JP2014515741A5

JP2014515741A5 -

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Publication number: JP2014515741A5
Authority: JP; Japan
Prior art keywords: compound; formula; bis; diboron; alkyl
Prior art date: 2012-03-23
Legal status : Granted

Application number

JP2014502638A

Other languages

English (en)

Japanese (ja)

Other versions

JP6058625B2 (ja

JP2014515741A (ja

Filing date

2012-03-23

Publication date

2015-04-30

2012-03-23 Application filed filed Critical

2012-03-23 Priority claimed from PCT/US2012/030269 external-priority patent/WO2012134989A1/en

2014-07-03 Publication of JP2014515741A publication Critical patent/JP2014515741A/ja

2015-04-30 Publication of JP2014515741A5 publication Critical patent/JP2014515741A5/ja

2017-01-11 Application granted granted Critical

2017-01-11 Publication of JP6058625B2 publication Critical patent/JP6058625B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-03-23 Anticipated expiration legal-status Critical

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238000000034 method Methods 0.000 claims description 225
150000001875 compounds Chemical class 0.000 claims description 224
239000002904 solvent Substances 0.000 claims description 120
125000000217 alkyl group Chemical group 0.000 claims description 115
239000003153 chemical reaction reagent Substances 0.000 claims description 107
-1 copper (II) halide Chemical class 0.000 claims description 107
125000001072 heteroaryl group Chemical group 0.000 claims description 76
239000003054 catalyst Substances 0.000 claims description 74
125000003118 aryl group Chemical group 0.000 claims description 68
229910052757 nitrogen Inorganic materials 0.000 claims description 52
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
125000004430 oxygen atom Chemical group O* 0.000 claims description 30
230000002140 halogenating effect Effects 0.000 claims description 28
ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical group 0.000 claims description 20
IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims description 18
LWXSPDVXDPRQED-UHFFFAOYSA-N [B+3].[B+3].C12(C(CCC(C1(C)C)C2)(C)[O-])[O-].C21(C(CCC(C2(C)C)C1)(C)[O-])[O-] Chemical compound [B+3].[B+3].C12(C(CCC(C1(C)C)C2)(C)[O-])[O-].C21(C(CCC(C2(C)C)C1)(C)[O-])[O-] LWXSPDVXDPRQED-UHFFFAOYSA-N 0.000 claims description 17
125000004122 cyclic group Chemical group 0.000 claims description 17
238000005885 boration reaction Methods 0.000 claims description 14
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 13
MDNDJMCSXOXBFZ-UHFFFAOYSA-N 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane Chemical compound O1CC(C)(C)COB1B1OCC(C)(C)CO1 MDNDJMCSXOXBFZ-UHFFFAOYSA-N 0.000 claims description 10
LJOXKUBPSYCAFX-BJDJZHNGSA-N diethyl (4s,5s)-2-[(4s,5s)-4,5-bis(ethoxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@H](C(=O)OCC)[C@@H](C(=O)OCC)OB1B1O[C@H](C(=O)OCC)[C@@H](C(=O)OCC)O1 LJOXKUBPSYCAFX-BJDJZHNGSA-N 0.000 claims description 10
230000008569 process Effects 0.000 claims 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 claims description 9
GDBJZTBFVNVAPH-VGWMRTNUSA-N dipropan-2-yl (4s,5s)-2-[(4s,5s)-4,5-bis(propan-2-yloxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@H](C(=O)OC(C)C)[C@@H](C(=O)OC(C)C)OB1B1O[C@H](C(=O)OC(C)C)[C@@H](C(=O)OC(C)C)O1 GDBJZTBFVNVAPH-VGWMRTNUSA-N 0.000 claims description 8
230000026045 iodination Effects 0.000 claims description 8
238000006192 iodination reaction Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
WYBQOWXCLDXZNR-UHFFFAOYSA-N 2-(1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole Chemical compound O1C2=CC=CC=C2OB1B1OC2=CC=CC=C2O1 WYBQOWXCLDXZNR-UHFFFAOYSA-N 0.000 claims description 7
UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical group CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims description 7
ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 claims description 7
GDBJZTBFVNVAPH-KLHDSHLOSA-N dipropan-2-yl (4r,5r)-2-[(4r,5r)-4,5-bis(propan-2-yloxycarbonyl)-1,3,2-dioxaborolan-2-yl]-1,3,2-dioxaborolane-4,5-dicarboxylate Chemical compound O1[C@@H](C(=O)OC(C)C)[C@H](C(=O)OC(C)C)OB1B1O[C@@H](C(=O)OC(C)C)[C@H](C(=O)OC(C)C)O1 GDBJZTBFVNVAPH-KLHDSHLOSA-N 0.000 claims description 7
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 4
101150003085 Pdcl gene Proteins 0.000 claims description 4
LANVQSVBEALBNB-BJDJZHNGSA-N (4s,5s)-2-[(4s,5s)-4,5-bis(dimethylcarbamoyl)-1,3,2-dioxaborolan-2-yl]-4-n,4-n,5-n,5-n-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide Chemical compound O1[C@H](C(=O)N(C)C)[C@@H](C(=O)N(C)C)OB1B1O[C@H](C(=O)N(C)C)[C@@H](C(=O)N(C)C)O1 LANVQSVBEALBNB-BJDJZHNGSA-N 0.000 claims description 3
NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 claims description 3
JQJOWILVGOJWJF-UHFFFAOYSA-N 2-[1-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]cyclohexyl]acetic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NCC1(CC(=O)O)CCCCC1 JQJOWILVGOJWJF-UHFFFAOYSA-N 0.000 claims description 3
UWJKMSTUOSZXAI-UHFFFAOYSA-N CC1OBOC1C Chemical compound CC1OBOC1C UWJKMSTUOSZXAI-UHFFFAOYSA-N 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
PDTRBCTYOYMYKK-RFIDALOWSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate;(2r,3r)-2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC.CC[C@](O)(C(O)=O)[C@](O)(CC)C(O)=O PDTRBCTYOYMYKK-RFIDALOWSA-N 0.000 claims description 3
229910001882 dioxygen Inorganic materials 0.000 claims description 3
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
239000000203 mixture Substances 0.000 description 60
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 46
125000002723 alicyclic group Chemical group 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 42
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 36
229910052723 transition metal Inorganic materials 0.000 description 36
150000003624 transition metals Chemical group 0.000 description 36
235000019441 ethanol Nutrition 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
125000001424 substituent group Chemical group 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
125000002619 bicyclic group Chemical group 0.000 description 22
125000000753 cycloalkyl group Chemical group 0.000 description 22
239000002798 polar solvent Substances 0.000 description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 21
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
125000003545 alkoxy group Chemical group 0.000 description 20
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 20
125000000592 heterocycloalkyl group Chemical group 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
125000003342 alkenyl group Chemical group 0.000 description 19
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 18
125000005843 halogen group Chemical group 0.000 description 17
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 16
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 16
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 16
239000003814 drug Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000000304 alkynyl group Chemical group 0.000 description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
239000012454 non-polar solvent Substances 0.000 description 15
125000003396 thiol group Chemical group [H]S* 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000011261 inert gas Substances 0.000 description 14
125000002252 acyl group Chemical group 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 12
125000003435 aroyl group Chemical group 0.000 description 12
238000000576 coating method Methods 0.000 description 12
125000004093 cyano group Chemical group *C#N 0.000 description 12
229910052763 palladium Inorganic materials 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
125000004104 aryloxy group Chemical group 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
125000005553 heteroaryloxy group Chemical group 0.000 description 11
208000015181 infectious disease Diseases 0.000 description 11
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 11
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 11
229910021590 Copper(II) bromide Inorganic materials 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
125000004356 hydroxy functional group Chemical group O* 0.000 description 10
125000004043 oxo group Chemical group O=* 0.000 description 10
239000003981 vehicle Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
125000001188 haloalkyl group Chemical group 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
KVNFSFSYJQTSQI-UHFFFAOYSA-N [Ir+].[Ir+].C1CC=CCCC=C1.C1CC=CCCC=C1 Chemical compound [Ir+].[Ir+].C1CC=CCCC=C1.C1CC=CCCC=C1 KVNFSFSYJQTSQI-UHFFFAOYSA-N 0.000 description 8
HHDBHSJOAURMII-UHFFFAOYSA-N [Ir].[Ir].C1CC=CCCC=C1 Chemical compound [Ir].[Ir].C1CC=CCCC=C1 HHDBHSJOAURMII-UHFFFAOYSA-N 0.000 description 8
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 8
125000003710 aryl alkyl group Chemical group 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 8
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
229910052741 iridium Inorganic materials 0.000 description 8
125000002950 monocyclic group Chemical group 0.000 description 8
229910052759 nickel Inorganic materials 0.000 description 8
229910052697 platinum Inorganic materials 0.000 description 8
229920001223 polyethylene glycol Polymers 0.000 description 8
239000000047 product Substances 0.000 description 8
229910052702 rhenium Inorganic materials 0.000 description 8
229910052703 rhodium Inorganic materials 0.000 description 8
229940124597 therapeutic agent Drugs 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
239000011248 coating agent Substances 0.000 description 7
125000000392 cycloalkenyl group Chemical group 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000012634 fragment Substances 0.000 description 7
125000002768 hydroxyalkyl group Chemical group 0.000 description 7
239000008101 lactose Substances 0.000 description 7
229910052724 xenon Inorganic materials 0.000 description 7
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 7
NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 6
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
229930006000 Sucrose Natural products 0.000 description 6
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002671 adjuvant Substances 0.000 description 6
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 6
125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 6
125000002102 aryl alkyloxo group Chemical group 0.000 description 6
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
125000002541 furyl group Chemical group 0.000 description 6
125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
239000008194 pharmaceutical composition Substances 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000002202 Polyethylene glycol Substances 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
125000004448 alkyl carbonyl group Chemical group 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
125000005605 benzo group Chemical group 0.000 description 5
239000012472 biological sample Substances 0.000 description 5
125000000707 boryl group Chemical group B* 0.000 description 5
230000031709 bromination Effects 0.000 description 5
238000005893 bromination reaction Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
125000004181 carboxyalkyl group Chemical group 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000011161 development Methods 0.000 description 5
239000003937 drug carrier Substances 0.000 description 5
125000004366 heterocycloalkenyl group Chemical group 0.000 description 5
125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 5
239000000463 material Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000006187 pill Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000007909 solid dosage form Substances 0.000 description 5
239000005720 sucrose Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
239000001993 wax Substances 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
RLMLFADXHJLPSQ-NPPFTVEMSA-N (3s,6s,9s,12s,15s,18s,21s,24r,27s)-3,6-dibenzyl-12,24-bis[(2r)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonon Chemical compound C([C@H]1C(=O)N2CCC[C@H]2C(=O)N[C@@H](C(N(C)[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N(C)[C@H](C(=O)O[C@H](C(=O)N(C)[C@@H](C(C)C)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N1C)[C@H](C)CC)C(C)(C)O)=O)[C@H](C)CC)C1=CC=CC=C1 RLMLFADXHJLPSQ-NPPFTVEMSA-N 0.000 description 4
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JP2014502638A 2011-04-01 2012-03-23 オーレオバシジン誘導体および合成方法 Expired - Fee Related JP6058625B2 (ja)