JP2019520415A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019520415A5 JP2019520415A5 JP2019500810A JP2019500810A JP2019520415A5 JP 2019520415 A5 JP2019520415 A5 JP 2019520415A5 JP 2019500810 A JP2019500810 A JP 2019500810A JP 2019500810 A JP2019500810 A JP 2019500810A JP 2019520415 A5 JP2019520415 A5 JP 2019520415A5
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- difluorophenyl
- fluoro
- aminopiperidin
- methylphenyl
- 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.)
- Granted
Links
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 183
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 163
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 229910052801 chlorine Inorganic materials 0.000 claims description 48
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- CUYKNJBYIJFRCU-UHFFFAOYSA-N pyridine-3-amine Natural products NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- CGWOEOXQHIMZEQ-UHFFFAOYSA-N 3-[1-[[4-(2-phenylquinolin-3-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 CGWOEOXQHIMZEQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- XNOGDVQTUUVEKD-DNQXCXABSA-N (3R,4R)-4-amino-1-[6-(3-cyano-2-hydroxyphenyl)-3-(3,5-difluorophenyl)quinolin-4-yl]piperidine-3-carboxylic acid Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C(=O)O XNOGDVQTUUVEKD-DNQXCXABSA-N 0.000 claims description 2
- IOLPVDHOVAVWTN-UHFFFAOYSA-N 1-[2-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-4,6-difluorophenyl]-3-methoxyurea Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)F)F IOLPVDHOVAVWTN-UHFFFAOYSA-N 0.000 claims description 2
- REMZNDYFYZWVDV-UHFFFAOYSA-N 1-[3-(3,5-difluorophenyl)-6-[5-fluoro-4-(oxetan-3-yloxy)pyridin-3-yl]quinolin-4-yl]piperidin-4-amine Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NC=C(C=1OC1COC1)F REMZNDYFYZWVDV-UHFFFAOYSA-N 0.000 claims description 2
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 2
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims description 2
- CAXDTJAYDWXHLK-UHFFFAOYSA-N 2-(methoxyiminomethyl)pyridin-4-amine Chemical compound CON=CC1=NC=CC(=C1)N CAXDTJAYDWXHLK-UHFFFAOYSA-N 0.000 claims description 2
- UZODABKGIQHGPB-UHFFFAOYSA-N 2-[2-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-6-cyanophenoxy]acetic acid Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(OCC(=O)O)C(=CC=C1)C#N)C1=CC(=CC(=C1)F)F UZODABKGIQHGPB-UHFFFAOYSA-N 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- POBRHBKAXUQOGD-UHFFFAOYSA-N 2-cyclopropylpyridin-4-amine Chemical compound NC1=CC=NC(C2CC2)=C1 POBRHBKAXUQOGD-UHFFFAOYSA-N 0.000 claims description 2
- BJQZVISGHDIVCW-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(2-hydroxyethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCCO)C1=CC(=CC(=C1)F)F BJQZVISGHDIVCW-UHFFFAOYSA-N 0.000 claims description 2
- TVSPGTRFDXDRHW-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(2-methoxyethoxymethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOCCOC)C1=CC(=CC(=C1)F)F TVSPGTRFDXDRHW-UHFFFAOYSA-N 0.000 claims description 2
- ULUQRQOMEBQOIC-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(methoxymethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F ULUQRQOMEBQOIC-UHFFFAOYSA-N 0.000 claims description 2
- GHILNKWBALQPDP-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F GHILNKWBALQPDP-UHFFFAOYSA-N 0.000 claims description 2
- MCEDWFWPINMPTJ-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-5-chloro-4-fluoro-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)Cl)O)C1=CC(=CC(=C1)F)F MCEDWFWPINMPTJ-UHFFFAOYSA-N 0.000 claims description 2
- BIEAVTSOLIAZKF-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-[3-fluoro-5-(oxetan-3-yloxy)phenyl]quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OC1COC1)F BIEAVTSOLIAZKF-UHFFFAOYSA-N 0.000 claims description 2
- BDMILXDVJXNJCW-AABVJFSESA-N 3-[4-(4-aminopiperidin-1-yl)-3-[3-fluoro-5-[(E)-methoxyiminomethyl]phenyl]quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)/C=N/OC)F BDMILXDVJXNJCW-AABVJFSESA-N 0.000 claims description 2
- HWLUDPGRVTYPHZ-DNQXCXABSA-N 3-[4-[(3R,4R)-4-amino-3-fluoropiperidin-1-yl]-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)F HWLUDPGRVTYPHZ-DNQXCXABSA-N 0.000 claims description 2
- YZICXZWMZPMDCN-IXCJQBJRSA-N 3-[4-[(3R,4R)-4-amino-3-methoxypiperidin-1-yl]-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(methoxymethoxy)benzonitrile Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)OC YZICXZWMZPMDCN-IXCJQBJRSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- JVSLFJAHSXCAAZ-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO JVSLFJAHSXCAAZ-UHFFFAOYSA-N 0.000 claims description 2
- CVWAYYSYVJGJQN-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NOC Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NOC CVWAYYSYVJGJQN-UHFFFAOYSA-N 0.000 claims description 2
- MIZXKKWBPVKUEJ-UHFFFAOYSA-N ClC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO Chemical compound ClC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO MIZXKKWBPVKUEJ-UHFFFAOYSA-N 0.000 claims description 2
- KPHYYFOYKPKVHA-IXCJQBJRSA-N FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1C[C@H]([C@@H](CC1)N)OC)C=NO Chemical compound FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1C[C@H]([C@@H](CC1)N)OC)C=NO KPHYYFOYKPKVHA-IXCJQBJRSA-N 0.000 claims description 2
- MFXJWJYASCWNOL-UHFFFAOYSA-N FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)OC)F)N1CCC(CC1)N)C=NO Chemical compound FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)OC)F)N1CCC(CC1)N)C=NO MFXJWJYASCWNOL-UHFFFAOYSA-N 0.000 claims description 2
- HZGJPRHVRRPXNX-UHFFFAOYSA-N FC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C=NO Chemical compound FC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C=NO HZGJPRHVRRPXNX-UHFFFAOYSA-N 0.000 claims description 2
- FGDFFXABWRUDRT-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NO FGDFFXABWRUDRT-UHFFFAOYSA-N 0.000 claims description 2
- HTXXHFQRIQBBFV-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NOC Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NOC HTXXHFQRIQBBFV-UHFFFAOYSA-N 0.000 claims description 2
- CHKNAHXXPPNOMM-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=CC(=NC=C1)C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=CC(=NC=C1)C=NO CHKNAHXXPPNOMM-UHFFFAOYSA-N 0.000 claims description 2
- PNMACYYKLZXQKQ-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=NC(=CC=C1)C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=NC(=CC=C1)C=NO PNMACYYKLZXQKQ-UHFFFAOYSA-N 0.000 claims description 2
- UDYYKULSAXUUMU-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=NC=CC=C1C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=NC=CC=C1C=NO UDYYKULSAXUUMU-UHFFFAOYSA-N 0.000 claims description 2
- GPPBICSIGYZNBU-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C(=NC=CC=1)C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C(=NC=CC=1)C=NO GPPBICSIGYZNBU-UHFFFAOYSA-N 0.000 claims description 2
- MBBXCEPWQDWOOT-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NC=C(C=1C=NO)F Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NC=C(C=1C=NO)F MBBXCEPWQDWOOT-UHFFFAOYSA-N 0.000 claims description 2
- NZHHISNTTBAEMW-UHFFFAOYSA-N FC=1C=C(C=C(C=1)OC)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)O)C1=C(C(=CC(=C1O)F)F)F Chemical compound FC=1C=C(C=C(C=1)OC)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)O)C1=C(C(=CC(=C1O)F)F)F NZHHISNTTBAEMW-UHFFFAOYSA-N 0.000 claims description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- RMVYXFMCRFPXKO-KAYWLYCHSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F RMVYXFMCRFPXKO-KAYWLYCHSA-N 0.000 claims description 2
- XAEZHQWQMQRORU-KAYWLYCHSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F XAEZHQWQMQRORU-KAYWLYCHSA-N 0.000 claims description 2
- PWPXWDPYVOSERY-CLJLJLNGSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F PWPXWDPYVOSERY-CLJLJLNGSA-N 0.000 claims description 2
- NTGRHURYMLRHBA-FQLXRVMXSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F NTGRHURYMLRHBA-FQLXRVMXSA-N 0.000 claims description 2
- NFXRBFCVJDQFHL-VSGBNLITSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F NFXRBFCVJDQFHL-VSGBNLITSA-N 0.000 claims description 2
- PLWPZSLWEIZFEY-FQLXRVMXSA-N N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OC)F Chemical compound N1[C@H]2[C@H](OCCC1)CN(CC2)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OC)F PLWPZSLWEIZFEY-FQLXRVMXSA-N 0.000 claims description 2
- GVWRIMYEDZJUHM-UHFFFAOYSA-N NC(C(F)(F)F)C1=C(C=CC=C1F)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N Chemical compound NC(C(F)(F)F)C1=C(C=CC=C1F)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N GVWRIMYEDZJUHM-UHFFFAOYSA-N 0.000 claims description 2
- GZRULTLGLIYHMQ-UHFFFAOYSA-N NC(C(F)(F)F)C=1C=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N Chemical compound NC(C(F)(F)F)C=1C=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N GZRULTLGLIYHMQ-UHFFFAOYSA-N 0.000 claims description 2
- HMEUGRRAZPSSGA-UHFFFAOYSA-N NC1=C(C#N)C=C(C(=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)F)F Chemical compound NC1=C(C#N)C=C(C(=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)F)F HMEUGRRAZPSSGA-UHFFFAOYSA-N 0.000 claims description 2
- KGJZXQIEQPFYQH-UHFFFAOYSA-N NC1=C(C#N)C=CC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N Chemical compound NC1=C(C#N)C=CC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N KGJZXQIEQPFYQH-UHFFFAOYSA-N 0.000 claims description 2
- QZICRXUZHBELLK-UHFFFAOYSA-N NC1=C(C=NC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C#N Chemical compound NC1=C(C=NC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C#N QZICRXUZHBELLK-UHFFFAOYSA-N 0.000 claims description 2
- WCUHUQBRZOYBBV-UHFFFAOYSA-N NC1=C(C=NC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C#N Chemical compound NC1=C(C=NC=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C#N WCUHUQBRZOYBBV-UHFFFAOYSA-N 0.000 claims description 2
- QYIFAMDGSGJUAV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)C#N)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)C#N)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F QYIFAMDGSGJUAV-UHFFFAOYSA-N 0.000 claims description 2
- FJPPLUJSKCDAGM-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)C=NOC)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)C=NOC)O)C1=CC(=CC(=C1)C)F FJPPLUJSKCDAGM-UHFFFAOYSA-N 0.000 claims description 2
- KOWKWGMDRZUMRD-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)C=NOC)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)C=NOC)O)C1=CC(=CC(=C1)F)F KOWKWGMDRZUMRD-UHFFFAOYSA-N 0.000 claims description 2
- YUULCUWFPGCJSN-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)Cl)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)Cl)O)C1=CC(=CC(=C1)F)F YUULCUWFPGCJSN-UHFFFAOYSA-N 0.000 claims description 2
- FABYYJRXXQHPQK-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)N(C)C)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)N(C)C)C1=CC(=CC(=C1)C)F FABYYJRXXQHPQK-UHFFFAOYSA-N 0.000 claims description 2
- QDCPKIFLYLFQFJ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F QDCPKIFLYLFQFJ-UHFFFAOYSA-N 0.000 claims description 2
- UDSFKFLKAYUXGP-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC(C)C)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC(C)C)C1=CC(=CC(=C1)C)F UDSFKFLKAYUXGP-UHFFFAOYSA-N 0.000 claims description 2
- KUUPFEPDXCVNRX-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)OC)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)OC)F KUUPFEPDXCVNRX-UHFFFAOYSA-N 0.000 claims description 2
- PHGVDLAVWUVGMC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOCC(F)(F)F)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOCC(F)(F)F)C1=CC(=CC(=C1)C)F PHGVDLAVWUVGMC-UHFFFAOYSA-N 0.000 claims description 2
- FZKAIJCONXSTCN-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOCC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOCC)C1=CC(=CC(=C1)C)F FZKAIJCONXSTCN-UHFFFAOYSA-N 0.000 claims description 2
- UVHOUEJPMRZZPU-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(COC)=O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(COC)=O)C1=CC(=CC(=C1)C)F UVHOUEJPMRZZPU-UHFFFAOYSA-N 0.000 claims description 2
- UUZYFFIQVIOYKZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NS(=O)(=O)C)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NS(=O)(=O)C)C1=CC(=CC(=C1)F)F UUZYFFIQVIOYKZ-UHFFFAOYSA-N 0.000 claims description 2
- VHGWSGXBJDJMLI-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F VHGWSGXBJDJMLI-UHFFFAOYSA-N 0.000 claims description 2
- WVJTWMQPFJXHQW-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)Br)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)Br)O)C1=CC(=CC(=C1)F)F WVJTWMQPFJXHQW-UHFFFAOYSA-N 0.000 claims description 2
- XMOVCFJVZUSMNZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F XMOVCFJVZUSMNZ-UHFFFAOYSA-N 0.000 claims description 2
- OSGZWGFZYPWFDO-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)N(C)OC)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)N(C)OC)C1=CC(=CC(=C1)F)F OSGZWGFZYPWFDO-UHFFFAOYSA-N 0.000 claims description 2
- OURFVYHDLSAPTE-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)NC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)NC(=O)NC)C1=CC(=CC(=C1)C)F OURFVYHDLSAPTE-UHFFFAOYSA-N 0.000 claims description 2
- HZAYODUPKJUWDH-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)F)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)F)O)C1=CC(=CC(=C1)F)F HZAYODUPKJUWDH-UHFFFAOYSA-N 0.000 claims description 2
- OVGIMQJNJNWDAZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C=NOC)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C=NOC)O)C1=CC(=CC(=C1)C)F OVGIMQJNJNWDAZ-UHFFFAOYSA-N 0.000 claims description 2
- RZVDHYXWKJBVLS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C=NOC)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C=NOC)O)C1=CC(=CC(=C1)F)F RZVDHYXWKJBVLS-UHFFFAOYSA-N 0.000 claims description 2
- VBHOAVNNEVNMLO-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)Cl)NC(=O)NOC)C1=CC(=CC(=C1)OC)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)Cl)NC(=O)NOC)C1=CC(=CC(=C1)OC)F VBHOAVNNEVNMLO-UHFFFAOYSA-N 0.000 claims description 2
- YOWRHRRNHIBJPK-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)Cl)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)Cl)O)C1=CC(=CC(=C1)F)F YOWRHRRNHIBJPK-UHFFFAOYSA-N 0.000 claims description 2
- ONWWIOOVPZJQCZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)N(C)OC)C1=CC(=CC(=C1)C)F ONWWIOOVPZJQCZ-UHFFFAOYSA-N 0.000 claims description 2
- VJFWIONKNGLTOY-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)N1CCC1)C1=CC(=CC(=C1)OC)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)N1CCC1)C1=CC(=CC(=C1)OC)F VJFWIONKNGLTOY-UHFFFAOYSA-N 0.000 claims description 2
- PNTLAAZMRHODQL-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)NOC)C1=CC(=CC(=C1)OC)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)NC(=O)NOC)C1=CC(=CC(=C1)OC)F PNTLAAZMRHODQL-UHFFFAOYSA-N 0.000 claims description 2
- ATNNYMIDYXCRLO-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C=CC(=C1)C#N)NC(=O)NOC)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C=CC(=C1)C#N)NC(=O)NOC)C1=CC(=CC(=C1)F)F ATNNYMIDYXCRLO-UHFFFAOYSA-N 0.000 claims description 2
- ISEVDBBZOFRQNF-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C=CC=C1)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C=CC=C1)O)C1=CC(=CC(=C1)F)F ISEVDBBZOFRQNF-UHFFFAOYSA-N 0.000 claims description 2
- YUXWPHMGHPBPND-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(OCCCC(=O)O)C(=CC=C1)C#N)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(OCCCC(=O)O)C(=CC=C1)C#N)C1=CC(=CC(=C1)F)F YUXWPHMGHPBPND-UHFFFAOYSA-N 0.000 claims description 2
- OWWIDTNDLSRFEC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC(=C(C=C1)O)C=NOC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC(=C(C=C1)O)C=NOC)C1=CC(=CC(=C1)C)F OWWIDTNDLSRFEC-UHFFFAOYSA-N 0.000 claims description 2
- NBVWPRKFADZWPB-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)C1=CC(=CC(=C1)C)F NBVWPRKFADZWPB-UHFFFAOYSA-N 0.000 claims description 2
- ROWRCTDRFOTHRH-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC=C(C=C1)NC(=O)NOC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC=C(C=C1)NC(=O)NOC)C1=CC(=CC(=C1)C)F ROWRCTDRFOTHRH-UHFFFAOYSA-N 0.000 claims description 2
- NYDNSRSLDMWKHR-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC=CC=2NC(NC=21)=O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=CC=CC=2NC(NC=21)=O)C1=CC(=CC(=C1)C)F NYDNSRSLDMWKHR-UHFFFAOYSA-N 0.000 claims description 2
- LWCRNGJOCNNTBZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=NC=CC(=C1N)C)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=NC=CC(=C1N)C)C1=CC(=CC(=C1)F)F LWCRNGJOCNNTBZ-UHFFFAOYSA-N 0.000 claims description 2
- FXNUUWBVEDWRMF-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F FXNUUWBVEDWRMF-UHFFFAOYSA-N 0.000 claims description 2
- VTTDYXLYODLROC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F VTTDYXLYODLROC-UHFFFAOYSA-N 0.000 claims description 2
- QBOKDKUUYQEZHE-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)OCOC)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)OCOC)C1=CC(=CC(=C1)F)F QBOKDKUUYQEZHE-UHFFFAOYSA-N 0.000 claims description 2
- CCEBLPSPBUMPHF-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F CCEBLPSPBUMPHF-UHFFFAOYSA-N 0.000 claims description 2
- KDUIYRMRJLHYPN-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F KDUIYRMRJLHYPN-UHFFFAOYSA-N 0.000 claims description 2
- NXAQRJKBVKXKGB-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)C=NO)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)C=NO)C1=CC(=CC(=C1)F)F NXAQRJKBVKXKGB-UHFFFAOYSA-N 0.000 claims description 2
- UJWVFOZDAGJLCH-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F UJWVFOZDAGJLCH-UHFFFAOYSA-N 0.000 claims description 2
- KLUOSXWSOBXPMG-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)C=NOCC Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)C=NOCC KLUOSXWSOBXPMG-UHFFFAOYSA-N 0.000 claims description 2
- MCWAEGHHRBXEQQ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OCCOC)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OCCOC)F MCWAEGHHRBXEQQ-UHFFFAOYSA-N 0.000 claims description 2
- NVCDBFBSPPOGQC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OC1COC1)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OC1COC1)C1=CC(=CC(=C1)F)F NVCDBFBSPPOGQC-UHFFFAOYSA-N 0.000 claims description 2
- AIBSABJXCQJHGM-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCC#N)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCC#N)C1=CC(=CC(=C1)F)F AIBSABJXCQJHGM-UHFFFAOYSA-N 0.000 claims description 2
- XXVBCHGKMBJSCV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCCOC)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCCOC)C1=CC(=CC(=C1)F)F XXVBCHGKMBJSCV-UHFFFAOYSA-N 0.000 claims description 2
- PSMDEOQGNGJXKY-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC(=CC=1)C)NC(=O)NOC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC(=CC=1)C)NC(=O)NOC)C1=CC(=CC(=C1)C)F PSMDEOQGNGJXKY-UHFFFAOYSA-N 0.000 claims description 2
- PLDNNRMJIRJYBL-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC=C(C=1)F)N)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC=C(C=1)F)N)C1=CC(=CC(=C1)C)F PLDNNRMJIRJYBL-UHFFFAOYSA-N 0.000 claims description 2
- SLHVTRGUCKEPAQ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC=C(C=1)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=NC=C(C=1)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F SLHVTRGUCKEPAQ-UHFFFAOYSA-N 0.000 claims description 2
- XZPVJOHSMQBKNV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C#N)C=CC=1)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C#N)C=CC=1)C1=CC(=CC(=C1)F)F XZPVJOHSMQBKNV-UHFFFAOYSA-N 0.000 claims description 2
- PXOGPHTVWQPIJS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)Cl)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)Cl)C1=CC(=CC(=C1)F)F PXOGPHTVWQPIJS-UHFFFAOYSA-N 0.000 claims description 2
- RJSXUDOXZZKYJT-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=CC2=C(NC(O2)=O)C=1)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=CC2=C(NC(O2)=O)C=1)C1=CC(=CC(=C1)F)F RJSXUDOXZZKYJT-UHFFFAOYSA-N 0.000 claims description 2
- HYFCLKRPHBGGBS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1N)Cl)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1N)Cl)C1=CC(=CC(=C1)C)F HYFCLKRPHBGGBS-UHFFFAOYSA-N 0.000 claims description 2
- QURDLRNMRFOOAA-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1N)F)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1N)F)C1=CC(=CC(=C1)C)F QURDLRNMRFOOAA-UHFFFAOYSA-N 0.000 claims description 2
- CLGPMUVHORFLFO-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)Cl)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)Cl)C1=CC(=CC(=C1)C)F CLGPMUVHORFLFO-UHFFFAOYSA-N 0.000 claims description 2
- XRLKSACYNSIOII-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)F)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)F)C1=CC(=CC(=C1)C)F XRLKSACYNSIOII-UHFFFAOYSA-N 0.000 claims description 2
- FGPJSARFAKGWAB-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=NC=C(C=1NC(=O)NOC)O)C1=CC(=CC(=C1)F)F FGPJSARFAKGWAB-UHFFFAOYSA-N 0.000 claims description 2
- AFRIMWUNASDEED-AHKZPQOWSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F)OC Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F)OC AFRIMWUNASDEED-AHKZPQOWSA-N 0.000 claims description 2
- PFOVWEACIOSCHZ-UKILVPOCSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F)O Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F)O PFOVWEACIOSCHZ-UKILVPOCSA-N 0.000 claims description 2
- DKMATUOOXFBVHA-UKILVPOCSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)O Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)O DKMATUOOXFBVHA-UKILVPOCSA-N 0.000 claims description 2
- IBYBYCAQCXHPOP-AZGAKELHSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC IBYBYCAQCXHPOP-AZGAKELHSA-N 0.000 claims description 2
- UUOZCXLCNXSLJZ-AHKZPQOWSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCO Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCO UUOZCXLCNXSLJZ-AHKZPQOWSA-N 0.000 claims description 2
- UBACKYQMNWHVII-XTEPFMGCSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCOC Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCOC UBACKYQMNWHVII-XTEPFMGCSA-N 0.000 claims description 2
- YIELGQHBQYVXNO-AHKZPQOWSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)O Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)O YIELGQHBQYVXNO-AHKZPQOWSA-N 0.000 claims description 2
- YZICXZWMZPMDCN-XTEPFMGCSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)OC YZICXZWMZPMDCN-XTEPFMGCSA-N 0.000 claims description 2
- AFRIMWUNASDEED-XNMGPUDCSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)C)F)OC AFRIMWUNASDEED-XNMGPUDCSA-N 0.000 claims description 2
- OEZFVIONUOMRME-AOYPEHQESA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)C)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)C)F)OC OEZFVIONUOMRME-AOYPEHQESA-N 0.000 claims description 2
- XUYQVKKAEHFLCU-ILBGXUMGSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1C)F)F)O)C1=CC(=CC(=C1)F)F)OC XUYQVKKAEHFLCU-ILBGXUMGSA-N 0.000 claims description 2
- LPQQVXSXBOFVBE-NTKDMRAZSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)O)C1=CC(=CC(=C1)C)F)C#N Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)O)C1=CC(=CC(=C1)C)F)C#N LPQQVXSXBOFVBE-NTKDMRAZSA-N 0.000 claims description 2
- YAMMCIMBNROCJX-UZUQRXQVSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)O)C1=CC(=CC(=C1)F)F)C#N Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)C#N)O)C1=CC(=CC(=C1)F)F)C#N YAMMCIMBNROCJX-UZUQRXQVSA-N 0.000 claims description 2
- QSLJMDIPVBJOKF-KBMIEXCESA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C#N Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C#N QSLJMDIPVBJOKF-KBMIEXCESA-N 0.000 claims description 2
- VSGPMJJJJMBFHQ-CLJLJLNGSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C(=O)N(C)C Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C(=O)N(C)C VSGPMJJJJMBFHQ-CLJLJLNGSA-N 0.000 claims description 2
- NJWRVWHZODPSPX-ILBGXUMGSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)C)F)OC NJWRVWHZODPSPX-ILBGXUMGSA-N 0.000 claims description 2
- INZKRZVGHQVZLV-ISKFKSNPSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)F)F)OC INZKRZVGHQVZLV-ISKFKSNPSA-N 0.000 claims description 2
- UUOZCXLCNXSLJZ-XNMGPUDCSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCO Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCO UUOZCXLCNXSLJZ-XNMGPUDCSA-N 0.000 claims description 2
- UBACKYQMNWHVII-IXCJQBJRSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCOC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OCCOC UBACKYQMNWHVII-IXCJQBJRSA-N 0.000 claims description 2
- RXLMOBGRSJQZJL-XNMGPUDCSA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C#N)C=CC=1)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C#N)C=CC=1)C1=CC(=CC(=C1)F)F)OC RXLMOBGRSJQZJL-XNMGPUDCSA-N 0.000 claims description 2
- IBYBYCAQCXHPOP-RSXGOPAZSA-N N[C@H]1[C@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@H]1[C@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC IBYBYCAQCXHPOP-RSXGOPAZSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- WUEQCIURKDKGHS-UHFFFAOYSA-N [2-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-6-cyanophenyl]methyl hydrogen carbonate Chemical compound C1CN(CCC1N)C2=C3C=C(C=CC3=NC=C2C4=CC(=CC(=C4)F)F)C5=CC=CC(=C5COC(=O)O)C#N WUEQCIURKDKGHS-UHFFFAOYSA-N 0.000 claims description 2
- HFAPRDSBZBOSLL-UHFFFAOYSA-N [3-[4-(4-aminopiperidin-1-yl)-3-(3-fluoro-5-methylphenyl)quinolin-6-yl]-2-hydroxyphenyl]-(azetidin-1-yl)methanone Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C(=O)N1CCC1)O)C1=CC(=CC(=C1)C)F HFAPRDSBZBOSLL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 17
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 8
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 4
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 201000011519 neuroendocrine tumor Diseases 0.000 claims 3
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 206010000599 Acromegaly Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000006187 pill Substances 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000003826 tablet Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- FGQWTMXGXZGRIT-UHFFFAOYSA-N 3-[3-(3-chloro-5-methylphenyl)-4-(1,7-diazaspiro[3.5]nonan-7-yl)cinnolin-6-yl]-5-fluorobenzamide Chemical compound ClC=1C=C(C=C(C=1)C)C=1N=NC2=CC=C(C=C2C=1N1CCC2(CCN2)CC1)C=1C=C(C(=O)N)C=C(C=1)F FGQWTMXGXZGRIT-UHFFFAOYSA-N 0.000 claims 1
- CNOYYMCCIYRPBZ-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-7-chloro-3-(3-fluoro-5-methylphenyl)cinnolin-6-yl]-5-fluorobenzamide Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F CNOYYMCCIYRPBZ-UHFFFAOYSA-N 0.000 claims 1
- ZGNBKACVBVCKDF-UHFFFAOYSA-N 3-[7-chloro-4-[4-(2-fluoroethylamino)piperidin-1-yl]-3-(3-fluoro-5-methylphenyl)cinnolin-6-yl]-5-fluorobenzamide Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)NCCF)C=1C=C(C(=O)N)C=C(C=1)F ZGNBKACVBVCKDF-UHFFFAOYSA-N 0.000 claims 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
- ALACVHMKHWHUTF-UHFFFAOYSA-N ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NC1COC1)C=1C(=C(C#N)C=C(C=1)F)O Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NC1COC1)C=1C(=C(C#N)C=C(C=1)F)O ALACVHMKHWHUTF-UHFFFAOYSA-N 0.000 claims 1
- YGLZMTRUQDJDEL-UHFFFAOYSA-N ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NC1COC1)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NC1COC1)C=1C=C(C(=O)N)C=C(C=1)F YGLZMTRUQDJDEL-UHFFFAOYSA-N 0.000 claims 1
- NIMMLYNFZKISET-UHFFFAOYSA-N ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCC(F)(F)F)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCC(F)(F)F)C=1C=C(C(=O)N)C=C(C=1)F NIMMLYNFZKISET-UHFFFAOYSA-N 0.000 claims 1
- SJRNYDCUBLQHSI-UHFFFAOYSA-N ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCF)C=1C(=C(C#N)C=C(C=1)F)O Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCF)C=1C(=C(C#N)C=C(C=1)F)O SJRNYDCUBLQHSI-UHFFFAOYSA-N 0.000 claims 1
- NZBMPMYMMZGGCM-UHFFFAOYSA-N ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCF)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound ClC1=C(C=C2C(=C(N=NC2=C1)C1=CC(=CC(=C1)C)Cl)N1CCC(CC1)NCCF)C=1C=C(C(=O)N)C=C(C=1)F NZBMPMYMMZGGCM-UHFFFAOYSA-N 0.000 claims 1
- BGNVDMZQASUIMJ-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)C)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NC1COC1)C=1C(=C(C#N)C=C(C=1)F)O Chemical compound ClC=1C=C(C=C(C=1)C)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NC1COC1)C=1C(=C(C#N)C=C(C=1)F)O BGNVDMZQASUIMJ-UHFFFAOYSA-N 0.000 claims 1
- HAVAMOMVLXTVFK-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)Cl)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NCCC(F)(F)F)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NCCC(F)(F)F)C=1C=C(C(=O)N)C=C(C=1)F HAVAMOMVLXTVFK-UHFFFAOYSA-N 0.000 claims 1
- NJKJDEGQPULFPH-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)Cl)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NCCF)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1N=NC2=CC=C(C=C2C=1N1CCC(CC1)NCCF)C=1C=C(C(=O)N)C=C(C=1)F NJKJDEGQPULFPH-UHFFFAOYSA-N 0.000 claims 1
- XULLNXLNOUNEPX-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NN(C=1C=NO)C Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NN(C=1C=NO)C XULLNXLNOUNEPX-UHFFFAOYSA-N 0.000 claims 1
- LEMAQGHXEOWTLZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)Cl)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1F)F)Cl)O)C1=CC(=CC(=C1)F)F LEMAQGHXEOWTLZ-UHFFFAOYSA-N 0.000 claims 1
- KNYGRSPZRRYACK-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=C(C=CC(=N1)C(=O)N)Cl)Cl)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=C(C=CC(=N1)C(=O)N)Cl)Cl)C1=CC(=CC(=C1)C)Cl KNYGRSPZRRYACK-UHFFFAOYSA-N 0.000 claims 1
- CHZABTMBLGNBAQ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)Cl)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)Cl)C1=CC(=CC(=C1)C)F CHZABTMBLGNBAQ-UHFFFAOYSA-N 0.000 claims 1
- ZPRAZTFNYOIBHS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=CC=CC=2NC(NC=21)=O)Cl)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C1=CC=CC=2NC(NC=21)=O)Cl)C1=CC(=CC(=C1)C)F ZPRAZTFNYOIBHS-UHFFFAOYSA-N 0.000 claims 1
- AAZMUNJKDDWXAV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)Cl)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)Cl)C1=CC(=CC(=C1)C)Cl AAZMUNJKDDWXAV-UHFFFAOYSA-N 0.000 claims 1
- QYWVXQOEHUNGIL-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)Cl)C1=CC(=CC(=C1)Cl)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)Cl)C1=CC(=CC(=C1)Cl)Cl QYWVXQOEHUNGIL-UHFFFAOYSA-N 0.000 claims 1
- GQPUXILMXGVYSV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)C)C Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)C)C GQPUXILMXGVYSV-UHFFFAOYSA-N 0.000 claims 1
- GSBUXLRRNGYKSQ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)C)F GSBUXLRRNGYKSQ-UHFFFAOYSA-N 0.000 claims 1
- PHKGCUAEGBKZOL-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)Cl)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C(=C(C#N)C=CC=1)O)Cl)C1=CC(=CC(=C1)Cl)Cl PHKGCUAEGBKZOL-UHFFFAOYSA-N 0.000 claims 1
- PJUFPGMBNQIKRC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)C Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)C PJUFPGMBNQIKRC-UHFFFAOYSA-N 0.000 claims 1
- LQVXFOTVJDCZOJ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)O)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=C(C(=CC=C1)F)O)C1=CC(=CC(=C1)C)Cl LQVXFOTVJDCZOJ-UHFFFAOYSA-N 0.000 claims 1
- UUWOHFAGTKVFQV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=C(C(=CC=C1C)F)O)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=C(C(=CC=C1C)F)O)C1=CC(=CC(=C1)C)Cl UUWOHFAGTKVFQV-UHFFFAOYSA-N 0.000 claims 1
- YCXIGIIQWRCOCC-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC(=CC(=C1)C)F)C=1C=C(C(=O)N)C=C(C=1)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC(=CC(=C1)C)F)C=1C=C(C(=O)N)C=C(C=1)F YCXIGIIQWRCOCC-UHFFFAOYSA-N 0.000 claims 1
- XKIFBHKRAQQLPA-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC(=CC=2NC(NC=21)=O)F)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC(=CC=2NC(NC=21)=O)F)C1=CC(=CC(=C1)C)Cl XKIFBHKRAQQLPA-UHFFFAOYSA-N 0.000 claims 1
- HXEGYXRNASKDCI-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C1=CC2=C(NC(N2)=O)C=C1)C1=CC(=CC(=C1)C)F HXEGYXRNASKDCI-UHFFFAOYSA-N 0.000 claims 1
- IYBHGCSXAVHYTA-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl IYBHGCSXAVHYTA-UHFFFAOYSA-N 0.000 claims 1
- ZFYDJWDTNUHEFN-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)Cl ZFYDJWDTNUHEFN-UHFFFAOYSA-N 0.000 claims 1
- LTDFTLJNJPMLKV-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)C)F LTDFTLJNJPMLKV-UHFFFAOYSA-N 0.000 claims 1
- BWDCXWIYMHWELZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)Cl)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)Cl)Cl BWDCXWIYMHWELZ-UHFFFAOYSA-N 0.000 claims 1
- UMVLNEQYMKONGS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)Cl UMVLNEQYMKONGS-UHFFFAOYSA-N 0.000 claims 1
- XHBCXJJBTDBOGD-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F XHBCXJJBTDBOGD-UHFFFAOYSA-N 0.000 claims 1
- NLENDTJLNUYNQO-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)C)F NLENDTJLNUYNQO-UHFFFAOYSA-N 0.000 claims 1
- QUTWYCQBGHFAAZ-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)Cl)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)Cl)Cl QUTWYCQBGHFAAZ-UHFFFAOYSA-N 0.000 claims 1
- QBDNMAMLIGQNKI-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)F)F QBDNMAMLIGQNKI-UHFFFAOYSA-N 0.000 claims 1
- OPXWTTHAVVESPS-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)F)C1=CC(=CC(=C1)C)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)F)C1=CC(=CC(=C1)C)Cl OPXWTTHAVVESPS-UHFFFAOYSA-N 0.000 claims 1
- DKGCRILBHPUOAX-UHFFFAOYSA-N NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)F)C1=CC(=CC(=C1)Cl)Cl Chemical compound NC1CCN(CC1)C1=C(N=NC2=CC=C(C=C12)C=1C=C(C2=C(NC(N2)=O)C=1)F)C1=CC(=CC(=C1)Cl)Cl DKGCRILBHPUOAX-UHFFFAOYSA-N 0.000 claims 1
- SUORKXNHYRILNZ-LADGPHEKSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)OC)F)O Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)F)O)C1=CC(=CC(=C1)OC)F)O SUORKXNHYRILNZ-LADGPHEKSA-N 0.000 claims 1
- PLBLUUNFOQMYEL-PKTZIBPZSA-N N[C@@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)F Chemical compound N[C@@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)F PLBLUUNFOQMYEL-PKTZIBPZSA-N 0.000 claims 1
- UUKZHMCFRRKIIM-DHIUTWEWSA-N N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)Cl)F Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)Cl)F UUKZHMCFRRKIIM-DHIUTWEWSA-N 0.000 claims 1
- PLBLUUNFOQMYEL-DHIUTWEWSA-N N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)F Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)F PLBLUUNFOQMYEL-DHIUTWEWSA-N 0.000 claims 1
- QDGGGHQHWKTAPK-ISKFKSNPSA-N N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)O Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)O QDGGGHQHWKTAPK-ISKFKSNPSA-N 0.000 claims 1
- FNWZCOVESZYGGO-ILBGXUMGSA-N N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(N=NC2=CC(=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)Cl)C1=CC(=CC(=C1)C)F)OC FNWZCOVESZYGGO-ILBGXUMGSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108050001286 Somatostatin Receptor Proteins 0.000 claims 1
- 102000011096 Somatostatin receptor Human genes 0.000 claims 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- MKXRJLGWTAYJKG-UHFFFAOYSA-N NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl Chemical compound NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl MKXRJLGWTAYJKG-UHFFFAOYSA-N 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- KVTUSMPNLUCCQO-UHFFFAOYSA-N 3,3-difluoropyrrolidine Chemical compound FC1(F)CCNC1 KVTUSMPNLUCCQO-UHFFFAOYSA-N 0.000 description 1
- VLKATFUFQAOXTR-UHFFFAOYSA-N 3-[3-(3-fluoro-5-methylphenyl)-4-(3-morpholin-3-ylazetidin-1-yl)quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound FC=1C=C(C=C(C=1)C)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)C1NCCOC1)C=1C(=C(C#N)C=CC=1)O VLKATFUFQAOXTR-UHFFFAOYSA-N 0.000 description 1
- RXYSZCNRMWNYGP-UHFFFAOYSA-N 3-[4-[3-(ethylaminomethyl)azetidin-1-yl]-3-(3-fluoro-5-methylphenyl)quinolin-6-yl]-5-fluoro-2-hydroxybenzonitrile Chemical compound C(C)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F RXYSZCNRMWNYGP-UHFFFAOYSA-N 0.000 description 1
- JCJPLTPHWLWKAS-SANMLTNESA-N 3-[4-[3-[(1S)-1-aminopropyl]azetidin-1-yl]-3-(3-fluoro-5-methylphenyl)quinolin-6-yl]-5-fluoro-2-hydroxybenzonitrile Chemical compound N[C@@H](CC)C1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F JCJPLTPHWLWKAS-SANMLTNESA-N 0.000 description 1
- OBCFLJCEYRGYPB-UHFFFAOYSA-N 3-[4-[3-[(cyclopropylamino)methyl]azetidin-1-yl]-3-(3-fluoro-5-methylphenyl)quinolin-6-yl]-5-fluoro-2-hydroxybenzonitrile Chemical compound C1(CC1)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F OBCFLJCEYRGYPB-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- GTLVBYHXXQDFTH-UHFFFAOYSA-N 5-fluoro-3-[3-(3-fluoro-5-methylphenyl)-4-[3-(pyrrolidin-1-ylmethyl)azetidin-1-yl]quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CN1CCCC1 GTLVBYHXXQDFTH-UHFFFAOYSA-N 0.000 description 1
- NRCQCFPRTOOWBQ-UHFFFAOYSA-N C(C)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1C)F)O)C1=CC(=CC(=C1)C)F Chemical compound C(C)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1C)F)O)C1=CC(=CC(=C1)C)F NRCQCFPRTOOWBQ-UHFFFAOYSA-N 0.000 description 1
- XDEOYCMFNQAYIA-UHFFFAOYSA-N C(C)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)C)F Chemical compound C(C)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C(=O)N)C=C(C=1)F)C1=CC(=CC(=C1)C)F XDEOYCMFNQAYIA-UHFFFAOYSA-N 0.000 description 1
- PHBJJRGPJKGNFS-UHFFFAOYSA-N C1(CCCC1)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F Chemical compound C1(CCCC1)NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F PHBJJRGPJKGNFS-UHFFFAOYSA-N 0.000 description 1
- LQQAGKUKYRVPHN-UHFFFAOYSA-N ClC=1C=C(C=C(C=1)Cl)C=1C=NC2=CC=CC=C2C=1N1CCC(CC1)N Chemical compound ClC=1C=C(C=C(C=1)Cl)C=1C=NC2=CC=CC=C2C=1N1CCC(CC1)N LQQAGKUKYRVPHN-UHFFFAOYSA-N 0.000 description 1
- QBRVSWBIJSYAKQ-UHFFFAOYSA-N FC1=C(C(=CC(=C1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC)F)O Chemical compound FC1=C(C(=CC(=C1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC)F)O QBRVSWBIJSYAKQ-UHFFFAOYSA-N 0.000 description 1
- KTJPCMIVPPTHDM-UHFFFAOYSA-N FC1=CC(=CC=2NC(NC=21)=O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC Chemical compound FC1=CC(=CC=2NC(NC=21)=O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC KTJPCMIVPPTHDM-UHFFFAOYSA-N 0.000 description 1
- SLMATAOCEFFAGE-UHFFFAOYSA-N FC=1C(=C(C(=CC=1)F)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC Chemical compound FC=1C(=C(C(=CC=1)F)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCCC SLMATAOCEFFAGE-UHFFFAOYSA-N 0.000 description 1
- GHWGOICYUMYXHB-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CN1CCCCC1 Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CN1CCCCC1 GHWGOICYUMYXHB-UHFFFAOYSA-N 0.000 description 1
- BQDHMKOCECZKIO-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CN1CCOCC1 Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CN1CCOCC1 BQDHMKOCECZKIO-UHFFFAOYSA-N 0.000 description 1
- BOWPBFRXLCDQON-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC(CO)CC Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC(CO)CC BOWPBFRXLCDQON-UHFFFAOYSA-N 0.000 description 1
- VOFRSXHIVZYFET-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC(COC)(C)C Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC(COC)(C)C VOFRSXHIVZYFET-UHFFFAOYSA-N 0.000 description 1
- SPOQQFXMJMDGAG-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1CCOCC1 Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1CCOCC1 SPOQQFXMJMDGAG-UHFFFAOYSA-N 0.000 description 1
- HHJJRUJUKRDIPS-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1COC1 Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1COC1 HHJJRUJUKRDIPS-UHFFFAOYSA-N 0.000 description 1
- YHKVOWYOQJLGLH-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1COCC1 Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNC1COCC1 YHKVOWYOQJLGLH-UHFFFAOYSA-N 0.000 description 1
- VKWUVAMOEIZEKU-UHFFFAOYSA-N FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCC(C)(C)O Chemical compound FC=1C=C(C(=C(C#N)C=1)O)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)CNCC(C)(C)O VKWUVAMOEIZEKU-UHFFFAOYSA-N 0.000 description 1
- OUFRCKUPEIKKBF-UHFFFAOYSA-N FC=1C=C(C=C(C=1)C)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)CN1CCNCC1)C=1C(=C(C#N)C=C(C=1)F)O Chemical compound FC=1C=C(C=C(C=1)C)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)CN1CCNCC1)C=1C(=C(C#N)C=C(C=1)F)O OUFRCKUPEIKKBF-UHFFFAOYSA-N 0.000 description 1
- XABQHQXZCGUCRN-UHFFFAOYSA-N FC=1C=C(C=C(C=1)C)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)CNCCOC)C=1C(=C(C#N)C=C(C=1)F)O Chemical compound FC=1C=C(C=C(C=1)C)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)CNCCOC)C=1C(=C(C#N)C=C(C=1)F)O XABQHQXZCGUCRN-UHFFFAOYSA-N 0.000 description 1
- OAFYIJMNLCKYFV-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)C1NCCOC1)C=1C(=C(C#N)C=CC=1)O Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CC(C1)C1NCCOC1)C=1C(=C(C#N)C=CC=1)O OAFYIJMNLCKYFV-UHFFFAOYSA-N 0.000 description 1
- NMNRXJWAURUMJP-UHFFFAOYSA-N NC1=NN(C=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C Chemical compound NC1=NN(C=C1C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C NMNRXJWAURUMJP-UHFFFAOYSA-N 0.000 description 1
- FBDPZFWUBLDUKU-XJECJHNESA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)/C=N/OC)C1=CC(=CC(=C1)F)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)/C=N/OC)C1=CC(=CC(=C1)F)F FBDPZFWUBLDUKU-XJECJHNESA-N 0.000 description 1
- DTEOEMVXUDJKQN-UHFFFAOYSA-N NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C=NC=1NCCOC)C#N)C1=CC(=CC(=C1)C)F Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C=C(C=NC=1NCCOC)C#N)C1=CC(=CC(=C1)C)F DTEOEMVXUDJKQN-UHFFFAOYSA-N 0.000 description 1
- UGYHPTQTLFGQCP-UHFFFAOYSA-N NC=1C(=NC=CC=1C#N)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)C1NCCOC1 Chemical compound NC=1C(=NC=CC=1C#N)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CC(C1)C1NCCOC1 UGYHPTQTLFGQCP-UHFFFAOYSA-N 0.000 description 1
- YVLVAKDNLVTXCT-UHFFFAOYSA-N NCC1(CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl)C Chemical compound NCC1(CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)Cl)C YVLVAKDNLVTXCT-UHFFFAOYSA-N 0.000 description 1
- KMHVHJYSRLJPOV-UHFFFAOYSA-N NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F Chemical compound NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)C)F KMHVHJYSRLJPOV-UHFFFAOYSA-N 0.000 description 1
- ZLRMLKDAKYCWIU-UHFFFAOYSA-N NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)Cl Chemical compound NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)Cl ZLRMLKDAKYCWIU-UHFFFAOYSA-N 0.000 description 1
- UVOZBAMWEOSEJA-UHFFFAOYSA-N NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F Chemical compound NCC1CN(C1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1)F)O)C1=CC(=CC(=C1)F)F UVOZBAMWEOSEJA-UHFFFAOYSA-N 0.000 description 1
- IBYBYCAQCXHPOP-AOYPEHQESA-N N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)OC IBYBYCAQCXHPOP-AOYPEHQESA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021173304A JP2022028675A (ja) | 2016-07-14 | 2021-10-22 | ソマトスタチンモジュレーターとその使用 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662362493P | 2016-07-14 | 2016-07-14 | |
| US62/362,493 | 2016-07-14 | ||
| US201662411338P | 2016-10-21 | 2016-10-21 | |
| US62/411,338 | 2016-10-21 | ||
| PCT/US2017/041694 WO2018013676A1 (en) | 2016-07-14 | 2017-07-12 | Somatostatin modulators and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021173304A Division JP2022028675A (ja) | 2016-07-14 | 2021-10-22 | ソマトスタチンモジュレーターとその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019520415A JP2019520415A (ja) | 2019-07-18 |
| JP2019520415A5 true JP2019520415A5 (enExample) | 2021-09-30 |
| JP6967577B2 JP6967577B2 (ja) | 2021-11-17 |
Family
ID=60941935
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019500810A Active JP6967577B2 (ja) | 2016-07-14 | 2017-07-12 | ソマトスタチンモジュレーターとその使用 |
| JP2021173304A Ceased JP2022028675A (ja) | 2016-07-14 | 2021-10-22 | ソマトスタチンモジュレーターとその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021173304A Ceased JP2022028675A (ja) | 2016-07-14 | 2021-10-22 | ソマトスタチンモジュレーターとその使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (6) | US9896432B2 (enExample) |
| EP (2) | EP4163276A1 (enExample) |
| JP (2) | JP6967577B2 (enExample) |
| KR (2) | KR102324042B1 (enExample) |
| CN (2) | CN109715612B (enExample) |
| AU (2) | AU2017296392B2 (enExample) |
| CA (1) | CA3030423A1 (enExample) |
| DK (1) | DK3484865T3 (enExample) |
| ES (1) | ES2931472T3 (enExample) |
| HR (1) | HRP20221279T1 (enExample) |
| HU (1) | HUE060182T2 (enExample) |
| IL (1) | IL264178B2 (enExample) |
| LT (1) | LT3484865T (enExample) |
| MX (1) | MX390120B (enExample) |
| NZ (1) | NZ750174A (enExample) |
| PL (1) | PL3484865T3 (enExample) |
| PT (1) | PT3484865T (enExample) |
| RS (1) | RS63776B1 (enExample) |
| SG (1) | SG11201900349VA (enExample) |
| SM (1) | SMT202200465T1 (enExample) |
| TW (1) | TWI789355B (enExample) |
| UA (1) | UA125393C2 (enExample) |
| WO (1) | WO2018013676A1 (enExample) |
| ZA (1) | ZA201900317B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3484865T3 (pl) | 2016-07-14 | 2023-01-09 | Crinetics Pharmaceuticals, Inc. | Modulatory somatostatyny i ich zastosowania |
| WO2018170284A1 (en) | 2017-03-16 | 2018-09-20 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| WO2019023278A1 (en) | 2017-07-25 | 2019-01-31 | Crinetics Pharmaceuticals, Inc. | MODULATORS OF SOMATOSTATIN AND USES THEREOF |
| CA3088658A1 (en) | 2018-01-17 | 2019-07-25 | Crinetics Pharmaceuticals, Inc. | Process of making somatostatin modulators |
| WO2019157458A1 (en) * | 2018-02-12 | 2019-08-15 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3807248A4 (en) * | 2018-05-29 | 2021-10-27 | Council of Scientific and Industrial Research | BICYCLIC TOPOISOMERASE I INHIBITOR COMPOUNDS, THEIR PREPARATION AND USE |
| JP7431813B2 (ja) | 2018-09-18 | 2024-02-15 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターとその使用 |
| JP2022540922A (ja) * | 2019-07-17 | 2022-09-20 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターの結晶形態 |
| TWI841768B (zh) * | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
| SMT202500315T1 (it) * | 2020-09-09 | 2025-11-10 | Crinetics Pharmaceuticals Inc | Formulazioni di un modulatore della somatostatina |
| CN117043149A (zh) | 2021-02-17 | 2023-11-10 | 克林提克斯医药股份有限公司 | 促生长素抑制素调节剂的结晶形式 |
| CA3216457A1 (en) * | 2021-05-25 | 2022-12-01 | Ajay Madan | Uses of a somatostatin modulator for the treatment of disease |
| EP4378971A4 (en) | 2021-09-28 | 2024-11-20 | Denka Company Limited | CHLOROPRENE BLOCK COPOLYMER, LATEX, LATEX COMPOSITION AND RUBBER COMPOSITION |
| AU2023207068A1 (en) * | 2022-01-11 | 2024-07-11 | Crinetics Pharmaceuticals, Inc. | Uses of a somatostatin modulator for the treatment of carcinoid syndrome |
| EP4547654A1 (en) | 2022-06-10 | 2025-05-07 | Assia Chemical Industries Ltd. | Solid state forms of paltusotine and process for preparation thereof |
| PE20251882A1 (es) * | 2022-10-28 | 2025-07-22 | Basecamp Bio Inc | Agonistas del receptor de la somatostatina 2 y usos de estos |
| US20240254106A1 (en) | 2022-12-13 | 2024-08-01 | Crinetics Pharmaceuticals, Inc. | Somatostatin subtype-2 receptor (sst2r) targeted therapeutics and uses thereof |
| KR20250162795A (ko) | 2023-03-28 | 2025-11-19 | 크리네틱스 파마슈티칼스, 인크. | 간 기능장애가 있는 환자에게 팔투소틴을 투여하기 위한 조성물 및 방법 |
| WO2025111318A1 (en) * | 2023-11-22 | 2025-05-30 | Crinetics Pharmaceuticals, Inc. | Somatostatin subtype receptor 3 (sstr3) agonists and uses thereof |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1035154A (en) | 1910-05-16 | 1912-08-13 | Ernest G Clark | Machine for rectifying perforated music and masters. |
| FR2802206B1 (fr) | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | Derives de 4-aminopiperidine et leur utilisation en tant que medicament |
| EP1451156A4 (en) | 2001-11-27 | 2005-05-25 | Merck & Co Inc | 4-AMINOCHINOLINVERBINDUNGEN |
| WO2003066055A1 (en) * | 2002-02-04 | 2003-08-14 | F. Hoffmann-La Roche Ag | Quinoline derivatives as npy antagonists |
| US7767817B2 (en) | 2003-09-05 | 2010-08-03 | Binghe Wang | Water soluble boronic acid fluorescent reporter compounds and methods of use thereof |
| EP1773343A4 (en) * | 2004-07-13 | 2009-05-13 | Glaxo Group Ltd | ANTIBACTERIAL AGENTS |
| US20060183763A1 (en) | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| CN101365439B (zh) | 2005-12-05 | 2012-12-26 | 克塞诺波特公司 | 左旋多巴前体药物甲磺酸盐、其组合物及其用途 |
| EP1991540A1 (en) | 2006-02-21 | 2008-11-19 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
| WO2007103554A1 (en) | 2006-03-08 | 2007-09-13 | Amgen Inc. | Quinoline and isoquinoline derivatives as phosphodiesterase 10 inhibitors |
| AU2007309708A1 (en) * | 2006-03-13 | 2008-05-02 | Merck Sharp & Dohme Corp. | Somatostatin agonists |
| MX2011002367A (es) | 2008-09-02 | 2011-04-04 | Novartis Ag | Inhibidores de cinasa biciclicos. |
| GB0818241D0 (en) | 2008-10-06 | 2008-11-12 | Cancer Res Technology | Compounds and their use |
| BR112013002182B8 (pt) * | 2010-07-30 | 2023-02-28 | Oncotherapy Science Inc | Compostos derivados de quinolina, composição farmacêutica, inibidor de melk, agente modulador de expressão de melk, agente antitumor, agente terapêutico e/ou preventivo para uma doença que envolve a superexpressão de melk contendo os mesmos e uso dos referidos compostos |
| AU2012258977A1 (en) | 2011-05-23 | 2014-01-16 | Imago Pharmaceuticals, Inc. | Inhibitors of LRRK2 kinase activity |
| US8871756B2 (en) | 2011-08-11 | 2014-10-28 | Hoffmann-La Roche Inc. | Compounds for the treatment and prophylaxis of Respiratory Syncytial Virus disease |
| DE102011113749A1 (de) | 2011-09-14 | 2013-03-14 | Aicuris Gmbh & Co. Kg | Sulfonsäuresalze Heterocyclylamid-substituiertr Imidazole |
| WO2013050996A2 (en) | 2011-10-05 | 2013-04-11 | Mapi Pharma Ltd. | Process and intermediates for the preparation of substituted 2-arylthiazole carboxylic acids |
| EP2871179A4 (en) * | 2012-07-03 | 2016-03-16 | Ono Pharmaceutical Co | CONNECTION WITH AGONISTIC EFFECT ON THE SOMATOSTATIN RECEPTOR AND ITS USE FOR MEDICAL PURPOSES |
| PE20151203A1 (es) * | 2012-10-16 | 2015-08-31 | Janssen Pharmaceutica Nv | MODULADORES DE QUINOLINILO UNIDOS A FENILO DE ROR-GAMMA-t |
| TWI628175B (zh) | 2013-09-30 | 2018-07-01 | 日商小野藥品工業股份有限公司 | 具有體抑素受體致效活性的化合物及其醫藥用途 |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| CA2943643A1 (en) | 2014-03-24 | 2015-10-01 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| WO2016049568A1 (en) | 2014-09-25 | 2016-03-31 | Araxes Pharma Llc | Methods and compositions for inhibition of ras |
| US9902703B2 (en) | 2015-07-01 | 2018-02-27 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| HK1255034A1 (zh) | 2015-07-01 | 2019-08-02 | Crinetics Pharmaceuticals, Inc. | 生长抑素调节剂及其用途 |
| EP3889145B1 (en) | 2015-12-17 | 2024-02-21 | Merck Patent GmbH | 8-cyano-5-piperidino-quinolines as tlr7/8 antagonists and their uses for treating immune disorders |
| US10597393B2 (en) | 2016-07-07 | 2020-03-24 | Plantex Ltd. | Solid state forms of Palbociclib dimesylate |
| PL3484865T3 (pl) * | 2016-07-14 | 2023-01-09 | Crinetics Pharmaceuticals, Inc. | Modulatory somatostatyny i ich zastosowania |
| CA3088658A1 (en) | 2018-01-17 | 2019-07-25 | Crinetics Pharmaceuticals, Inc. | Process of making somatostatin modulators |
| JP7431813B2 (ja) | 2018-09-18 | 2024-02-15 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターとその使用 |
| JP2022540922A (ja) | 2019-07-17 | 2022-09-20 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターの結晶形態 |
| SMT202500315T1 (it) | 2020-09-09 | 2025-11-10 | Crinetics Pharmaceuticals Inc | Formulazioni di un modulatore della somatostatina |
-
2017
- 2017-07-12 PL PL17828375.0T patent/PL3484865T3/pl unknown
- 2017-07-12 EP EP22194733.6A patent/EP4163276A1/en not_active Withdrawn
- 2017-07-12 CN CN201780056677.9A patent/CN109715612B/zh active Active
- 2017-07-12 HR HRP20221279TT patent/HRP20221279T1/hr unknown
- 2017-07-12 JP JP2019500810A patent/JP6967577B2/ja active Active
- 2017-07-12 LT LTEPPCT/US2017/041694T patent/LT3484865T/lt unknown
- 2017-07-12 RS RS20221103A patent/RS63776B1/sr unknown
- 2017-07-12 WO PCT/US2017/041694 patent/WO2018013676A1/en not_active Ceased
- 2017-07-12 SG SG11201900349VA patent/SG11201900349VA/en unknown
- 2017-07-12 HU HUE17828375A patent/HUE060182T2/hu unknown
- 2017-07-12 IL IL264178A patent/IL264178B2/en unknown
- 2017-07-12 PT PT178283750T patent/PT3484865T/pt unknown
- 2017-07-12 SM SM20220465T patent/SMT202200465T1/it unknown
- 2017-07-12 EP EP17828375.0A patent/EP3484865B1/en active Active
- 2017-07-12 CA CA3030423A patent/CA3030423A1/en active Pending
- 2017-07-12 CN CN202211105259.3A patent/CN115557929A/zh active Pending
- 2017-07-12 US US15/647,758 patent/US9896432B2/en active Active
- 2017-07-12 UA UAA201901274A patent/UA125393C2/uk unknown
- 2017-07-12 ES ES17828375T patent/ES2931472T3/es active Active
- 2017-07-12 DK DK17828375.0T patent/DK3484865T3/da active
- 2017-07-12 KR KR1020197004427A patent/KR102324042B1/ko active Active
- 2017-07-12 MX MX2019000588A patent/MX390120B/es unknown
- 2017-07-12 KR KR1020217035692A patent/KR20210134838A/ko not_active Ceased
- 2017-07-12 AU AU2017296392A patent/AU2017296392B2/en active Active
- 2017-07-12 NZ NZ750174A patent/NZ750174A/en unknown
- 2017-07-14 TW TW106123557A patent/TWI789355B/zh active
- 2017-12-20 US US15/849,409 patent/US10351547B2/en active Active
-
2019
- 2019-01-16 ZA ZA2019/00317A patent/ZA201900317B/en unknown
- 2019-05-08 US US16/407,031 patent/US10597377B2/en active Active
- 2019-12-12 US US16/712,620 patent/US10875839B2/en active Active
-
2020
- 2020-10-26 US US17/080,358 patent/US11414397B2/en active Active
- 2020-11-24 AU AU2020277122A patent/AU2020277122A1/en not_active Abandoned
-
2021
- 2021-10-22 JP JP2021173304A patent/JP2022028675A/ja not_active Ceased
-
2022
- 2022-07-01 US US17/810,497 patent/US20220380337A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019520415A5 (enExample) | ||
| HRP20221279T1 (hr) | Modulatori somatostatina i njihove uporabe | |
| CA2628490A1 (en) | 5-lipoxygenase-activating protein (flap) inhibitors | |
| US9051310B2 (en) | Nicotinamide derivative or salt thereof | |
| KR101825543B1 (ko) | 유기 광전자 소자 및 표시장치 | |
| JP2015502967A5 (enExample) | ||
| EP3392236B1 (en) | Method for producing aromatic amide derivative | |
| EP3041841B1 (en) | Triazolopyridine compounds, compositions and methods of use thereof | |
| US5843973A (en) | Thiazolidinone compounds and composition for angina pectoris comprising the compounds as an active ingredient | |
| JP3058945B2 (ja) | Ｎ−（３，３−ジ置換アクリロイル）ピペラジン誘導体 | |
| JPH0770072A (ja) | チオウレア誘導体 | |
| Das | Generated Tables by BIVNOR | |
| KR20250088869A (ko) | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 | |
| Cee | 3a roAi. 1937-1938 | |
| TW200418858A (en) | Carbapenem derivatives | |
| JPH08217765A (ja) | チアゾリジノン化合物 | |
| JP2006045153A (ja) | カルバペネム誘導体を含有する医薬 | |
| JP2004262923A (ja) | カルバペネム誘導体 |