HRP20000544A2 - 2-arylethyl-(piperidin-4-ylmethyl)amine derivatives as muscarinic receptor antagonists - Google Patents

Info

Publication number

HRP20000544A2

HRP20000544A2 HR20000544A HRP20000544A HRP20000544A2 HR P20000544 A2 HRP20000544 A2 HR P20000544A2 HR 20000544 A HR20000544 A HR 20000544A HR P20000544 A HRP20000544 A HR P20000544A HR P20000544 A2 HRP20000544 A2 HR P20000544A2

Authority

HR

Croatia

Prior art keywords

methylethyl

ylmethyl

piperidin

ethyl

amine

Prior art date

1998-02-27

Links

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• 150000001412 amines Chemical class 0.000 title claims description 65
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 title description 14
• 150000001875 compounds Chemical class 0.000 claims description 284
• -1 morpholino, piperidinyl Chemical group 0.000 claims description 168
• 238000000034 method Methods 0.000 claims description 116
• 239000000203 mixture Substances 0.000 claims description 95
• 238000006243 chemical reaction Methods 0.000 claims description 79
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 16
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 239000003638 chemical reducing agent Substances 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 230000008569 process Effects 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 230000009467 reduction Effects 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• HBVWMOGNXHPWGZ-UHFFFAOYSA-N [4-[[ethyl-[1-[3-(trifluoromethyl)phenyl]propan-2-yl]amino]methyl]piperidin-1-yl]-piperidin-1-ylmethanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC(C)N(CC)CC(CC1)CCN1C(=O)N1CCCCC1 HBVWMOGNXHPWGZ-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• QAHJUTBPGXSPCC-SFHVURJKSA-N n-[3-[4-[[[(2s)-1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-yl]-ethylamino]methyl]piperidin-1-yl]-3-oxopropyl]methanesulfonamide Chemical compound CCN([C@@H](C)CC=1C=C2CCOC2=CC=1)CC1CCN(C(=O)CCNS(C)(=O)=O)CC1 QAHJUTBPGXSPCC-SFHVURJKSA-N 0.000 claims description 4
• YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 3
• VMPIQPNZNZOWAB-UHFFFAOYSA-N 4-[[ethyl-[1-[3-(trifluoromethyl)phenyl]propan-2-yl]amino]methyl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC(C)N(CC)CC1CCN(C(=O)N(C)C)CC1 VMPIQPNZNZOWAB-UHFFFAOYSA-N 0.000 claims description 3
• UKWFQJXUZNUXMU-UHFFFAOYSA-N 4-[[ethyl-[1-[4-(trifluoromethyl)phenyl]propan-2-yl]amino]methyl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1CC(C)N(CC)CC1CCN(C(=O)N(C)C)CC1 UKWFQJXUZNUXMU-UHFFFAOYSA-N 0.000 claims description 3
• 239000005864 Sulphur Substances 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• 238000010511 deprotection reaction Methods 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• ALRQEPDILNRIMT-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-yl)-n-[(1-methylsulfonylpiperidin-4-yl)methyl]-n-propylpropan-2-amine Chemical compound C=1C=C2OCCC2=CC=1CC(C)N(CCC)CC1CCN(S(C)(=O)=O)CC1 ALRQEPDILNRIMT-UHFFFAOYSA-N 0.000 claims description 2
• DUHKKBBESXCBNM-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-yl)-n-ethyl-n-[(1-methylsulfonylpiperidin-4-yl)methyl]propan-2-amine Chemical compound C=1C=C2OCCC2=CC=1CC(C)N(CC)CC1CCN(S(C)(=O)=O)CC1 DUHKKBBESXCBNM-UHFFFAOYSA-N 0.000 claims description 2
• JZGAHILTHVMHGV-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-n-[(1-methylsulfonylpiperidin-4-yl)methyl]-n-propylpropan-2-amine Chemical compound C=1C=C2CCCC2=CC=1CC(C)N(CCC)CC1CCN(S(C)(=O)=O)CC1 JZGAHILTHVMHGV-UHFFFAOYSA-N 0.000 claims description 2
• QXDNBCTTWROWNA-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-n-ethyl-n-[(1-methylsulfonylpiperidin-4-yl)methyl]propan-2-amine Chemical compound C=1C=C2CCCC2=CC=1CC(C)N(CC)CC1CCN(S(C)(=O)=O)CC1 QXDNBCTTWROWNA-UHFFFAOYSA-N 0.000 claims description 2
• LHTCPKXIIAMQCY-UHFFFAOYSA-N 4-[[ethyl-[1-(4-methoxyphenyl)propan-2-yl]amino]methyl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C=1C=C(OC)C=CC=1CC(C)N(CC)CC1CCN(C(=O)N(C)C)CC1 LHTCPKXIIAMQCY-UHFFFAOYSA-N 0.000 claims description 2
• RIBAXXIYZLISAM-UHFFFAOYSA-N 4-methoxy-n-[3-[2-[[1-(morpholine-4-carbonyl)piperidin-4-yl]methyl-propylamino]propyl]phenyl]benzamide Chemical compound C=1C=CC(NC(=O)C=2C=CC(OC)=CC=2)=CC=1CC(C)N(CCC)CC(CC1)CCN1C(=O)N1CCOCC1 RIBAXXIYZLISAM-UHFFFAOYSA-N 0.000 claims description 2
• RDJRIOZXPOIIJA-UHFFFAOYSA-N 4-methyl-n-[3-[2-[[1-(morpholine-4-carbonyl)piperidin-4-yl]methyl-propylamino]propyl]phenyl]benzamide Chemical compound C=1C=CC(NC(=O)C=2C=CC(C)=CC=2)=CC=1CC(C)N(CCC)CC(CC1)CCN1C(=O)N1CCOCC1 RDJRIOZXPOIIJA-UHFFFAOYSA-N 0.000 claims description 2
• YRVAVJKNANTQRT-UHFFFAOYSA-N [4-[[1-(2,3-dihydro-1,4-benzodioxin-6-yl)propan-2-yl-ethylamino]methyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OCCOC2=CC=1CC(C)N(CC)CC(CC1)CCN1C(=O)N1CCOCC1 YRVAVJKNANTQRT-UHFFFAOYSA-N 0.000 claims description 2
• WIFKFHIASQHPNT-UHFFFAOYSA-N [4-[[1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-yl-ethylamino]methyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OCCC2=CC=1CC(C)N(CC)CC(CC1)CCN1C(=O)N1CCOCC1 WIFKFHIASQHPNT-UHFFFAOYSA-N 0.000 claims description 2
• DLMOQDVDJCDVCV-UHFFFAOYSA-N [4-[[1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-yl-propylamino]methyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OCCC2=CC=1CC(C)N(CCC)CC(CC1)CCN1C(=O)N1CCOCC1 DLMOQDVDJCDVCV-UHFFFAOYSA-N 0.000 claims description 2
• NPFVCJFOGGKLLC-UHFFFAOYSA-N [4-[[1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-yl-propylamino]methyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2CCOC2=CC=1CC(C)N(CCC)CC(CC1)CCN1C(=O)N1CCOCC1 NPFVCJFOGGKLLC-UHFFFAOYSA-N 0.000 claims description 2
• PLJVGHYPEMWTCT-UHFFFAOYSA-N [4-[[1-(3-chlorophenyl)propan-2-yl-ethylamino]methyl]piperidin-1-yl]-piperidin-1-ylmethanone Chemical compound C=1C=CC(Cl)=CC=1CC(C)N(CC)CC(CC1)CCN1C(=O)N1CCCCC1 PLJVGHYPEMWTCT-UHFFFAOYSA-N 0.000 claims description 2
• FHBYZVZPZZUPKP-UHFFFAOYSA-N [4-[[ethyl-[1-[3-(trifluoromethyl)phenyl]propan-2-yl]amino]methyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC(C)N(CC)CC(CC1)CCN1C(=O)N1CCOCC1 FHBYZVZPZZUPKP-UHFFFAOYSA-N 0.000 claims description 2
• PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 2
• WADLOJAPSURZGG-UHFFFAOYSA-N morpholin-4-yl-[4-[[propyl-[1-[3-(trifluoromethyl)phenyl]propan-2-yl]amino]methyl]piperidin-1-yl]methanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC(C)N(CCC)CC(CC1)CCN1C(=O)N1CCOCC1 WADLOJAPSURZGG-UHFFFAOYSA-N 0.000 claims description 2
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical group CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims 1
• BTSVMLPWCFPJJL-UHFFFAOYSA-N ethoxy-methoxy-propoxy-lambda3-chlorane Chemical group CCCOCl(OC)OCC BTSVMLPWCFPJJL-UHFFFAOYSA-N 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 190
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
• 239000000243 solution Substances 0.000 description 78
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
• 238000002360 preparation method Methods 0.000 description 61
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 239000002904 solvent Substances 0.000 description 52
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 230000002829 reductive effect Effects 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• 238000002844 melting Methods 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
• 230000008018 melting Effects 0.000 description 27
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• 235000019198 oils Nutrition 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 20
• 238000009472 formulation Methods 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• 239000003960 organic solvent Substances 0.000 description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 239000002585 base Substances 0.000 description 17
• 239000012074 organic phase Substances 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 13
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 13
• 239000000843 powder Substances 0.000 description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 238000010992 reflux Methods 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 11
• 239000002775 capsule Substances 0.000 description 11
• 239000012280 lithium aluminium hydride Substances 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 238000006268 reductive amination reaction Methods 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000004615 ingredient Substances 0.000 description 10
• 150000002576 ketones Chemical class 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 125000006239 protecting group Chemical group 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 239000002552 dosage form Substances 0.000 description 9
• 238000002474 experimental method Methods 0.000 description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 8
• 239000003054 catalyst Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 150000008282 halocarbons Chemical class 0.000 description 8
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 210000003932 urinary bladder Anatomy 0.000 description 8
• HYDZLHMFYXHQRK-HNNXBMFYSA-N (2s)-1-(2,3-dihydro-1-benzofuran-5-yl)-n-ethyl-n-(piperidin-4-ylmethyl)propan-2-amine Chemical compound CCN([C@@H](C)CC=1C=C2CCOC2=CC=1)CC1CCNCC1 HYDZLHMFYXHQRK-HNNXBMFYSA-N 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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