KR101045154B1 - 치환된 아자인돌옥소아세틱 피페라진 유도체의 조성물 및항바이러스 활성 - Google Patents
치환된 아자인돌옥소아세틱 피페라진 유도체의 조성물 및항바이러스 활성 Download PDFInfo
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- KR101045154B1 KR101045154B1 KR1020057002158A KR20057002158A KR101045154B1 KR 101045154 B1 KR101045154 B1 KR 101045154B1 KR 1020057002158 A KR1020057002158 A KR 1020057002158A KR 20057002158 A KR20057002158 A KR 20057002158A KR 101045154 B1 KR101045154 B1 KR 101045154B1
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- precursor
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- alkyl
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- azaindole
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- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 12
- 150000004885 piperazines Chemical class 0.000 title abstract description 20
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 title description 99
- 150000001875 compounds Chemical class 0.000 claims abstract description 208
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims description 74
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 199
- 208000030507 AIDS Diseases 0.000 abstract description 15
- 239000003814 drug Substances 0.000 abstract description 14
- 239000003112 inhibitor Substances 0.000 abstract description 14
- 229940079593 drug Drugs 0.000 abstract description 10
- 239000003443 antiviral agent Substances 0.000 abstract description 7
- 230000009545 invasion Effects 0.000 abstract description 6
- 229960005475 antiinfective agent Drugs 0.000 abstract description 5
- 239000004599 antimicrobial Substances 0.000 abstract description 5
- 239000002955 immunomodulating agent Substances 0.000 abstract description 5
- 229940124425 anti-infective immunomodulator Drugs 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 description 557
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 263
- -1 azaindole piperazine diamide derivatives Chemical class 0.000 description 262
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- 238000006243 chemical reaction Methods 0.000 description 176
- 125000001072 heteroaryl group Chemical group 0.000 description 136
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 127
- 238000007429 general method Methods 0.000 description 122
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 99
- 125000000217 alkyl group Chemical group 0.000 description 96
- 229910052736 halogen Inorganic materials 0.000 description 90
- 238000002360 preparation method Methods 0.000 description 89
- 229910052739 hydrogen Inorganic materials 0.000 description 88
- 239000002904 solvent Substances 0.000 description 86
- 150000002367 halogens Chemical class 0.000 description 84
- 239000000543 intermediate Substances 0.000 description 81
- 239000011541 reaction mixture Substances 0.000 description 72
- 125000003118 aryl group Chemical group 0.000 description 71
- 239000000243 solution Substances 0.000 description 71
- 239000001257 hydrogen Substances 0.000 description 70
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 68
- 125000001424 substituent group Chemical group 0.000 description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 49
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- 239000002253 acid Substances 0.000 description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 45
- 229910052796 boron Inorganic materials 0.000 description 44
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 43
- 235000019439 ethyl acetate Nutrition 0.000 description 42
- 239000003153 chemical reaction reagent Substances 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- 125000000753 cycloalkyl group Chemical group 0.000 description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 36
- 238000002953 preparative HPLC Methods 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 35
- 238000010168 coupling process Methods 0.000 description 35
- 125000000623 heterocyclic group Chemical group 0.000 description 35
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000005859 coupling reaction Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- 150000001299 aldehydes Chemical group 0.000 description 30
- 150000001412 amines Chemical class 0.000 description 30
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 29
- 239000000047 product Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 27
- 125000004093 cyano group Chemical group *C#N 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 230000008878 coupling Effects 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 25
- 238000004811 liquid chromatography Methods 0.000 description 25
- 238000004949 mass spectrometry Methods 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 22
- 125000003545 alkoxy group Chemical group 0.000 description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 21
- 238000010898 silica gel chromatography Methods 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 20
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000000284 extract Substances 0.000 description 19
- 125000001544 thienyl group Chemical group 0.000 description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 18
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 17
- 150000001204 N-oxides Chemical class 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- 125000001153 fluoro group Chemical group F* 0.000 description 17
- 125000002541 furyl group Chemical group 0.000 description 17
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 17
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 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 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000004007 reversed phase HPLC Methods 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 15
- 125000004076 pyridyl group Chemical group 0.000 description 15
- 238000005755 formation reaction Methods 0.000 description 14
- 150000002431 hydrogen Chemical class 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 150000002825 nitriles Chemical class 0.000 description 14
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 13
- 229960004132 diethyl ether Drugs 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 229910000080 stannane Inorganic materials 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- 235000019270 ammonium chloride Nutrition 0.000 description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 12
- 150000003852 triazoles Chemical group 0.000 description 12
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 11
- WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 229910052744 lithium Inorganic materials 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 10
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 10
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 9
- 229910018594 Si-Cu Inorganic materials 0.000 description 9
- 229910008465 Si—Cu Inorganic materials 0.000 description 9
- 244000309464 bull Species 0.000 description 9
- 150000001805 chlorine compounds Chemical class 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 229960002555 zidovudine Drugs 0.000 description 9
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 8
- SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 description 8
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 208000031886 HIV Infections Diseases 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 8
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 230000000670 limiting effect Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
- 150000003536 tetrazoles Chemical group 0.000 description 8
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical group O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 208000037357 HIV infectious disease Diseases 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
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- 125000001246 bromo group Chemical group Br* 0.000 description 7
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- DRMNEFTZEKEZHE-UHFFFAOYSA-M potassium;2-(7-chloro-4-fluoropyrrolo[3,2-b]pyridin-3-yl)-2-oxoacetate Chemical compound [K+].C1=CN(F)C2=C(C(=O)C(=O)[O-])C=NC2=C1Cl DRMNEFTZEKEZHE-UHFFFAOYSA-M 0.000 description 1
- WTHPPDHMSZQUEP-UHFFFAOYSA-M potassium;2-[7-(4-methoxyphenyl)-1h-pyrrolo[3,2-b]pyridin-3-yl]-2-oxoacetate Chemical compound [K+].C1=CC(OC)=CC=C1C1=CC=NC2=C1NC=C2C(=O)C([O-])=O WTHPPDHMSZQUEP-UHFFFAOYSA-M 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 238000006478 transmetalation reaction Methods 0.000 description 1
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- DJPWGOLOEFKKFC-UHFFFAOYSA-N tributyl(1h-pyrazol-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NN1 DJPWGOLOEFKKFC-UHFFFAOYSA-N 0.000 description 1
- UDLLSOQWYYRFPP-UHFFFAOYSA-N tributyl(pyridazin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NN=C1 UDLLSOQWYYRFPP-UHFFFAOYSA-N 0.000 description 1
- DINAKCGOEKXDTP-UHFFFAOYSA-N tributyl-(1-methylpyrrol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CN1C DINAKCGOEKXDTP-UHFFFAOYSA-N 0.000 description 1
- IEBXUMIXNUUCFJ-UHFFFAOYSA-N tributyl-(1-phenyltriazol-4-yl)stannane Chemical compound N1=NC([Sn](CCCC)(CCCC)CCCC)=CN1C1=CC=CC=C1 IEBXUMIXNUUCFJ-UHFFFAOYSA-N 0.000 description 1
- VQXIHWMSSWMZTM-UHFFFAOYSA-N tributyl-(4,6-dimethoxy-1,3,5-triazin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC(OC)=NC(OC)=N1 VQXIHWMSSWMZTM-UHFFFAOYSA-N 0.000 description 1
- PPJFSRBPGMKFLO-UHFFFAOYSA-N tributyl-(5,6-dichloropyrazin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=C(Cl)C(Cl)=N1 PPJFSRBPGMKFLO-UHFFFAOYSA-N 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- PIQMEENHEITNKH-UHFFFAOYSA-N trimethyl-(1-methylimidazol-2-yl)stannane Chemical compound CN1C=CN=C1[Sn](C)(C)C PIQMEENHEITNKH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 230000007306 turnover Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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Abstract
Description
EC50에 대한 생물학적 데이타 부호 | |||
5 μM 초과의 EC50을 갖는 화합물* | 1 μM 초과 5 μM 미만의 EC50을 갖는 화합물 | 50 nM 초과의 EC50을 갖는 화합물. 더 높은 농도에서는 시험하지 않음. | 1 μM 미만의 EC50을 갖는 화합물 |
군 C | 군 B | 군 A' | 군 A |
표 A2 내지 A7에서 EC50에 대한 생물학적 데이타 부호 | ||
1 μM 초과의 EC50을 갖는 화합물* |
0.2 nM 초과 1 μM 미만의 EC50을 갖는 화합물 | 0.20 nM 이하의 EC50을 갖는 화합물 |
군 3 | 군 2 | 군 1 |
놀라운 우수한 특성을 갖는, R4로서 N 연결된 트리아졸 | |||||
실시예 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
216 | 1 | 예 | 낮음 | 32±12 | 1.6±0.2 |
188 | 1 | 예 | 낮음 | 20±4.6 | 2.4±0.08 |
187 | 1 | 예 | 낮음 | 22.4±7.2 | 2.4±0.5 |
215,303 | 1 | 예 | 낮음 | 83.7±9.8 | 0.7±0.12 |
245 | 1 | 예 | 낮음 | 12.1±1.3 | 5.6±1.8 |
313 | 1 | 예 | 낮음 | ||
316 | 1 | 예 | 낮음 | 52±12 | 1.3±0.19 |
317 | 1 | 예 | 낮음 | 43±12 | 1.9±0.26 |
306 | 1 | 예 | 낮음 | 160±11 | 0.39±0.07 |
321 | 1 | 예 | 낮음 | ||
322 | 1 | 예 | 낮음 | 82±23 | 1.8±0.4 |
314 | 1 | 예 | 낮음 | ||
315 | 1 | 예 | 낮음 | ||
352 | 1 | 예 | 낮음 | ||
325 | 1 | 예 | 낮음 | ||
326 | 1 | 예 | 낮음 | 9.8±2.9 | 8.3 |
274 | 1 | 예 | 낮음 | ||
273 | 1 | 예 | 낮음 | ||
324 | 1 | 예 | 낮음 | ||
275 | 1 | 예 | 낮음 |
비교물로서 R4에서 몇몇 기타 다르게 치환된 N 연결된 트리아졸 | |||||
실시예 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
217 | 2 | 예 | NT | NT | NT |
307 | 2 | 예 | NT | NT | NT |
256 | 2 | 예 | NT | NT | NT |
350 | 2 | 예 | 낮음 | NT | NT |
327 | 2 | 예 | 낮음 | NT | NT |
328 | 1 | 예 | 낮음 | NT | NT |
351 | NT | NT | 낮음 | 1.5±0.14 | 16.6±1.4 |
비교물로서 R4에서 몇몇 기타 관련된 N 연결된 헤테로아릴 | |||||
실시예 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
139 | 2 | 예 | 높음 | ||
219,305 | 1 | 예 | 높음 | ||
193 | 1 | 아니오 | 낮음 | 14±8 | 4.5±0.4 |
189 | 2 | 예 | 낮음 | ||
222 | 2 | 예 | 낮음 | ||
221 | 2 | 예 | 낮음 | ||
220 | 2 | 예 | NT | ||
218,304 | 2 | 예 | 낮음 | ||
190 | 1 | 예 | 낮음 | 7.4±3.4* | 3.7±1.0 |
191 | 2 | 예 | NT | ||
309 | 1 | 예 | 낮음 | 0.09±0.05 | 34.3±2.6 |
318 | 2 | 예 | 낮음 | ||
310 | 1 | 예 | 낮음 | 2.1±0.4* | 16.5±3.3 |
241 | 1 | 예 | 낮음 | 6.4±4.2* | 11.2±0.9 |
312 | 2 | 예 | 낮음 | ||
241 | 1 | 예 | 낮음 | 0.0086±0.005** | 131±4.3 |
236 | 1 | 예 | 낮음 | 0.56±0.25 | 29±6.7 |
251 | 1 | 예 | 낮음 | ||
230 | 1 | 예 | 중간 | ||
343 | 1 | 예 | 낮음 | ||
344 | 2 | 아니오 | 낮음 | ||
276 | 1 | 예 | NT | ||
255 | 1 | 예 | 중간 | ||
258 | 1 | 예 | 낮음 | ||
314 | 1 | 예 | 낮음 | ||
315 | 1 | 예 | 낮음 | ||
352 | 1 | 예 | 낮음 | ||
326 | 1 | 예 | 낮음 | 9.8±2.9 | 8.3 |
274 | 1 | 예 | |||
273 | 1 | 예 | |||
275 | 1 | 예 |
몇몇 관련된 C 연결된 헤테로아릴 비교물 | |||||
실시예 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
40 | 2 | 아니오 | 낮음 | ||
42 | 2 | 예 | 낮음 | ||
22 | 1 | 아니오 | 중간 | ||
35 | 1 | 예 | 중간 | ||
37 | 1 | 아니오 | NT | ||
38 | 1 | 아니오 | 낮음 | ||
39 | 2 | 아니오 | 중간 | ||
28 | 3 | 아니오 | NT | ||
29 | 2 | 아니오 | 높음 | ||
22 | 2 | 아니오 | 높음 | ||
74 | 2 | 아니오 | 중간 | ||
71 | 1 | 예 | 중간 | ||
73 | 1 | 예 | 중간 | ||
78 | 2 | 예 | 중간 | ||
94 | 1 | 예 | NT | ||
102 | 2 | 예 | 낮음 | 6.9±1.3 | 12±5.5 |
163 | 2 | 예 | 어려움 | ||
95 | 1 | 예 | 중간 | ||
140 | 2 | 예 | 중간 | ||
146 | 2 | 예 | 중간 | ||
145 | 1 | 예 | 어려움 | 12±3.8 | 1.4±0.29 |
148 | 2 | 예 | NT | ||
210 | 1 | 예 | 중간 | ||
211 | 1 | 아니오 | 중간 | ||
212 | 1 | 예 | 낮음 | ||
223 | 2 | 예 | 낮음 | ||
224 | 2 | 예 | 낮음 | ||
225 | 2 | 예 | NT | ||
227 | 2 | 예 | 낮음 | 3.8±0.83 | 8.8±3.7 |
226 | 1 | 예 | 낮음 | 0.5±0.13* | 24.5±3 |
299 | 1 | 아니오 | 낮음 | ||
300 | 2 | 예 | 낮음 | ||
266 | 1 | 예 | 낮음 | 0.16±0.04* | 37.4±3.2 |
345 | 2 | 예 | 낮음 | ||
301 | 2 | 예 | NT | ||
346 | 2 | 예 | NT | ||
347 | 2 | 예 | 낮음 | ||
334 | 2 | 예 | NT | ||
348 | 2 | 예 | 낮음 | ||
349 | 2 | 예 | NT | ||
342 | 1 | 예 | 낮음 |
몇몇 관련된 4-아자인돌 비교물 및 데이타 | |||||
실시예 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
204 | 2 | 예 | 낮음 | 12±1.4 | 10±1.3 |
161 | 1 | 예 | 높음 | ||
205 | 2 | 예 | 낮음 | 9.6±1.2 | 5.4±0.4 |
207 | 2 | 예 | 낮음 | ||
206 | 2 | 예 | NT | ||
208 | 2 | 예 | NT | ||
353 | 2 | 예 | 낮음 | 1363±307 | 5.6±1.1* |
354 | 2 | 예 | 낮음 | 1.26 0.18* |
11.2±0.8 |
355 | 2 | 예 | 낮음 | 3.3±0.77* | 13.9±5.3 |
356 | 2 | 예 | 낮음 | ||
357 | 2 | 예 | 중간 | ||
358 | 2 | 예 | 높음 | ||
359 | 2 | 예 | NT | ||
360 | 2 | 예 | 낮음 | ||
361 | 2 | 예 | NT |
미국 특허 제6476034호(참고 문헌 94)로부터의 몇몇 관련된 비교물 및 데이타 | |||||
참고 화합물 번호 | EC50 카테고리 | CC50 > 100 μM |
HLM에서 예상된 인간에서의 제거 등급 | AUC 24시간 (㎍.hr/mL) |
CL, iv (mL/분/kg) |
1 | 2 | 예 | 낮음 | 0.5 | 32±1.8 |
2 | 2 | 예 | 중간 | ||
3 | 2 | 예 | 낮음 | 6.3±2.7 | 13±4.0 |
4 | 2 | 예 | 낮음 | ||
5 | 1 | 예 | 중간 | ||
6 | 2 | 예 | 낮음 | 1.7±0.58 | 31±5.9 |
7 | 1 | 예 | 낮음 | 2.6±0.12* | 19.3±0.65 |
8 | 1 | 예 | 낮음 | 1.03±0.07* | 47.2±11.5 |
9 | 2 | 예 | 낮음 | 5.9±2.2 | 5.9±2.2 |
10 | 2 | 예 | 낮음 | 2.9±0.3 | 11.7±1.0 |
11 | 1 | 예 | 1.4±0.2* | 24.8±0.41 | |
12 | 1 | 예 | 낮음 | 4.7±1.1 | 11.9±1.8 |
13 | 2 | 예 | NT |
Claims (93)
- 항바이러스 유효량의 제1항의 화합물 및 제약상 허용가능한 담체를 포함하는, HIV 바이러스에 감염된 포유동물을 치료하기 위한 제약 제제.
- 항바이러스 유효량의 제2항의 화합물 및 제약상 허용가능한 담체를 포함하는, HIV 바이러스에 감염된 포유동물을 치료하기 위한 제약 제제.
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US10/214,982 US20030207910A1 (en) | 2001-02-02 | 2002-08-07 | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
US10/214,982 | 2002-08-07 | ||
PCT/US2003/024415 WO2004014380A1 (en) | 2002-08-07 | 2003-08-05 | Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives |
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Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0307834D0 (en) * | 2003-04-04 | 2003-05-14 | Ta Contrast Ab | Composition |
US20050075364A1 (en) * | 2003-07-01 | 2005-04-07 | Kap-Sun Yeung | Indole, azaindole and related heterocyclic N-substituted piperazine derivatives |
US20050124623A1 (en) * | 2003-11-26 | 2005-06-09 | Bender John A. | Diazaindole-dicarbonyl-piperazinyl antiviral agents |
US7745625B2 (en) | 2004-03-15 | 2010-06-29 | Bristol-Myers Squibb Company | Prodrugs of piperazine and substituted piperidine antiviral agents |
US20050215544A1 (en) * | 2004-03-24 | 2005-09-29 | Pin-Fang Lin | Methods of treating HIV infection |
US7776863B2 (en) * | 2004-03-24 | 2010-08-17 | Bristol-Myers Squibb Company | Methods of treating HIV infection |
DE602005010698D1 (de) | 2004-06-09 | 2008-12-11 | Glaxo Group Ltd | Pyrrolopyridinderivate |
US20060100209A1 (en) * | 2004-11-09 | 2006-05-11 | Chong-Hui Gu | Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
US20060100432A1 (en) * | 2004-11-09 | 2006-05-11 | Matiskella John D | Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione |
US7183284B2 (en) * | 2004-12-29 | 2007-02-27 | Bristol-Myers Squibb Company | Aminium salts of 1,2,3-triazoles as prodrugs of drugs including antiviral agents |
US7601715B2 (en) | 2005-06-22 | 2009-10-13 | Bristol-Myers Squibb Company | Process for preparing triazole substituted azaindoleoxoacetic piperazine derivatives and novel salt forms produced therein |
US7598380B2 (en) * | 2005-08-03 | 2009-10-06 | Bristol-Myers Squibb Company | Method of preparation of azaindole derivatives |
US7851476B2 (en) * | 2005-12-14 | 2010-12-14 | Bristol-Myers Squibb Company | Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine |
US7807671B2 (en) | 2006-04-25 | 2010-10-05 | Bristol-Myers Squibb Company | Diketo-piperazine and piperidine derivatives as antiviral agents |
US7504399B2 (en) * | 2006-06-08 | 2009-03-17 | Bristol-Meyers Squibb Company | Piperazine enamines as antiviral agents |
US8318941B2 (en) * | 2006-07-06 | 2012-11-27 | Bristol-Myers Squibb Company | Pyridone/hydroxypyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
EP2346508B1 (en) | 2008-09-26 | 2016-08-24 | Intellikine, LLC | Heterocyclic kinase inhibitors |
GB0910667D0 (en) * | 2009-06-19 | 2009-08-05 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
WO2012019003A1 (en) * | 2010-08-06 | 2012-02-09 | Bristol-Myers Squibb Company | Substituted indole and azaindole oxoacetyl piperazinamide derivatives |
ES2585396T3 (es) * | 2010-12-02 | 2016-10-05 | VIIV Healthcare UK (No.5) Limited | Alquilamidas como inhibidores de la unión del VIH |
CN102718692B (zh) * | 2012-07-03 | 2014-01-08 | 苏州和健医药科技有限公司 | 一种7位甲基-5位氧取代吲哚化合物的制备方法 |
WO2016004272A1 (en) | 2014-07-02 | 2016-01-07 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
EP3194387B1 (en) * | 2014-09-17 | 2019-07-31 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
CA2983927A1 (en) | 2015-05-06 | 2016-11-10 | The Regents Of The University Of California | K-ras modulators |
EP4340839A1 (fr) * | 2021-05-21 | 2024-03-27 | Centre National de la Recherche Scientifique (CNRS) | Nouveaux derives azaindole en tant qu'agents antiviraux |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020061892A1 (en) | 2000-02-22 | 2002-05-23 | Tao Wang | Antiviral azaindole derivatives |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2761201A (en) | 1952-05-02 | 1956-09-04 | Griffin Wheel Co | Renewing molds |
US3830602A (en) | 1973-03-14 | 1974-08-20 | Commercial Shearing | Rotary pumps and motors |
US5023265A (en) * | 1990-06-01 | 1991-06-11 | Schering Corporation | Substituted 1-H-pyrrolopyridine-3-carboxamides |
IL99843A0 (en) | 1990-11-01 | 1992-08-18 | Merck & Co Inc | Synergistic combination of hiv reverse transcriptase inhibitors |
US5811432A (en) | 1990-11-09 | 1998-09-22 | Pfizer Inc | Azaoxindole derivatives |
JP3119485B2 (ja) | 1991-07-03 | 2000-12-18 | ファルマシア・アンド・アップジョン・カンパニー | 抗−エイズ薬としての置換インドール類 |
US5124327A (en) * | 1991-09-06 | 1992-06-23 | Merck & Co., Inc. | HIV reverse transcriptase |
WO1993005020A1 (en) | 1991-09-06 | 1993-03-18 | Merck & Co., Inc. | Indoles as inhibitors of hiv reverse transcriptase |
US5413999A (en) | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
IT1265057B1 (it) | 1993-08-05 | 1996-10-28 | Dompe Spa | Tropil 7-azaindolil-3-carbossiamidi |
US5424329A (en) * | 1993-08-18 | 1995-06-13 | Warner-Lambert Company | Indole-2-carboxamides as inhibitors of cell adhesion |
GB9420521D0 (en) | 1994-10-12 | 1994-11-30 | Smithkline Beecham Plc | Novel compounds |
IL146309A0 (en) | 1999-05-21 | 2002-07-25 | Scios Inc | Indole-type derivatives as inhibitors of p38 kinase |
US6469006B1 (en) | 1999-06-15 | 2002-10-22 | Bristol-Myers Squibb Company | Antiviral indoleoxoacetyl piperazine derivatives |
US6476034B2 (en) | 2000-02-22 | 2002-11-05 | Bristol-Myers Squibb Company | Antiviral azaindole derivatives |
ES2250422T3 (es) | 2000-07-10 | 2006-04-16 | Bristol-Myers Squibb Company | Composicion y actividad antiviral de derivados de piperazina indoloxoaceticos sustituidos. |
US6403211B1 (en) | 2000-07-18 | 2002-06-11 | 3M Innovative Properties Company | Liquid crystal polymer for flexible circuits |
EE05424B1 (et) * | 2001-02-02 | 2011-06-15 | Bristol-Myers Squibb Company | Asendatud asaindooloksoatseetpiperasiini derivaadid, neid sisaldav ravimpreparaat ning nende kasutamine ravis |
AU2003217604A1 (en) * | 2002-02-23 | 2003-09-09 | Bristol-Myers Squibb Company | Method of treating hiv infection by preventing interaction of cd4 and gp120 |
-
2002
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020061892A1 (en) | 2000-02-22 | 2002-05-23 | Tao Wang | Antiviral azaindole derivatives |
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