JP2019501937A5 - - Google Patents
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- Publication number
- JP2019501937A5 JP2019501937A5 JP2018536436A JP2018536436A JP2019501937A5 JP 2019501937 A5 JP2019501937 A5 JP 2019501937A5 JP 2018536436 A JP2018536436 A JP 2018536436A JP 2018536436 A JP2018536436 A JP 2018536436A JP 2019501937 A5 JP2019501937 A5 JP 2019501937A5
- Authority
- JP
- Japan
- Prior art keywords
- diazaspiro
- phenyl
- dimethylamino
- decane
- sith
- 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
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- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 100
- 229920006395 saturated elastomer Polymers 0.000 claims description 99
- -1 2 -cyclobutyl Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 15
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 11
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- BQKQLYGFPMLQNZ-UHFFFAOYSA-N 8-benzyl-8-(dimethylamino)-3-[4-methyl-6-(trifluoromethyl)pyridin-3-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CC2=CC=CC=C2)CCC2(CN(C(=O)N2)C2=C(C)C=C(N=C2)C(F)(F)F)CC1 BQKQLYGFPMLQNZ-UHFFFAOYSA-N 0.000 claims description 2
- SEFLPUFNIBPPKQ-UHFFFAOYSA-N COC=1N=CC(=NC=1)N1C(NCC11CCC(CC1)(C1=CC=CC=C1)NC)=O Chemical compound COC=1N=CC(=NC=1)N1C(NCC11CCC(CC1)(C1=CC=CC=C1)NC)=O SEFLPUFNIBPPKQ-UHFFFAOYSA-N 0.000 claims description 2
- ZKYZFWZNKIBTKU-UHFFFAOYSA-N FC(CCN1C(NCC11CCCCC1)=O)(F)F Chemical compound FC(CCN1C(NCC11CCCCC1)=O)(F)F ZKYZFWZNKIBTKU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
- 125000006707 (C3-C12) heterocycloalkyl group Chemical group 0.000 description 13
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 9
- CSKUCUPFMABMFT-UHFFFAOYSA-N 1-(cyclobutylmethyl)-8-(dimethylamino)-3,8-diphenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2CC2CCC2)c2ccccc2)CC1)c1ccccc1 CSKUCUPFMABMFT-UHFFFAOYSA-N 0.000 description 2
- MNYSSPRUXOCYDU-UHFFFAOYSA-N 8-(dimethylamino)-8-thiophen-2-yl-3-[2-(trifluoromethyl)pyrimidin-5-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)C2=CN=C(N=C2)C(F)(F)F)CC1)C1=CC=CS1 MNYSSPRUXOCYDU-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- CKKXZTIXJMGOAZ-UHFFFAOYSA-N 1-(cyclobutylmethyl)-3-(2,4-dimethoxyphenyl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound COc1ccc(N2CC3(CCC(CC3)(N(C)C)c3ccccc3)N(CC3CCC3)C2=O)c(OC)c1 CKKXZTIXJMGOAZ-UHFFFAOYSA-N 0.000 description 1
- NOLRBXWDANQFCG-UHFFFAOYSA-N 1-(cyclobutylmethyl)-8-(dimethylamino)-3-(2-methoxypyrimidin-5-yl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound COc1ncc(cn1)N1CC2(CCC(CC2)(N(C)C)c2ccccc2)N(CC2CCC2)C1=O NOLRBXWDANQFCG-UHFFFAOYSA-N 0.000 description 1
- YPZMUMXKXNDMHK-UHFFFAOYSA-N 1-(cyclobutylmethyl)-8-(dimethylamino)-3-(6-methylsulfanylpyrimidin-4-yl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CSc1cc(ncn1)N1CC2(CCC(CC2)(N(C)C)c2ccccc2)N(CC2CCC2)C1=O YPZMUMXKXNDMHK-UHFFFAOYSA-N 0.000 description 1
- NCTOFCIDKRISKV-UHFFFAOYSA-N 1-(cyclopropylmethyl)-8-(dimethylamino)-8-(3-fluorophenyl)-3-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2CC2CC2)c2cc(nn2C)C(F)(F)F)CC1)c1cccc(F)c1 NCTOFCIDKRISKV-UHFFFAOYSA-N 0.000 description 1
- BUYHFLCMNKRRSM-UHFFFAOYSA-N 2-[2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]phenoxy]acetamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccccc2OCC(N)=O)CC1)c1ccccc1 BUYHFLCMNKRRSM-UHFFFAOYSA-N 0.000 description 1
- LVWOFVXIWGACRB-UHFFFAOYSA-N 2-[2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]phenoxy]acetic acid Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccccc2OCC(O)=O)CC1)c1ccccc1 LVWOFVXIWGACRB-UHFFFAOYSA-N 0.000 description 1
- CGECKWRCJVJAHZ-UHFFFAOYSA-N 2-[3-(2-cyanopyrimidin-4-yl)-8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-1-yl]-N,N-dimethylacetamide Chemical compound CN(C)C(=O)CN1C(=O)N(CC11CCC(CC1)(N(C)C)c1ccccc1)c1ccnc(n1)C#N CGECKWRCJVJAHZ-UHFFFAOYSA-N 0.000 description 1
- DNGKPPIKCUWYAV-UHFFFAOYSA-N 2-[3-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyridin-4-yl]acetamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnccc2CC(N)=O)CC1)c1ccccc1 DNGKPPIKCUWYAV-UHFFFAOYSA-N 0.000 description 1
- NQNQMZJYUXTBNX-UHFFFAOYSA-N 2-[8-(dimethylamino)-1-(oxetan-3-ylmethyl)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2CC2COC2)c2ccccc2C(N)=O)CC1)c1ccccc1 NQNQMZJYUXTBNX-UHFFFAOYSA-N 0.000 description 1
- OKRJYYYMSSJJGI-UHFFFAOYSA-N 2-[8-(dimethylamino)-2-oxo-3,8-diphenyl-1,3-diazaspiro[4.5]decan-1-yl]-N,N-dimethylacetamide Chemical compound CN(C)C(=O)CN1C(=O)N(CC11CCC(CC1)(N(C)C)c1ccccc1)c1ccccc1 OKRJYYYMSSJJGI-UHFFFAOYSA-N 0.000 description 1
- NXCXFLGHMYLNRY-UHFFFAOYSA-N 2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccccc2C(N)=O)CC1)c1ccccc1 NXCXFLGHMYLNRY-UHFFFAOYSA-N 0.000 description 1
- KMWSREQVPPLMOU-UHFFFAOYSA-N 2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccccc2C#N)CC1)c1ccccc1 KMWSREQVPPLMOU-UHFFFAOYSA-N 0.000 description 1
- CUPYIRNLIXSDHZ-UHFFFAOYSA-N 2-[8-(ethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzamide Chemical compound CCNC1(CCC2(CN(C(=O)N2)C2=C(C=CC=C2)C(N)=O)CC1)C1=CC=CC=C1 CUPYIRNLIXSDHZ-UHFFFAOYSA-N 0.000 description 1
- WSFPMDMXXIJPTJ-UHFFFAOYSA-N 2-[8-(ethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzonitrile Chemical compound CCNC1(CCC2(CN(C(=O)N2)c2ccccc2C#N)CC1)c1ccccc1 WSFPMDMXXIJPTJ-UHFFFAOYSA-N 0.000 description 1
- WVKSTAIMCCMIKC-UHFFFAOYSA-N 2-[[5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-2-methylpyrimidin-4-yl]amino]acetamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(C)nc2NCC(N)=O)CC1)c1ccccc1 WVKSTAIMCCMIKC-UHFFFAOYSA-N 0.000 description 1
- CQVFLODBZLZRGK-LHHJGKSTSA-N 2-[[5-[8-[(E)-but-2-en-2-yl]-8-(dimethylamino)-2-oxo-1,3-diazaspiro[4.5]decan-3-yl]pyrimidin-2-yl]amino]acetamide Chemical compound C/C=C(\C)/C1(CCC2(CC1)CN(C(=O)N2)C3=CN=C(N=C3)NCC(=O)N)N(C)C CQVFLODBZLZRGK-LHHJGKSTSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UJQAOVXBODKERF-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc3OCOc3c2)CC1)c1ccccc1 UJQAOVXBODKERF-UHFFFAOYSA-N 0.000 description 1
- FTRCLQAOUNRTQF-UHFFFAOYSA-N 3-(1,3-benzothiazol-7-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccc3ncsc23)CC1)c1ccccc1 FTRCLQAOUNRTQF-UHFFFAOYSA-N 0.000 description 1
- TXYHBBZZCGMODR-UHFFFAOYSA-N 3-(1-acetylindol-3-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound C(C)(=O)N1C=C(C2=CC=CC=C12)N1C(NC2(C1)CCC(CC2)(C1=CC=CC=C1)N(C)C)=O TXYHBBZZCGMODR-UHFFFAOYSA-N 0.000 description 1
- ZAXNOFYSLPQJMM-UHFFFAOYSA-N 3-(1-acetylindol-4-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccc3n(ccc23)C(C)=O)CC1)c1ccccc1 ZAXNOFYSLPQJMM-UHFFFAOYSA-N 0.000 description 1
- QXDNBFMPLPHMQA-UHFFFAOYSA-N 3-(2,1,3-benzoxadiazol-5-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc3nonc3c2)CC1)c1ccccc1 QXDNBFMPLPHMQA-UHFFFAOYSA-N 0.000 description 1
- LHNTVISNPRPSQF-UHFFFAOYSA-N 3-(2-aminopyrimidin-5-yl)-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(N)nc2)CC1)c1ccccc1 LHNTVISNPRPSQF-UHFFFAOYSA-N 0.000 description 1
- KIWWMLBEXMMCDQ-UHFFFAOYSA-N 3-[2-(3,4-difluorophenyl)pyrimidin-5-yl]-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)-c2ccc(F)c(F)c2)CC1)c1ccccc1 KIWWMLBEXMMCDQ-UHFFFAOYSA-N 0.000 description 1
- AAGSZPWMYDLUMO-UHFFFAOYSA-N 3-[2-[benzyl(methyl)amino]pyrimidin-5-yl]-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)N(C)Cc2ccccc2)CC1)c1ccccc1 AAGSZPWMYDLUMO-UHFFFAOYSA-N 0.000 description 1
- PLLSZWYBVYTYDL-UHFFFAOYSA-N 3-[4-(azetidin-1-yl)-2-methylpyrimidin-5-yl]-8-(dimethylamino)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(C)nc2N2CCC2)CC1)c1ccccc1 PLLSZWYBVYTYDL-UHFFFAOYSA-N 0.000 description 1
- LXNMNUCHEDRFIA-UHFFFAOYSA-N 3-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyridine-4-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnccc2C#N)CC1)c1ccccc1 LXNMNUCHEDRFIA-UHFFFAOYSA-N 0.000 description 1
- XDNFBBSFXLEXEM-UHFFFAOYSA-N 3-methoxy-4-[8-(methylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzonitrile Chemical compound CNC1(CCC2(CN(C(=O)N2)c2ccc(cc2OC)C#N)CC1)c1ccccc1 XDNFBBSFXLEXEM-UHFFFAOYSA-N 0.000 description 1
- PFYXXCONQFAJRQ-UHFFFAOYSA-N 4-[1-(cyclobutylmethyl)-8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-N-methylbenzamide Chemical compound CNC(=O)c1ccc(cc1)N1CC2(CCC(CC2)(N(C)C)c2ccccc2)N(CC2CCC2)C1=O PFYXXCONQFAJRQ-UHFFFAOYSA-N 0.000 description 1
- QRVYQPUGWHQTPP-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-3,5-difluorobenzamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2c(F)cc(cc2F)C(N)=O)CC1)c1ccccc1 QRVYQPUGWHQTPP-UHFFFAOYSA-N 0.000 description 1
- GGJKOEXVYUYJGW-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-3,5-difluorobenzonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2c(F)cc(cc2F)C#N)CC1)c1ccccc1 GGJKOEXVYUYJGW-UHFFFAOYSA-N 0.000 description 1
- CQQRPYSJQCSPDB-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-3-fluorobenzamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cc2F)C(N)=O)CC1)c1ccccc1 CQQRPYSJQCSPDB-UHFFFAOYSA-N 0.000 description 1
- JRHMRLSDOLLTRV-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-3-fluorobenzonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cc2F)C#N)CC1)c1ccccc1 JRHMRLSDOLLTRV-UHFFFAOYSA-N 0.000 description 1
- RBQOGZGCRIKZGD-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cc2)C(N)=O)CC1)c1ccccc1 RBQOGZGCRIKZGD-UHFFFAOYSA-N 0.000 description 1
- CJPHJXLWJKUGGU-UHFFFAOYSA-N 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cc2)C#N)CC1)c1ccccc1 CJPHJXLWJKUGGU-UHFFFAOYSA-N 0.000 description 1
- QXQNVFBFSDMJPR-UHFFFAOYSA-N 4-[8-(ethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-3-methoxybenzonitrile Chemical compound CCNC1(CCC2(CN(C(=O)N2)C2=C(OC)C=C(C=C2)C#N)CC1)C1=CC=CC=C1 QXQNVFBFSDMJPR-UHFFFAOYSA-N 0.000 description 1
- FUDFISYBABRXMK-UHFFFAOYSA-N 4-methoxy-5-[8-(methylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyrimidine-2-carbonitrile Chemical compound CNC1(CCC2(CN(C(=O)N2)c2cnc(nc2OC)C#N)CC1)c1ccccc1 FUDFISYBABRXMK-UHFFFAOYSA-N 0.000 description 1
- AWUNDZYQWVOFCN-UHFFFAOYSA-N 5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyridine-2-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(nc2)C#N)CC1)c1ccccc1 AWUNDZYQWVOFCN-UHFFFAOYSA-N 0.000 description 1
- LXLXWBPWTYZIDO-UHFFFAOYSA-N 5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyridine-3-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cncc(c2)C#N)CC1)c1ccccc1 LXLXWBPWTYZIDO-UHFFFAOYSA-N 0.000 description 1
- XWYPZJNHTKUZFS-UHFFFAOYSA-N 6-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-5-fluoropyridine-3-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ncc(cc2F)C#N)CC1)c1ccccc1 XWYPZJNHTKUZFS-UHFFFAOYSA-N 0.000 description 1
- VLQNXWSIQLBTEB-UHFFFAOYSA-N 6-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]-5-methylpyridine-3-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ncc(cc2C)C#N)CC1)c1ccccc1 VLQNXWSIQLBTEB-UHFFFAOYSA-N 0.000 description 1
- WMPJCCHJFFMIRK-UHFFFAOYSA-N 6-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyridine-3-carbonitrile Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cn2)C#N)CC1)c1ccccc1 WMPJCCHJFFMIRK-UHFFFAOYSA-N 0.000 description 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 1
- NFYNBCKQUICERP-UHFFFAOYSA-N 8-(dimethylamino)-1-(2-methoxyethyl)-3,8-diphenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound COCCN1C(=O)N(CC11CCC(CC1)(N(C)C)c1ccccc1)c1ccccc1 NFYNBCKQUICERP-UHFFFAOYSA-N 0.000 description 1
- KXYBTRGQMWJJDO-UHFFFAOYSA-N 8-(dimethylamino)-1-[(1-hydroxycyclobutyl)methyl]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2CC2(O)CCC2)c2cnc(nc2)N2CCN(C)CC2)CC1)c1ccccc1 KXYBTRGQMWJJDO-UHFFFAOYSA-N 0.000 description 1
- LQVRSOKDJLDEBD-UHFFFAOYSA-N 8-(dimethylamino)-3-(1H-indol-3-yl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C1(CCC2(CN(C(N2)=O)C2=CNC3=CC=CC=C23)CC1)C1=CC=CC=C1)C LQVRSOKDJLDEBD-UHFFFAOYSA-N 0.000 description 1
- KYKHIFQWYLTJFS-UHFFFAOYSA-N 8-(dimethylamino)-3-(1H-indol-4-yl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccc3[nH]ccc23)CC1)c1ccccc1 KYKHIFQWYLTJFS-UHFFFAOYSA-N 0.000 description 1
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- QTCQAFPZJSXNIS-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-(2-pyrrolidin-1-ylpyrimidin-5-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)N2CCCC2)CC1)c1ccccc1 QTCQAFPZJSXNIS-UHFFFAOYSA-N 0.000 description 1
- NNYAULQLLWEBGI-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-(4-phenyl-1,3-thiazol-2-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2nc(cs2)-c2ccccc2)CC1)c1ccccc1 NNYAULQLLWEBGI-UHFFFAOYSA-N 0.000 description 1
- QGGIIHGZICEMHD-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-(5-phenylthiophen-2-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(s2)-c2ccccc2)CC1)c1ccccc1 QGGIIHGZICEMHD-UHFFFAOYSA-N 0.000 description 1
- VKIBGUZLHGQDKQ-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-(5-pyridin-4-ylthiophen-2-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(s2)-c2ccncc2)CC1)c1ccccc1 VKIBGUZLHGQDKQ-UHFFFAOYSA-N 0.000 description 1
- POBDASBECHXJEO-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-(6-piperazin-1-ylpyridin-3-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(nc2)N2CCNCC2)CC1)c1ccccc1 POBDASBECHXJEO-UHFFFAOYSA-N 0.000 description 1
- VTLRTHQVGSMLCZ-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[2-(trifluoromethyl)pyrimidin-5-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)C(F)(F)F)CC1)c1ccccc1 VTLRTHQVGSMLCZ-UHFFFAOYSA-N 0.000 description 1
- RNMQZSJYJDLESV-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[2-[4-(trifluoromethyl)triazol-1-yl]pyrimidin-5-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)-n2cc(nn2)C(F)(F)F)CC1)c1ccccc1 RNMQZSJYJDLESV-UHFFFAOYSA-N 0.000 description 1
- PLPISDYOAFLWKY-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[3-(trifluoromethoxy)phenyl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccc(OC(F)(F)F)c2)CC1)c1ccccc1 PLPISDYOAFLWKY-UHFFFAOYSA-N 0.000 description 1
- WCVHXBVDIAFTNA-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[4-(trifluoromethoxy)phenyl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(OC(F)(F)F)cc2)CC1)c1ccccc1 WCVHXBVDIAFTNA-UHFFFAOYSA-N 0.000 description 1
- KSXZLTPRBZTFIK-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[4-(trifluoromethyl)phenyl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cc2)C(F)(F)F)CC1)c1ccccc1 KSXZLTPRBZTFIK-UHFFFAOYSA-N 0.000 description 1
- JPWCPNJWPYNXKS-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[5-(trifluoromethoxy)pyridin-2-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(OC(F)(F)F)cn2)CC1)c1ccccc1 JPWCPNJWPYNXKS-UHFFFAOYSA-N 0.000 description 1
- YLAJTUUOGVUBGU-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-[5-(trifluoromethyl)pyridin-2-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc(cn2)C(F)(F)F)CC1)c1ccccc1 YLAJTUUOGVUBGU-UHFFFAOYSA-N 0.000 description 1
- PVZGQKBRJDRGTO-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-pyrazin-2-yl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnccn2)CC1)c1ccccc1 PVZGQKBRJDRGTO-UHFFFAOYSA-N 0.000 description 1
- LQWDOKWCGUDDHD-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-pyridazin-3-yl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccnn2)CC1)c1ccccc1 LQWDOKWCGUDDHD-UHFFFAOYSA-N 0.000 description 1
- FHYPCPJVPPOUPZ-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-pyrimidin-5-yl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cncnc2)CC1)c1ccccc1 FHYPCPJVPPOUPZ-UHFFFAOYSA-N 0.000 description 1
- FOAMOCVCNSSHPL-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-quinazolin-6-yl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2ccc3ncncc3c2)CC1)c1ccccc1 FOAMOCVCNSSHPL-UHFFFAOYSA-N 0.000 description 1
- KHWWBYLKAQPTGB-UHFFFAOYSA-N 8-(dimethylamino)-8-phenyl-3-quinolin-5-yl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cccc3ncccc23)CC1)c1ccccc1 KHWWBYLKAQPTGB-UHFFFAOYSA-N 0.000 description 1
- RMNYCOWXJNBCBZ-UHFFFAOYSA-N 8-(methylamino)-3-(4-methyl-2-morpholin-4-ylpyrimidin-5-yl)-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CNC1(CCC2(CN(C(=O)N2)c2cnc(nc2C)N2CCOCC2)CC1)c1ccccc1 RMNYCOWXJNBCBZ-UHFFFAOYSA-N 0.000 description 1
- YPLPWBKLYQWANT-UHFFFAOYSA-N 8-[methyl(oxolan-3-ylmethyl)amino]-3-[2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-8-phenyl-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(CC1CCOC1)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)N2CCN(C)CC2)CC1)c1ccccc1 YPLPWBKLYQWANT-UHFFFAOYSA-N 0.000 description 1
- LITAUHRDJJGFIL-UHFFFAOYSA-N 8-benzyl-8-(dimethylamino)-3-(2-morpholin-4-ylpyrimidin-5-yl)-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CC2=CC=CC=C2)CCC2(CN(C(=O)N2)C2=CN=C(N=C2)N2CCOCC2)CC1 LITAUHRDJJGFIL-UHFFFAOYSA-N 0.000 description 1
- XIJOHGWRYRZBLL-UHFFFAOYSA-N 8-benzyl-8-(dimethylamino)-3-[2-(trifluoromethyl)pyrimidin-5-yl]-1,3-diazaspiro[4.5]decan-2-one Chemical compound CN(C)C1(CC2=CC=CC=C2)CCC2(CN(C(=O)N2)C2=CN=C(N=C2)C(F)(F)F)CC1 XIJOHGWRYRZBLL-UHFFFAOYSA-N 0.000 description 1
- VOWCKZPZDMVQFX-UHFFFAOYSA-N N,N-dimethyl-2-[8-(methylamino)-2-oxo-3,8-diphenyl-1,3-diazaspiro[4.5]decan-1-yl]acetamide Chemical compound CNC1(CCC2(CN(C(=O)N2CC(=O)N(C)C)c2ccccc2)CC1)c1ccccc1 VOWCKZPZDMVQFX-UHFFFAOYSA-N 0.000 description 1
- CLWJCWXJPFKIPP-UHFFFAOYSA-N N-[5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyrimidin-2-yl]-N,2,5-trimethylpyrazole-3-carboxamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)N(C)C(=O)c2cc(C)nn2C)CC1)c1ccccc1 CLWJCWXJPFKIPP-UHFFFAOYSA-N 0.000 description 1
- LNFCBHVRAJCJTK-UHFFFAOYSA-N N-[5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyrimidin-2-yl]-N-methyloxane-4-carboxamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(nc2)N(C)C(=O)C2CCOCC2)CC1)c1ccccc1 LNFCBHVRAJCJTK-UHFFFAOYSA-N 0.000 description 1
- MTDDHZWFSNBZGQ-UHFFFAOYSA-N N-[5-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]pyrimidin-2-yl]acetamide Chemical compound CN(C)C1(CCC2(CN(C(=O)N2)c2cnc(NC(C)=O)nc2)CC1)c1ccccc1 MTDDHZWFSNBZGQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- SAMWUWRYNMIGPZ-UHFFFAOYSA-N methyl 2-[2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]phenoxy]acetate Chemical compound COC(=O)COc1ccccc1N1CC2(CCC(CC2)(N(C)C)c2ccccc2)NC1=O SAMWUWRYNMIGPZ-UHFFFAOYSA-N 0.000 description 1
- FTXLMENZIRBTKI-UHFFFAOYSA-N methyl 2-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzoate Chemical compound COC(=O)c1ccccc1N1CC2(CCC(CC2)(N(C)C)c2ccccc2)NC1=O FTXLMENZIRBTKI-UHFFFAOYSA-N 0.000 description 1
- RPAKHAFKMVQQKP-UHFFFAOYSA-N methyl 3-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzoate Chemical compound COC(=O)c1cccc(c1)N1CC2(CCC(CC2)(N(C)C)c2ccccc2)NC1=O RPAKHAFKMVQQKP-UHFFFAOYSA-N 0.000 description 1
- SFDULQWBDDNZMO-UHFFFAOYSA-N methyl 4-[8-(dimethylamino)-2-oxo-8-phenyl-1,3-diazaspiro[4.5]decan-3-yl]benzoate Chemical compound COC(=O)c1ccc(cc1)N1CC2(CCC(CC2)(N(C)C)c2ccccc2)NC1=O SFDULQWBDDNZMO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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| SI3402782T1 (sl) | 2016-01-13 | 2020-11-30 | Grunenthal Gmbh | 8-amino-2-okso-1,3-diaza-spiro-(4,5)-dekanski derivati |
| JP6854823B2 (ja) | 2016-01-13 | 2021-04-07 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ３−（カルボキシメチル）−８−アミノ−２−オキソ−１，３−ジアザ−スピロ−［４．５］−デカン誘導体 |
| EP3722284B1 (en) | 2016-01-13 | 2025-01-22 | Grünenthal GmbH | 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives |
| US20170197947A1 (en) | 2016-01-13 | 2017-07-13 | Gruenenthal Gmbh | 3-((Hetero-)Aryl)-Alkyl-8-Amino-2-Oxo-1,3-Diaza-Spiro-[4.5]-Decane Derivatives |
| US10961242B2 (en) * | 2017-05-17 | 2021-03-30 | Legochem Biosciences, Inc. | Compounds as autotaxin inhibitors and pharmaceutical compositions comprising the same |
| JP7446316B2 (ja) | 2019-01-11 | 2024-03-08 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 置換ピロリジンアミドｉｉｉ |
| CN110862395B (zh) * | 2019-11-13 | 2020-09-29 | 株洲千金药业股份有限公司 | 一种制备他达拉非重要杂质的原料化合物的制备方法 |
| US20240400537A1 (en) | 2023-04-25 | 2024-12-05 | Gruenenthal Gmbh | Cis-8-(3,5-difluorophenyl)-8-(dimethylamino)-1,3-diazaspiro[4.5]decan-2-one derivatives |
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| DE102006019597A1 (de) | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
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| WO2008092878A1 (en) * | 2007-02-01 | 2008-08-07 | Glaxo Group Limited | Glyt1 transporter inhibitors and uses thereof in treatment of neurological and neuropsychiatric disorders |
| JP5490677B2 (ja) | 2007-04-09 | 2014-05-14 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 不安及び鬱病の処置のためのｏｒｌ−１受容体リガンドとしての１，３，８−三置換−１，３，８−トリアザ−スピロ［４．５］デカン−４−オン誘導体 |
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| TW201038572A (en) | 2009-03-25 | 2010-11-01 | Gruenenthal Gmbh | Substituted spiro-amide compounds |
| WO2010151815A2 (en) | 2009-06-25 | 2010-12-29 | Abbott Laboratories | 3,9-diazaspiro[5,5]undecane amides and ureas and methods of use thereof |
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2017
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