JP2013542960A5 - - Google Patents
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- Publication number
- JP2013542960A5 JP2013542960A5 JP2013537904A JP2013537904A JP2013542960A5 JP 2013542960 A5 JP2013542960 A5 JP 2013542960A5 JP 2013537904 A JP2013537904 A JP 2013537904A JP 2013537904 A JP2013537904 A JP 2013537904A JP 2013542960 A5 JP2013542960 A5 JP 2013542960A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- sulfonyl
- diazaspiro
- oxa
- alkyl
- 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.)
- Pending
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- -1 C 1 -C 4 alkoxy Chemical compound 0.000 claims 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims 44
- 229910052736 halogen Inorganic materials 0.000 claims 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- IEQSBUAMMARFCO-UHFFFAOYSA-N 4-cyclopropyl-9-(2-fluoro-4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C=C3N=CC=CC3=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 IEQSBUAMMARFCO-UHFFFAOYSA-N 0.000 claims 2
- VHEFCIONPXNYGE-UHFFFAOYSA-N 4-cyclopropyl-9-(4-isoquinolin-6-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3C=CN=CC3=CC=2)CN1C1CC1 VHEFCIONPXNYGE-UHFFFAOYSA-N 0.000 claims 2
- OGGOWHOQMIINAZ-UHFFFAOYSA-N 4-cyclopropyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1CC1 OGGOWHOQMIINAZ-UHFFFAOYSA-N 0.000 claims 2
- XGPGVXWKVITNPQ-UHFFFAOYSA-N 4-cyclopropyl-9-[2-fluoro-4-(1h-indazol-5-yl)phenyl]sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C=C3C=NNC3=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 XGPGVXWKVITNPQ-UHFFFAOYSA-N 0.000 claims 2
- SXOKNWOSOOZNPR-UHFFFAOYSA-N 9-[4-(1,3-benzothiazol-5-yl)-2-fluorophenyl]sulfonyl-4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C=C3N=CSC3=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 SXOKNWOSOOZNPR-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 2
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- JKJUOFYGPOINCA-UHFFFAOYSA-N 1-[3-oxo-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl]cyclopropane-1-carbonitrile Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1(C#N)CC1 JKJUOFYGPOINCA-UHFFFAOYSA-N 0.000 claims 1
- KKTFNTDYEBJDKV-UHFFFAOYSA-N 1-[3-oxo-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl]cyclopropane-1-carboxamide Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)OCC(=O)N1C1(C(=O)N)CC1 KKTFNTDYEBJDKV-UHFFFAOYSA-N 0.000 claims 1
- IOCKXBKEVSYCSW-UHFFFAOYSA-N 1-[6-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]-1h-indazol-3-yl]-3-methylurea Chemical compound C=1C=C2C(NC(=O)NC)=NNC2=CC=1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 IOCKXBKEVSYCSW-UHFFFAOYSA-N 0.000 claims 1
- SGAHVIAOLVTASZ-UHFFFAOYSA-N 2-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]thieno[3,2-b]pyridine-6-carboxamide Chemical compound S1C2=CC(C(=O)N)=CN=C2C=C1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 SGAHVIAOLVTASZ-UHFFFAOYSA-N 0.000 claims 1
- UQGIVLGWIVLABY-UHFFFAOYSA-N 2-cyclopropyl-9-(4-quinolin-7-ylphenyl)sulfonyl-2,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1CCC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1CC1 UQGIVLGWIVLABY-UHFFFAOYSA-N 0.000 claims 1
- SCTOXQQLCCTTGT-UHFFFAOYSA-N 3-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N2CCC3(CC2)OCC(=O)N(C2CC2)C3)=C1 SCTOXQQLCCTTGT-UHFFFAOYSA-N 0.000 claims 1
- IGRSEAWPYLFQKZ-UHFFFAOYSA-N 3-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N2CCC3(CC2)OCC(=O)N(C2CC2)C3)=C1 IGRSEAWPYLFQKZ-UHFFFAOYSA-N 0.000 claims 1
- WQMHNOFTTIECSS-UHFFFAOYSA-N 4-(1-methylcyclobutyl)-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)OCC(=O)N1C1(C)CCC1 WQMHNOFTTIECSS-UHFFFAOYSA-N 0.000 claims 1
- QQPVAPGCXRFLIM-UHFFFAOYSA-N 4-(1-methylcyclopropyl)-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)OCC(=O)N1C1(C)CC1 QQPVAPGCXRFLIM-UHFFFAOYSA-N 0.000 claims 1
- XAAXWUSZWCDYTI-UHFFFAOYSA-N 4-(2-methoxyethyl)-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O1CC(=O)N(CCOC)CC11CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CC1 XAAXWUSZWCDYTI-UHFFFAOYSA-N 0.000 claims 1
- KWUFDPPTJKWREY-UHFFFAOYSA-N 4-(furan-2-ylmethyl)-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1CC1=CC=CO1 KWUFDPPTJKWREY-UHFFFAOYSA-N 0.000 claims 1
- YSBFAESHTFUOGJ-UHFFFAOYSA-N 4-(oxetan-3-yl)-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1COC1 YSBFAESHTFUOGJ-UHFFFAOYSA-N 0.000 claims 1
- LYRYZFWSKRNUBG-UHFFFAOYSA-N 4-[1-(hydroxymethyl)cyclopropyl]-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)OCC(=O)N1C1(CO)CC1 LYRYZFWSKRNUBG-UHFFFAOYSA-N 0.000 claims 1
- WMVUIELQWYFKDE-UHFFFAOYSA-N 4-[1-(hydroxymethyl)cyclopropyl]-9-[4-(3-methoxyquinolin-7-yl)phenyl]sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1=CC2=CC(OC)=CN=C2C=C1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1(CO)CC1 WMVUIELQWYFKDE-UHFFFAOYSA-N 0.000 claims 1
- BWNLFGVJHBDVBD-UHFFFAOYSA-N 4-[1-(methoxymethyl)cyclopropyl]-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)OCC(=O)N1C1(COC)CC1 BWNLFGVJHBDVBD-UHFFFAOYSA-N 0.000 claims 1
- PWHYXPQCZXHUEN-UHFFFAOYSA-N 4-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]-3-fluorophenyl]benzonitrile Chemical compound FC1=CC(C=2C=CC(=CC=2)C#N)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 PWHYXPQCZXHUEN-UHFFFAOYSA-N 0.000 claims 1
- HLOGNKVVHRNTFT-UHFFFAOYSA-N 4-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]-2-methylbenzonitrile Chemical compound C1=C(C#N)C(C)=CC(C=2C=CC(=CC=2)S(=O)(=O)N2CCC3(CC2)OCC(=O)N(C2CC2)C3)=C1 HLOGNKVVHRNTFT-UHFFFAOYSA-N 0.000 claims 1
- JUGZRHBBAVDJCP-UHFFFAOYSA-N 4-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]benzonitrile Chemical compound C1N(C2CC2)C(=O)COC1(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 JUGZRHBBAVDJCP-UHFFFAOYSA-N 0.000 claims 1
- HOKDMQRIALWUJL-UHFFFAOYSA-N 4-benzyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1CC1=CC=CC=C1 HOKDMQRIALWUJL-UHFFFAOYSA-N 0.000 claims 1
- YPWZTZZKLKASLG-UHFFFAOYSA-N 4-cyclobutyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1COC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1CCC1 YPWZTZZKLKASLG-UHFFFAOYSA-N 0.000 claims 1
- ZYTKGBLPKCQUJC-UHFFFAOYSA-N 4-cyclopropyl-1-methyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1,4,9-triazaspiro[5.5]undecan-3-one Chemical compound C1C2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)N(C)CC(=O)N1C1CC1 ZYTKGBLPKCQUJC-UHFFFAOYSA-N 0.000 claims 1
- BKNCFYTYIBOWSC-UHFFFAOYSA-N 4-cyclopropyl-10-methyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)C(C)CC1(OCC1=O)CN1C1CC1 BKNCFYTYIBOWSC-UHFFFAOYSA-N 0.000 claims 1
- KOOPLJSDYQGLCU-UHFFFAOYSA-N 4-cyclopropyl-11-fluoro-9-(4-imidazo[1,2-a]pyridin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1CN(S(=O)(=O)C=2C=CC(=CC=2)C2=CC3=NC=CN3C=C2)CCC1(OCC1=O)CN1C1CC1 KOOPLJSDYQGLCU-UHFFFAOYSA-N 0.000 claims 1
- WTUJCWZTEHENHS-UHFFFAOYSA-N 4-cyclopropyl-11-fluoro-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CCC1(OCC1=O)CN1C1CC1 WTUJCWZTEHENHS-UHFFFAOYSA-N 0.000 claims 1
- LSURXAVWXPTLKP-UHFFFAOYSA-N 4-cyclopropyl-11-methyl-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound CC1CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CCC1(OCC1=O)CN1C1CC1 LSURXAVWXPTLKP-UHFFFAOYSA-N 0.000 claims 1
- OGGOWHOQMIINAZ-DBTGQBASSA-N 4-cyclopropyl-2,2,5,5-tetradeuterio-9-(4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound O=C1C([2H])([2H])OC2(CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)C([2H])([2H])N1C1CC1 OGGOWHOQMIINAZ-DBTGQBASSA-N 0.000 claims 1
- JWGZWGICDZONRC-UHFFFAOYSA-N 4-cyclopropyl-9-(2,3-dimethyl-4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C(C)=C(C)C=1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 JWGZWGICDZONRC-UHFFFAOYSA-N 0.000 claims 1
- ICDPARPQOGUITJ-UHFFFAOYSA-N 4-cyclopropyl-9-(2,5-difluoro-4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC=1C=C(C=2C=C3N=CC=CC3=CC=2)C(F)=CC=1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 ICDPARPQOGUITJ-UHFFFAOYSA-N 0.000 claims 1
- LDUKTLFHWBUIBP-UHFFFAOYSA-N 4-cyclopropyl-9-(2-fluoro-4-quinolin-5-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C3=CC=CN=C3C=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 LDUKTLFHWBUIBP-UHFFFAOYSA-N 0.000 claims 1
- GOESEFQHHGAYHW-UHFFFAOYSA-N 4-cyclopropyl-9-(2-fluoro-4-quinolin-6-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C=C3C=CC=NC3=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 GOESEFQHHGAYHW-UHFFFAOYSA-N 0.000 claims 1
- VNLKLRBSLZXOJP-UHFFFAOYSA-N 4-cyclopropyl-9-(2-methyl-4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound CC1=CC(C=2C=C3N=CC=CC3=CC=2)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 VNLKLRBSLZXOJP-UHFFFAOYSA-N 0.000 claims 1
- DYHCAEWSIXLUTR-UHFFFAOYSA-N 4-cyclopropyl-9-(3,5-difluoro-4-quinolin-7-ylphenyl)sulfonyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C(F)=C(C=2C=C3N=CC=CC3=CC=2)C(F)=CC=1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 DYHCAEWSIXLUTR-UHFFFAOYSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
- ZFHWXXCNUCZDNQ-UHFFFAOYSA-N n-[5-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]-1-methylindazol-3-yl]methanesulfonamide Chemical compound C=1C=C2N(C)N=C(NS(C)(=O)=O)C2=CC=1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 ZFHWXXCNUCZDNQ-UHFFFAOYSA-N 0.000 claims 1
- CFGHSSHAOOZQBT-UHFFFAOYSA-N n-[7-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]quinolin-3-yl]acetamide Chemical compound C1=CC2=CC(NC(=O)C)=CN=C2C=C1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 CFGHSSHAOOZQBT-UHFFFAOYSA-N 0.000 claims 1
- PGGGJNBSMCZLGZ-UHFFFAOYSA-N n-[7-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]quinolin-3-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(C=C1C=C2)=CN=C1C=C2C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 PGGGJNBSMCZLGZ-UHFFFAOYSA-N 0.000 claims 1
- SRGZJJNKPNEGME-UHFFFAOYSA-N n-[7-[4-[(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)sulfonyl]phenyl]quinolin-3-yl]methanesulfonamide Chemical compound C1=CC2=CC(NS(=O)(=O)C)=CN=C2C=C1C(C=C1)=CC=C1S(=O)(=O)N(CC1)CCC1(OCC1=O)CN1C1CC1 SRGZJJNKPNEGME-UHFFFAOYSA-N 0.000 claims 1
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| US41111010P | 2010-11-08 | 2010-11-08 | |
| US61/411,110 | 2010-11-08 | ||
| PCT/US2011/059563 WO2012064642A1 (en) | 2010-11-08 | 2011-11-07 | Fatty acid synthase inhibitors |
Publications (2)
| Publication Number | Publication Date |
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| JP2013542960A JP2013542960A (ja) | 2013-11-28 |
| JP2013542960A5 true JP2013542960A5 (https=) | 2014-10-23 |
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| US (1) | US20130237535A1 (https=) |
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| JP (1) | JP2013542960A (https=) |
| WO (1) | WO2012064642A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5964426B2 (ja) * | 2011-08-19 | 2016-08-03 | グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー２、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｎｏ．２ Ｌｉｍｉｔｅｄ | 脂肪酸シンターゼ阻害剤 |
| WO2013177253A2 (en) * | 2012-05-22 | 2013-11-28 | Glaxosmithkline Llc | Fatty acid synthase inhibitors |
| AR092211A1 (es) | 2012-09-24 | 2015-04-08 | Merck Patent Ges Mit Beschränkter Haftung | Derivados de hidropirrolopirrol |
| ES2651331T3 (es) | 2013-01-10 | 2018-01-25 | Glaxosmithkline Intellectual Property (No. 2) Limited | Inhibidores de la sintasa de ácidos grasos |
| SG10201707409PA (en) | 2013-03-13 | 2017-10-30 | Forma Therapeutics Inc | Novel compounds and compositions for inhibition of fasn |
| ES2849951T3 (es) | 2015-06-18 | 2021-08-24 | 89Bio Ltd | Derivados de piperidina 4-bencil y 4-benzoil sustituidos |
| EA201890086A1 (ru) | 2015-06-18 | 2018-06-29 | Сефалон, Инк. | 1,4-замещенные производные пиперидина |
| JP7007374B2 (ja) | 2016-09-23 | 2022-01-24 | ノバルティス アーゲー | 腱及び／又は靭帯損傷に使用するためのインダゾール化合物 |
| JOP20190053A1 (ar) | 2016-09-23 | 2019-03-21 | Novartis Ag | مركبات أزا إندازول للاستخدام في إصابات الأوتار و/ أو الرباط |
| CN107628968B (zh) * | 2017-10-10 | 2019-09-06 | 北京汇康博源医药科技有限公司 | 一种简便合成1-氨基-1-腈基-环丙烷的方法 |
| CN112154561B (zh) | 2018-05-30 | 2025-10-14 | 罗伯特·博世有限公司 | 包括具有由支撑框架支撑的边缘绝缘装置的双极电池单元的电池 |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| US10793554B2 (en) | 2018-10-29 | 2020-10-06 | Forma Therapeutics, Inc. | Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone |
| CN114286676A (zh) * | 2019-08-22 | 2022-04-05 | 密歇根大学董事会 | 治疗kras相关癌症的方法 |
| CN111574414A (zh) * | 2020-05-20 | 2020-08-25 | 上海毕得医药科技有限公司 | 一种4-溴-2-甲氧基苯磺酰氯的合成方法 |
| US20250084062A1 (en) * | 2021-12-27 | 2025-03-13 | Astellas Pharma Inc. | Substituted quinoline derivative |
| CN116478158A (zh) * | 2023-04-26 | 2023-07-25 | 湖南警察学院 | 一种制备螺环化合物的方法 |
| US20250375429A1 (en) | 2024-05-29 | 2025-12-11 | Smarter Not Harder, Inc. | Obligate pairing of orthosteric and non-orthosteric gaba ligands in pharmaceutical formulations |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE69633245T2 (de) * | 1995-09-29 | 2005-09-08 | Eli Lilly And Co., Indianapolis | Spiroverbindungen als Inhibitoren der Fibrinogen-abhängigen Blutplättchenaggregation |
| CO5180605A1 (es) * | 1999-06-23 | 2002-07-30 | Smithkline Beecham Corp | Compuestos de indol |
| ATE250604T1 (de) * | 1999-10-27 | 2003-10-15 | Millennium Pharm Inc | Pyridyl enthaltende spirocyclische verbindungen als inhibitoren der fibrinogen-abhängigen blutplättchen aggregation |
| US7498323B2 (en) * | 2003-04-18 | 2009-03-03 | Ono Pharmaceuticals Co., Ltd. | Spiro-piperidine compounds and medicinal use thereof |
| WO2006006490A1 (ja) * | 2004-07-08 | 2006-01-19 | Ono Pharmaceutical Co., Ltd. | スピロ化合物 |
| TW200831092A (en) * | 2006-12-21 | 2008-08-01 | Astrazeneca Ab | Therapeutic agents |
| WO2008088692A2 (en) * | 2007-01-12 | 2008-07-24 | Merck & Co., Inc. | Spirochromanon derivatives |
| CN101835779B (zh) * | 2007-10-26 | 2014-01-29 | 霍夫曼-拉罗奇有限公司 | 作为pi3激酶抑制剂的嘌呤衍生物 |
| US8450350B2 (en) * | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
-
2011
- 2011-11-07 JP JP2013537904A patent/JP2013542960A/ja active Pending
- 2011-11-07 EP EP11839403.0A patent/EP2637660A4/en not_active Withdrawn
- 2011-11-07 WO PCT/US2011/059563 patent/WO2012064642A1/en not_active Ceased
- 2011-11-07 US US13/883,877 patent/US20130237535A1/en not_active Abandoned
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