TWI591064B - ２－吡啶酮化合物 - Google Patents

Info

Publication number

TWI591064B

TWI591064B TW102141288A TW102141288A TWI591064B TW I591064 B TWI591064 B TW I591064B TW 102141288 A TW102141288 A TW 102141288A TW 102141288 A TW102141288 A TW 102141288A TW I591064 B TWI591064 B TW I591064B

Authority

TW

Taiwan

Prior art keywords

compound

cyclopropyl

phenyl

ethyl

difluoroethyl

Prior art date

2012-11-13

Links

• Espacenet
• Global Dossier
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• -1 2-pyridone compound Chemical class 0.000 title claims description 48
• 150000001875 compounds Chemical class 0.000 claims description 168
• 239000002904 solvent Substances 0.000 claims description 41
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
• 239000013078 crystal Substances 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 238000004519 manufacturing process Methods 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 206010012601 diabetes mellitus Diseases 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• 239000008280 blood Substances 0.000 claims description 16
• 210000004369 blood Anatomy 0.000 claims description 16
• 239000000126 substance Substances 0.000 claims description 16
• 230000004913 activation Effects 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 229940079593 drug Drugs 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• 238000000862 absorption spectrum Methods 0.000 claims description 9
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 9
• 239000012453 solvate Substances 0.000 claims description 9
• 229910017488 Cu K Inorganic materials 0.000 claims description 8
• 229910017541 Cu-K Inorganic materials 0.000 claims description 8
• 238000002844 melting Methods 0.000 claims description 8
• 230000008018 melting Effects 0.000 claims description 8
• 230000000704 physical effect Effects 0.000 claims description 8
• 238000010521 absorption reaction Methods 0.000 claims description 7
• 230000009471 action Effects 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 239000000843 powder Substances 0.000 claims description 4
• 102000030595 Glucokinase Human genes 0.000 claims description 3
• 108010021582 Glucokinase Proteins 0.000 claims description 3
• 230000001976 improved effect Effects 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 239000003125 aqueous solvent Substances 0.000 claims description 2
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 1
• 238000002441 X-ray diffraction Methods 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 238000000034 method Methods 0.000 description 64
• 239000000243 solution Substances 0.000 description 33
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 21
• 238000012360 testing method Methods 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 17
• 239000008103 glucose Substances 0.000 description 17
• 239000003112 inhibitor Substances 0.000 description 16
• 239000000203 mixture Substances 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 239000012442 inert solvent Substances 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 238000001819 mass spectrum Methods 0.000 description 12
• 125000006239 protecting group Chemical group 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• 238000002425 crystallisation Methods 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 230000008025 crystallization Effects 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
• 229910052763 palladium Inorganic materials 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• 229940126585 therapeutic drug Drugs 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 238000010511 deprotection reaction Methods 0.000 description 9
• 210000004185 liver Anatomy 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 230000008569 process Effects 0.000 description 9
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 9
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 150000001728 carbonyl compounds Chemical class 0.000 description 8
• 230000002829 reductive effect Effects 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
• 229910052744 lithium Inorganic materials 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 150000001340 alkali metals Chemical class 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 230000006870 function Effects 0.000 description 6
• 201000001421 hyperglycemia Diseases 0.000 description 6
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
• 238000005259 measurement Methods 0.000 description 6
• 239000000758 substrate Substances 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• 229920002554 vinyl polymer Polymers 0.000 description 6
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 5
• 241000699670 Mus sp. Species 0.000 description 5
• 208000008589 Obesity Diseases 0.000 description 5
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 238000004440 column chromatography Methods 0.000 description 5
• 239000000499 gel Substances 0.000 description 5
• 230000004153 glucose metabolism Effects 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 230000001965 increasing effect Effects 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• 235000020824 obesity Nutrition 0.000 description 5
• ABERLDAQFUZISG-SJLPKXTDSA-N 3-cyclopropyl-6-[(1r)-1-[4-(1,1-difluoroethyl)phenyl]-2-[(2r)-5-oxopyrrolidin-2-yl]ethyl]-1h-pyridin-2-one Chemical compound C1=CC(C(F)(F)C)=CC=C1[C@H](C=1NC(=O)C(C2CC2)=CC=1)C[C@@H]1NC(=O)CC1 ABERLDAQFUZISG-SJLPKXTDSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 229910052783 alkali metal Inorganic materials 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 229910000420 cerium oxide Inorganic materials 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000002274 desiccant Substances 0.000 description 4
• 229910003460 diamond Inorganic materials 0.000 description 4
• 239000010432 diamond Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 230000002440 hepatic effect Effects 0.000 description 4
• 230000003914 insulin secretion Effects 0.000 description 4
• 239000012299 nitrogen atmosphere Substances 0.000 description 4
• BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 229960003975 potassium Drugs 0.000 description 4
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• CXONXVMMINSQBV-NNYOXOHSSA-N (2r,3r,4s,5r)-5-[[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxymethyl]-2-(3-carbamothioylpyridin-1-ium-1-yl)-4-hydroxyoxolan-3-olate Chemical compound NC(=S)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)[O-])=C1 CXONXVMMINSQBV-NNYOXOHSSA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 3
• APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 3
• 102100031126 6-phosphogluconolactonase Human genes 0.000 description 3
• 108010029731 6-phosphogluconolactonase Proteins 0.000 description 3
• 206010003210 Arteriosclerosis Diseases 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000004215 Carbon black (E152) Substances 0.000 description 3
• 208000002249 Diabetes Complications Diseases 0.000 description 3
• 206010012655 Diabetic complications Diseases 0.000 description 3
• 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 3
• 206010020772 Hypertension Diseases 0.000 description 3
• 102000004877 Insulin Human genes 0.000 description 3
• 108090001061 Insulin Proteins 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
• 208000017442 Retinal disease Diseases 0.000 description 3
• 206010038923 Retinopathy Diseases 0.000 description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000002835 absorbance Methods 0.000 description 3
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
• 150000001450 anions Chemical class 0.000 description 3
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• 208000011775 arteriosclerosis disease Diseases 0.000 description 3
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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• 150000002430 hydrocarbons Chemical class 0.000 description 3
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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
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• 230000003449 preventive effect Effects 0.000 description 3
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• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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• 238000010898 silica gel chromatography Methods 0.000 description 3
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
• MYRUIMMRTFRSLX-MRVPVSSYSA-N (5r)-5-(1,3-benzothiazol-2-ylsulfonylmethyl)pyrrolidin-2-one Chemical compound N1C(=O)CC[C@@H]1CS(=O)(=O)C1=NC2=CC=CC=C2S1 MYRUIMMRTFRSLX-MRVPVSSYSA-N 0.000 description 2
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
• QXIBKCFAFRHORF-UHFFFAOYSA-N 1-bromo-4-(1,1-difluoroethyl)benzene Chemical compound CC(F)(F)C1=CC=C(Br)C=C1 QXIBKCFAFRHORF-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• BUXMGIUSFIVYHE-UHFFFAOYSA-N 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde Chemical compound COC1=NC(C=O)=CC=C1C1CC1 BUXMGIUSFIVYHE-UHFFFAOYSA-N 0.000 description 2
• ZYOCLLKGLHOQTP-UHFFFAOYSA-N 6-bromo-3-cyclopropyl-2-methoxypyridine Chemical compound COC1=NC(Br)=CC=C1C1CC1 ZYOCLLKGLHOQTP-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
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