MD3976597T2 - Inhibitori cu molecula mică ai kinazei care induce NF-kB - Google Patents

Info

Publication number

MD3976597T2

MD3976597T2 MDE20220374T MDE20220374T MD3976597T2 MD 3976597 T2 MD3976597 T2 MD 3976597T2 MD E20220374 T MDE20220374 T MD E20220374T MD E20220374 T MDE20220374 T MD E20220374T MD 3976597 T2 MD3976597 T2 MD 3976597T2

Authority

MD

Moldova

Prior art keywords

ethynyl

phenyl

pyrimidin

hydroxy

amino

Prior art date

2019-05-31

Links

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• 239000003112 inhibitor Substances 0.000 title description 8
• 230000001939 inductive effect Effects 0.000 title description 4
• 108091000080 Phosphotransferase Proteins 0.000 title description 2
• 102000020233 phosphotransferase Human genes 0.000 title description 2
• 150000003384 small molecules Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 227
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 47
• 238000000034 method Methods 0.000 claims abstract description 25
• 208000035475 disorder Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 23
• 238000011282 treatment Methods 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 6
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 6
• 208000008589 Obesity Diseases 0.000 claims abstract description 4
• 206010037575 Pustular psoriasis Diseases 0.000 claims abstract description 4
• 201000011510 cancer Diseases 0.000 claims abstract description 4
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 4
• 208000002557 hidradenitis Diseases 0.000 claims abstract description 4
• 201000007162 hidradenitis suppurativa Diseases 0.000 claims abstract description 4
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 4
• 235000020824 obesity Nutrition 0.000 claims abstract description 4
• 201000010914 pustulosis of palm and sole Diseases 0.000 claims abstract description 4
• 208000011797 pustulosis palmaris et plantaris Diseases 0.000 claims abstract description 4
• 150000003254 radicals Chemical class 0.000 claims description 141
• 150000003839 salts Chemical class 0.000 claims description 118
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
• 102000019148 NF-kappaB-inducing kinase activity proteins Human genes 0.000 claims description 54
• 108040008091 NF-kappaB-inducing kinase activity proteins Proteins 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• RLDYBDXGTWEFJZ-NRFANRHFSA-N NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O RLDYBDXGTWEFJZ-NRFANRHFSA-N 0.000 claims description 15
• FKVSVHKPLBGNQS-FQEVSTJZSA-N NC1=NC=CC2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC1=NC=CC2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O FKVSVHKPLBGNQS-FQEVSTJZSA-N 0.000 claims description 13
• IRWCCQNHZKTMBC-HXUWFJFHSA-N NC1=NC=NC2=C1N=C(N=C2C)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O Chemical compound NC1=NC=NC2=C1N=C(N=C2C)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O IRWCCQNHZKTMBC-HXUWFJFHSA-N 0.000 claims description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 12
• SYDSHTZOHFOVFO-VXQWRZFRSA-N (3R)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O SYDSHTZOHFOVFO-VXQWRZFRSA-N 0.000 claims description 11
• CXTMHGLFUDUJLE-IBGZPJMESA-N NC=1C2=C(N=CN=1)SC(=N2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=CN=1)SC(=N2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O CXTMHGLFUDUJLE-IBGZPJMESA-N 0.000 claims description 11
• SYDSHTZOHFOVFO-WRLIODQTSA-N (3S)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O SYDSHTZOHFOVFO-WRLIODQTSA-N 0.000 claims description 10
• 229910052805 deuterium Inorganic materials 0.000 claims description 10
• 230000001404 mediated effect Effects 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• DZTZPLQFQOSNIE-FQEVSTJZSA-N NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)Cl Chemical compound NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)Cl DZTZPLQFQOSNIE-FQEVSTJZSA-N 0.000 claims description 8
• LJGVSTKZALQANF-NRFANRHFSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C LJGVSTKZALQANF-NRFANRHFSA-N 0.000 claims description 8
• CIRHIKZELFNGMU-NRFANRHFSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)NC Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)NC CIRHIKZELFNGMU-NRFANRHFSA-N 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• FYMBEUHVWDUXRB-QFIPXVFZSA-N NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)CC Chemical compound NC1=NC=C(C2=C1N=C(N=C2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)CC FYMBEUHVWDUXRB-QFIPXVFZSA-N 0.000 claims description 7
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
• MFUBQMZDXKAVSA-NRFANRHFSA-N NC1=NC=NC2=CC=C(C=C12)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC1=NC=NC2=CC=C(C=C12)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O MFUBQMZDXKAVSA-NRFANRHFSA-N 0.000 claims description 6
• RLDYBDXGTWEFJZ-OAQYLSRUSA-N NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=C(N=1)C)C=CC(=N2)C=1C=C(C=CC=1)C#C[C@@]1(C(N(CC1)C)=O)O RLDYBDXGTWEFJZ-OAQYLSRUSA-N 0.000 claims description 6
• PVFOYAHXMWIDAG-IBGZPJMESA-N NC=1C2=C(N=CN=1)C=NC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=CN=1)C=NC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O PVFOYAHXMWIDAG-IBGZPJMESA-N 0.000 claims description 6
• BMGCLNUWPNEMRQ-NRFANRHFSA-N NC=1C2=C(N=CN=1)CCN(C2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O Chemical compound NC=1C2=C(N=CN=1)CCN(C2)C=1C=C(C=CC=1C)C#C[C@]1(C(N(CC1)C)=O)O BMGCLNUWPNEMRQ-NRFANRHFSA-N 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• LZAUFLQEOZGLBG-WNBCCLPKSA-N (3R)-3-[2-[3-(2-deuterio-8-ethyl-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)CC LZAUFLQEOZGLBG-WNBCCLPKSA-N 0.000 claims description 5
• DYUIILDYMFTFPP-MUPYNFCXSA-N (3R)-3-[2-[3-(8-cyclopentyl-2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1-methylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C1CCCC1 DYUIILDYMFTFPP-MUPYNFCXSA-N 0.000 claims description 5
• 208000009329 Graft vs Host Disease Diseases 0.000 claims description 5
• IJKFNPMPERZKIV-QHCPKHFHSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C1CC1 Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C1CC1 IJKFNPMPERZKIV-QHCPKHFHSA-N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 208000024908 graft versus host disease Diseases 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• LJGVSTKZALQANF-SHKVTDPKSA-N NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C([2H])([2H])[2H] Chemical compound NC=1C2=C(N=CN=1)C(=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N(CC1)C)=O)O)C([2H])([2H])[2H] LJGVSTKZALQANF-SHKVTDPKSA-N 0.000 claims description 3
• 201000011152 Pemphigus Diseases 0.000 claims description 3
• 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 201000001976 pemphigus vulgaris Diseases 0.000 claims description 3
• DRSHHHLTFNAOGN-KIKSHYFBSA-N (3R,5R)-3-[2-[3-(2-deuterio-4-imino-1H-pyrido[3,2-d]pyrimidin-6-yl)phenyl]ethynyl]-3-hydroxy-1,5-dimethylpyrrolidin-2-one Chemical compound NC=1C2=C(N=C(N=1)[2H])C=CC(=N2)C=1C=C(C=CC=1)C#C[C@]1(C(N([C@@H](C1)C)C)=O)O DRSHHHLTFNAOGN-KIKSHYFBSA-N 0.000 claims 1
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
• 210000003719 b-lymphocyte Anatomy 0.000 abstract description 4
• 206010025323 Lymphomas Diseases 0.000 abstract description 2
• 206010035226 Plasma cell myeloma Diseases 0.000 abstract description 2
• 208000032839 leukemia Diseases 0.000 abstract description 2
• 230000036210 malignancy Effects 0.000 abstract description 2
• 201000000050 myeloid neoplasm Diseases 0.000 abstract description 2
• 230000002265 prevention Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 511
• 239000000203 mixture Substances 0.000 description 340
• 239000007787 solid Substances 0.000 description 276
• 239000000243 solution Substances 0.000 description 197
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
• 238000000132 electrospray ionisation Methods 0.000 description 177
• 235000019439 ethyl acetate Nutrition 0.000 description 172
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 152
• 238000005160 1H NMR spectroscopy Methods 0.000 description 120
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 116
• -1 (R)-3-[2-[3-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-4-methyl-phenyl]ethynyl]-3-hydroxy-1-methyl-pyrrolidin- Chemical compound 0.000 description 113
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 110
• 238000003818 flash chromatography Methods 0.000 description 102
• 239000012044 organic layer Substances 0.000 description 89
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 88
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 73
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 70
• 239000012267 brine Substances 0.000 description 69
• 238000001914 filtration Methods 0.000 description 69
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 69
• 239000003208 petroleum Substances 0.000 description 68
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
• 229920006395 saturated elastomer Polymers 0.000 description 50
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 45
• 239000012299 nitrogen atmosphere Substances 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 229910052938 sodium sulfate Inorganic materials 0.000 description 33
• 235000011152 sodium sulphate Nutrition 0.000 description 33
• 238000003756 stirring Methods 0.000 description 32
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 31
• 239000007832 Na2SO4 Substances 0.000 description 29
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 29
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
• 239000003921 oil Substances 0.000 description 27
• 235000019198 oils Nutrition 0.000 description 27
• 235000017557 sodium bicarbonate Nutrition 0.000 description 27
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
• 239000000725 suspension Substances 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 25
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000000284 extract Substances 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
• 239000011541 reaction mixture Substances 0.000 description 23
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
• 125000001424 substituent group Chemical group 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 19
• 235000019270 ammonium chloride Nutrition 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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• 238000000746 purification Methods 0.000 description 15
• 238000001816 cooling Methods 0.000 description 14
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 14
• 238000004808 supercritical fluid chromatography Methods 0.000 description 14
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 13
• 239000012071 phase Substances 0.000 description 13
• 230000002829 reductive effect Effects 0.000 description 13
• SECXISVLQFMRJM-FIBGUPNXSA-N 1-(trideuteriomethyl)pyrrolidin-2-one Chemical compound [2H]C([2H])([2H])N1CCCC1=O SECXISVLQFMRJM-FIBGUPNXSA-N 0.000 description 12
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• 239000013543 active substance Substances 0.000 description 12
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
• 229910000027 potassium carbonate Inorganic materials 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• 238000000926 separation method Methods 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 239000005909 Kieselgur Substances 0.000 description 11
• 238000010438 heat treatment Methods 0.000 description 11
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• VUHVCMJKJLGRJX-UHFFFAOYSA-N tert-butyl n-(2-chloropyridin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CN=C1Cl VUHVCMJKJLGRJX-UHFFFAOYSA-N 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 230000037361 pathway Effects 0.000 description 10
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• 230000001225 therapeutic effect Effects 0.000 description 10
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
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