JP2005501856A5

JP2005501856A5 -

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Publication number: JP2005501856A5
Authority: JP; Japan
Prior art keywords: mmol; amine; added; mixture; alkyl
Prior art date: 2002-08-06
Legal status : Pending

Application number

JP2003521230A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005501856A (ja

Filing date

2002-08-06

Publication date

2006-01-05

2002-08-06 Application filed filed Critical

2002-08-06 Priority claimed from PCT/US2002/021317 external-priority patent/WO2003016307A1/en

2005-01-20 Publication of JP2005501856A publication Critical patent/JP2005501856A/ja

2006-01-05 Publication of JP2005501856A5 publication Critical patent/JP2005501856A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 161
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 60
-1 C 1 -C 6 alkyl Chemical group 0.000 claims description 50
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000002904 solvent Substances 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 32
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
208000008589 Obesity Diseases 0.000 claims description 15
235000020824 obesity Nutrition 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
150000003536 tetrazoles Chemical class 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 8
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 396
150000001412 amines Chemical class 0.000 description 227
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
239000000203 mixture Substances 0.000 description 180
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 167
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 162
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 150
239000000243 solution Substances 0.000 description 131
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
150000002118 epoxides Chemical class 0.000 description 75
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
239000011541 reaction mixture Substances 0.000 description 63
238000000034 method Methods 0.000 description 51
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
238000006243 chemical reaction Methods 0.000 description 49
239000012267 brine Substances 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000011734 sodium Substances 0.000 description 46
230000002829 reductive effect Effects 0.000 description 42
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
239000012458 free base Substances 0.000 description 36
238000002360 preparation method Methods 0.000 description 35
239000012044 organic layer Substances 0.000 description 34
239000007787 solid Substances 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
239000000047 product Substances 0.000 description 29
238000003818 flash chromatography Methods 0.000 description 28
238000010992 reflux Methods 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
238000000434 field desorption mass spectrometry Methods 0.000 description 23
239000000706 filtrate Substances 0.000 description 23
239000010410 layer Substances 0.000 description 22
108020003175 receptors Proteins 0.000 description 21
102000005962 receptors Human genes 0.000 description 21
229910052938 sodium sulfate Inorganic materials 0.000 description 21
235000011152 sodium sulphate Nutrition 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
229910004298 SiO 2 Inorganic materials 0.000 description 20
239000000284 extract Substances 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
238000003756 stirring Methods 0.000 description 20
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 14
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 14
238000010828 elution Methods 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000002002 slurry Substances 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 10
150000001502 aryl halides Chemical class 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
ZEMSPQCZQNWQGR-UHFFFAOYSA-N [3-[2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1h-indol-7-yl] trifluoromethanesulfonate Chemical compound C1=CC=C2C(CC(C)(C)NC(=O)OC(C)(C)C)=CNC2=C1OS(=O)(=O)C(F)(F)F ZEMSPQCZQNWQGR-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
229910052786 argon Inorganic materials 0.000 description 9
238000001816 cooling Methods 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
239000003814 drug Substances 0.000 description 8
239000003480 eluent Substances 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
HMLYQQCFTUQZAX-UHFFFAOYSA-N tert-butyl n-[1-(7-hydroxy-1h-indol-3-yl)-2-methylpropan-2-yl]carbamate Chemical compound C1=CC=C2C(CC(C)(C)NC(=O)OC(C)(C)C)=CNC2=C1O HMLYQQCFTUQZAX-UHFFFAOYSA-N 0.000 description 8
239000000556 agonist Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
125000001153 fluoro group Chemical group F* 0.000 description 7
238000009472 formulation Methods 0.000 description 7
238000000746 purification Methods 0.000 description 7
FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 6
0 CCc1ccccc1OCC(CNC(C)(C)Cc1c[n](*)c2c1cccc2)O Chemical compound CCc1ccccc1OCC(CNC(C)(C)Cc1c[n](*)c2c1cccc2)O 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
238000004007 reversed phase HPLC Methods 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
238000006069 Suzuki reaction reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
244000309464 bull Species 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
201000010099 disease Diseases 0.000 description 5
229940079593 drug Drugs 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000005457 ice water Substances 0.000 description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
244000144972 livestock Species 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 5
GLDWVEMBLRENOV-UHFFFAOYSA-N tert-butyl n-[1-[7-(cyanomethoxy)-1h-indol-3-yl]-2-methylpropan-2-yl]carbamate Chemical compound C1=CC=C2C(CC(C)(C)NC(=O)OC(C)(C)C)=CNC2=C1OCC#N GLDWVEMBLRENOV-UHFFFAOYSA-N 0.000 description 5
ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 4
KLAIOABSDQUNSA-WUKNDPDISA-N 3-[(e)-octadec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCC\C=C\CC1CC(=O)OC1=O KLAIOABSDQUNSA-WUKNDPDISA-N 0.000 description 4
108060003345 Adrenergic Receptor Proteins 0.000 description 4
102000017910 Adrenergic receptor Human genes 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
238000005576 amination reaction Methods 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
150000001543 aryl boronic acids Chemical class 0.000 description 4
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000005341 cation exchange Methods 0.000 description 4
239000010779 crude oil Substances 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000012467 final product Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
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 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000010791 quenching Methods 0.000 description 4
239000000018 receptor agonist Substances 0.000 description 4
229940044601 receptor agonist Drugs 0.000 description 4
230000004044 response Effects 0.000 description 4
238000004366 reverse phase liquid chromatography Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 4
XVGGRPOVHXFOLK-UHFFFAOYSA-N tert-butyl n-[2-methyl-1-[7-(trifluoromethylsulfonylmethyl)-1h-indol-3-yl]propan-2-yl]carbamate Chemical compound C1=CC=C2C(CC(C)(C)NC(=O)OC(C)(C)C)=CNC2=C1CS(=O)(=O)C(F)(F)F XVGGRPOVHXFOLK-UHFFFAOYSA-N 0.000 description 4
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JP2003521230A 2001-08-14 2002-08-06 β３アドレナリン作動性アゴニスト Pending JP2005501856A (ja)