JP2009528986A5

JP2009528986A5 -

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Publication number: JP2009528986A5
Authority: JP; Japan
Prior art keywords: aliphatic; optionally substituted; hydrogen; ring; compound
Prior art date: 2007-01-31
Legal status : Granted

Application number

JP2008553310A

Other languages

English (en)

Japanese (ja)

Other versions

JP5231251B2 (ja

JP2009528986A (ja

Filing date

2007-01-31

Publication date

2010-03-18

2007-01-31 Application filed filed Critical

2007-01-31 Priority claimed from PCT/US2007/002560 external-priority patent/WO2007092213A2/en

2009-08-13 Publication of JP2009528986A publication Critical patent/JP2009528986A/ja

2010-03-18 Publication of JP2009528986A5 publication Critical patent/JP2009528986A5/ja

2013-07-10 Application granted granted Critical

2013-07-10 Publication of JP5231251B2 publication Critical patent/JP5231251B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-01-31 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 474
125000001931 aliphatic group Chemical group 0.000 claims description 222
229910052739 hydrogen Inorganic materials 0.000 claims description 195
239000001257 hydrogen Substances 0.000 claims description 195
238000000034 method Methods 0.000 claims description 155
239000000203 mixture Substances 0.000 claims description 144
-1 benzfuranyl Chemical group 0.000 claims description 123
150000002431 hydrogen Chemical class 0.000 claims description 113
125000001153 fluoro group Chemical group F* 0.000 claims description 101
125000003118 aryl group Chemical group 0.000 claims description 98
229910052799 carbon Inorganic materials 0.000 claims description 86
125000000623 heterocyclic group Chemical group 0.000 claims description 78
125000001072 heteroaryl group Chemical group 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 73
229910052757 nitrogen Inorganic materials 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 66
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 63
102000004190 Enzymes Human genes 0.000 claims description 56
108090000790 Enzymes Proteins 0.000 claims description 56
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
201000010099 disease Diseases 0.000 claims description 43
230000000694 effects Effects 0.000 claims description 41
125000005843 halogen group Chemical group 0.000 claims description 41
229920006395 saturated elastomer Polymers 0.000 claims description 39
206010028980 Neoplasm Diseases 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 36
125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
238000011282 treatment Methods 0.000 claims description 33
125000002947 alkylene group Chemical group 0.000 claims description 29
125000005842 heteroatom Chemical group 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
201000011510 cancer Diseases 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 23
150000002009 diols Chemical group 0.000 claims description 22
125000003709 fluoroalkyl group Chemical group 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
125000003107 substituted aryl group Chemical group 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 19
125000004122 cyclic group Chemical group 0.000 claims description 17
125000002950 monocyclic group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
125000006413 ring segment Chemical group 0.000 claims description 13
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
125000002971 oxazolyl group Chemical group 0.000 claims description 8
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
125000000532 dioxanyl group Chemical class 0.000 claims description 6
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
125000001786 isothiazolyl group Chemical group 0.000 claims description 6
125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
238000000338 in vitro Methods 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 5
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
206010009944 Colon cancer Diseases 0.000 claims description 4
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
206010033128 Ovarian cancer Diseases 0.000 claims description 4
206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
230000028993 immune response Effects 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
125000005956 isoquinolyl group Chemical group 0.000 claims description 4
201000005202 lung cancer Diseases 0.000 claims description 4
208000020816 lung neoplasm Diseases 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000005493 quinolyl group Chemical group 0.000 claims description 4
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 3
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 3
125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 3
125000005879 dioxolanyl group Chemical group 0.000 claims description 3
201000005787 hematologic cancer Diseases 0.000 claims description 3
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 3
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims description 3
125000004306 triazinyl group Chemical group 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
125000002636 imidazolinyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims 3
229910021386 carbon form Inorganic materials 0.000 claims 2
125000001113 thiadiazolyl group Chemical group 0.000 claims 2
210000005167 vascular cell Anatomy 0.000 claims 2
208000035269 cancer or benign tumor Diseases 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 222
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 215
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 163
239000000243 solution Substances 0.000 description 131
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 117
235000019439 ethyl acetate Nutrition 0.000 description 101
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 description 98
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
238000010898 silica gel chromatography Methods 0.000 description 79
238000006243 chemical reaction Methods 0.000 description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
150000001721 carbon Chemical group 0.000 description 53
239000011541 reaction mixture Substances 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
239000007787 solid Substances 0.000 description 37
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
108090000623 proteins and genes Proteins 0.000 description 31
239000000047 product Substances 0.000 description 30
102000004169 proteins and genes Human genes 0.000 description 30
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
239000002904 solvent Substances 0.000 description 28
239000012299 nitrogen atmosphere Substances 0.000 description 26
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210000004027 cell Anatomy 0.000 description 25
230000005764 inhibitory process Effects 0.000 description 22
239000000725 suspension Substances 0.000 description 22
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239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
239000012044 organic layer Substances 0.000 description 21
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
108010091546 Ubiquitin-Activating Enzymes Proteins 0.000 description 20
102000018478 Ubiquitin-Activating Enzymes Human genes 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
239000002585 base Substances 0.000 description 19
239000003112 inhibitor Substances 0.000 description 19
239000010410 layer Substances 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
235000018102 proteins Nutrition 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
230000003213 activating effect Effects 0.000 description 15
239000012300 argon atmosphere Substances 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
102000044159 Ubiquitin Human genes 0.000 description 14
108090000848 Ubiquitin Proteins 0.000 description 14
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
238000010992 reflux Methods 0.000 description 13
239000000126 substance Substances 0.000 description 13
239000000758 substrate Substances 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
238000003556 assay Methods 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
230000006663 ubiquitin-proteasome pathway Effects 0.000 description 12
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239000003795 chemical substances by application Substances 0.000 description 11
239000000284 extract Substances 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
238000004809 thin layer chromatography Methods 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
238000010511 deprotection reaction Methods 0.000 description 10
239000002532 enzyme inhibitor Substances 0.000 description 10
230000037361 pathway Effects 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
229940124597 therapeutic agent Drugs 0.000 description 10
210000001519 tissue Anatomy 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
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238000004458 analytical method Methods 0.000 description 9
238000009472 formulation Methods 0.000 description 9
238000001727 in vivo Methods 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
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235000011152 sodium sulphate Nutrition 0.000 description 9
238000003756 stirring Methods 0.000 description 9
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
230000034512 ubiquitination Effects 0.000 description 9
238000010798 ubiquitination Methods 0.000 description 9
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
125000003342 alkenyl group Chemical group 0.000 description 8
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
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230000002062 proliferating effect Effects 0.000 description 8
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 8
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
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JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
150000003138 primary alcohols Chemical class 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
238000000746 purification Methods 0.000 description 7
230000009467 reduction Effects 0.000 description 7
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
102100031911 NEDD8 Human genes 0.000 description 6
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JP2008553310A 2006-02-02 2007-01-31 Ｅ１活性化酵素の阻害剤 Expired - Fee Related JP5231251B2 (ja)