IL303170A

IL303170A - 4-fluoro-(4-(4-benzyl)piperidin-1-yl)(2-(pyrimidin-4-yl)pyridin-3-yl)methanone derivatives and similar compounds as cyp46a1 inhibitors for the treatment of neurodegenerative disorders

4-fluoro-(4-(4-benzyl)piperidin-1-yl)(2-(pyrimidin-4-yl)pyridin-3-yl)methanone derivatives and similar compounds as cyp46a1 inhibitors for the treatment of neurodegenerative disorders

Info

Publication number: IL303170A
Authority: IL; Israel
Prior art keywords: compound; pct; disease; disorder; mmol
Prior art date: 2020-11-25

Application number

IL303170A

Other languages

English (en)

Hebrew (he)

Original Assignee

Sage Therapeutics Inc

Priority date

2020-11-25

Filing date

2021-11-24

Publication date

2023-07-01

2021-11-24 Application filed by Sage Therapeutics Inc filed Critical Sage Therapeutics Inc

2023-07-01 Publication of IL303170A publication Critical patent/IL303170A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 290
-1 2-(pyrimidin-4-yl)pyridin-3-yl Chemical group 0.000 title claims description 203
108091022871 Cholesterol 24-Hydroxylase Proteins 0.000 title claims description 50
102000020038 Cholesterol 24-Hydroxylase Human genes 0.000 title claims description 49
208000015122 neurodegenerative disease Diseases 0.000 title claims description 42
CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 title description 40
238000011282 treatment Methods 0.000 title description 33
239000003112 inhibitor Substances 0.000 title description 14
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 title 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 127
125000000623 heterocyclic group Chemical group 0.000 claims description 88
201000006417 multiple sclerosis Diseases 0.000 claims description 88
150000003839 salts Chemical class 0.000 claims description 88
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 86
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 81
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 74
201000010099 disease Diseases 0.000 claims description 70
238000000034 method Methods 0.000 claims description 58
208000035475 disorder Diseases 0.000 claims description 57
125000000753 cycloalkyl group Chemical group 0.000 claims description 51
230000005764 inhibitory process Effects 0.000 claims description 50
239000003814 drug Substances 0.000 claims description 49
125000004093 cyano group Chemical group *C#N 0.000 claims description 44
239000008194 pharmaceutical composition Substances 0.000 claims description 41
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 39
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 33
206010015037 epilepsy Diseases 0.000 claims description 31
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 30
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 29
208000020016 psychiatric disease Diseases 0.000 claims description 29
208000005392 Spasm Diseases 0.000 claims description 28
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
208000013257 developmental and epileptic encephalopathy Diseases 0.000 claims description 22
125000004076 pyridyl group Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 19
201000000980 schizophrenia Diseases 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
229910052701 rubidium Inorganic materials 0.000 claims description 18
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 17
208000029560 autism spectrum disease Diseases 0.000 claims description 17
125000002098 pyridazinyl group Chemical group 0.000 claims description 16
125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
208000007101 Muscle Cramp Diseases 0.000 claims description 15
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
208000024827 Alzheimer disease Diseases 0.000 claims description 13
208000018737 Parkinson disease Diseases 0.000 claims description 13
125000003373 pyrazinyl group Chemical group 0.000 claims description 13
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
208000023105 Huntington disease Diseases 0.000 claims description 12
206010008118 cerebral infarction Diseases 0.000 claims description 12
208000010877 cognitive disease Diseases 0.000 claims description 12
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 12
125000001425 triazolyl group Chemical group 0.000 claims description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
208000030886 Traumatic Brain injury Diseases 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000004306 triazinyl group Chemical group 0.000 claims description 11
208000010412 Glaucoma Diseases 0.000 claims description 10
208000028017 Psychotic disease Diseases 0.000 claims description 10
208000026106 cerebrovascular disease Diseases 0.000 claims description 10
230000009529 traumatic brain injury Effects 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000000842 isoxazolyl group Chemical group 0.000 claims description 9
208000027061 mild cognitive impairment Diseases 0.000 claims description 9
125000002971 oxazolyl group Chemical group 0.000 claims description 9
125000000168 pyrrolyl group Chemical group 0.000 claims description 9
208000022610 schizoaffective disease Diseases 0.000 claims description 9
125000003831 tetrazolyl group Chemical group 0.000 claims description 9
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
208000024254 Delusional disease Diseases 0.000 claims description 8
208000002851 paranoid schizophrenia Diseases 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
229910052702 rhenium Inorganic materials 0.000 claims description 8
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 8
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Chemical group C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 3
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims 13
239000000203 mixture Substances 0.000 description 354
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 157
239000000243 solution Substances 0.000 description 141
235000019439 ethyl acetate Nutrition 0.000 description 113
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 103
239000007832 Na2SO4 Substances 0.000 description 102
229910052938 sodium sulfate Inorganic materials 0.000 description 102
235000011152 sodium sulphate Nutrition 0.000 description 102
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 97
239000012044 organic layer Substances 0.000 description 97
238000005160 1H NMR spectroscopy Methods 0.000 description 95
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 93
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
239000012267 brine Substances 0.000 description 89
229910001868 water Inorganic materials 0.000 description 89
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 88
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 77
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 74
101150041968 CDC13 gene Proteins 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 63
229910052757 nitrogen Inorganic materials 0.000 description 62
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 54
125000000217 alkyl group Chemical group 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
125000005843 halogen group Chemical group 0.000 description 49
125000004452 carbocyclyl group Chemical group 0.000 description 47
238000006243 chemical reaction Methods 0.000 description 47
125000005842 heteroatom Chemical group 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 46
238000003786 synthesis reaction Methods 0.000 description 45
230000015572 biosynthetic process Effects 0.000 description 42
125000003118 aryl group Chemical group 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
239000004698 Polyethylene Substances 0.000 description 38
238000010898 silica gel chromatography Methods 0.000 description 38
238000004293 19F NMR spectroscopy Methods 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
208000005809 status epilepticus Diseases 0.000 description 35
DNUSEHOQLBQBRR-UHFFFAOYSA-N 2-pyrimidin-4-ylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C1=CC=NC=N1 DNUSEHOQLBQBRR-UHFFFAOYSA-N 0.000 description 33
125000001072 heteroaryl group Chemical group 0.000 description 33
125000001424 substituent group Chemical group 0.000 description 33
125000004432 carbon atom Chemical group C* 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 30
229910000041 hydrogen chloride Inorganic materials 0.000 description 30
235000017557 sodium bicarbonate Nutrition 0.000 description 30
229910000030 sodium bicarbonate Inorganic materials 0.000 description 30
238000002953 preparative HPLC Methods 0.000 description 28
229940079593 drug Drugs 0.000 description 27
238000003756 stirring Methods 0.000 description 27
229910017906 NH3H2O Inorganic materials 0.000 description 26
238000001474 liquid chromatography-evaporative light scattering detection Methods 0.000 description 26
239000003795 chemical substances by application Substances 0.000 description 23
229920006395 saturated elastomer Polymers 0.000 description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 20
239000005457 ice water Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000007821 HATU Substances 0.000 description 18
235000012538 ammonium bicarbonate Nutrition 0.000 description 18
230000004770 neurodegeneration Effects 0.000 description 18
229910052760 oxygen Inorganic materials 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
239000004480 active ingredient Substances 0.000 description 17
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239000001301 oxygen Chemical group 0.000 description 17
208000024891 symptom Diseases 0.000 description 17
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 17
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
238000002360 preparation method Methods 0.000 description 16
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
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239000000546 pharmaceutical excipient Substances 0.000 description 15
206010010904 Convulsion Diseases 0.000 description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
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238000004808 supercritical fluid chromatography Methods 0.000 description 14
125000003342 alkenyl group Chemical group 0.000 description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
239000011593 sulfur Chemical group 0.000 description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
235000019270 ammonium chloride Nutrition 0.000 description 12
238000004128 high performance liquid chromatography Methods 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
108090000623 proteins and genes Proteins 0.000 description 12
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
239000002253 acid Substances 0.000 description 11
125000002947 alkylene group Chemical group 0.000 description 11
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 11
239000011777 magnesium Substances 0.000 description 11
229960005486 vaccine Drugs 0.000 description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
229940124597 therapeutic agent Drugs 0.000 description 10
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 9
235000019345 sodium thiosulphate Nutrition 0.000 description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
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238000010511 deprotection reaction Methods 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
238000001990 intravenous administration Methods 0.000 description 6
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