KR20060088534A - Ｃｒｆ1 수용체 리간드로서의 헤테로아릴 융합된 피리딘,피라진 및 피리미딘 - Google Patents
Ｃｒｆ1 수용체 리간드로서의 헤테로아릴 융합된 피리딘,피라진 및 피리미딘 Download PDFInfo
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- KR20060088534A KR20060088534A KR1020067004564A KR20067004564A KR20060088534A KR 20060088534 A KR20060088534 A KR 20060088534A KR 1020067004564 A KR1020067004564 A KR 1020067004564A KR 20067004564 A KR20067004564 A KR 20067004564A KR 20060088534 A KR20060088534 A KR 20060088534A
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- KR
- South Korea
- Prior art keywords
- pyridin
- alkyl
- pyrrolo
- methoxy
- ethyl
- Prior art date
- 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.)
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 62
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 36
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 108091005471 CRHR1 Proteins 0.000 title abstract description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title abstract description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 title abstract description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 222
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 239000000523 sample Substances 0.000 claims abstract description 22
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 208000035475 disorder Diseases 0.000 claims abstract description 10
- 238000001525 receptor binding assay Methods 0.000 claims abstract description 10
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 8
- 208000030814 Eating disease Diseases 0.000 claims abstract description 7
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 7
- -1 tri-substituted phenyl Chemical group 0.000 claims description 455
- 239000000203 mixture Substances 0.000 claims description 238
- 229910052736 halogen Inorganic materials 0.000 claims description 140
- 150000002367 halogens Chemical class 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 110
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 100
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 97
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
- 150000003839 salts Chemical class 0.000 claims description 86
- 125000001424 substituent group Chemical group 0.000 claims description 83
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 82
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 76
- 150000002431 hydrogen Chemical class 0.000 claims description 71
- 229910052760 oxygen Inorganic materials 0.000 claims description 66
- 150000003462 sulfoxides Chemical class 0.000 claims description 61
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 60
- 229910052717 sulfur Inorganic materials 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 125000004043 oxo group Chemical group O=* 0.000 claims description 45
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 210000004027 cell Anatomy 0.000 claims description 28
- 125000003282 alkyl amino group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 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
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 230000027455 binding Effects 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 17
- 238000000338 in vitro Methods 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 16
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 16
- 239000011436 cob Substances 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 16
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 15
- 238000001514 detection method Methods 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000005843 halogen group Chemical group 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
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 14
- 125000004890 (C1-C6) alkylamino group Chemical group 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
- 238000012360 testing method Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000013068 control sample Substances 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 150000003457 sulfones Chemical class 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl 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
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 238000005553 drilling Methods 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
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
- BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 7
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 6
- 238000003556 assay Methods 0.000 claims description 6
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 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 4
- 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 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
- UZZILCFUGXUHIG-AWEZNQCLSA-N 3-bromo-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(Br)C2=NC=1C1=CC=C(C(C)C)N=C1OC UZZILCFUGXUHIG-AWEZNQCLSA-N 0.000 claims description 3
- 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 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
- 238000005406 washing Methods 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 2
- 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 2
- 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
- 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 2
- 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 2
- 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 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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
- 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 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
- 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 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
- 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
- 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 2
- 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 description 2
- 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 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
- DDOAQOPGSIIJHR-HNNXBMFYSA-N 6-bromo-1-[(2s)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-yl)-3-methylpyrrolo[3,2-b]pyridine Chemical compound BrC=1C=C2N([C@H](COC)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1OC DDOAQOPGSIIJHR-HNNXBMFYSA-N 0.000 claims description 2
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- 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
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- 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
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- 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
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- 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
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- 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
- SLRZBOISAYCZLK-SFHVURJKSA-N 1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethyl-5-(6-propan-2-yl-2-propan-2-yloxypyridin-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=C1OC(C)C SLRZBOISAYCZLK-SFHVURJKSA-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
- LQMIXVMYCWOSMI-HNNXBMFYSA-N 1-[(2s)-1-methoxypropan-2-yl]-6-methyl-5-[2-(methylamino)-6-propan-2-ylpyridin-3-yl]pyrrolo[3,2-b]pyridine-3-carbonitrile Chemical compound CNC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C#N LQMIXVMYCWOSMI-HNNXBMFYSA-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
- 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 1
- NAOAPEWNXZRUJX-UHFFFAOYSA-N 1-[2-(2-fluoroethoxy)ethyl]-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(CCOCCF)C=C2C NAOAPEWNXZRUJX-UHFFFAOYSA-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
- 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
- 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
- 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
- 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 class 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 class 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 class 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
- 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
- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
- KBLJODRRWZCXLM-SFHVURJKSA-N 3-[1-[(2s)-1-ethoxybutan-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](CC)COCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC KBLJODRRWZCXLM-SFHVURJKSA-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
- LLWDZRFGJCISAL-INIZCTEOSA-N 3-[1-[(2s)-1-fluorobutan-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](CF)CC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC LLWDZRFGJCISAL-INIZCTEOSA-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-HXUWFJFHSA-N 3-[3,6-dimethyl-1-[(2r)-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-HXUWFJFHSA-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
- KYCPYYIUPNKMAN-OAHLLOKOSA-N 3-[3-chloro-1-[(2r)-1-methoxybutan-2-yl]-6-methylpyrrolo[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(Cl)C2=NC=1C1=CC=C(C(C)C)N=C1NC KYCPYYIUPNKMAN-OAHLLOKOSA-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
- ZOLDVIDWHMZEAI-QGZVFWFLSA-N 3-[5-[(2r)-1-ethoxybutan-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](CC)COCC)C=C(C)C2=NC=1C1=CC=C(C(C)C)N=C1NC ZOLDVIDWHMZEAI-QGZVFWFLSA-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
- 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
- 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
- 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
- KBWMEXYKKXIFPN-OAHLLOKOSA-N 3-chloro-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=C(Cl)C2=NC=1C1=CC=C(C(C)C)N=C1OC KBWMEXYKKXIFPN-OAHLLOKOSA-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
- KFSKDZXQPPJKNE-HNNXBMFYSA-N 3-chloro-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-methoxypropan-2-yl]-6-methylpyrrolo[3,2-b]pyridine Chemical compound CCC1=NC(C(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2Cl KFSKDZXQPPJKNE-HNNXBMFYSA-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
- 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
- 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
- UFBJCWKEEOUCET-MRXNPFEDSA-N 5-(2-ethoxy-6-ethyl-5-methylsulfonylpyridin-3-yl)-6-ethyl-1-[(2r)-1-methoxypropan-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](C)COC)C=C2C UFBJCWKEEOUCET-MRXNPFEDSA-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
- 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
- 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
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- 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
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- 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
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- 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
- JYQVVBFTFIMJRQ-UHFFFAOYSA-N 5-(3-chloro-7-methyl-5-pentan-3-ylpyrrolo[2,3-b]pyrazin-2-yl)-n,4-diethyl-n-methylpyridin-2-amine Chemical compound ClC=1N=C2N(C(CC)CC)C=C(C)C2=NC=1C1=CN=C(N(C)CC)C=C1CC JYQVVBFTFIMJRQ-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
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- 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
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- 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
- 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
- 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
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- 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
- 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 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
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- 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
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- 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
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- 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
- 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
- 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 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
- 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
- LOYSZMCHLFVUPX-HNNXBMFYSA-N 6-chloro-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2s)-1-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](C)COC)C=C2C LOYSZMCHLFVUPX-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
- DVUPIDFYTZIBRD-GOSISDBHSA-N 6-ethyl-1-[(2r)-1-methoxybutan-2-yl]-5-(2-methoxy-6-propan-2-ylpyridin-3-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=C1OC DVUPIDFYTZIBRD-GOSISDBHSA-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
- 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
- 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
- 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-QGZVFWFLSA-N 6-ethyl-5-(2-ethyl-6-propan-2-ylpyridin-3-yl)-1-[(2r)-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-QGZVFWFLSA-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
- 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
- DOONOYDSPGMBNN-INIZCTEOSA-N 6-ethyl-5-[1-[(2s)-1-methoxypropan-2-yl]-3,6-dimethylpyrrolo[3,2-b]pyridin-5-yl]-n,n-dimethylpyridin-2-amine Chemical compound CCC1=NC(N(C)C)=CC=C1C(C(=C1)C)=NC2=C1N([C@@H](C)COC)C=C2C DOONOYDSPGMBNN-INIZCTEOSA-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
- RKOUCPMGBBKLNK-UHFFFAOYSA-N Auxin A Natural products CCC(C)C1CC(C(C)CC)C(C(O)CC(O)C(O)C(O)=O)=C1 RKOUCPMGBBKLNK-UHFFFAOYSA-N 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
- 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
- XVVCAKGMAVBCNQ-IBGZPJMESA-N [(2s)-2-[5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrrolo[3,2-b]pyridin-1-yl]butyl] n-ethyl-n-(2-methoxyethyl)carbamate Chemical compound CC=1C=C2N([C@H](COC(=O)N(CC)CCOC)CC)C=C(C)C2=NC=1C1=CC=C(OC(F)(F)F)C=C1OC XVVCAKGMAVBCNQ-IBGZPJMESA-N 0.000 claims 1
- MEOZFUYXLCDYGA-UHFFFAOYSA-N azepane-1-carboxylic acid Chemical compound OC(=O)N1CCCCCC1 MEOZFUYXLCDYGA-UHFFFAOYSA-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
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 235000013601 eggs Nutrition 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
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- 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
- 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
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50041403P | 2003-09-05 | 2003-09-05 | |
| US60/500,414 | 2003-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060088534A true KR20060088534A (ko) | 2006-08-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067004564A Withdrawn KR20060088534A (ko) | 2003-09-05 | 2004-09-03 | Ｃｒｆ1 수용체 리간드로서의 헤테로아릴 융합된 피리딘,피라진 및 피리미딘 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US20050113379A1 (https=) |
| EP (1) | EP1680424A2 (https=) |
| JP (1) | JP2007504271A (https=) |
| KR (1) | KR20060088534A (https=) |
| CN (1) | CN1878773A (https=) |
| AP (1) | AP2006003559A0 (https=) |
| AR (1) | AR045582A1 (https=) |
| AU (1) | AU2004270713A1 (https=) |
| BR (1) | BRPI0414087A (https=) |
| CA (1) | CA2537829A1 (https=) |
| CR (1) | CR8274A (https=) |
| EA (1) | EA200600372A1 (https=) |
| EC (1) | ECSP066408A (https=) |
| IL (1) | IL174084A0 (https=) |
| MA (1) | MA28086A1 (https=) |
| NO (1) | NO20061180L (https=) |
| TW (1) | TW200530232A (https=) |
| WO (1) | WO2005023806A2 (https=) |
| ZA (1) | ZA200601978B (https=) |
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| WO2005028480A2 (en) * | 2003-09-03 | 2005-03-31 | Neurogen Corporation | 5-aryl-pyrazolo[4,3-d]pyrimidines, pyridines, and pyrazines and related compounds |
| US8273750B2 (en) | 2005-06-06 | 2012-09-25 | Takeda Pharmaceutical Company Limited | Organic compounds |
| RU2008110941A (ru) * | 2005-08-25 | 2009-09-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | ИНГИБИТОРЫ КИНАЗЫ p38 МАР И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| US8143285B2 (en) | 2005-09-06 | 2012-03-27 | Shionogi & Co., Ltd. | Indolecarboxylic acid derivative having PGD2 receptor antagonistic activity |
| US7405302B2 (en) * | 2005-10-11 | 2008-07-29 | Amira Pharmaceuticals, Inc. | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| CN102775396B (zh) | 2005-11-08 | 2014-10-08 | 沃泰克斯药物股份有限公司 | Atp-结合弹夹转运蛋白的杂环调控剂 |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| EP1961754A4 (en) | 2005-12-15 | 2009-11-11 | Ono Pharmaceutical Co | BICYCLIC HETEROCYCLIC COMPOUND |
| TW200812588A (en) * | 2006-05-15 | 2008-03-16 | Neurogen Corp | CRF1 receptor ligands comprising heteroaryl fused bicycles |
| TWI398252B (zh) | 2006-05-26 | 2013-06-11 | 諾華公司 | 吡咯并嘧啶化合物及其用途 |
| US9006258B2 (en) | 2006-12-05 | 2015-04-14 | Intra-Cellular Therapies, Inc. | Method of treating female sexual dysfunction with a PDE1 inhibitor |
| WO2008076446A1 (en) * | 2006-12-18 | 2008-06-26 | Coleman Peter R | Accelerated opiate dependence detoxification process |
| JP2010513370A (ja) * | 2006-12-19 | 2010-04-30 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾロ［３，４−ｄ］ピリミジンｐ３８ＭＡＰキナーゼインヒビター |
| WO2008083070A1 (en) * | 2006-12-29 | 2008-07-10 | Neurogen Corporation | Crf1 receptor ligands comprising fused bicyclic heteroaryl moieties |
| CN104447716A (zh) | 2007-05-09 | 2015-03-25 | 沃泰克斯药物股份有限公司 | Cftr调节剂 |
| ES2588238T3 (es) * | 2007-12-06 | 2016-10-31 | Intra-Cellular Therapies, Inc. | Derivados de pirazolopirimidin-4,6-diona y su uso como producto farmacéutico |
| MX365732B (es) | 2007-12-07 | 2019-06-12 | Vertex Pharma | Procesos para producir acidos cicloalquilcarboxamido-piridin benzoicos. |
| EP3683218B1 (en) | 2007-12-07 | 2024-09-18 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| NZ720282A (en) | 2008-02-28 | 2017-12-22 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| ES2522346T3 (es) | 2008-08-22 | 2014-11-14 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de CDK |
| MX2011005936A (es) * | 2008-12-06 | 2011-12-16 | Intra Cellular Therapies Inc | Compuestos organicos. |
| AU2009322904A1 (en) | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP5989993B2 (ja) | 2008-12-06 | 2016-09-07 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| KR20110098732A (ko) | 2008-12-06 | 2011-09-01 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| WO2010065147A1 (en) | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| CN102231953A (zh) | 2008-12-06 | 2011-11-02 | 细胞内治疗公司 | 有机化合物 |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US8551996B2 (en) * | 2009-02-20 | 2013-10-08 | Emory University | Compounds, compositions, methods of synthesis, and methods of treatment |
| US9468637B2 (en) | 2009-05-13 | 2016-10-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| UY33227A (es) | 2010-02-19 | 2011-09-30 | Novartis Ag | Compuestos de pirrolopirimidina como inhibidores de la cdk4/6 |
| JP2013523833A (ja) | 2010-04-07 | 2013-06-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | ３−（６−（１−（２，２−ジフルオロベンゾ［ｄ］［１，３］ジオキソール−５−イル）シクロプロパンカルボキサミド）−３−メチルピリジン−２−イル）安息香酸の医薬組成物およびその投与 |
| WO2011153135A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9763948B2 (en) | 2010-05-31 | 2017-09-19 | Intra-Cellular Therapies, Inc. | PDE1 inhibitory compounds and methods |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| RU2013120966A (ru) | 2010-10-08 | 2014-11-20 | Эббви Инк. | ФУРО[3,2-d]ПИРИМИДИНОВЫЕ СОЕДИНЕНИЯ |
| AR086554A1 (es) | 2011-05-27 | 2014-01-08 | Novartis Ag | Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina |
| EP2717877B1 (en) | 2011-06-10 | 2017-11-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| NZ727015A (en) | 2012-01-25 | 2017-12-22 | Vertex Pharma | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
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| RU2153494C2 (ru) * | 1993-10-12 | 2000-07-27 | Дзе Дюпон Мерк Фармасьютикал Компани | 1-n-алкил-n-арилпиримидинамины, способ лечения заболеваний, фармацевтическая композиция |
| US6020492A (en) * | 1995-05-12 | 2000-02-01 | Neurogen Corporation | Deazapurine derivatives; a new class of CRF1 specific ligands |
| JP3964478B2 (ja) * | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
| IL127566A0 (en) * | 1996-08-28 | 1999-10-28 | Pfizer | Substituted 6,5-hetero- bicyclic derivatives |
| JP2002510687A (ja) * | 1998-04-02 | 2002-04-09 | ニューロゲン コーポレイション | アミノアルキル置換ピロロ［２，３−ｂ］ピリジンおよびピロロ［２，３−ｄ］ピリミジン誘導体：ｃｒｆ１レセプタのモジュレータ |
| WO2002000623A2 (en) * | 2000-06-26 | 2002-01-03 | Neurogen Corporation | Aryl fused substituted 4-oxy-pyridines |
| DE10229777A1 (de) * | 2002-07-03 | 2004-01-29 | Bayer Ag | Indolin-Phenylsulfonamid-Derivate |
| EP1620095A4 (en) * | 2003-04-24 | 2009-04-01 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
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- 2004-09-03 KR KR1020067004564A patent/KR20060088534A/ko not_active Withdrawn
- 2004-09-03 EA EA200600372A patent/EA200600372A1/ru unknown
- 2004-09-03 WO PCT/US2004/028899 patent/WO2005023806A2/en not_active Ceased
- 2004-09-03 AU AU2004270713A patent/AU2004270713A1/en not_active Abandoned
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- 2004-09-03 ZA ZA200601978A patent/ZA200601978B/en unknown
- 2004-09-03 BR BRPI0414087-7A patent/BRPI0414087A/pt not_active IP Right Cessation
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- 2004-09-03 AR ARP040103174A patent/AR045582A1/es unknown
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- 2006-03-24 US US11/389,646 patent/US20060199823A1/en not_active Abandoned
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| JP2007504271A (ja) | 2007-03-01 |
| AP2006003559A0 (en) | 2006-04-30 |
| AR045582A1 (es) | 2005-11-02 |
| CR8274A (es) | 2008-06-10 |
| EP1680424A2 (en) | 2006-07-19 |
| TW200530232A (en) | 2005-09-16 |
| ZA200601978B (en) | 2007-05-30 |
| MA28086A1 (fr) | 2006-08-01 |
| AU2004270713A1 (en) | 2005-03-17 |
| WO2005023806A3 (en) | 2005-06-02 |
| CA2537829A1 (en) | 2005-03-17 |
| US20060199823A1 (en) | 2006-09-07 |
| NO20061180L (no) | 2006-03-31 |
| US20050113379A1 (en) | 2005-05-26 |
| ECSP066408A (es) | 2006-09-18 |
| WO2005023806A2 (en) | 2005-03-17 |
| BRPI0414087A (pt) | 2006-10-31 |
| IL174084A0 (en) | 2008-02-09 |
| EA200600372A1 (ru) | 2006-08-25 |
| CN1878773A (zh) | 2006-12-13 |
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