JP2014521748A5 - - Google Patents
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- Publication number
- JP2014521748A5 JP2014521748A5 JP2014526199A JP2014526199A JP2014521748A5 JP 2014521748 A5 JP2014521748 A5 JP 2014521748A5 JP 2014526199 A JP2014526199 A JP 2014526199A JP 2014526199 A JP2014526199 A JP 2014526199A JP 2014521748 A5 JP2014521748 A5 JP 2014521748A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- oxo
- diazaspiro
- oxa
- 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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- -1 C 1 -C 4 alkoxy Chemical compound 0.000 claims 113
- 125000000753 cycloalkyl group Chemical group 0.000 claims 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 19
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 19
- 229910052805 deuterium Inorganic materials 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000004043 oxo group Chemical group O=* 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 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 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- 229910052717 sulfur Inorganic materials 0.000 claims 9
- 239000011593 sulfur Substances 0.000 claims 9
- 125000001425 triazolyl group Chemical group 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims 4
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 206010038389 Renal cancer Diseases 0.000 claims 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 206010017758 gastric cancer Diseases 0.000 claims 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000001041 indolyl group Chemical group 0.000 claims 4
- 201000010982 kidney cancer Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000005493 quinolyl group Chemical group 0.000 claims 4
- 201000011549 stomach cancer Diseases 0.000 claims 4
- KLMXZFVYNBASQE-UHFFFAOYSA-N 4-cyclopropyl-9-[(2-fluoro-4-quinolin-7-ylphenyl)-(1h-1,2,4-triazol-5-yl)methyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC1=CC(C=2C=C3N=CC=CC3=CC=2)=CC=C1C(C=1NC=NN=1)N(CC1)CCC1(OCC1=O)CN1C1CC1 KLMXZFVYNBASQE-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- YYFLDZZDOUDZQM-UHFFFAOYSA-N 3-[1-[[4-(3-phenylquinolin-2-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 YYFLDZZDOUDZQM-UHFFFAOYSA-N 0.000 claims 2
- UFIGOYSEDNHKGT-UHFFFAOYSA-N 3-fluoroquinoline Chemical compound C1=CC=CC2=CC(F)=CN=C21 UFIGOYSEDNHKGT-UHFFFAOYSA-N 0.000 claims 2
- AQCRFDKOKZGTDE-UHFFFAOYSA-N 3-methoxyquinoline Chemical compound C1=CC=CC2=CC(OC)=CN=C21 AQCRFDKOKZGTDE-UHFFFAOYSA-N 0.000 claims 2
- JACUAQUJJLQAQT-UHFFFAOYSA-N 4-cyclopropyl-9-[1-(2,6-difluoro-4-quinolin-7-ylphenyl)-2-hydroxyethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound FC=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(CO)N(CC1)CCC1(OCC1=O)CN1C1CC1 JACUAQUJJLQAQT-UHFFFAOYSA-N 0.000 claims 2
- PMWLYCQCNDUYNC-UHFFFAOYSA-N 4-cyclopropyl-9-[1-(2-fluoro-4-quinolin-7-ylphenyl)-2-hydroxyethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(CO)N(CC1)CCC1(OCC1=O)CN1C1CC1 PMWLYCQCNDUYNC-UHFFFAOYSA-N 0.000 claims 2
- NTRJVOBNGBYMKA-UHFFFAOYSA-N 4-cyclopropyl-9-[1-(2-fluoro-4-quinolin-7-ylphenyl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(C)N(CC1)CCC1(OCC1=O)CN1C1CC1 NTRJVOBNGBYMKA-UHFFFAOYSA-N 0.000 claims 2
- RNAAXKYOTPSFGV-UHFFFAOYSA-N 8-fluoroquinoline Chemical compound C1=CN=C2C(F)=CC=CC2=C1 RNAAXKYOTPSFGV-UHFFFAOYSA-N 0.000 claims 2
- ZLKGGEBOALGXJZ-UHFFFAOYSA-N 8-methoxyquinoline Chemical compound C1=CN=C2C(OC)=CC=CC2=C1 ZLKGGEBOALGXJZ-UHFFFAOYSA-N 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010014967 Ependymoma Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 208000032612 Glial tumor Diseases 0.000 claims 2
- 206010018338 Glioma Diseases 0.000 claims 2
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 claims 2
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 208000000172 Medulloblastoma Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000008383 Wilms tumor Diseases 0.000 claims 2
- 229960001171 acetohydroxamic acid Drugs 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=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
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 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
- 201000004653 inflammatory breast carcinoma Diseases 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
- 125000005956 isoquinolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 201000007270 liver cancer Diseases 0.000 claims 2
- 208000014018 liver neoplasm Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 201000008026 nephroblastoma Diseases 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 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
- 125000004076 pyridyl 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003831 tetrazolyl 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
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- AUOFURGFEWUADQ-UHFFFAOYSA-N 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-quinolin-7-ylphenyl)acetic acid Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(C(=O)O)N(CC1)CCC1(OCC1=O)CN1C1CC1 AUOFURGFEWUADQ-UHFFFAOYSA-N 0.000 claims 1
- KBXMSZHYPWVJDC-UHFFFAOYSA-N 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(4-quinolin-7-ylphenyl)acetic acid Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(C(=O)O)N(CC1)CCC1(OCC1=O)CN1C1CC1 KBXMSZHYPWVJDC-UHFFFAOYSA-N 0.000 claims 1
- QJSMKGKRGZPBPG-UHFFFAOYSA-N 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(4-quinolin-7-ylphenyl)acetonitrile Chemical compound O=C1COC2(CCN(CC2)C(C#N)C=2C=CC(=CC=2)C=2C=C3N=CC=CC3=CC=2)CN1C1CC1 QJSMKGKRGZPBPG-UHFFFAOYSA-N 0.000 claims 1
- GYVAUQIFVFTHLW-UHFFFAOYSA-N 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-[2-fluoro-4-(2-oxo-1h-quinolin-7-yl)phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=C(O)C=CC3=CC=2)C=C(F)C=1C(C(=O)N)N(CC1)CCC1(OCC1=O)CN1C1CC1 GYVAUQIFVFTHLW-UHFFFAOYSA-N 0.000 claims 1
- OZLQSDYARSBPRE-UHFFFAOYSA-N 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-[2-fluoro-4-(3-fluoroquinolin-7-yl)phenyl]acetamide Chemical compound C=1C=C(C=2C=C3N=CC(F)=CC3=CC=2)C=C(F)C=1C(C(=O)N)N(CC1)CCC1(OCC1=O)CN1C1CC1 OZLQSDYARSBPRE-UHFFFAOYSA-N 0.000 claims 1
- MNTAVEXBTONKEA-UHFFFAOYSA-N 2-[4-(3-chloroquinolin-7-yl)-2-fluorophenyl]-2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetamide Chemical compound C=1C=C(C=2C=C3N=CC(Cl)=CC3=CC=2)C=C(F)C=1C(C(=O)N)N(CC1)CCC1(OCC1=O)CN1C1CC1 MNTAVEXBTONKEA-UHFFFAOYSA-N 0.000 claims 1
- KNDOHCXNTLOCEK-UHFFFAOYSA-N 2-[4-(3-chloroquinolin-7-yl)-2-fluorophenyl]-2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetamide Chemical compound O1CC(=O)N(CC)CC11CCN(C(C(N)=O)C=2C(=CC(=CC=2)C=2C=C3N=CC(Cl)=CC3=CC=2)F)CC1 KNDOHCXNTLOCEK-UHFFFAOYSA-N 0.000 claims 1
- NIXSHEWEBYWJAX-UHFFFAOYSA-N 3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-quinolin-7-ylphenyl)propanamide Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(CC(=O)N)N(CC1)CCC1(OCC1=O)CN1C1CC1 NIXSHEWEBYWJAX-UHFFFAOYSA-N 0.000 claims 1
- RWTDADOILACFPR-UHFFFAOYSA-N 3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-quinolin-7-ylphenyl)propanoic acid Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(CC(=O)O)N(CC1)CCC1(OCC1=O)CN1C1CC1 RWTDADOILACFPR-UHFFFAOYSA-N 0.000 claims 1
- BQDYVCDTTGKUHT-UHFFFAOYSA-N 4-cyclopropyl-9-[1-(4-quinolin-7-ylphenyl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(C)N(CC1)CCC1(OCC1=O)CN1C1CC1 BQDYVCDTTGKUHT-UHFFFAOYSA-N 0.000 claims 1
- JDELODMNZUZMER-UHFFFAOYSA-N 4-cyclopropyl-9-[1-[2-fluoro-4-(4-methoxyphenyl)phenyl]ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C1=CC(OC)=CC=C1C(C=C1F)=CC=C1C(C)N1CCC2(OCC(=O)N(C3CC3)C2)CC1 JDELODMNZUZMER-UHFFFAOYSA-N 0.000 claims 1
- MKCLRYWQUNHZEV-UHFFFAOYSA-N 4-cyclopropyl-9-[2-hydroxy-1-(4-quinolin-7-ylphenyl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(CO)N(CC1)CCC1(OCC1=O)CN1C1CC1 MKCLRYWQUNHZEV-UHFFFAOYSA-N 0.000 claims 1
- BHIMESFIENCDNE-UHFFFAOYSA-N 4-cyclopropyl-9-[2-oxo-1-(4-quinolin-7-ylphenyl)propyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(C(=O)C)N(CC1)CCC1(OCC1=O)CN1C1CC1 BHIMESFIENCDNE-UHFFFAOYSA-N 0.000 claims 1
- 208000002966 Giant Cell Tumor of Bone Diseases 0.000 claims 1
- 208000007569 Giant Cell Tumors Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 201000011143 bone giant cell tumor Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LVMXTXRVXCHNQB-UHFFFAOYSA-N ethyl 2-(4-ethyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(2-fluoro-4-quinolin-7-ylphenyl)acetate Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(C(=O)OCC)N(CC1)CCC21CN(CC)C(=O)CO2 LVMXTXRVXCHNQB-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- WOPSXTHGVTZKEL-UHFFFAOYSA-N methyl 2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-[2-fluoro-4-(3-methoxyquinolin-7-yl)phenyl]acetate Chemical compound C=1C=C(C=2C=C3N=CC(OC)=CC3=CC=2)C=C(F)C=1C(C(=O)OC)N(CC1)CCC1(OCC1=O)CN1C1CC1 WOPSXTHGVTZKEL-UHFFFAOYSA-N 0.000 claims 1
- NVNZLOKUZZEDRR-UHFFFAOYSA-N methyl 3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(2-fluoro-4-quinolin-7-ylphenyl)propanoate Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=C(F)C=1C(CC(=O)OC)N(CC1)CCC1(OCC1=O)CN1C1CC1 NVNZLOKUZZEDRR-UHFFFAOYSA-N 0.000 claims 1
- GFPNHOLMUGOVTH-UHFFFAOYSA-N methyl 3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-3-(4-quinolin-7-ylphenyl)propanoate Chemical compound C=1C=C(C=2C=C3N=CC=CC3=CC=2)C=CC=1C(CC(=O)OC)N(CC1)CCC1(OCC1=O)CN1C1CC1 GFPNHOLMUGOVTH-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 208000013076 thyroid tumor Diseases 0.000 claims 1
- 0 CC**(CC(C(C)(*)C1)(C(*)(*)C*1C(C)(**)C(C)=CC(C)(C)C=C(**)*C=C)OC1)C1=O Chemical compound CC**(CC(C(C)(*)C1)(C(*)(*)C*1C(C)(**)C(C)=CC(C)(C)C=C(**)*C=C)OC1)C1=O 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161525402P | 2011-08-19 | 2011-08-19 | |
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| US20150329524A1 (en) | 2013-01-10 | 2015-11-19 | Glaxosmithkline Intellectual Property (No.2) Limited | Fatty acid synthase inhibitors |
| JP6616934B2 (ja) * | 2014-05-22 | 2019-12-04 | 株式会社 資生堂 | レナリドミドの光学分割方法 |
| TW201615643A (zh) * | 2014-06-02 | 2016-05-01 | 伊史帝夫博士實驗室股份有限公司 | 具有多重模式抗疼痛活性之１－氧雜－４，９－二氮雜螺十一烷化合物之烷基與芳基衍生物 |
| KR20180026459A (ko) | 2015-06-18 | 2018-03-12 | 세파론, 인코포레이티드 | 1,4-치환된 피페리딘 유도체 |
| WO2016205590A1 (en) | 2015-06-18 | 2016-12-22 | Cephalon, Inc. | Substituted 4-benzyl and 4-benzoyl piperidine derivatives |
| US10689398B2 (en) | 2015-10-23 | 2020-06-23 | Esteve Pharmaceuticals, S.A. | OXA-Diazaspiro compounds having activity against pain |
| SMT202200396T1 (it) | 2017-12-13 | 2022-11-18 | Lupin Ltd | Composti eterociclici biciclici sostituiti come inibitori di prmt5 |
| EP3636637A1 (en) * | 2018-10-10 | 2020-04-15 | Forma Therapeutics, Inc. | Inhibiting fatty acid synthase (fasn) |
| 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) |
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| US4353900A (en) | 1981-10-19 | 1982-10-12 | Syntex (U.S.A.) Inc. | 9-(Arylalkyl or aroylalkyl)-1-oxa-4,9-diazaspiro(5.5)undecan-3-ones |
| WO1997011940A1 (en) * | 1995-09-29 | 1997-04-03 | Eli Lilly And Company | Spiro compounds as inhibitors of fibrinogen-dependent platelet aggregation |
| ATE250604T1 (de) * | 1999-10-27 | 2003-10-15 | Millennium Pharm Inc | Pyridyl enthaltende spirocyclische verbindungen als inhibitoren der fibrinogen-abhängigen blutplättchen aggregation |
| WO2004037800A1 (en) * | 2002-10-22 | 2004-05-06 | Glaxo Group Limited | Aryloxyalkylamine derivates as h3 receptor ligands |
| WO2006105217A2 (en) * | 2005-03-31 | 2006-10-05 | Schering Corporation | Spirocyclic thrombin receptor antagonists |
| WO2007058322A1 (ja) * | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | 塩基性基を含有する化合物およびその用途 |
| TW200831092A (en) | 2006-12-21 | 2008-08-01 | Astrazeneca Ab | Therapeutic agents |
| WO2012064642A1 (en) | 2010-11-08 | 2012-05-18 | Glaxosmithkline Llc | Fatty acid synthase inhibitors |
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- 2012-08-16 US US14/238,418 patent/US9084794B2/en not_active Expired - Fee Related
- 2012-08-16 JP JP2014526199A patent/JP5964426B2/ja not_active Expired - Fee Related