JPH069623A - ピロリルベンゾジアゼピノン類 - Google Patents
ピロリルベンゾジアゼピノン類Info
- Publication number
- JPH069623A JPH069623A JP5024953A JP2495393A JPH069623A JP H069623 A JPH069623 A JP H069623A JP 5024953 A JP5024953 A JP 5024953A JP 2495393 A JP2495393 A JP 2495393A JP H069623 A JPH069623 A JP H069623A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- pyrrol
- methyl
- compounds
- 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.)
- Pending
Links
- GSXUYTBBSZWMRY-UHFFFAOYSA-N 4-(1H-pyrrol-2-yl)-1,2-benzodiazepin-3-one Chemical class N1C(=CC=C1)C=1C(N=NC2=C(C=1)C=CC=C2)=O GSXUYTBBSZWMRY-UHFFFAOYSA-N 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 206010038997 Retroviral infections Diseases 0.000 claims abstract description 8
- MDGWIRCXFXDNBJ-UHFFFAOYSA-N 7-methyl-5-(1h-pyrrol-2-yl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)CN=C1C1=CC=CN1 MDGWIRCXFXDNBJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 7
- WRPBNGDPQRHZHC-UHFFFAOYSA-N 7-fluoro-5-(1h-pyrrol-2-yl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(F)=CC=C2NC(=O)CN=C1C1=CC=CN1 WRPBNGDPQRHZHC-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 14
- 229910021529 ammonia Inorganic materials 0.000 abstract description 6
- 230000037396 body weight Effects 0.000 abstract description 5
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000840 anti-viral effect Effects 0.000 abstract description 4
- QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical compound NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- FAMYUDNLRDWZIN-UHFFFAOYSA-N 2-bromo-n-[2-(1h-pyrrole-2-carbonyl)phenyl]acetamide Chemical compound BrCC(=O)NC1=CC=CC=C1C(=O)C1=CC=CN1 FAMYUDNLRDWZIN-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- 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 9
- 239000000460 chlorine Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 102100034343 Integrase Human genes 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229960004793 sucrose Drugs 0.000 description 4
- 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 4
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- SLLPGPRVJRMPTI-UHFFFAOYSA-N (2-amino-5-fluorophenyl)-(1h-pyrrol-2-yl)methanone Chemical compound NC1=CC=C(F)C=C1C(=O)C1=CC=CN1 SLLPGPRVJRMPTI-UHFFFAOYSA-N 0.000 description 2
- MTFDYPDPBUHGSX-UHFFFAOYSA-N 2-bromo-n-[4-fluoro-2-(1h-pyrrole-2-carbonyl)phenyl]acetamide Chemical compound FC1=CC=C(NC(=O)CBr)C(C(=O)C=2NC=CC=2)=C1 MTFDYPDPBUHGSX-UHFFFAOYSA-N 0.000 description 2
- GUINCXDKUOHPHI-UHFFFAOYSA-N 3-oxo-n-phenyl-3-(1h-pyrrol-2-yl)propanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CN1 GUINCXDKUOHPHI-UHFFFAOYSA-N 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
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- 239000008215 water for injection Substances 0.000 description 2
- UCRXMAVIQOENGE-UHFFFAOYSA-N (2-amino-5-methylphenyl)-(1h-pyrrol-2-yl)methanone Chemical compound CC1=CC=C(N)C(C(=O)C=2NC=CC=2)=C1 UCRXMAVIQOENGE-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- CISRHMUOOJKICE-UHFFFAOYSA-N 1-(fluoromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CF CISRHMUOOJKICE-UHFFFAOYSA-N 0.000 description 1
- -1 1H-Pyrrol-2-ylcarbonyl Chemical group 0.000 description 1
- WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- PAHAIHXVVJMZKU-UHFFFAOYSA-N 4-bromo-2-methyl-1-nitrobenzene Chemical compound CC1=CC(Br)=CC=C1[N+]([O-])=O PAHAIHXVVJMZKU-UHFFFAOYSA-N 0.000 description 1
- GHYZIXDKAPMFCS-UHFFFAOYSA-N 5-fluoro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1[N+]([O-])=O GHYZIXDKAPMFCS-UHFFFAOYSA-N 0.000 description 1
- REAWYHMDDZZSSJ-UHFFFAOYSA-N 6-fluoro-2-methyl-3,1-benzoxazin-4-one Chemical compound C1=C(F)C=C2C(=O)OC(C)=NC2=C1 REAWYHMDDZZSSJ-UHFFFAOYSA-N 0.000 description 1
- ZBYGWMKGKCTSSF-UHFFFAOYSA-N 7-bromo-5-(1h-pyrrol-2-yl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CN1 ZBYGWMKGKCTSSF-UHFFFAOYSA-N 0.000 description 1
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- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
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- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 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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- 239000002324 mouth wash Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 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
- 235000015205 orange juice Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82547592A | 1992-01-24 | 1992-01-24 | |
| US825475 | 1992-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH069623A true JPH069623A (ja) | 1994-01-18 |
Family
ID=25244088
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5024953A Pending JPH069623A (ja) | 1992-01-24 | 1993-01-21 | ピロリルベンゾジアゼピノン類 |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7507200B2 (en) | 2003-01-31 | 2009-03-24 | Olympus Corporation | Diathermic snare, medical instrument system using the snare, and method of assembling the medical instrument system |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2446696A1 (fr) | 2001-06-07 | 2002-12-12 | Neuro3D | Inhibiteurs des phosphodiesterases des nucleotides cycliques, preparation et utilisations de ces inhibiteurs |
| CN107056760A (zh) * | 2017-01-22 | 2017-08-18 | 苏州楚凯药业有限公司 | 5,7位取代的1H‑苯并[e][1,4]二氮杂‑2(3H)‑酮衍生物的制备方法 |
| CN106831726A (zh) * | 2017-01-22 | 2017-06-13 | 苏州楚凯药业有限公司 | 抗病毒药物中间体苯并二氮杂酮衍生物的制备方法 |
| KR20200144870A (ko) | 2019-06-19 | 2020-12-30 | 김상은 | 항곰팡이 및 항균성이 우수한 수지 조성물 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04305578A (ja) * | 1990-09-10 | 1992-10-28 | F Hoffmann La Roche Ag | ベンゾジアゼピン、その製造法、及び薬剤としての利用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE903879A1 (en) * | 1989-10-30 | 1991-05-08 | Hoffmann La Roche | Use of a benzodiazepine and a phenylpyrrylketone derivative |
| EP0491218A1 (en) * | 1990-12-17 | 1992-06-24 | F. Hoffmann-La Roche Ag | Benzodiazepinones |
-
1992
- 1992-12-16 TW TW081110081A patent/TW221687B/zh active
- 1992-12-17 CZ CS923727A patent/CZ372792A3/cs unknown
- 1992-12-29 CA CA002086368A patent/CA2086368A1/en not_active Abandoned
-
1993
- 1993-01-14 EP EP93100451A patent/EP0552665A1/en not_active Withdrawn
- 1993-01-15 ZA ZA93285A patent/ZA93285B/xx unknown
- 1993-01-18 HU HU939300117A patent/HUT63162A/hu unknown
- 1993-01-18 IL IL104424A patent/IL104424A0/xx unknown
- 1993-01-18 AU AU31856/93A patent/AU3185693A/en not_active Abandoned
- 1993-01-20 MX MX9300260A patent/MX9300260A/es unknown
- 1993-01-20 CN CN93100812A patent/CN1074905A/zh active Pending
- 1993-01-21 KR KR1019930000793A patent/KR930016417A/ko not_active Withdrawn
- 1993-01-21 FI FI930244A patent/FI930244A7/fi not_active Application Discontinuation
- 1993-01-21 JP JP5024953A patent/JPH069623A/ja active Pending
- 1993-01-22 BR BR9300250A patent/BR9300250A/pt not_active Application Discontinuation
- 1993-01-22 NO NO93930224A patent/NO930224L/no unknown
- 1993-01-22 UY UY23540A patent/UY23540A1/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04305578A (ja) * | 1990-09-10 | 1992-10-28 | F Hoffmann La Roche Ag | ベンゾジアゼピン、その製造法、及び薬剤としての利用 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7507200B2 (en) | 2003-01-31 | 2009-03-24 | Olympus Corporation | Diathermic snare, medical instrument system using the snare, and method of assembling the medical instrument system |
Also Published As
| Publication number | Publication date |
|---|---|
| HUT63162A (en) | 1993-07-28 |
| IL104424A0 (en) | 1993-05-13 |
| FI930244L (fi) | 1993-07-25 |
| UY23540A1 (es) | 1993-07-16 |
| CN1074905A (zh) | 1993-08-04 |
| KR930016417A (ko) | 1993-08-26 |
| BR9300250A (pt) | 1993-07-27 |
| MX9300260A (es) | 1993-07-01 |
| HU9300117D0 (en) | 1993-04-28 |
| TW221687B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-03-11 |
| CA2086368A1 (en) | 1993-07-25 |
| NO930224L (no) | 1993-07-26 |
| EP0552665A1 (en) | 1993-07-28 |
| FI930244A0 (fi) | 1993-01-21 |
| AU3185693A (en) | 1993-07-29 |
| CZ372792A3 (en) | 1993-12-15 |
| NO930224D0 (no) | 1993-01-22 |
| ZA93285B (en) | 1993-08-19 |
| FI930244A7 (fi) | 1993-07-25 |
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