 4-[(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl]thiomorpholine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCSCC1 MJZMDIMPTONIJD-SFHVURJKSA-N 0.000 claims 1
• IRELQQYECLKMPH-UHFFFAOYSA-N 4-[2-[3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]propyl]morpholine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1C(C(C)CN1CCOCC1)=CN2C IRELQQYECLKMPH-UHFFFAOYSA-N 0.000 claims 1
• JTNWJSHBHUAFRP-UHFFFAOYSA-N 4-[2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]ethyl]morpholine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCN1CCOCC1)C=C2C JTNWJSHBHUAFRP-UHFFFAOYSA-N 0.000 claims 1
• VFOVWUIDQLMZQN-UHFFFAOYSA-N 4-ethyl-5-(2-ethyl-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazin-3-yl)-n,n-dimethylpyridin-2-amine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CN=C(N(C)C)C=C1CC VFOVWUIDQLMZQN-UHFFFAOYSA-N 0.000 claims 1
• BUZJYJICIXGDJA-INIZCTEOSA-N 5-(2,6-diethylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(CC)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C BUZJYJICIXGDJA-INIZCTEOSA-N 0.000 claims 1
• ZFXUXPCSZDOPAO-UHFFFAOYSA-N 5-(2,6-diethylpyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(CC)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C ZFXUXPCSZDOPAO-UHFFFAOYSA-N 0.000 claims 1
• WPZJHBZRNNJFEF-GOSISDBHSA-N 5-(2-ethoxy-6-ethyl-5-methylsulfonylpyridin-3-yl)-6-ethyl-1-[(2r)-1-methoxybutan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCOC1=NC(CC)=C(S(C)(=O)=O)C=C1C(C(=C1)CC)=NC2=C1N([C@H](CC)COC)C=C2C WPZJHBZRNNJFEF-GOSISDBHSA-N 0.000 claims 1
• OJHYFPFDOPBNIW-KRWDZBQOSA-N 5-(2-ethoxy-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCOC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C OJHYFPFDOPBNIW-KRWDZBQOSA-N 0.000 claims 1
• ISXBDNYPSSJCSY-MRXNPFEDSA-N 5-(2-ethyl-6-methoxypyridin-3-yl)-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(OC)N=C1CC ISXBDNYPSSJCSY-MRXNPFEDSA-N 0.000 claims 1
• BJYQAYITEAAPIJ-UHFFFAOYSA-N 5-(2-ethyl-6-methoxypyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OC)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C BJYQAYITEAAPIJ-UHFFFAOYSA-N 0.000 claims 1
• ZVVFOVHNFIKRIO-GOSISDBHSA-N 5-(2-ethyl-6-propan-2-yloxypyridin-3-yl)-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(OC(C)C)N=C1CC ZVVFOVHNFIKRIO-GOSISDBHSA-N 0.000 claims 1
• MGPQAZVGRKYZNV-KRWDZBQOSA-N 5-(2-ethyl-6-propan-2-yloxypyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OC(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C MGPQAZVGRKYZNV-KRWDZBQOSA-N 0.000 claims 1
• CFXSBGRQSBGRSH-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-yloxypyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OC(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C CFXSBGRQSBGRSH-UHFFFAOYSA-N 0.000 claims 1
• YGQHICHYUOKNQZ-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-(1-methoxy-2-methylpropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)(C)COC)C=C2C YGQHICHYUOKNQZ-UHFFFAOYSA-N 0.000 claims 1
• DJMBLQFKNGLOHF-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-(1-methoxypropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)COC)C=C2C DJMBLQFKNGLOHF-UHFFFAOYSA-N 0.000 claims 1
• RELJMCALYJBEGQ-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-(2-fluoroethyl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCF)C=C2C RELJMCALYJBEGQ-UHFFFAOYSA-N 0.000 claims 1
• MODROGVJKMWPKL-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-(3-fluoropropyl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CCCF)C=C2C MODROGVJKMWPKL-UHFFFAOYSA-N 0.000 claims 1
• LVACYZHUNJTICC-KRWDZBQOSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](CF)COC)C=C2C LVACYZHUNJTICC-KRWDZBQOSA-N 0.000 claims 1
• AKRWGVOKHNUHMM-GOSISDBHSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC AKRWGVOKHNUHMM-GOSISDBHSA-N 0.000 claims 1
• UTLJDDJRHZVEPW-LJQANCHMSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-methoxypentan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC UTLJDDJRHZVEPW-LJQANCHMSA-N 0.000 claims 1
• DJMBLQFKNGLOHF-QGZVFWFLSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](C)COC)C=C2C DJMBLQFKNGLOHF-QGZVFWFLSA-N 0.000 claims 1
• UCWXMWMDETYNQC-KRWDZBQOSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-fluorobutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@H](CF)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC UCWXMWMDETYNQC-KRWDZBQOSA-N 0.000 claims 1
• DKGRCPTVYLHBPD-INIZCTEOSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6,7-trimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1C)C)=NC2=C1N([C@@H](C)COC)C=C2C DKGRCPTVYLHBPD-INIZCTEOSA-N 0.000 claims 1
• DJMBLQFKNGLOHF-KRWDZBQOSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C DJMBLQFKNGLOHF-KRWDZBQOSA-N 0.000 claims 1
• QATFVCJVPUJALI-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-(2-methylpropyl)pyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC(C)C)C=C2C QATFVCJVPUJALI-UHFFFAOYSA-N 0.000 claims 1
• PTOHVGGCUOWQTP-UHFFFAOYSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C PTOHVGGCUOWQTP-UHFFFAOYSA-N 0.000 claims 1
• LEQOTVLTIWTFIF-INIZCTEOSA-N 5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)OC)=NC2=C1N([C@@H](C)COC)C=C2C LEQOTVLTIWTFIF-INIZCTEOSA-N 0.000 claims 1
• BRRYOWQCLPLFME-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1,3,6-trimethylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C)C=C2C BRRYOWQCLPLFME-UHFFFAOYSA-N 0.000 claims 1
• ILLSRBNJNNRVSD-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1-(3-methoxyprop-1-en-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(=C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ILLSRBNJNNRVSD-UHFFFAOYSA-N 0.000 claims 1
• NLDODZBEVHWDED-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1-(3-methoxypropyl)-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCCOC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NLDODZBEVHWDED-UHFFFAOYSA-N 0.000 claims 1
• NNUPVIYNNXPDCM-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-(2-methylpropyl)pyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(CC(C)C)C=C2C NNUPVIYNNXPDCM-UHFFFAOYSA-N 0.000 claims 1
• PDWMFLICFWTMQJ-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC PDWMFLICFWTMQJ-UHFFFAOYSA-N 0.000 claims 1
• IGQDJDAFJXCHCF-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C IGQDJDAFJXCHCF-UHFFFAOYSA-N 0.000 claims 1
• ASWVXKDUIXVNDT-UHFFFAOYSA-N 5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ASWVXKDUIXVNDT-UHFFFAOYSA-N 0.000 claims 1
• XKBLDZHMNXPXLE-UHFFFAOYSA-N 5-(3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridin-5-yl)-4-ethyl-n,n-dimethylpyridin-2-amine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1CC XKBLDZHMNXPXLE-UHFFFAOYSA-N 0.000 claims 1
• CXIODZDEAVSXCR-UHFFFAOYSA-N 5-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-6-ethyl-n,n-dimethylpyridin-2-amine Chemical compound CCC1=NC(N(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C CXIODZDEAVSXCR-UHFFFAOYSA-N 0.000 claims 1
• MJYXSUXGGLUAMB-UHFFFAOYSA-N 5-(3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-4-ethyl-n,n-dimethylpyridin-2-amine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1CC MJYXSUXGGLUAMB-UHFFFAOYSA-N 0.000 claims 1
• IGUJBUALTFQKST-UHFFFAOYSA-N 5-(3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-4-methoxy-n,n-dimethylpyridin-2-amine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1OC IGUJBUALTFQKST-UHFFFAOYSA-N 0.000 claims 1
• OOFULEJUQPYEHB-UHFFFAOYSA-N 5-(3,7-dimethyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-n,4-diethyl-n-methylpyridin-2-amine Chemical compound CC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)CC)C=C1CC OOFULEJUQPYEHB-UHFFFAOYSA-N 0.000 claims 1
• JPRSGGQOZPPJDX-UHFFFAOYSA-N 5-(3-chloro-7-methyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-4-ethyl-n,n-dimethylpyridin-2-amine Chemical compound ClC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)C)C=C1CC JPRSGGQOZPPJDX-UHFFFAOYSA-N 0.000 claims 1
• KYMXIIPWIUIJQU-UHFFFAOYSA-N 5-(3-chloro-7-methyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-n,n,4-triethylpyridin-2-amine Chemical compound ClC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(CC)CC)C=C1CC KYMXIIPWIUIJQU-UHFFFAOYSA-N 0.000 claims 1
• ODQZETYAUCYANV-INIZCTEOSA-N 5-(6-cyclopropyl-2-ethylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound C=1C=C(C=2C(=CC=3N([C@@H](C)COC)C=C(C)C=3N=2)C)C(CC)=NC=1C1CC1 ODQZETYAUCYANV-INIZCTEOSA-N 0.000 claims 1
• YEQAPKHQMHIDKI-QGZVFWFLSA-N 5-(6-ethoxy-2-ethylpyridin-3-yl)-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OCC)=CC=C1C(C(=C1)C)=NC2=C1N([C@H](CC)COC)C=C2C YEQAPKHQMHIDKI-QGZVFWFLSA-N 0.000 claims 1
• FOUNAHFZXVLJSX-INIZCTEOSA-N 5-(6-ethoxy-2-ethylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OCC)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C FOUNAHFZXVLJSX-INIZCTEOSA-N 0.000 claims 1
• XXHNBMYNAPCAKC-QGZVFWFLSA-N 5-[(2r)-1-ethoxybutan-2-yl]-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@H](CC)COCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC XXHNBMYNAPCAKC-QGZVFWFLSA-N 0.000 claims 1
• FKFLERGWUKXYPV-QGZVFWFLSA-N 5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethyl-2-(2-methyl-6-propan-2-ylpyridin-3-yl)pyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1C FKFLERGWUKXYPV-QGZVFWFLSA-N 0.000 claims 1
• UPQLNKCPPNVHAJ-QGZVFWFLSA-N 5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethyl-2-(6-propan-2-ylpyridin-3-yl)pyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 UPQLNKCPPNVHAJ-QGZVFWFLSA-N 0.000 claims 1
• FCCGIKZKBIBAQS-INIZCTEOSA-N 5-[(2s)-1-methoxybutan-2-yl]-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC FCCGIKZKBIBAQS-INIZCTEOSA-N 0.000 claims 1
• LQSRYJXSXDGLFL-KRWDZBQOSA-N 5-[2-(3,3-difluoroazetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CC(F)(F)C1 LQSRYJXSXDGLFL-KRWDZBQOSA-N 0.000 claims 1
• HVELZZIJZOWEEQ-LJQANCHMSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 HVELZZIJZOWEEQ-LJQANCHMSA-N 0.000 claims 1
• CLWBVPMWTLOQJU-KRWDZBQOSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-1-[(2s)-1-methoxypropan-2-yl]-3,6,7-trimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C(C)=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 CLWBVPMWTLOQJU-KRWDZBQOSA-N 0.000 claims 1
• DCDSCEDRPOPAKG-SFHVURJKSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 DCDSCEDRPOPAKG-SFHVURJKSA-N 0.000 claims 1
• GATNJLXVZNSEMQ-UHFFFAOYSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound N=1C(C(C)C)=CC=C(C=2C(=CC=3N(C(C)C)C=C(C)C=3N=2)C)C=1N1CCC1 GATNJLXVZNSEMQ-UHFFFAOYSA-N 0.000 claims 1
• QOKORLHVSDGFCX-UHFFFAOYSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-3,6-dimethyl-1-propylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N(CCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 QOKORLHVSDGFCX-UHFFFAOYSA-N 0.000 claims 1
• ILPUKNBASIZXRD-HXUWFJFHSA-N 5-[2-(azetidin-1-yl)-6-propan-2-ylpyridin-3-yl]-6-ethyl-1-[(2r)-1-methoxybutan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1N1CCC1 ILPUKNBASIZXRD-HXUWFJFHSA-N 0.000 claims 1
• SVUZACDZPFPBJJ-KRWDZBQOSA-N 5-[2-ethyl-6-(2-methoxyethoxy)pyridin-3-yl]-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(OCCOC)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C SVUZACDZPFPBJJ-KRWDZBQOSA-N 0.000 claims 1
• ZXYFIFIEVQQMMO-IBGZPJMESA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-[(2s)-1-(4-methylpiperazin-1-yl)butan-2-yl]pyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCN(C)CC1 ZXYFIFIEVQQMMO-IBGZPJMESA-N 0.000 claims 1
• YRDSHJLAAKUPPS-IBGZPJMESA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-[(2s)-1-piperidin-1-ylbutan-2-yl]pyrrolo[3,2-b]pyridine Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)N1CCCCC1 YRDSHJLAAKUPPS-IBGZPJMESA-N 0.000 claims 1
• VTIWKXSKWGNOQI-UHFFFAOYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C VTIWKXSKWGNOQI-UHFFFAOYSA-N 0.000 claims 1
• ZFDJRZWPQXLEKH-UHFFFAOYSA-N 5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethyl-1h-pyrrolo[3,2-b]pyridine Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C(C(=C1)C)=NC2=C1NC=C2C ZFDJRZWPQXLEKH-UHFFFAOYSA-N 0.000 claims 1
• IRHHFPSUEJWNGL-LJQANCHMSA-N 5-[6-(cyclopropylmethoxy)-2-ethylpyridin-3-yl]-1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound CC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C(C(=N1)CC)=CC=C1OCC1CC1 IRHHFPSUEJWNGL-LJQANCHMSA-N 0.000 claims 1
• GHIBRASGXPADBI-KRWDZBQOSA-N 5-[6-(cyclopropylmethoxy)-2-ethylpyridin-3-yl]-1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridine Chemical compound C=1C=C(C=2C(=CC=3N([C@@H](C)COC)C=C(C)C=3N=2)C)C(CC)=NC=1OCC1CC1 GHIBRASGXPADBI-KRWDZBQOSA-N 0.000 claims 1
• PGJGDXYZPJOSMX-HNNXBMFYSA-N 5-bromo-3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=C(Br)C=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C PGJGDXYZPJOSMX-HNNXBMFYSA-N 0.000 claims 1
• BZQIBOXGFHDAPB-OAHLLOKOSA-N 5-bromo-3-[6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC(Br)=C(C(C)C)N=C1NC BZQIBOXGFHDAPB-OAHLLOKOSA-N 0.000 claims 1
• ZLVVETTVDNSOQI-UHFFFAOYSA-N 5-bromo-6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1-methyl-3-propan-2-ylpyrrolo[2,3-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)Br)=NC2=C1C(C(C)C)=CN2C ZLVVETTVDNSOQI-UHFFFAOYSA-N 0.000 claims 1
• VUVWOBORYVROMA-UHFFFAOYSA-N 5-bromo-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-1-methyl-3-pentan-3-ylpyrrolo[2,3-b]pyridine Chemical compound BrC=1C=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC VUVWOBORYVROMA-UHFFFAOYSA-N 0.000 claims 1
• MFUKVRLBOHKDJK-UHFFFAOYSA-N 5-but-1-en-2-yl-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(C(=C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC MFUKVRLBOHKDJK-UHFFFAOYSA-N 0.000 claims 1
• OHSMISVBZTXXRT-UHFFFAOYSA-N 5-butan-2-yl-2-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,7-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2N(C(C)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC OHSMISVBZTXXRT-UHFFFAOYSA-N 0.000 claims 1
• XOIOAGDHULRXGP-UHFFFAOYSA-N 5-chloro-3-(3,6-dimethyl-1-propan-2-ylpyrrolo[3,2-b]pyridin-5-yl)-n-ethyl-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=C(Cl)C=C1C(C(=C1)C)=NC2=C1N(C(C)C)C=C2C XOIOAGDHULRXGP-UHFFFAOYSA-N 0.000 claims 1
• SDEINDYKOHDZSF-HNNXBMFYSA-N 5-chloro-3-[1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CNC1=NC(C(C)C)=C(Cl)C=C1C(C(=C1)C)=NC2=C1N([C@@H](CF)COC)C=C2C SDEINDYKOHDZSF-HNNXBMFYSA-N 0.000 claims 1
• KSEWSCJGCXRALS-OAHLLOKOSA-N 5-chloro-3-[6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC(Cl)=C(C(C)C)N=C1NC KSEWSCJGCXRALS-OAHLLOKOSA-N 0.000 claims 1
• TWACFDHFCAXAMF-CQSZACIVSA-N 5-chloro-3-[7-chloro-6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=C(Cl)C=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC(Cl)=C(C(C)C)N=C1NC TWACFDHFCAXAMF-CQSZACIVSA-N 0.000 claims 1
• FPGZVAIIVQQNBR-UHFFFAOYSA-N 5-chloro-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-1-methyl-3-pentan-3-ylpyrrolo[2,3-b]pyridine Chemical compound ClC=1C=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC FPGZVAIIVQQNBR-UHFFFAOYSA-N 0.000 claims 1
• FPVHEVAEGCYSLO-QGZVFWFLSA-N 5-cyclopropyl-3-[6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C(C(=NC=1C(C)C)NC)=CC=1C1CC1 FPVHEVAEGCYSLO-QGZVFWFLSA-N 0.000 claims 1
• XXTLMISVKFCECJ-KRWDZBQOSA-N 5-ethyl-3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound N1=C(C(C)C)C(CC)=CC(C=2C(=CC=3N([C@@H](C)COC)C=C(C)C=3N=2)C)=C1NC XXTLMISVKFCECJ-KRWDZBQOSA-N 0.000 claims 1
• MAKHVWYFAUKTHA-QGZVFWFLSA-N 5-ethyl-3-[6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-n-methyl-6-propan-2-ylpyridin-2-amine Chemical compound N1=C(C(C)C)C(CC)=CC(C=2C(=CC=3N([C@H](C)COC)C=C(C)C=3N=2)CC)=C1NC MAKHVWYFAUKTHA-QGZVFWFLSA-N 0.000 claims 1
• SSCSHVKGXVCWTF-UHFFFAOYSA-N 5-ethyl-6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1-methyl-3-propan-2-ylpyrrolo[2,3-b]pyridine Chemical compound CCC1=CC=2C(C(C)C)=CN(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC SSCSHVKGXVCWTF-UHFFFAOYSA-N 0.000 claims 1
• CUHUVVKJCWITNC-UHFFFAOYSA-N 6-(2-ethyl-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazin-3-yl)-5-methoxy-3-propan-2-yl-2,3-dihydrofuro[3,2-b]pyridine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C(C(=N1)OC)=CC2=C1C(C(C)C)CO2 CUHUVVKJCWITNC-UHFFFAOYSA-N 0.000 claims 1
• JIJWBWVQXZWPPV-UHFFFAOYSA-N 6-(2-methoxy-6-propan-2-ylpyridin-3-yl)-1,5-dimethyl-3-propan-2-ylpyrrolo[2,3-b]pyridine Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1C(C(C)C)=CN2C JIJWBWVQXZWPPV-UHFFFAOYSA-N 0.000 claims 1
• DCAFQRHBYKTYEE-UHFFFAOYSA-N 6-(3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridin-5-yl)-2,5-diethyl-3-propan-2-ylimidazo[4,5-b]pyridine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C(C(=N1)CC)=CC2=C1N(C(C)C)C(CC)=N2 DCAFQRHBYKTYEE-UHFFFAOYSA-N 0.000 claims 1
• STAORVHVYBSHFV-UHFFFAOYSA-N 6-(3,6-dimethyl-1-pentan-3-ylpyrrolo[3,2-b]pyridin-5-yl)-5-ethyl-3-propan-2-ylimidazo[4,5-b]pyridine Chemical compound CC=1C=C2N(C(CC)CC)C=C(C)C2=NC=1C(C(=N1)CC)=CC2=C1N(C(C)C)C=N2 STAORVHVYBSHFV-UHFFFAOYSA-N 0.000 claims 1
• GFZCWLDGWODXFJ-UHFFFAOYSA-N 6-(3-chloro-7-methyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-5-methoxy-3-propan-2-yl-2,3-dihydrofuro[3,2-b]pyridine Chemical compound ClC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C(C(=N1)OC)=CC2=C1C(C(C)C)CO2 GFZCWLDGWODXFJ-UHFFFAOYSA-N 0.000 claims 1
• YLKDIGYWXHIZNY-YNNZGITBSA-N 6-chloro-1-[(1R)-1-fluoro-2-methoxypropyl]-3-methyl-5-(2-methyl-6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound ClC=1C=C2C(=NC1C=1C(=NC(=CC1)C(C)C)C)C(=CN2[C@@H](C(OC)C)F)C YLKDIGYWXHIZNY-YNNZGITBSA-N 0.000 claims 1
• QCVAGDDOEHAQJH-AWEZNQCLSA-N 6-chloro-1-[(2s)-1-methoxypropan-2-yl]-3-methyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound ClC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 QCVAGDDOEHAQJH-AWEZNQCLSA-N 0.000 claims 1
• ZTENRSIEYBRFLL-AWEZNQCLSA-N 6-chloro-1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound ClC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC ZTENRSIEYBRFLL-AWEZNQCLSA-N 0.000 claims 1
• ZHLPYNGPPHBMPD-HNNXBMFYSA-N 6-chloro-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)Cl)=NC2=C1N([C@@H](CF)COC)C=C2C ZHLPYNGPPHBMPD-HNNXBMFYSA-N 0.000 claims 1
• ZLYITIUZCKESAL-KRWDZBQOSA-N 6-ethyl-1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@@H](CF)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC ZLYITIUZCKESAL-KRWDZBQOSA-N 0.000 claims 1
• GEXGMAHPJDMLJI-MRXNPFEDSA-N 6-ethyl-1-[(2r)-1-fluoropropan-2-yl]-5-(2-methoxy-4-propan-2-ylphenyl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@H](C)CF)C=C(C)C=2N=C1C1=CC=C(C(C)C)C=C1OC GEXGMAHPJDMLJI-MRXNPFEDSA-N 0.000 claims 1
• AGKNKHOVXYLXGD-QGZVFWFLSA-N 6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-5-(2-methoxy-4-propan-2-ylphenyl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)C=C1OC AGKNKHOVXYLXGD-QGZVFWFLSA-N 0.000 claims 1
• RYFDUQLUWOMJBO-MRXNPFEDSA-N 6-ethyl-1-[(2r)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC RYFDUQLUWOMJBO-MRXNPFEDSA-N 0.000 claims 1
• DSZGLCUJROBHCD-INIZCTEOSA-N 6-ethyl-1-[(2s)-1-methoxypropan-2-yl]-3-methyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1 DSZGLCUJROBHCD-INIZCTEOSA-N 0.000 claims 1
• RYFDUQLUWOMJBO-INIZCTEOSA-N 6-ethyl-1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC RYFDUQLUWOMJBO-INIZCTEOSA-N 0.000 claims 1
• PTDQNSILPABWCA-HNNXBMFYSA-N 6-ethyl-2-methoxy-5-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n-methylpyridine-3-carboxamide Chemical compound CCC1=NC(OC)=C(C(=O)NC)C=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C PTDQNSILPABWCA-HNNXBMFYSA-N 0.000 claims 1
• CQVPITRLKKHHQI-INIZCTEOSA-N 6-ethyl-5-(2-ethyl-6-methoxypyridin-3-yl)-1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@@H](CF)COC)C=C(C)C=2N=C1C1=CC=C(OC)N=C1CC CQVPITRLKKHHQI-INIZCTEOSA-N 0.000 claims 1
• MBFNADMNENQLKP-LJQANCHMSA-N 6-ethyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-1-methoxybutan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC=1C=C2N([C@@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1CC MBFNADMNENQLKP-LJQANCHMSA-N 0.000 claims 1
• CILMDPNIWCCAIW-KRWDZBQOSA-N 6-ethyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N([C@@H](C)COC)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1CC CILMDPNIWCCAIW-KRWDZBQOSA-N 0.000 claims 1
• RAVROSITPQJDOR-UHFFFAOYSA-N 6-ethyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-3-methyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N(C(C)C)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1CC RAVROSITPQJDOR-UHFFFAOYSA-N 0.000 claims 1
• JDIHANWLCRAFSD-UHFFFAOYSA-N 6-ethyl-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methyl-1-propan-2-ylpyrrolo[3,2-b]pyridine Chemical compound CCC1=CC=2N(C(C)C)C=C(C)C=2N=C1C1=CC=C(C(C)C)N=C1OC JDIHANWLCRAFSD-UHFFFAOYSA-N 0.000 claims 1
• CMVFHSXRPSQLGG-GOSISDBHSA-N 6-ethyl-7-[1-[(2r)-1-hydroxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-2-methyl-4-propan-2-ylpyrido[2,3-b]pyrazin-3-one Chemical compound N1=C(C)C(=O)N(C(C)C)C(N=C2CC)=C1C=C2C1=C(C)C=C2N([C@@H](CO)CC)C=C(C)C2=N1 CMVFHSXRPSQLGG-GOSISDBHSA-N 0.000 claims 1
• SOLHJJQRCDOQNG-HXUWFJFHSA-N 6-ethyl-7-[1-[(2r)-1-methoxybutan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-2,4-di(propan-2-yl)pyrido[2,3-b]pyrazin-3-one Chemical compound N1=C(C(C)C)C(=O)N(C(C)C)C(N=C2CC)=C1C=C2C1=C(C)C=C2N([C@@H](COC)CC)C=C(C)C2=N1 SOLHJJQRCDOQNG-HXUWFJFHSA-N 0.000 claims 1
• REYCHCAIKSTEGD-KRWDZBQOSA-N 6-ethyl-7-[6-ethyl-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-2-methyl-4-propan-2-ylpyrido[2,3-b]pyrazin-3-one Chemical compound N1=C(C)C(=O)N(C(C)C)C(N=C2CC)=C1C=C2C1=NC(C(C)=CN2[C@@H](C)COC)=C2C=C1CC REYCHCAIKSTEGD-KRWDZBQOSA-N 0.000 claims 1
• HSKQEQVONJGCCS-HNNXBMFYSA-N 6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-3-methyl-5-(6-propan-2-ylpyridin-3-yl)pyrrolo[3,2-b]pyridine Chemical compound COC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1 HSKQEQVONJGCCS-HNNXBMFYSA-N 0.000 claims 1
• NSLLUMXCTAFJEA-HNNXBMFYSA-N 6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound COC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC NSLLUMXCTAFJEA-HNNXBMFYSA-N 0.000 claims 1
• PGUKSOHJZKJMJY-UHFFFAOYSA-N 7-(1-methoxybutan-2-yl)-3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2C(C(COC)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC PGUKSOHJZKJMJY-UHFFFAOYSA-N 0.000 claims 1
• SVUGPJQVHUKYGA-UHFFFAOYSA-N 7-(1-methoxypropan-2-yl)-3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2C(C(C)COC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC SVUGPJQVHUKYGA-UHFFFAOYSA-N 0.000 claims 1
• ZGEWRFAULOTQNL-UHFFFAOYSA-N 7-(1-methoxypropan-2-yl)-3-[2-methoxy-4-(trifluoromethoxy)phenyl]-2,5-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2C(C(C)COC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC ZGEWRFAULOTQNL-UHFFFAOYSA-N 0.000 claims 1
• JVQFFISKMLCKND-UHFFFAOYSA-N 7-butan-2-yl-3-(2-methoxy-6-propan-2-ylpyridin-3-yl)-2,5-dimethylpyrrolo[2,3-b]pyrazine Chemical compound CC=1N=C2C(C(C)CC)=CN(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC JVQFFISKMLCKND-UHFFFAOYSA-N 0.000 claims 1
• 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 1
• AJTNATHUESAWIU-KRWDZBQOSA-N [(2s)-2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] methanesulfonate Chemical compound CC=1C=C2N([C@H](COS(C)(=O)=O)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC AJTNATHUESAWIU-KRWDZBQOSA-N 0.000 claims 1
• WSNJCLABWDSADF-FQEVSTJZSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] 4-acetylpiperazine-1-carboxylate Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)OC(=O)N1CCN(C(C)=O)CC1 WSNJCLABWDSADF-FQEVSTJZSA-N 0.000 claims 1
• RIQQKDPUSITTFF-IBGZPJMESA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] 4-methylpiperazine-1-carboxylate Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)OC(=O)N1CCN(C)CC1 RIQQKDPUSITTFF-IBGZPJMESA-N 0.000 claims 1
• KKQUFGJPRBYYCN-FQEVSTJZSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] azepane-1-carboxylate Chemical compound C([C@H](CC)N1C2=CC(C)=C(N=C2C(C)=C1)C=1C(=CC(OC(F)(F)F)=CC=1)OC)OC(=O)N1CCCCCC1 KKQUFGJPRBYYCN-FQEVSTJZSA-N 0.000 claims 1
• ZGPDTDJVDQTGPO-SFHVURJKSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] n,n-diethylcarbamate Chemical compound CC=1C=C2N([C@H](COC(=O)N(CC)CC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC ZGPDTDJVDQTGPO-SFHVURJKSA-N 0.000 claims 1
• COTFGMMGCHJUMH-KRWDZBQOSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] n-(2-methoxyethyl)carbamate Chemical compound CC=1C=C2N([C@H](COC(=O)NCCOC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC COTFGMMGCHJUMH-KRWDZBQOSA-N 0.000 claims 1
• GAGCCGCZBDFUQH-KRWDZBQOSA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] n-ethyl-n-methylcarbamate Chemical compound CC=1C=C2N([C@H](COC(=O)N(C)CC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC GAGCCGCZBDFUQH-KRWDZBQOSA-N 0.000 claims 1
• VYNSMJZUJLTAEU-VPUSJEBWSA-N benzyl (3s,4r)-3-(2-fluoroethoxy)-4-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]pyrrolidine-1-carboxylate Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C(C(=C1)C)=NC2=C1N([C@H]1[C@H](CN(C1)C(=O)OCC=1C=CC=CC=1)OCCF)C=C2C VYNSMJZUJLTAEU-VPUSJEBWSA-N 0.000 claims 1
• VKEOLSRHORITAD-UHFFFAOYSA-N ethyl 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]acetate Chemical compound CC=1C=C2N(CC(=O)OCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC VKEOLSRHORITAD-UHFFFAOYSA-N 0.000 claims 1
• KPOJIIQQDBDCJC-UHFFFAOYSA-N ethyl 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]propanoate Chemical compound CC=1C=C2N(C(C)C(=O)OCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC KPOJIIQQDBDCJC-UHFFFAOYSA-N 0.000 claims 1
• QBYPSKRXHGGTHH-UHFFFAOYSA-N ethyl(2-methoxyethyl)carbamic acid Chemical compound CCN(C(O)=O)CCOC QBYPSKRXHGGTHH-UHFFFAOYSA-N 0.000 claims 1
• XIKDEXWRZLRDKE-CTNGQTDRSA-N methyl (3s,4r)-3-(2-fluoroethoxy)-4-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC)C[C@H](OCCF)[C@@H]1N1C2=CC(C)=C(C=3C(=CC(OC(F)(F)F)=CC=3)OC)N=C2C(C)=C1 XIKDEXWRZLRDKE-CTNGQTDRSA-N 0.000 claims 1
• FNKYEEIFHZMGIB-UHFFFAOYSA-N methyl 2-[3-[2-methoxy-4-(trifluoromethoxy)phenyl]-2,5-dimethylpyrrolo[2,3-b]pyrazin-7-yl]propanoate Chemical compound CC=1N=C2C(C(C)C(=O)OC)=CN(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC FNKYEEIFHZMGIB-UHFFFAOYSA-N 0.000 claims 1
• XOUYACVJAKAKOE-UHFFFAOYSA-N n,n,4-triethyl-5-(2-ethyl-5-methyl-7-pentan-3-ylpyrrolo[2,3-b]pyrazin-3-yl)pyridin-2-amine Chemical compound CCC=1N=C2C(C(CC)CC)=CN(C)C2=NC=1C1=CN=C(N(CC)CC)C=C1CC XOUYACVJAKAKOE-UHFFFAOYSA-N 0.000 claims 1
• VRRBIKYSOLXFRE-UHFFFAOYSA-N n-(2-methoxyethyl)-3-[1-(1-methoxypropan-2-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-6-propan-2-ylpyridin-2-amine Chemical compound COCCNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)COC)C=C2C VRRBIKYSOLXFRE-UHFFFAOYSA-N 0.000 claims 1
• WMTDJOKBWYIVFH-KRWDZBQOSA-N n-cyclopropyl-3-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-6-propan-2-ylpyridin-2-amine Chemical compound CC=1C=C2N([C@@H](C)COC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC1CC1 WMTDJOKBWYIVFH-KRWDZBQOSA-N 0.000 claims 1
• GVSXJLYHRYMJNY-KRWDZBQOSA-N n-ethyl-3-[1-[(2r)-1-fluoro-3-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](CF)COC)C=C2C GVSXJLYHRYMJNY-KRWDZBQOSA-N 0.000 claims 1
• VROHHNKNINEJKL-QGZVFWFLSA-N n-ethyl-3-[5-[(2r)-1-methoxybutan-2-yl]-3,7-dimethylpyrrolo[2,3-b]pyrazin-2-yl]-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC=C1C(C(=N1)C)=NC2=C1N([C@H](CC)COC)C=C2C VROHHNKNINEJKL-QGZVFWFLSA-N 0.000 claims 1
• GCSMZSULZUXJCN-INIZCTEOSA-N n-ethyl-3-[6-methoxy-1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrrolo[3,2-b]pyridin-5-yl]-6-propan-2-ylpyridin-2-amine Chemical compound CCNC1=NC(C(C)C)=CC=C1C(C(=C1)OC)=NC2=C1N([C@@H](C)COC)C=C2C GCSMZSULZUXJCN-INIZCTEOSA-N 0.000 claims 1
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
• RTEAKYUCTSARHM-UHFFFAOYSA-N tert-butyl 2-[5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]propanoate Chemical compound COC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N(C(C)C(=O)OC(C)(C)C)C=C2C RTEAKYUCTSARHM-UHFFFAOYSA-N 0.000 claims 1
• 102000005962 receptors Human genes 0.000 abstract description 13
• 108020003175 receptors Proteins 0.000 abstract description 13
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract description 9
• 238000003556 assay Methods 0.000 abstract description 9
• 230000036506 anxiety Effects 0.000 abstract description 6
• 230000004807 localization Effects 0.000 abstract description 5
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 4
• 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 269
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 190
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 117
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• 239000000243 solution Substances 0.000 description 88
• 238000000746 purification Methods 0.000 description 83
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