AU758563B2 - Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof - Google Patents
Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof Download PDFInfo
- Publication number
- AU758563B2 AU758563B2 AU47152/99A AU4715299A AU758563B2 AU 758563 B2 AU758563 B2 AU 758563B2 AU 47152/99 A AU47152/99 A AU 47152/99A AU 4715299 A AU4715299 A AU 4715299A AU 758563 B2 AU758563 B2 AU 758563B2
- Authority
- AU
- Australia
- Prior art keywords
- loweralkyl
- pharmaceutically acceptable
- acceptable salts
- alkylaryl
- aryl
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 90
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 title abstract description 15
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- -1 dibenzofuran compound Chemical class 0.000 claims abstract description 51
- 208000005384 Pneumocystis Pneumonia Diseases 0.000 claims abstract description 38
- 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 claims abstract description 36
- 201000000317 pneumocystosis Diseases 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 35
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 33
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 30
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 27
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000005001 aminoaryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 5
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 102100021850 Nardilysin Human genes 0.000 claims 24
- 108090000970 Nardilysin Proteins 0.000 claims 24
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
- 239000000243 solution Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 42
- 239000007787 solid Substances 0.000 description 40
- 238000004128 high performance liquid chromatography Methods 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 229910001868 water Inorganic materials 0.000 description 31
- 230000000694 effects Effects 0.000 description 30
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 239000000725 suspension Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 239000012458 free base Substances 0.000 description 17
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 229960004448 pentamidine Drugs 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000003389 potentiating effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 150000003457 sulfones Chemical class 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 230000004568 DNA-binding Effects 0.000 description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001716 carbazoles Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 231100000419 toxicity Toxicity 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 7
- 244000309466 calf Species 0.000 description 6
- VPEXKVZOURGOKV-UHFFFAOYSA-N dibenzofuran-3,7-dicarbonitrile Chemical compound N#CC1=CC=C2C3=CC=C(C#N)C=C3OC2=C1 VPEXKVZOURGOKV-UHFFFAOYSA-N 0.000 description 6
- 150000004826 dibenzofurans Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 210000001541 thymus gland Anatomy 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000027455 binding Effects 0.000 description 5
- LHRXOUZBYQFVMV-UHFFFAOYSA-N dibenzofuran-2,8-dicarbonitrile Chemical compound C1=C(C#N)C=C2C3=CC(C#N)=CC=C3OC2=C1 LHRXOUZBYQFVMV-UHFFFAOYSA-N 0.000 description 5
- IQFOWQNSBODWQI-UHFFFAOYSA-N dibenzothiophene-2,8-dicarbonitrile Chemical compound C1=C(C#N)C=C2C3=CC(C#N)=CC=C3SC2=C1 IQFOWQNSBODWQI-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000002502 liposome Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000011552 rat model Methods 0.000 description 5
- GBCYJXFJGQKMPY-UHFFFAOYSA-N 3,7-dibromodibenzofuran Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3OC2=C1 GBCYJXFJGQKMPY-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 206010061598 Immunodeficiency Diseases 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 238000003482 Pinner synthesis reaction Methods 0.000 description 4
- 206010035664 Pneumonia Diseases 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 208000031513 cyst Diseases 0.000 description 4
- BNNWPSAGYXTUAC-UHFFFAOYSA-N dibenzothiophene-3,7-dicarbonitrile Chemical compound N#CC1=CC=C2C3=CC=C(C#N)C=C3SC2=C1 BNNWPSAGYXTUAC-UHFFFAOYSA-N 0.000 description 4
- 125000000950 dibromo group Chemical group Br* 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 230000000813 microbial effect Effects 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 210000003462 vein Anatomy 0.000 description 4
- CHDZNTSBYBEBTQ-UHFFFAOYSA-N 1-[8-(4,5-dihydroimidazol-1-yl)dibenzothiophen-2-yl]-4,5-dihydroimidazole;dihydrochloride Chemical compound Cl.Cl.C1=NCCN1C1=CC=C(SC=2C3=CC(=CC=2)N2C=NCC2)C3=C1 CHDZNTSBYBEBTQ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KMNBVODPWIFUSS-UHFFFAOYSA-N 3,7-dibromodibenzothiophene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3SC2=C1 KMNBVODPWIFUSS-UHFFFAOYSA-N 0.000 description 3
- VCLKJLSWRBGUTI-UHFFFAOYSA-N 4-bromo-1-(4-bromo-2-methoxyphenyl)-2-nitrobenzene Chemical group COC1=CC(Br)=CC=C1C1=CC=C(Br)C=C1[N+]([O-])=O VCLKJLSWRBGUTI-UHFFFAOYSA-N 0.000 description 3
- DSDSVHLSVVQUSM-UHFFFAOYSA-N 5-bromo-2-(4-bromo-2-methoxyphenyl)aniline Chemical group COC1=CC(Br)=CC=C1C1=CC=C(Br)C=C1N DSDSVHLSVVQUSM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 241000233872 Pneumocystis carinii Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
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- 238000013459 approach Methods 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
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- 238000005516 engineering process Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
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- 238000003305 oral gavage Methods 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
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- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
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- 230000002829 reductive effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- RRCIJLBMQJGTJN-UHFFFAOYSA-N (E)-[amino-[7-[(E)-amino(hydroxyazaniumylidene)methyl]dibenzothiophen-3-yl]methylidene]-hydroxyazanium dichloride Chemical compound Cl.Cl.ONC(=N)C1=CC=C2C3=CC=C(C(=N)NO)C=C3SC2=C1 RRCIJLBMQJGTJN-UHFFFAOYSA-N 0.000 description 2
- KXWXLOCZOYLYKC-UHFFFAOYSA-N (z)-[amino-[7-[(z)-amino(propan-2-ylazaniumylidene)methyl]dibenzothiophen-3-yl]methylidene]-propan-2-ylazanium;dichloride Chemical compound Cl.Cl.CC(C)NC(=N)C1=CC=C2C3=CC=C(C(=N)NC(C)C)C=C3SC2=C1 KXWXLOCZOYLYKC-UHFFFAOYSA-N 0.000 description 2
- HJVIIKACDCRZHM-UHFFFAOYSA-N 1-n',7-n'-di(propan-2-yl)-9h-carbazole-1,7-dicarboximidamide;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C3=CC=C(C(=N)NC(C)C)C=C3NC2=C1C(=N)NC(C)C HJVIIKACDCRZHM-UHFFFAOYSA-N 0.000 description 2
- VLBCMZRPFFBRCK-UHFFFAOYSA-N 1-n',7-n'-dihydroxy-9h-carbazole-1,7-dicarboximidamide Chemical compound C1=CC=C2C3=CC=C(C(=N)NO)C=C3NC2=C1C(=N)NO VLBCMZRPFFBRCK-UHFFFAOYSA-N 0.000 description 2
- LEEHEYFEAYBKDK-UHFFFAOYSA-N 1-n',7-n'-dihydroxy-9h-carbazole-1,7-dicarboximidamide;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C3=CC=C(C(=N)NO)C=C3NC2=C1C(=N)NO LEEHEYFEAYBKDK-UHFFFAOYSA-N 0.000 description 2
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- REUCYFQYHWKXPH-UHFFFAOYSA-N 4-bromo-1-(4-bromo-2-nitrophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1[N+]([O-])=O REUCYFQYHWKXPH-UHFFFAOYSA-N 0.000 description 2
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- 206010011953 Decreased activity Diseases 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 2
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- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003473 anti-pneumocystis Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- NCMHKCKGHRPLCM-UHFFFAOYSA-N caesium(1+) Chemical compound [Cs+] NCMHKCKGHRPLCM-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 2
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- NLSVKIDQAOBZNB-UHFFFAOYSA-N dibenzofuran-2,8-dicarboximidamide;dihydrochloride Chemical compound Cl.Cl.C1=C(C(N)=N)C=C2C3=CC(C(=N)N)=CC=C3OC2=C1 NLSVKIDQAOBZNB-UHFFFAOYSA-N 0.000 description 1
- HGWSGYCOFMSZFU-UHFFFAOYSA-N dibenzofuran-3,7-dicarboximidamide Chemical compound NC(=N)C1=CC=C2C3=CC=C(C(=N)N)C=C3OC2=C1 HGWSGYCOFMSZFU-UHFFFAOYSA-N 0.000 description 1
- YSWFIUHDUKUSGJ-UHFFFAOYSA-N dibenzofuran-3,7-dicarboximidamide;dihydrochloride Chemical compound Cl.Cl.NC(=N)C1=CC=C2C3=CC=C(C(=N)N)C=C3OC2=C1 YSWFIUHDUKUSGJ-UHFFFAOYSA-N 0.000 description 1
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 description 1
- YFQKVQDMYAXRRC-UHFFFAOYSA-N dibenzothiophene-3,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3SC2=C1 YFQKVQDMYAXRRC-UHFFFAOYSA-N 0.000 description 1
- YDGINKIBVCFVKP-UHFFFAOYSA-N dibenzothiophene-3,7-diamine;dihydrochloride Chemical compound Cl.Cl.NC1=CC=C2C3=CC=C(N)C=C3SC2=C1 YDGINKIBVCFVKP-UHFFFAOYSA-N 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- OIIWPAYIXDCDNL-UHFFFAOYSA-M sodium 3-(trimethylsilyl)propionate Chemical compound [Na+].C[Si](C)(C)CCC([O-])=O OIIWPAYIXDCDNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/08—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis for Pneumocystis carinii
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9727398P | 1998-08-20 | 1998-08-20 | |
| US60/097273 | 1998-08-20 | ||
| PCT/US1999/014313 WO2000010990A2 (en) | 1998-08-20 | 1999-06-24 | Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4715299A AU4715299A (en) | 2000-03-14 |
| AU758563B2 true AU758563B2 (en) | 2003-03-27 |
Family
ID=22262567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU47152/99A Ceased AU758563B2 (en) | 1998-08-20 | 1999-06-24 | Dicationic dibenzofuran and dibenzothiophene compounds and methods of use thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6172104B1 (enExample) |
| EP (1) | EP1105381B1 (enExample) |
| JP (1) | JP2003523927A (enExample) |
| AT (1) | ATE239003T1 (enExample) |
| AU (1) | AU758563B2 (enExample) |
| CA (1) | CA2340912C (enExample) |
| DE (1) | DE69907476T2 (enExample) |
| ES (1) | ES2198139T3 (enExample) |
| WO (1) | WO2000010990A2 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2784678B1 (fr) * | 1998-09-23 | 2002-11-29 | Sod Conseils Rech Applic | Nouveaux derives de n-(iminomethyl)amines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
| US6569853B1 (en) * | 2000-11-06 | 2003-05-27 | Combinatorx, Incorporated | Combinations of chlorpromazine and pentamidine for the treatment of neoplastic disorders |
| GB2380192B8 (en) * | 2001-02-09 | 2005-09-14 | Sumitomo Chemical Co | Phenylacetylene compounds liquid crystal compositions polymers optically anisotropic products & optical & liquid crystal elements derived therefrom |
| JP2002255960A (ja) * | 2001-02-27 | 2002-09-11 | Sumitomo Chem Co Ltd | ジベンゾチオフェン化合物、中間体およびその製造方法 |
| JP2005505508A (ja) * | 2001-06-13 | 2005-02-24 | ジーンソフト ファーマシューティカルズ インコーポレイテッド | 抗感染活性を有するベンゾチオフェン化合物 |
| BR0212078A (pt) * | 2001-08-31 | 2004-09-28 | Neurochem Int Ltd | Método de tratar ou prevenir uma doença relacionada com amilóide em um paciente, composição farmacêutica, composto quìmico, e, uso de um composto |
| SG124249A1 (en) * | 2001-12-07 | 2006-08-30 | Sumitomo Chemical Co | New polymer and polymer light-emitting device using the same |
| JP4957669B2 (ja) * | 2002-03-15 | 2012-06-20 | 住友化学株式会社 | 高分子化合物およびそれを用いた高分子発光素子 |
| AU2003258022A1 (en) | 2002-08-02 | 2004-02-23 | Genesoft Pharmaceuticals, Inc. | Biaryl compounds having anti-infective activity |
| US7265129B2 (en) * | 2002-10-25 | 2007-09-04 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
| EP1587529A4 (en) | 2002-12-10 | 2009-08-12 | Oscient Pharmaceuticals Corp | ANTIBACTERIAL COMPOUNDS WITH (PYROCARBOXAMIDE) - (BENZAMID) - (IMIDAZOLE CARBOXAMIDE) MOTIVE |
| US20050054708A1 (en) * | 2003-07-28 | 2005-03-10 | Nichols Matthew James | Combinations of drugs for the treatment of neoplasms |
| US20050080075A1 (en) * | 2003-08-25 | 2005-04-14 | Nichols M. James | Formulations, conjugates, and combinations of drugs for the treatment of neoplasms |
| US20050158320A1 (en) * | 2003-11-12 | 2005-07-21 | Nichols M. J. | Combinations for the treatment of proliferative diseases |
| US20050100508A1 (en) * | 2003-11-12 | 2005-05-12 | Nichols M. J. | Methods for identifying drug combinations for the treatment of proliferative diseases |
| WO2005051296A2 (en) * | 2003-11-24 | 2005-06-09 | University Of North Carolina At Chapel Hill | Fused ring dicationic anti-protozoan agents and their prodrugs |
| US7262223B2 (en) * | 2004-01-23 | 2007-08-28 | Neurochem (International) Limited | Amidine derivatives for treating amyloidosis |
| US7365193B2 (en) | 2004-02-04 | 2008-04-29 | Abbott Laboratories | Amino-substituted tricyclic derivatives and methods of use |
| US7994225B2 (en) * | 2004-03-17 | 2011-08-09 | Rempex Pharmaceuticals, Inc. | Bacterial efflux pump inhibitors for the treatment of ophthalmic and otic infections |
| CA2559208A1 (en) * | 2004-03-17 | 2005-09-29 | Mpex Pharmaceuticals, Inc. | Use and administration of bacterial efflux pump inhibitors |
| DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
| GB0619325D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| US20090092574A1 (en) | 2006-12-29 | 2009-04-09 | Scott Richard W | Ophthalmic And Otic Compositions Of Facially Amphiphilic Polymers And Oligomers And Uses Thereof |
| DE102007013854A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Tetrahydrochinoline |
| DE102007013855A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydrochinoline |
| DE102007013856A1 (de) | 2007-03-20 | 2008-09-25 | Merck Patent Gmbh | Substituierte Tetrahydropyrrolochinoline |
| CA2732572A1 (en) * | 2008-07-28 | 2010-02-04 | Polymedix, Inc. | Anti-malarial compounds |
| US8278309B2 (en) | 2008-10-27 | 2012-10-02 | Polymedix, Inc. | Synthetic mimetics of host defense and uses thereof |
| BR112012016570A2 (pt) * | 2010-01-07 | 2016-04-05 | Polymedix Inc | composto, composição farmacêutica, método para antagonizar a heparina não fracionada, heparina de peso molecular baixo, ou derivado de heparina /heparina de peso molecular baixo, e, uso do composto |
| TWI520951B (zh) | 2011-05-16 | 2016-02-11 | 塞爾西優蒂克斯公司 | 用於治療粘膜炎的化合物 |
| US11771694B2 (en) | 2020-06-05 | 2023-10-03 | Innovation Pharmaceuticals Inc. | Arylamide compounds for treatment and prevention of viral infections |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500734A (en) * | 1946-06-13 | 1950-03-14 | Gen Electric | Process of preparing 2-ethyldibenzofuran |
| GB932813A (en) * | 1960-12-01 | 1963-07-31 | Monsanto Chemicals | New heterocyclic chemical compounds |
| GB951797A (en) * | 1960-12-20 | 1964-03-11 | Monsanto Chemicals | Heterocyclic compounds |
| US4362883A (en) * | 1981-10-28 | 1982-12-07 | The Halcon Sd Group, Inc. | Preparation of dibenzofuran |
| AU626033B2 (en) | 1988-10-25 | 1992-07-23 | Government Of The United States Of America, As Represented By The Secretary Of The Army, The | Methods for the treatment and prophylaxis of pneumocystis carinii pneumonia and other diseases and compounds and formulations for use in said methods |
| IL115875A (en) | 1994-11-14 | 2000-12-06 | Univ Georgia State Res Found | Methods of inhibiting pneumocystis carinii pneumonia giardia lamblia and cryptosporidium parvum in an animal subject and compounds useful therefor |
| US5668166A (en) * | 1995-06-07 | 1997-09-16 | Georgia State University Research Foundation, Inc. | Methods of inhibiting pneumocystis carinii pneumonia and compounds useful therefor |
| WO1996040117A1 (en) | 1995-06-07 | 1996-12-19 | The University Of North Carolina At Chapel Hill | Methods of treating microbial infections |
| US5723495A (en) * | 1995-11-16 | 1998-03-03 | The University Of North Carolina At Chapel Hill | Benzamidoxime prodrugs as antipneumocystic agents |
-
1999
- 1999-06-24 JP JP2000566263A patent/JP2003523927A/ja active Pending
- 1999-06-24 AT AT99930662T patent/ATE239003T1/de not_active IP Right Cessation
- 1999-06-24 ES ES99930662T patent/ES2198139T3/es not_active Expired - Lifetime
- 1999-06-24 DE DE69907476T patent/DE69907476T2/de not_active Expired - Fee Related
- 1999-06-24 US US09/344,143 patent/US6172104B1/en not_active Expired - Lifetime
- 1999-06-24 CA CA002340912A patent/CA2340912C/en not_active Expired - Fee Related
- 1999-06-24 AU AU47152/99A patent/AU758563B2/en not_active Ceased
- 1999-06-24 WO PCT/US1999/014313 patent/WO2000010990A2/en not_active Ceased
- 1999-06-24 EP EP99930662A patent/EP1105381B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69907476D1 (de) | 2003-06-05 |
| ES2198139T3 (es) | 2004-01-16 |
| EP1105381B1 (en) | 2003-05-02 |
| AU4715299A (en) | 2000-03-14 |
| WO2000010990A3 (en) | 2003-04-17 |
| US6172104B1 (en) | 2001-01-09 |
| WO2000010990A2 (en) | 2000-03-02 |
| ATE239003T1 (de) | 2003-05-15 |
| CA2340912C (en) | 2008-11-18 |
| JP2003523927A (ja) | 2003-08-12 |
| CA2340912A1 (en) | 2000-03-02 |
| DE69907476T2 (de) | 2004-04-15 |
| EP1105381A1 (en) | 2001-06-13 |
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