IL38451A - Antiviral ureidophenyl-guanidine compounds - Google Patents
Antiviral ureidophenyl-guanidine compoundsInfo
- Publication number
- IL38451A IL38451A IL38451A IL3845171A IL38451A IL 38451 A IL38451 A IL 38451A IL 38451 A IL38451 A IL 38451A IL 3845171 A IL3845171 A IL 3845171A IL 38451 A IL38451 A IL 38451A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- benzene
- compound
- chlorophenyl
- isobutylguanidino
- Prior art date
Links
- 230000000840 anti-viral effect Effects 0.000 title description 11
- ZLTGPVKZBBPOIZ-UHFFFAOYSA-N (N-carbamimidoylanilino)urea Chemical class N(C(=O)N)N(C(=N)N)C1=CC=CC=C1 ZLTGPVKZBBPOIZ-UHFFFAOYSA-N 0.000 title description 2
- -1 ethoxyphenyl Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000000243 solution Substances 0.000 claims description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical group [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007937 lozenge Substances 0.000 claims description 9
- 125000004799 bromophenyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229940101209 mercuric oxide Drugs 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 7
- 239000007922 nasal spray Substances 0.000 claims description 7
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 6
- 229940050410 gluconate Drugs 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- CYYRMFOTFFNLCL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-[[n'-(2-methylpropyl)carbamimidoyl]amino]phenyl]urea Chemical compound CC(C)CN=C(N)NC1=CC=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1 CYYRMFOTFFNLCL-UHFFFAOYSA-N 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims description 3
- XPWXMUWNIKWKDB-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[3-[[n'-(2-methylpropyl)carbamimidoyl]amino]phenyl]urea Chemical compound CC(C)CNC(=N)NC1=CC=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1 XPWXMUWNIKWKDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 229940006460 bromide ion Drugs 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000007923 nasal drop Substances 0.000 claims description 2
- 229940100662 nasal drops Drugs 0.000 claims description 2
- 229940097496 nasal spray Drugs 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- HCDDQQLNMJHPRT-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[3-[[N'-(2-methylpropyl)carbamimidoyl]amino]phenyl]urea Chemical compound CC(C)CNC(=N)NC1=CC=CC(NC(=O)NC=2C=CC(Br)=CC=2)=C1 HCDDQQLNMJHPRT-UHFFFAOYSA-N 0.000 claims 1
- MINHVFHWWIHNTA-UHFFFAOYSA-N 1-[3-[[N'-(4-chlorophenyl)carbamimidoyl]amino]phenyl]-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NC1=CC=CC(NC(=N)NC=2C=CC(Cl)=CC=2)=C1 MINHVFHWWIHNTA-UHFFFAOYSA-N 0.000 claims 1
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 4
- 241000709661 Enterovirus Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZPHQBFRCXUIIAZ-UHFFFAOYSA-N benzene;hydrochloride Chemical compound Cl.C1=CC=CC=C1 ZPHQBFRCXUIIAZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 201000009240 nasopharyngitis Diseases 0.000 description 4
- NNZVKALEGZPYKL-UHFFFAOYSA-N 1-isocyanato-2-methylpropane Chemical compound CC(C)CN=C=O NNZVKALEGZPYKL-UHFFFAOYSA-N 0.000 description 3
- 206010061494 Rhinovirus infection Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- HBRWURIJURVVAM-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-(propan-2-ylcarbamothioylamino)phenyl]urea Chemical compound CC(C)NC(=S)NC1=CC=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1 HBRWURIJURVVAM-UHFFFAOYSA-N 0.000 description 2
- VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NHQYLBJSZDQSFK-UHFFFAOYSA-N [amino-[3-[(4-chlorophenyl)carbamoylamino]anilino]methylidene]-(2-methylpropyl)azanium;chloride Chemical compound Cl.CC(C)CN=C(N)NC1=CC=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1 NHQYLBJSZDQSFK-UHFFFAOYSA-N 0.000 description 2
- JDXKTOBMLZLCSB-UHFFFAOYSA-N anilinothiourea Chemical compound NC(=S)NNC1=CC=CC=C1 JDXKTOBMLZLCSB-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 101150009274 nhr-1 gene Proteins 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- IKHKMGSVONNVKU-UHFFFAOYSA-N 1-(2-methylpropyl)-3-phenylurea Chemical compound CC(C)CNC(=O)NC1=CC=CC=C1 IKHKMGSVONNVKU-UHFFFAOYSA-N 0.000 description 1
- OFUSFWFRFWJRFF-UHFFFAOYSA-N 1-(3-aminophenyl)-3-(4-chlorophenyl)urea Chemical compound NC1=CC=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=C1 OFUSFWFRFWJRFF-UHFFFAOYSA-N 0.000 description 1
- STNKQKYMUWXKQG-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[[N'-(2-methylpropyl)carbamimidoyl]amino]phenyl]urea Chemical compound C1=CC(NC(=N)NCC(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 STNKQKYMUWXKQG-UHFFFAOYSA-N 0.000 description 1
- ORBJETIFXFIXKK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-phenylurea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC=C1 ORBJETIFXFIXKK-UHFFFAOYSA-N 0.000 description 1
- FYDWITHHZRSNSG-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[4-[[n'-(2-methylpropyl)carbamimidoyl]amino]phenyl]urea Chemical compound C1=CC(NC(=N)NCC(C)C)=CC=C1NC(=O)NC1=CC=C(C)C=C1 FYDWITHHZRSNSG-UHFFFAOYSA-N 0.000 description 1
- AGWCZLGCTUBHLR-UHFFFAOYSA-N 1-anilino-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NNC1=CC=CC=C1 AGWCZLGCTUBHLR-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- DIDRYWGNFXWZPW-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(NC1=CC(=CC=C1)NC(=O)NCCCC)=N Chemical compound ClC1=CC=C(C=C1)NC(NC1=CC(=CC=C1)NC(=O)NCCCC)=N DIDRYWGNFXWZPW-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 241000700605 Viruses Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 description 1
- XUPANCKBBOYIKC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=C=CC=C[CH]1 XUPANCKBBOYIKC-UHFFFAOYSA-N 0.000 description 1
- FNLYVHPPASFNNC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=C[C]=CC=C1 FNLYVHPPASFNNC-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000007821 culture assay Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 229960003681 gluconolactone Drugs 0.000 description 1
- CALVPZNSFFEPJG-UHFFFAOYSA-N guanidine;dihydrochloride Chemical compound Cl.Cl.NC(N)=N CALVPZNSFFEPJG-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- NSDDRJXKROCWRZ-UHFFFAOYSA-N isobutyl isothiocyanate Natural products CC(C)CN=C=S NSDDRJXKROCWRZ-UHFFFAOYSA-N 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000005265 lung cell Anatomy 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000133 nasal decongestant Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000003253 viricidal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/04—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from ammonium thiocyanate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB77771 | 1971-01-07 | ||
| AT256273A AT319266B (de) | 1971-01-07 | 1972-01-07 | Verfahren zur Herstellung von neuen Guanidinophenylharnstoffderivaten sowie von deren Säureadditionssalzen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38451A0 IL38451A0 (en) | 1972-03-28 |
| IL38451A true IL38451A (en) | 1974-12-31 |
Family
ID=59268403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38451A IL38451A (en) | 1971-01-07 | 1971-12-26 | Antiviral ureidophenyl-guanidine compounds |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4024183A (en:Method) |
| AR (3) | AR192732A1 (en:Method) |
| AT (3) | AT313300B (en:Method) |
| AU (1) | AU452832B2 (en:Method) |
| BE (1) | BE777781A (en:Method) |
| BR (1) | BR7200100D0 (en:Method) |
| CA (1) | CA973891A (en:Method) |
| CH (3) | CH577962A5 (en:Method) |
| CS (3) | CS171248B2 (en:Method) |
| DE (1) | DE2200722A1 (en:Method) |
| DK (1) | DK133149C (en:Method) |
| ES (4) | ES398676A1 (en:Method) |
| FR (1) | FR2121621B1 (en:Method) |
| GB (1) | GB1311432A (en:Method) |
| HU (1) | HU163287B (en:Method) |
| IE (1) | IE35903B1 (en:Method) |
| IL (1) | IL38451A (en:Method) |
| NL (1) | NL7200239A (en:Method) |
| NO (1) | NO136358C (en:Method) |
| SE (1) | SE374107B (en:Method) |
| SU (2) | SU486508A3 (en:Method) |
| ZA (1) | ZA718494B (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4327244A1 (de) * | 1993-08-13 | 1995-02-16 | Hoechst Ag | Harnstoffsubstituierte Benzoylguandine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| EP1148048B1 (en) * | 1997-04-10 | 2005-06-29 | Pharmacia & Upjohn Company LLC | Polyaromatic compounds for treating herpes viral infections |
| ITTO20010110A1 (it) * | 2001-02-08 | 2002-08-08 | Rotta Research Lab | Nuovi derivati benzamidinici dotati di attivita' anti-infiammatoria ed immunosoppressiva. |
| AU2008267081B2 (en) * | 2007-06-12 | 2013-05-09 | Provid Pharmaceuticals, Inc. | Kinase inhibitors, compositions thereof, and methods of use therewith |
| CN107652210B (zh) * | 2017-09-30 | 2021-01-01 | 瑞阳（上海）新药研发有限公司 | 一种胍类化合物或其药学上可接受的盐、其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH474486A (de) * | 1965-11-19 | 1969-06-30 | Ciba Geigy | Verfahren zur Herstellung neuer Diphenylharnstoffe |
| US3673241A (en) * | 1968-04-04 | 1972-06-27 | Ciba Geigy Corp | Substituted benzaldehyde guanylhydrazones |
-
1971
- 1971-01-07 GB GB77771A patent/GB1311432A/en not_active Expired
- 1971-12-16 IE IE1594/71A patent/IE35903B1/xx unknown
- 1971-12-20 CA CA130,595A patent/CA973891A/en not_active Expired
- 1971-12-20 ZA ZA718494A patent/ZA718494B/xx unknown
- 1971-12-26 IL IL38451A patent/IL38451A/en unknown
- 1971-12-27 NO NO4851/71A patent/NO136358C/no unknown
- 1971-12-28 SE SE7116738A patent/SE374107B/xx unknown
- 1971-12-30 AU AU37454/71A patent/AU452832B2/en not_active Expired
- 1971-12-30 AR AR239892A patent/AR192732A1/es active
-
1972
- 1972-01-05 DK DK5072*#A patent/DK133149C/da active
- 1972-01-06 CH CH863075A patent/CH577962A5/xx not_active IP Right Cessation
- 1972-01-06 CS CS3313*A patent/CS171248B2/cs unknown
- 1972-01-06 SU SU1962679A patent/SU486508A3/ru active
- 1972-01-06 CS CS73*BA patent/CS171246B2/cs unknown
- 1972-01-06 CS CS3312*A patent/CS171247B2/cs unknown
- 1972-01-06 CH CH19072A patent/CH568280A5/xx not_active IP Right Cessation
- 1972-01-06 FR FR7200312A patent/FR2121621B1/fr not_active Expired
- 1972-01-06 CH CH862975A patent/CH572465A5/xx not_active IP Right Cessation
- 1972-01-06 SU SU1737801A patent/SU484685A3/ru active
- 1972-01-06 BE BE777781A patent/BE777781A/xx unknown
- 1972-01-07 HU HUIE486A patent/HU163287B/hu unknown
- 1972-01-07 BR BR000100/72A patent/BR7200100D0/pt unknown
- 1972-01-07 AT AT10572A patent/AT313300B/de not_active IP Right Cessation
- 1972-01-07 ES ES398676A patent/ES398676A1/es not_active Expired
- 1972-01-07 AT AT256373A patent/AT322568B/de not_active IP Right Cessation
- 1972-01-07 DE DE19722200722 patent/DE2200722A1/de active Pending
- 1972-01-07 AT AT256273A patent/AT319266B/de not_active IP Right Cessation
- 1972-01-07 NL NL7200239A patent/NL7200239A/xx unknown
- 1972-08-11 AR AR243554A patent/AR192970A1/es active
- 1972-08-11 AR AR243553A patent/AR192969A1/es active
-
1974
- 1974-04-30 ES ES425830A patent/ES425830A1/es not_active Expired
- 1974-04-30 ES ES0425831A patent/ES425831A1/es not_active Expired
-
1975
- 1975-10-06 US US05/620,049 patent/US4024183A/en not_active Expired - Lifetime
-
1976
- 1976-01-22 ES ES444526A patent/ES444526A1/es not_active Expired
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