CA2792234C - 2,3 dihydro-1h-inden-1-yl-2,7-diazaspiro [3.5] nonane derivatives and their use as antagonists or inverse agonists of the ghrelin receptor - Google Patents
2,3 dihydro-1h-inden-1-yl-2,7-diazaspiro [3.5] nonane derivatives and their use as antagonists or inverse agonists of the ghrelin receptor Download PDFInfo
- Publication number
- CA2792234C CA2792234C CA2792234A CA2792234A CA2792234C CA 2792234 C CA2792234 C CA 2792234C CA 2792234 A CA2792234 A CA 2792234A CA 2792234 A CA2792234 A CA 2792234A CA 2792234 C CA2792234 C CA 2792234C
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- CA
- Canada
- Prior art keywords
- dihydro
- inden
- diazaspiro
- acetyl
- nonane
- 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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- 239000000556 agonist Substances 0.000 title abstract description 29
- 239000005557 antagonist Substances 0.000 title abstract description 23
- 102000000393 Ghrelin Receptors Human genes 0.000 title abstract description 15
- 108010016122 Ghrelin Receptors Proteins 0.000 title abstract description 15
- XVWYVEFVHFPPNL-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonane Chemical class C1NC(C2C3=CC=CC=C3CC2)C11CCNCC1 XVWYVEFVHFPPNL-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 193
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- -1 (C1-C3)alkyl-S(O)- Chemical class 0.000 claims description 201
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 21
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000006274 (C1-C3)alkoxy group Chemical class 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 claims description 3
- BPZZEFRSUJCCBU-UHFFFAOYSA-N imidazo[1,2-b][1,2,4]triazine Chemical compound N1=CC=NN2[C]=CN=C21 BPZZEFRSUJCCBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- ZIUDADZJCKGWKR-AREMUKBSSA-N 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[(1r)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C([C@H](C1=CC=2)N3CC4(CCN(CC4)C(=O)CC4=CN5C=C(SC5=N4)C)C3)CC1=CC=2C1=CC(C)=NC=N1 ZIUDADZJCKGWKR-AREMUKBSSA-N 0.000 claims 2
- MMNYYGXTGFMPKP-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1CC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CCN1C(=O)CC(C=C1)=CC=C1C1CC1 MMNYYGXTGFMPKP-UHFFFAOYSA-N 0.000 claims 2
- FZDGCONCFPFRTK-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(6-methoxypyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CN=C(OC)C=2)CC1 FZDGCONCFPFRTK-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- GWDCIJWWUFGGLC-UHFFFAOYSA-N 1-[2-(2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]-2-(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=CC=C3CC2)CC1 GWDCIJWWUFGGLC-UHFFFAOYSA-N 0.000 claims 1
- QYADLOJJPSWKMO-UHFFFAOYSA-N 1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]-2-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)ethanone Chemical compound C1=C2CCCCN2N=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 QYADLOJJPSWKMO-UHFFFAOYSA-N 0.000 claims 1
- ZKEWARJGCKGLNM-UHFFFAOYSA-N 1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 ZKEWARJGCKGLNM-UHFFFAOYSA-N 0.000 claims 1
- CWWWNUAQMXMSGC-MUUNZHRXSA-N 1-[2-[(1r)-5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(5-methoxypyridin-2-yl)ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2N=C(C)N=C(C)C=2)CC1 CWWWNUAQMXMSGC-MUUNZHRXSA-N 0.000 claims 1
- JYDQZHGILUYIQT-HHHXNRCGSA-N 1-[2-[(1r)-5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(5-methoxypyridin-2-yl)ethanone Chemical compound N1=CC(CC)=CN=C1C1=CC=C([C@@H](CC2)N3CC4(C3)CCN(CC4)C(=O)CC=3N=CC(OC)=CC=3)C2=C1 JYDQZHGILUYIQT-HHHXNRCGSA-N 0.000 claims 1
- XVFKFWHXYIULGU-UHFFFAOYSA-N 1-[2-[5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=CC(C)=NC(C)=N1 XVFKFWHXYIULGU-UHFFFAOYSA-N 0.000 claims 1
- CWWWNUAQMXMSGC-UHFFFAOYSA-N 1-[2-[5-(2,6-dimethylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(5-methoxypyridin-2-yl)ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)N=C(C)C=2)CC1 CWWWNUAQMXMSGC-UHFFFAOYSA-N 0.000 claims 1
- GICZZLVWIFQHBI-UHFFFAOYSA-N 1-[2-[5-(4,6-dimethylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC(C)=CC(C)=N1 GICZZLVWIFQHBI-UHFFFAOYSA-N 0.000 claims 1
- SSEJKRASVRMOGH-UHFFFAOYSA-N 1-[2-[5-(4,6-dimethylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(5-methoxypyridin-2-yl)ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)C=C(C)N=2)CC1 SSEJKRASVRMOGH-UHFFFAOYSA-N 0.000 claims 1
- ASKMOXIOMBPHAM-UHFFFAOYSA-N 1-[2-[5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(4-methoxyphenyl)ethanone Chemical compound N1=CC(CC)=CN=C1C1=CC=C(C(CC2)N3CC4(C3)CCN(CC4)C(=O)CC=3C=CC(OC)=CC=3)C2=C1 ASKMOXIOMBPHAM-UHFFFAOYSA-N 0.000 claims 1
- JYDQZHGILUYIQT-UHFFFAOYSA-N 1-[2-[5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]-2-(5-methoxypyridin-2-yl)ethanone Chemical compound N1=CC(CC)=CN=C1C1=CC=C(C(CC2)N3CC4(C3)CCN(CC4)C(=O)CC=3N=CC(OC)=CC=3)C2=C1 JYDQZHGILUYIQT-UHFFFAOYSA-N 0.000 claims 1
- MIFZJIVJINQISU-UHFFFAOYSA-N 2-(1-ethylpyrazol-3-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound CCN1C=CC(CC(=O)N2CCC3(CN(C3)C3C4=CC=C(C=C4CC3)C=3N=CC=CN=3)CC2)=N1 MIFZJIVJINQISU-UHFFFAOYSA-N 0.000 claims 1
- DWSZMRNLAZPKCF-UHFFFAOYSA-N 2-(1-ethylpyrazolo[3,4-b]pyridin-3-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C12=CC=CN=C2N(CC)N=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=CC(C)=NC=N1 DWSZMRNLAZPKCF-UHFFFAOYSA-N 0.000 claims 1
- MGFASSGEYPHPRF-UHFFFAOYSA-N 2-(1-methylpyrazolo[3,4-b]pyridin-3-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=NC(C)=CC(C=2C=C3CCC(C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2C3=CC=CN=C3N(C)N=2)=N1 MGFASSGEYPHPRF-UHFFFAOYSA-N 0.000 claims 1
- IYUPVYBKECLVFA-UHFFFAOYSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C=1C=C2OCCOC2=NC=1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 IYUPVYBKECLVFA-UHFFFAOYSA-N 0.000 claims 1
- PBVRUVRSOOCILV-AREMUKBSSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)-1-[2-[(1r)-5-(2-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound CC1=NC=CC(C=2C=C3CC[C@H](C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2N=C3OCCOC3=CC=2)=N1 PBVRUVRSOOCILV-AREMUKBSSA-N 0.000 claims 1
- LLRPBMJXTUIESQ-AREMUKBSSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)-1-[2-[(1r)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=NC(C)=CC(C=2C=C3CC[C@H](C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2N=C3OCCOC3=CC=2)=N1 LLRPBMJXTUIESQ-AREMUKBSSA-N 0.000 claims 1
- CKPHCWMDJDXUIZ-UHFFFAOYSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)-1-[2-[5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound CC1=CC=NC(C=2C=C3CCC(C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2N=C3OCCOC3=CC=2)=N1 CKPHCWMDJDXUIZ-UHFFFAOYSA-N 0.000 claims 1
- LLRPBMJXTUIESQ-UHFFFAOYSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=NC(C)=CC(C=2C=C3CCC(C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2N=C3OCCOC3=CC=2)=N1 LLRPBMJXTUIESQ-UHFFFAOYSA-N 0.000 claims 1
- VEMJWZXCAXTYFN-UHFFFAOYSA-N 2-(2,3-dimethylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C=1N2C(C)=C(C)SC2=NC=1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=CC(C)=NC=N1 VEMJWZXCAXTYFN-UHFFFAOYSA-N 0.000 claims 1
- OGTLKNQYOXIJTG-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 OGTLKNQYOXIJTG-UHFFFAOYSA-N 0.000 claims 1
- RIMZMWDWQJSJAV-RUZDIDTESA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-[(1r)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C([C@H](C1=CC=2)N3CC4(CCN(CC4)C(=O)CC4=CN5N=C(SC5=N4)C)C3)CC1=CC=2C1=CC(C)=NC=N1 RIMZMWDWQJSJAV-RUZDIDTESA-N 0.000 claims 1
- OQVBASJYMACOAZ-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-[5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC(C)=N1 OQVBASJYMACOAZ-UHFFFAOYSA-N 0.000 claims 1
- WQJCZDBHAQXLCJ-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-[5-(5-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=C(C)C=N1 WQJCZDBHAQXLCJ-UHFFFAOYSA-N 0.000 claims 1
- RIMZMWDWQJSJAV-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=CC(C)=NC=N1 RIMZMWDWQJSJAV-UHFFFAOYSA-N 0.000 claims 1
- KNCRMAGUHWPSCE-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=NN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2N1N=CC=N1 KNCRMAGUHWPSCE-UHFFFAOYSA-N 0.000 claims 1
- KMTPPHHBYJEXPO-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=CN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 KMTPPHHBYJEXPO-UHFFFAOYSA-N 0.000 claims 1
- KMTPPHHBYJEXPO-XMMPIXPASA-N 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[(1r)-5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C([C@H](C1=CC=2)N3CC4(CCN(CC4)C(=O)CC4=CN5C=C(SC5=N4)C)C3)CC1=CC=2C1=NC=CC=N1 KMTPPHHBYJEXPO-XMMPIXPASA-N 0.000 claims 1
- PYWPVRIBEOXIKN-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=CN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC(C)=N1 PYWPVRIBEOXIKN-UHFFFAOYSA-N 0.000 claims 1
- IHFYSFFWDWXLJS-UHFFFAOYSA-N 2-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2SC(C)=CN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2N1N=CC=N1 IHFYSFFWDWXLJS-UHFFFAOYSA-N 0.000 claims 1
- LAHGWWGYBMWICT-UHFFFAOYSA-N 2-(2h-indazol-3-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N=1NC2=CC=CC=C2C=1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 LAHGWWGYBMWICT-UHFFFAOYSA-N 0.000 claims 1
- RQUMQZKTCZFHMQ-UHFFFAOYSA-N 2-(4-ethylphenyl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(CC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 RQUMQZKTCZFHMQ-UHFFFAOYSA-N 0.000 claims 1
- UHUCZYJVWVZKAH-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 UHUCZYJVWVZKAH-UHFFFAOYSA-N 0.000 claims 1
- TYYSKYJWHWZGJF-RUZDIDTESA-N 2-(4-methoxyphenyl)-1-[2-[(1r)-5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 TYYSKYJWHWZGJF-RUZDIDTESA-N 0.000 claims 1
- TVENWCAZFIVAQU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-[2-[5-(1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2OC=CN=2)CC1 TVENWCAZFIVAQU-UHFFFAOYSA-N 0.000 claims 1
- CLTAVKBEIJFCFL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-[2-[5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)C=CN=2)CC1 CLTAVKBEIJFCFL-UHFFFAOYSA-N 0.000 claims 1
- OQRWNJSOQBYYNP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-[2-[5-(5-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC(C)=CN=2)CC1 OQRWNJSOQBYYNP-UHFFFAOYSA-N 0.000 claims 1
- TYYSKYJWHWZGJF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 TYYSKYJWHWZGJF-UHFFFAOYSA-N 0.000 claims 1
- DQSNXAIILIABRG-UHFFFAOYSA-N 2-(4-methylphenyl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 DQSNXAIILIABRG-UHFFFAOYSA-N 0.000 claims 1
- ZXPSCCPTTACNLO-UHFFFAOYSA-N 2-(5-cyclopropylpyridin-2-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1CC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CCN1C(=O)CC(N=C1)=CC=C1C1CC1 ZXPSCCPTTACNLO-UHFFFAOYSA-N 0.000 claims 1
- JBUITHYDAROGHQ-UHFFFAOYSA-N 2-(5-cyclopropylpyridin-2-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound C1=NC(C)=CC(C=2C=C3CCC(C3=CC=2)N2CC3(C2)CCN(CC3)C(=O)CC=2N=CC(=CC=2)C2CC2)=N1 JBUITHYDAROGHQ-UHFFFAOYSA-N 0.000 claims 1
- WUKHDLMVEFYYHY-UHFFFAOYSA-N 2-(5-ethylpyridin-2-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(CC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 WUKHDLMVEFYYHY-UHFFFAOYSA-N 0.000 claims 1
- WUKHDLMVEFYYHY-AREMUKBSSA-N 2-(5-ethylpyridin-2-yl)-1-[2-[(1r)-5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(CC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 WUKHDLMVEFYYHY-AREMUKBSSA-N 0.000 claims 1
- ZVUBFVANBXNXQF-UHFFFAOYSA-N 2-(5-ethylpyridin-2-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(CC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 ZVUBFVANBXNXQF-UHFFFAOYSA-N 0.000 claims 1
- HYUFHCRKSXZQFA-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-(5-phenoxy-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(OC=4C=CC=CC=4)C=C3CC2)CC1 HYUFHCRKSXZQFA-UHFFFAOYSA-N 0.000 claims 1
- HDIKVQIWPWELLR-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-(5-pyrazin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=NC=2)CC1 HDIKVQIWPWELLR-UHFFFAOYSA-N 0.000 claims 1
- BUCKSSXJIHVQBK-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 BUCKSSXJIHVQBK-UHFFFAOYSA-N 0.000 claims 1
- CSNLTDSMWBAFOG-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-(5-pyrimidin-4-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CN=CC=2)CC1 CSNLTDSMWBAFOG-UHFFFAOYSA-N 0.000 claims 1
- JSJHUXMAZWAWGK-XMMPIXPASA-N 2-(5-methoxypyridin-2-yl)-1-[2-[(1r)-5-(1,3-thiazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2SC=CN=2)CC1 JSJHUXMAZWAWGK-XMMPIXPASA-N 0.000 claims 1
- KEHVZGBXBDJDMH-AREMUKBSSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[(1r)-5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2N=C(C)C=CN=2)CC1 KEHVZGBXBDJDMH-AREMUKBSSA-N 0.000 claims 1
- SEGKTHKDKIHNOM-AREMUKBSSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[(1r)-5-(5-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2N=CC(C)=CN=2)CC1 SEGKTHKDKIHNOM-AREMUKBSSA-N 0.000 claims 1
- NATXGJPPVHDYCP-HHHXNRCGSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[(1r)-5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)C=2N=CN=C(C)C=2)CC1 NATXGJPPVHDYCP-HHHXNRCGSA-N 0.000 claims 1
- NOLZCWDIRAGCGH-XMMPIXPASA-N 2-(5-methoxypyridin-2-yl)-1-[2-[(1r)-5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 NOLZCWDIRAGCGH-XMMPIXPASA-N 0.000 claims 1
- AOJIUAXHDWSDNH-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(1,3-oxazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2OC=CN=2)CC1 AOJIUAXHDWSDNH-UHFFFAOYSA-N 0.000 claims 1
- JSJHUXMAZWAWGK-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(1,3-thiazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2SC=CN=2)CC1 JSJHUXMAZWAWGK-UHFFFAOYSA-N 0.000 claims 1
- AFINYXHHVZECAJ-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(1-methylpyrazol-3-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C2=NN(C)C=C2)CC1 AFINYXHHVZECAJ-UHFFFAOYSA-N 0.000 claims 1
- HKXFLLQSNOMBPN-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(2-methylpyridin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2C=C(C)N=CC=2)CC1 HKXFLLQSNOMBPN-UHFFFAOYSA-N 0.000 claims 1
- ILOLVOUTASXFQF-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(2-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)N=CC=2)CC1 ILOLVOUTASXFQF-UHFFFAOYSA-N 0.000 claims 1
- FACDMDNBMDTNTQ-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(4-methylpyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=C(C)C=2)CC1 FACDMDNBMDTNTQ-UHFFFAOYSA-N 0.000 claims 1
- VILPWEXVCIBXHV-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(5-methoxypyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC(OC)=CC=2)CC1 VILPWEXVCIBXHV-UHFFFAOYSA-N 0.000 claims 1
- PLRCFGZWIUHBAA-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(5-methoxypyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC(OC)=CN=2)CC1 PLRCFGZWIUHBAA-UHFFFAOYSA-N 0.000 claims 1
- MQWBBDPTDCTKIV-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(5-methyl-1,3-thiazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2SC(C)=CN=2)CC1 MQWBBDPTDCTKIV-UHFFFAOYSA-N 0.000 claims 1
- ZFBVFLGNDAWLDS-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(5-methylpyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC(C)=CC=2)CC1 ZFBVFLGNDAWLDS-UHFFFAOYSA-N 0.000 claims 1
- IDTDGFHEYCPFTC-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(6-methylpyridin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)C=CC=2)CC1 IDTDGFHEYCPFTC-UHFFFAOYSA-N 0.000 claims 1
- NOLZCWDIRAGCGH-UHFFFAOYSA-N 2-(5-methoxypyridin-2-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(OC)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 NOLZCWDIRAGCGH-UHFFFAOYSA-N 0.000 claims 1
- GRPPJCVJSHBBPO-UHFFFAOYSA-N 2-(5-methyl-1h-pyrazol-3-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1N=C(C)C=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 GRPPJCVJSHBBPO-UHFFFAOYSA-N 0.000 claims 1
- AAJDKMBUXCOQNC-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CC=CN=2)CC1 AAJDKMBUXCOQNC-UHFFFAOYSA-N 0.000 claims 1
- ZWFXCKJHCJRMDP-XMMPIXPASA-N 2-(5-methylpyridin-2-yl)-1-[2-[(1r)-5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)[C@H]2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 ZWFXCKJHCJRMDP-XMMPIXPASA-N 0.000 claims 1
- WAIPAVUHTDBUHG-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-1-[2-[5-(4-methylpyrimidin-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=C(C)C=CN=2)CC1 WAIPAVUHTDBUHG-UHFFFAOYSA-N 0.000 claims 1
- IFFQMYNBTIKRNQ-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-1-[2-[5-(6-methylpyrimidin-4-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)C=2N=CN=C(C)C=2)CC1 IFFQMYNBTIKRNQ-UHFFFAOYSA-N 0.000 claims 1
- ZWFXCKJHCJRMDP-UHFFFAOYSA-N 2-(5-methylpyridin-2-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=CC(C)=CC=C1CC(=O)N1CCC2(CN(C2)C2C3=CC=C(C=C3CC2)N2N=CC=N2)CC1 ZWFXCKJHCJRMDP-UHFFFAOYSA-N 0.000 claims 1
- NJEQEHJPTUJTNH-UHFFFAOYSA-N 2-(7-methylimidazo[1,2-a]pyridin-2-yl)-1-[2-(5-pyrimidin-2-yl-2,3-dihydro-1h-inden-1-yl)-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2C=C(C)C=CN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2C1=NC=CC=N1 NJEQEHJPTUJTNH-UHFFFAOYSA-N 0.000 claims 1
- PFWOQLAHXHLNOA-UHFFFAOYSA-N 2-(7-methylimidazo[1,2-a]pyridin-2-yl)-1-[2-[5-(triazol-2-yl)-2,3-dihydro-1h-inden-1-yl]-2,7-diazaspiro[3.5]nonan-7-yl]ethanone Chemical compound N1=C2C=C(C)C=CN2C=C1CC(=O)N(CC1)CCC1(C1)CN1C(C1=CC=2)CCC1=CC=2N1N=CC=N1 PFWOQLAHXHLNOA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D471/10—Spiro-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
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| RS59512B1 (sr) | 2012-09-25 | 2019-12-31 | Hoffmann La Roche | Derivati heksahidropirolo[3,4−c]pirola i srodna jedinjenja kao inhibitori autotaksina (atx) i kao inhibitori proizvodnje lizofosfatidne kiseline (lpa) za lečenje npr. bubrežnih bolesti |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
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| CA2941196C (en) * | 2014-03-17 | 2019-09-03 | Remynd Nv | 2,7-diazaspiro[3.5]nonane compounds |
| CN106103446B (zh) | 2014-03-26 | 2019-07-30 | 豪夫迈·罗氏有限公司 | 作为自分泌运动因子(atx)和溶血磷脂酸(lpa)生产抑制剂的二环化合物 |
| KR20160128428A (ko) | 2014-03-26 | 2016-11-07 | 에프. 호프만-라 로슈 아게 | 오토탁신(atx) 및 리소포스파티드산(lpa) 생성 억제제로서의 축합형 [1,4]다이아제핀 화합물 |
| CN106749002A (zh) * | 2015-02-12 | 2017-05-31 | 佛山市赛维斯医药科技有限公司 | 一种含硝基喹啉结构的葡萄糖激酶活化剂及其用途 |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| CN108026077B (zh) | 2015-09-04 | 2021-11-05 | 豪夫迈·罗氏有限公司 | 苯氧基甲基衍生物 |
| KR20180054635A (ko) | 2015-09-24 | 2018-05-24 | 에프. 호프만-라 로슈 아게 | 오토탁신(atx) 억제제로서 이환형 화합물 |
| CR20180143A (es) | 2015-09-24 | 2018-05-03 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de atx/ca |
| EP3353178B1 (en) | 2015-09-24 | 2021-07-14 | F. Hoffmann-La Roche AG | Bicyclic compounds as dual atx/ca inhibitors |
| PE20180461A1 (es) | 2015-09-24 | 2018-03-06 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores de la atx |
| KR102882225B1 (ko) | 2017-02-21 | 2025-11-07 | 엘지전자 주식회사 | 냉장고 |
| RU2019132254A (ru) | 2017-03-16 | 2021-04-16 | Ф. Хоффманн-Ля Рош Аг | Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca |
| CN110382484B (zh) | 2017-03-16 | 2022-12-06 | 豪夫迈·罗氏有限公司 | 新的作为atx抑制剂的二环化合物 |
| CN111225896B (zh) * | 2017-07-28 | 2024-03-26 | 凯莫森特里克斯股份有限公司 | 免疫调节剂化合物 |
| CN108588215A (zh) * | 2018-05-03 | 2018-09-28 | 成都中创清科医学检验所有限公司 | 一种用于检测家族性高胆固醇血症易感性相关的snp位点的引物及其检测方法 |
| CN109970631A (zh) * | 2019-03-26 | 2019-07-05 | 上海吉奉生物科技有限公司 | 一种5-碘-2-吡啶乙酸的合成方法 |
| AR118555A1 (es) | 2019-04-03 | 2021-10-20 | Vertex Pharma | Agentes moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| CN111777559B (zh) * | 2019-04-23 | 2021-11-09 | 苏州大学 | 基于端炔制备多取代吡唑的方法 |
| CN110172062B (zh) * | 2019-06-21 | 2022-01-07 | 南京药石科技股份有限公司 | 一种单氟代螺环化合物的合成方法及其中间体 |
| CA3150162A1 (en) * | 2019-08-14 | 2021-02-18 | Vertex Pharmaceuticals Incorporated | Crystalline forms of cftr modulators |
| CA3200245A1 (en) | 2020-11-27 | 2022-06-02 | Junjun Wu | Benzimidazole derivative and preparation method therefor and medical use thereof |
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| KR20220001745U (ko) | 2021-01-06 | 2022-07-13 | 성보라 | 자동차시트 후면 보호용 보조커버 |
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| UA99882C2 (uk) | 2009-03-11 | 2012-10-10 | Пфайзер Інк. | Похідні бензофуранілу, фармацевтична композиція та спосіб лікування захворювань (варіанти) |
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