JP2000513750A - ヒドラジン誘導体 - Google Patents
ヒドラジン誘導体Info
- Publication number
- JP2000513750A JP2000513750A JP11506230A JP50623099A JP2000513750A JP 2000513750 A JP2000513750 A JP 2000513750A JP 11506230 A JP11506230 A JP 11506230A JP 50623099 A JP50623099 A JP 50623099A JP 2000513750 A JP2000513750 A JP 2000513750A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- phenyl
- butenyl
- methanesulfonyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002429 hydrazines Chemical class 0.000 title description 20
- -1 cyano, amino, hydroxy Chemical group 0.000 claims abstract description 394
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 98
- 125000003118 aryl group Chemical group 0.000 claims abstract description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 208000032843 Hemorrhage Diseases 0.000 claims abstract description 10
- 206010061218 Inflammation Diseases 0.000 claims abstract description 10
- 206010037660 Pyrexia Diseases 0.000 claims abstract description 10
- 206010040047 Sepsis Diseases 0.000 claims abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
- 208000034158 bleeding Diseases 0.000 claims abstract description 10
- 230000000740 bleeding effect Effects 0.000 claims abstract description 10
- 230000004054 inflammatory process Effects 0.000 claims abstract description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 10
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 150000003950 cyclic amides Chemical class 0.000 claims abstract description 7
- 125000006850 spacer group Chemical group 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 6
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 105
- PJBQYCIDGYKEMN-UHFFFAOYSA-N pentanehydrazide Chemical compound CCCCC(=O)NN PJBQYCIDGYKEMN-UHFFFAOYSA-N 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- NKITXADAXHOCIE-VSLSUTFFSA-N (2s,3r)-n-hydroxy-5-methyl-3-[[[(2s)-2-methylbutyl]-methylsulfonylamino]carbamoyl]-2-[(e)-3-phenylprop-2-enyl]hexanamide Chemical compound CC[C@H](C)CN(S(C)(=O)=O)NC(=O)[C@H](CC(C)C)[C@@H](C(=O)NO)C\C=C\C1=CC=CC=C1 NKITXADAXHOCIE-VSLSUTFFSA-N 0.000 claims description 5
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- QDPZFEJNJGEFBC-ONAORTGXSA-N (2s,3r)-n-hydroxy-5-methyl-3-[(n-methylsulfonylanilino)carbamoyl]-2-[(e)-3-phenylprop-2-enyl]hexanamide Chemical compound C([C@@H]([C@@H](CC(C)C)C(=O)NN(C=1C=CC=CC=1)S(C)(=O)=O)C(=O)NO)\C=C\C1=CC=CC=C1 QDPZFEJNJGEFBC-ONAORTGXSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 208000014268 psoriasis 15 Diseases 0.000 claims description 2
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 208000032170 Congenital Abnormalities Diseases 0.000 claims 1
- 206010061619 Deformity Diseases 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 102000006747 Transforming Growth Factor alpha Human genes 0.000 abstract description 9
- 101800004564 Transforming growth factor alpha Proteins 0.000 abstract description 9
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract description 6
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract description 5
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract description 4
- 210000002510 keratinocyte Anatomy 0.000 abstract description 4
- 230000035755 proliferation Effects 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 108010009583 Transforming Growth Factors Proteins 0.000 abstract description 2
- 102000009618 Transforming Growth Factors Human genes 0.000 abstract description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 102000003390 tumor necrosis factor Human genes 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 761
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 530
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 273
- 239000007787 solid Substances 0.000 description 265
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 214
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 207
- 239000000243 solution Substances 0.000 description 184
- 238000010828 elution Methods 0.000 description 158
- 238000004128 high performance liquid chromatography Methods 0.000 description 140
- 230000014759 maintenance of location Effects 0.000 description 139
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 132
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 132
- 239000000203 mixture Substances 0.000 description 111
- 239000007858 starting material Substances 0.000 description 106
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 73
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 67
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 65
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 51
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 31
- 235000017557 sodium bicarbonate Nutrition 0.000 description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- 238000003756 stirring Methods 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 239000002253 acid Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- VOBMACGBVNTRGF-UHFFFAOYSA-N 4-methylpentanehydrazide Chemical compound CC(C)CCC(=O)NN VOBMACGBVNTRGF-UHFFFAOYSA-N 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 239000006260 foam Substances 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 10
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 9
- ACMPWZQOUILVFB-UHFFFAOYSA-N 4-methylpentanamide Chemical compound CC(C)CCC(N)=O ACMPWZQOUILVFB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229940098779 methanesulfonic acid Drugs 0.000 description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- FIUBFKICQZPDKF-UHFFFAOYSA-N S(=O)(=O)=C(C(=O)NNC1=CC=CC=C1)CC(C)C Chemical compound S(=O)(=O)=C(C(=O)NNC1=CC=CC=C1)CC(C)C FIUBFKICQZPDKF-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- 150000008282 halocarbons Chemical group 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- NGSOWKPBNFOQCR-UHFFFAOYSA-N 2-methylpropylhydrazine Chemical compound CC(C)CNN NGSOWKPBNFOQCR-UHFFFAOYSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 5
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000012738 dissolution medium Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000001288 lysyl group Chemical group 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KPWQPKZCNKGDNE-MCOCGALXSA-N (2S,3R)-3-(methanesulfonamidocarbamoyl)-5-methyl-N-(oxan-2-yloxy)-2-(3-phenylprop-2-enyl)hexanamide Chemical compound O1C(CCCC1)ONC(=O)[C@@H](CC=CC1=CC=CC=C1)[C@H](C(=O)NNS(=O)(=O)C)CC(C)C KPWQPKZCNKGDNE-MCOCGALXSA-N 0.000 description 4
- FHLSOVFMGZUSSR-JKSUJKDBSA-N (2S,3R)-N-hydroxy-3-(methanesulfonamidocarbamoyl)-5-methyl-2-(3-phenylprop-2-enyl)hexanamide Chemical compound ONC(=O)[C@@H](CC=CC1=CC=CC=C1)[C@H](C(=O)NNS(=O)(=O)C)CC(C)C FHLSOVFMGZUSSR-JKSUJKDBSA-N 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- SMYJDEGFDGDPFB-UHFFFAOYSA-N 2-(2-methylpropyl)-n'-methylsulfonylhexanehydrazide Chemical compound CCCCC(CC(C)C)C(=O)NNS(C)(=O)=O SMYJDEGFDGDPFB-UHFFFAOYSA-N 0.000 description 4
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical group [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- PQLMSZJNMODGKX-WQEUXLNQSA-N methyl (2s,3r)-5-methyl-2-[(e)-3-phenylprop-2-enyl]-3-(thiazinan-2-ylcarbamoyl)hexanoate Chemical compound C([C@H](C(=O)OC)[C@@H](CC(C)C)C(=O)NN1SCCCC1)\C=C\C1=CC=CC=C1 PQLMSZJNMODGKX-WQEUXLNQSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
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- MSFVDZMTLMMTCI-WQEUXLNQSA-N methyl n-[[(e,2r,3s)-3-(hydroxycarbamoyl)-2-(2-methylpropyl)-6-phenylhex-5-enoyl]amino]-n-(2-methylpropyl)carbamate Chemical compound COC(=O)N(CC(C)C)NC(=O)[C@H](CC(C)C)[C@@H](C(=O)NO)C\C=C\C1=CC=CC=C1 MSFVDZMTLMMTCI-WQEUXLNQSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- UBLQIESZTDNNAO-UHFFFAOYSA-N n,n-diethylethanamine;phosphoric acid Chemical compound [O-]P([O-])([O-])=O.CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC UBLQIESZTDNNAO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBCIOBSQHJYVBQ-UHFFFAOYSA-N naphthalen-1-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=CC2=C1 XBCIOBSQHJYVBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- ANWKYMULRIVEJC-QXBFXKENSA-N oxan-2-yl (2s,3r)-5-methyl-3-[(n-methylsulfonylanilino)carbamoyl]-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound C([C@@H]([C@@H](CC(C)C)C(=O)NN(C=1C=CC=CC=1)S(C)(=O)=O)C(=O)OC1OCCCC1)\C=C\C1=CC=CC=C1 ANWKYMULRIVEJC-QXBFXKENSA-N 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
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- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000005475 oxolanyl group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- DNDTZRSLSJSECH-UHFFFAOYSA-N phenyl n-aminocarbamate Chemical compound NNC(=O)OC1=CC=CC=C1 DNDTZRSLSJSECH-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- XLCISDOVNFLSGO-VONOSFMSSA-N phorbol-12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(O)C1(C)C XLCISDOVNFLSGO-VONOSFMSSA-N 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
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- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical compound NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 description 1
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- QMVCLSHKMIGEFN-UHFFFAOYSA-N quinolin-2-ylhydrazine Chemical compound C1=CC=CC2=NC(NN)=CC=C21 QMVCLSHKMIGEFN-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 108091007196 stromelysin Proteins 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DFLMFSOZCQWBPD-ZWKOTPCHSA-N tert-butyl (2S,3R)-3-(hydrazinecarbonyl)-5-methyl-2-(3-phenylprop-2-enyl)hexanoate Chemical compound C(C)(C)(C)OC(=O)[C@@H](CC=CC1=CC=CC=C1)[C@H](C(=O)NN)CC(C)C DFLMFSOZCQWBPD-ZWKOTPCHSA-N 0.000 description 1
- BWLFJQHJPKBXRD-PKTZIBPZSA-N tert-butyl (2r,3r)-2-[(1,3-dioxoisoindol-2-yl)methyl]-5-methyl-3-[(n-methylsulfonylanilino)carbamoyl]hexanoate Chemical compound O=C([C@@H]([C@H](CN1C(C2=CC=CC=C2C1=O)=O)C(=O)OC(C)(C)C)CC(C)C)NN(S(C)(=O)=O)C1=CC=CC=C1 BWLFJQHJPKBXRD-PKTZIBPZSA-N 0.000 description 1
- DPMOFXVJHWKRJJ-XZOQPEGZSA-N tert-butyl (2s,3r)-2-(3-cyclohexylpropyl)-5-methyl-3-[[2-methylpropyl(methylsulfonyl)amino]carbamoyl]hexanoate Chemical compound CC(C)CN(S(C)(=O)=O)NC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)CCCC1CCCCC1 DPMOFXVJHWKRJJ-XZOQPEGZSA-N 0.000 description 1
- YZGLGBBVCMXEOP-PXUCQJMWSA-N tert-butyl (2s,3r)-3-(anilinocarbamoyl)-5-methyl-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound C([C@@H]([C@@H](CC(C)C)C(=O)NNC=1C=CC=CC=1)C(=O)OC(C)(C)C)\C=C\C1=CC=CC=C1 YZGLGBBVCMXEOP-PXUCQJMWSA-N 0.000 description 1
- JMAVYZIHRVUGCZ-BDPQSKBNSA-N tert-butyl (2s,3r)-3-[(1,3-dioxoisoindol-2-yl)carbamoyl]-5-methyl-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound C([C@@H]([C@@H](CC(C)C)C(=O)NN1C(C2=CC=CC=C2C1=O)=O)C(=O)OC(C)(C)C)\C=C\C1=CC=CC=C1 JMAVYZIHRVUGCZ-BDPQSKBNSA-N 0.000 description 1
- VBSQKQMFYHTJLQ-WCWNVHNDSA-N tert-butyl (2s,3r)-3-[(3-chloropropylsulfonylamino)carbamoyl]-5-methyl-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound ClCCCS(=O)(=O)NNC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)C\C=C\C1=CC=CC=C1 VBSQKQMFYHTJLQ-WCWNVHNDSA-N 0.000 description 1
- HLKNOHKOBGXUPP-XEGGGDOUSA-N tert-butyl (2s,3r)-3-[(butylsulfonylamino)carbamoyl]-5-methyl-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound CCCCS(=O)(=O)NNC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)C\C=C\C1=CC=CC=C1 HLKNOHKOBGXUPP-XEGGGDOUSA-N 0.000 description 1
- BHUNPCSPRNJRHB-UEVQAURSSA-N tert-butyl (2s,3r)-3-[[methoxycarbonyl(2-methylpropyl)amino]carbamoyl]-5-methyl-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound COC(=O)N(CC(C)C)NC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)C\C=C\C1=CC=CC=C1 BHUNPCSPRNJRHB-UEVQAURSSA-N 0.000 description 1
- IYRZDBZAVZBYTQ-LEWJYISDSA-N tert-butyl (2s,3r)-5-methyl-3-[(2-methylpropylamino)carbamoyl]-2-(3-pyridin-3-ylpropyl)hexanoate Chemical compound CC(C)CNNC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)CCCC1=CC=CN=C1 IYRZDBZAVZBYTQ-LEWJYISDSA-N 0.000 description 1
- NMCWNAOWRKTRQX-GUYDGBRCSA-N tert-butyl (2s,3r)-5-methyl-3-[[2-methylpropanoyl(2-methylpropyl)amino]carbamoyl]-2-[(e)-3-phenylprop-2-enyl]hexanoate Chemical compound CC(C)CN(C(=O)C(C)C)NC(=O)[C@H](CC(C)C)[C@@H](C(=O)OC(C)(C)C)C\C=C\C1=CC=CC=C1 NMCWNAOWRKTRQX-GUYDGBRCSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- BWBONKHPVHMQHE-UHFFFAOYSA-N tiocarlide Chemical group C1=CC(OCCC(C)C)=CC=C1NC(=S)NC1=CC=C(OCCC(C)C)C=C1 BWBONKHPVHMQHE-UHFFFAOYSA-N 0.000 description 1
- 229960002171 tiocarlide Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LDJBOXSVVWHBLS-UHFFFAOYSA-M triphenyl(1,3-thiazol-2-ylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=NC=CS1 LDJBOXSVVWHBLS-UHFFFAOYSA-M 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
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- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式、 [式中、 Yは、CO又はSO2を表し; R1は、低級アルキル、低級アルケニル、低級シクロアルキル、低級シクロアル キル−低級アルキル、アリール又はアリール−低級アルキルを表し; R2は、YがSO2を表す場合には、低級アルキル、ハロ−低級アルキル、アリー ル−低級アルキル、アリール−低級アルケニル又はアリールを表し、そしてYが COを表す場合には、低級アルキル、ハロ−低級アルキル、低級アルコキシ、低 級アルコキシカルボニル、アシル、低級シクロアルキル、アリール、アリール− 低級アルキル、アリール−低級アルコキシ、又はNR5R6を表し; そして R3は、水素、場合によりシアノ、アミノ、ヒドロキシ、低級アルコキシ、低級 アルコキシカルボニル、ヘテロシクリル若しくはヘテロシクリルカルボニルによ り置換されている低級アルキル、低級アルケニル、低級アルキニル、低級シクロ アルキル、低級シクロアルキル−低級アルキル、アリール−低級アルキル、アリ ール−低級アルケニル、アリール又はヘテロシクリルを表し;あるいは R2及びR3は、一緒になって5−、6−又は7−員の環式アミド、環式イミド、 環式スルホンアミド又は環式ウレタン基を形成し; R4は、低級アルキル、低級アルケニル、低級シクロアルキル、低級シクロアル キル−低級アルキル、又は式X−アリール、X−ヘテロアリール若しくは−(C H2)1-2−CH=CR7R8の基を表し; Xは、スペーサ基を表し; R5及びR6は、それぞれ独立して水素、低級アルキル又はアリール−低級アルキ ルを表し;そして R7及びR8は、一緒になって低級アルキレン基を表し、ここで1個のメチレン基 は、場合によりへテロ原子により置換されている] の化合物、並びにそれらの医薬的に許容される塩。 2.YがCO、又はSO2を表し;R1が低級アルキル、低級シクロアルキル、低 級シクロアルキル−低級アルキル、アリール又はアリール−低級アルキルを表し ;R2が、YがSO2を表す場合に低級アルキル、アリール−低級アルキル又はア リールを表し、YがCOを表す場合に低級アルキル、低級アルコキシ、低級シク ロアルキル、アリール−低級アルコキシ又はNR5R6を表し;R3が、水素、場 合によりシアノ、アミノ若しくはフタルイミドにより置換されている低級アルキ ル、低級アルケニル、低級アルキニル、低級シクロアルキル、低級シクロアルキ ル−低級アルキル、アリール−低級アルキル、アリール又はヘテロシクリルを表 し;あるいはR2及びR3が、一緒になって5−、6−又は7−員の環式アミド、 環式イミド又は環式スルホンアミド基を形成し;R4がフタルイミド−低級アル キル又は式X−アリール若しくはX−ヘテロアリールの基を表し;Xがスペーサ 基を表し;ヘテロアリール基がC原子で結合しており;そしてR5及びR6がそれ ぞれに水素、低級アルキル又はアリール−低級アルキルを表す、請求項1に記載 の式(I)の化合物、並びにそれらの医薬的に許容される塩。 3.YがCOを表し、そしてR2が低級アルコキシを表すか、あるいはYがSO2 を表し、そしてR2が低級アルキルを表す、請求項1又は2に記載の化合物。 4.YがCOを表し、そしてR2がメトキシを表す、請求項3に記載の化合物。 5.YがSO2を表し、そしてR2がメチルを表す、請求項3に記載の化合物。 6.R1が低級アルキルを表す、請求項1〜5のいずれか1項に記載の化合物。 7.R1がイソブチルを表す、請求項1〜6のいずれか1項に記載の化合物。 8.R3が低級アルキル、低級アルケニル、アリール−低級アルキル又はアリー ルを表す、請求項1〜7のいずれか1項に記載の化合物。 9.R3がイソブチル、2−メチルブチル、2−メチルアリル、非置換ベンジル 又は非置換フェニルを表す、請求項8に記載の化合物。 10.Xが、式−(CH2)1-5−、−CH2−CH=CH−、−CH2−C≡C−、 −CH2NHCO−、−(CH2)1 又は2NHCONH−、−(CH2)1-5−S−、− CH2NHSO2−、−CH2NHCH2−、−(CH2)1-5−O−、−O−(CH2)1 -5 −又は−S−の基である、請求項1〜9のいずれか1項に記載の化合物。 11.Xが、式−(CH2)1-5−、−CH2−CH=CH−、−CH2−C≡C−、 −CH2NHCO−、−(CH2)1 又は2NHCONH−、−CH2S−、−CH2N HSO2−又は−CH2NHCH2−の基である、請求項10に記載の化合物。 12.R4が式X−アリールの基を表す、請求項1〜11のいずれか1項に記載 の化合物。 13.Xが式−CH2−CH=CH−の基を表し、アリールが非置換フェニルを 表す、請求項12に記載の化合物。 14.(E)−2(R)−[1(S)−(ヒドロキシカルバモイル)−4−フェ ニル−3−ブテニル]−2’−イソブチル−2’−(メタンスルホニル)−4− メチルバレロヒドラジド; (E)−2(R)−[1(S)−(ヒドロキシカルバモイル)−4−フェニル −3−ブテニル]−2’−(メタンスルホニル)−4−メチル−2’−フェニル バレロヒドラジド; (E)−2(R)−[1(S)−(ヒドロキシカルバモイル)−4−フェニル −3−ブテニル]−2’−(メタンスルホニル)−4−メチル−2’−[2(S )−メチルブチル]バレロヒドラジド; (E)−2(R)−[1(S)−(ヒドロキシカルバモイル)−4−フェニル −3−ブテニル]−2’−(メタンスルホニル)−4−メチル−2’−(2−メ チルアリル)バレロヒドラジド;及び メチル(E)−3−[2(R)−[1(S)−(ヒドロキシカルバモイル)− 4−フェニル−3−ブテニル]−4−メチルバレリル]−2−イソブチルカルバ ゼート からなる群から選択される化合物。 15.一般式、[式中、Y、R1、R2、R3及びR4は、請求項1に示される意味を有し、R9は 保護基を表す]の化合物。 16.R9がテトラヒドロピラニル、4−メトキシベンジル、ベンジル又はトリ (低級アルキル)シリルを表す、請求項15に記載の化合物。 17.一般式、 [式中、Y、R1、R2、R3及びR4は、請求項1に示される意味を有する]のカ ルボン酸。 18.治療的活性物質として使用するための、特には炎症、熱、出血、敗血症、 慢性関節リウマチ、変形性関節症、多発性硬化症又は乾癬の処置における治療的 活性物質として使用するための、請求項1〜14のいずれか1項に記載の化合物 。 19.請求項1〜14のいずれか1項に記載の化合物の製造方法であって、一般 式、 [式中、Y、R1、R2、R3及びR4は請求項1に示される意味を有し、R9は保 護基を表す] の化合物を脱保護し、所望により、得られた式(I)の化合物を医薬的に許容さ れる塩に変換する方法。 20.請求項1〜14のいずれか1項に記載の化合物、及び治療的に不活性な担 体物質を含む医薬。 21.請求項1〜14のいずれか1項に記載の化合物、及び治療的に不活性な担 体物質を含む、炎症、熱、出血、敗血症、慢性関節リウマチ、変形性関節症、多 発性硬化症又は乾癬の処置用医薬。 22.医薬、特には炎症、熱、出血、敗血症、慢性関節リウマチ、変形性関節症 、多発性硬化症又は乾癬の処置用医薬の製造方法であって、請求項1〜14のい ずれか1項に記載の化合物を、治療的に不活性な担体物質及び所望により1種以 上の付加的な治療的活性物質と共に製剤化する製造方法。 23.病気の処置、特には炎症、熱、出血、敗血症、慢性関節リウマチ、変形性 関節症、多発性硬化症又は乾癬の処置のための、請求項1〜14のいずれか1項 に記載の化合物の使用。 24.請求項19に記載の方法、又はそれに均等な方法により製造される、請求 項1〜14のいずれか1項に記載の化合物。 25.ここに記載される新規化合物、中間体、方法、医薬及び方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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GB9713833.3 | 1997-06-30 | ||
GBGB9713833.3A GB9713833D0 (en) | 1997-06-30 | 1997-06-30 | Novel hydrazine derivatives |
GB9803335.0 | 1998-02-17 | ||
GBGB9803335.0A GB9803335D0 (en) | 1997-06-30 | 1998-02-17 | Novel hydrazine derivatives |
PCT/EP1998/003683 WO1999001428A1 (en) | 1997-06-30 | 1998-06-18 | Hydrazine derivatives |
Publications (2)
Publication Number | Publication Date |
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JP2000513750A true JP2000513750A (ja) | 2000-10-17 |
JP3801653B2 JP3801653B2 (ja) | 2006-07-26 |
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JP50623099A Expired - Fee Related JP3801653B2 (ja) | 1997-06-30 | 1998-06-18 | ヒドラジン誘導体 |
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US (1) | US6235787B1 (ja) |
EP (1) | EP0993442B1 (ja) |
JP (1) | JP3801653B2 (ja) |
CN (1) | CN1161331C (ja) |
AT (1) | ATE238277T1 (ja) |
AU (1) | AU725039B2 (ja) |
BG (1) | BG104050A (ja) |
BR (1) | BR9810952A (ja) |
CA (1) | CA2295062A1 (ja) |
DE (2) | DE69813815T2 (ja) |
DK (1) | DK0993442T3 (ja) |
ES (2) | ES2195365T3 (ja) |
FR (1) | FR2765219B1 (ja) |
GB (1) | GB2326881A (ja) |
HU (1) | HUP0002424A3 (ja) |
ID (1) | ID24705A (ja) |
IL (1) | IL133712A0 (ja) |
IS (1) | IS5322A (ja) |
IT (1) | IT1301792B1 (ja) |
MA (1) | MA26517A1 (ja) |
NO (1) | NO996534L (ja) |
NZ (1) | NZ501455A (ja) |
PL (1) | PL337793A1 (ja) |
PT (1) | PT993442E (ja) |
SK (1) | SK180699A3 (ja) |
TR (1) | TR199903281T2 (ja) |
WO (1) | WO1999001428A1 (ja) |
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JP2006501155A (ja) * | 2002-05-31 | 2006-01-12 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害剤 |
JP2010518003A (ja) * | 2007-02-02 | 2010-05-27 | セラヴァンス, インコーポレーテッド | 二重作用性抗高血圧剤 |
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CA2604907A1 (en) * | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Combination cancer therapy with bis(thiohydrazide) amide compounds |
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DE102005038344A1 (de) * | 2005-08-13 | 2007-02-15 | Tetra Laval Holdings & Finance S.A. | Vorrichtung zum Ultraschallbearbeiten von Werkstücken |
NZ565996A (en) | 2005-08-16 | 2011-04-29 | Synta Pharmaceuticals Corp | Bis(thio-hydrazide amide) formulation |
EP2041181B1 (en) * | 2006-06-08 | 2011-05-18 | Helmholtz Zentrum München Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Specific protease inhibitors and their use in cancer therapy |
AU2007288338B2 (en) | 2006-08-21 | 2012-05-03 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
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WO2008033494A2 (en) * | 2006-09-15 | 2008-03-20 | Synta Pharmaceuticals Corp. | Purification of bis(thiohydrazide amides) |
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CN104031081B (zh) * | 2014-03-06 | 2017-03-29 | 苏州大学 | 一种多酰胺抗菌剂、制备方法及其应用 |
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- 1998-06-18 PL PL98337793A patent/PL337793A1/xx unknown
- 1998-06-24 IT IT1998MI001441A patent/IT1301792B1/it active IP Right Grant
- 1998-06-26 FR FR9808124A patent/FR2765219B1/fr not_active Expired - Lifetime
- 1998-06-29 GB GB9814027A patent/GB2326881A/en not_active Withdrawn
- 1998-06-29 ES ES009801359A patent/ES2140348B1/es not_active Expired - Lifetime
- 1998-06-30 MA MA25147A patent/MA26517A1/fr unknown
- 1998-06-30 DE DE19829229A patent/DE19829229A1/de not_active Withdrawn
-
1999
- 1999-12-23 IS IS5322A patent/IS5322A/is unknown
- 1999-12-28 BG BG104050A patent/BG104050A/bg unknown
- 1999-12-29 NO NO996534A patent/NO996534L/no not_active Application Discontinuation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006501155A (ja) * | 2002-05-31 | 2006-01-12 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害剤 |
JP2010518003A (ja) * | 2007-02-02 | 2010-05-27 | セラヴァンス, インコーポレーテッド | 二重作用性抗高血圧剤 |
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