IL38451A - Antiviral ureidophenyl-guanidine compounds - Google Patents

Antiviral ureidophenyl-guanidine compounds

Info

Publication number: IL38451A
Authority: IL; Israel
Prior art keywords: radical; benzene; compound; chlorophenyl; isobutylguanidino
Prior art date: 1971-01-07

Application number

IL38451A

Other languages

English (en)

Other versions

IL38451A0 (en

Original Assignee

Ici Ltd

Priority date (The priority date 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 date listed.)

1971-01-07

Filing date

1971-12-26

Publication date

1974-12-31

1971-12-26 Application filed by Ici Ltd filed Critical Ici Ltd

1972-03-28 Publication of IL38451A0 publication Critical patent/IL38451A0/xx

1974-12-31 Publication of IL38451A publication Critical patent/IL38451A/en

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

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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)

IL38451A 1971-01-07 1971-12-26 Antiviral ureidophenyl-guanidine compounds IL38451A (en)

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 (de)
AR (3)	AR192732A1 (de)
AT (3)	AT319266B (de)
AU (1)	AU452832B2 (de)
BE (1)	BE777781A (de)
BR (1)	BR7200100D0 (de)
CA (1)	CA973891A (de)
CH (3)	CH577962A5 (de)
CS (3)	CS171248B2 (de)
DE (1)	DE2200722A1 (de)
DK (1)	DK133149C (de)
ES (4)	ES398676A1 (de)
FR (1)	FR2121621B1 (de)
GB (1)	GB1311432A (de)
HU (1)	HU163287B (de)
IE (1)	IE35903B1 (de)
IL (1)	IL38451A (de)
NL (1)	NL7200239A (de)
NO (1)	NO136358C (de)
SE (1)	SE374107B (de)
SU (2)	SU484685A3 (de)
ZA (1)	ZA718494B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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 (de) *	1997-04-10	2005-06-29	Pharmacia & Upjohn Company LLC	Polyaromatische Verbindungen zur Behandlung von Herpes-Infektionen
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)

* Cited by examiner, † Cited by third party
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 ZA ZA718494A patent/ZA718494B/xx unknown
- 1971-12-20 CA CA130,595A patent/CA973891A/en not_active Expired
- 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 SU SU1737801A patent/SU484685A3/ru active
- 1972-01-06 BE BE777781A patent/BE777781A/xx unknown
- 1972-01-06 CS CS3313*A patent/CS171248B2/cs unknown
- 1972-01-06 CH CH863075A patent/CH577962A5/xx not_active IP Right Cessation
- 1972-01-06 CS CS3312*A patent/CS171247B2/cs unknown
- 1972-01-06 FR FR7200312A patent/FR2121621B1/fr not_active Expired
- 1972-01-06 SU SU1962679A patent/SU486508A3/ru active
- 1972-01-06 CH CH862975A patent/CH572465A5/xx not_active IP Right Cessation
- 1972-01-06 CH CH19072A patent/CH568280A5/xx not_active IP Right Cessation
- 1972-01-06 CS CS73*BA patent/CS171246B2/cs unknown
- 1972-01-07 HU HUIE486A patent/HU163287B/hu unknown
- 1972-01-07 AT AT256273A patent/AT319266B/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 AT AT10572A patent/AT313300B/de not_active IP Right Cessation
- 1972-01-07 BR BR000100/72A patent/BR7200100D0/pt unknown
- 1972-01-07 DE DE19722200722 patent/DE2200722A1/de active Pending
- 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

Also Published As

Publication number	Publication date
AT322568B (de)	1975-05-26
FR2121621B1 (de)	1975-08-01
ES425830A1 (es)	1976-07-01
US4024183A (en)	1977-05-17
BE777781A (fr)	1972-07-06
DE2200722A1 (de)	1972-07-20
ZA718494B (en)	1972-09-27
DK133149B (da)	1976-03-29
AR192970A1 (es)	1973-03-21
CH572465A5 (de)	1976-02-13
CS171246B2 (de)	1976-10-29
AU3745471A (en)	1973-07-05
CH577962A5 (de)	1976-07-30
AR192732A1 (es)	1973-03-14
AT319266B (de)	1974-12-10
ES425831A1 (es)	1976-07-01
CA973891A (en)	1975-09-02
SU484685A3 (ru)	1975-09-15
AT313300B (de)	1974-02-11
CS171247B2 (de)	1976-10-29
NL7200239A (de)	1972-07-11
CS171248B2 (de)	1976-10-29
HU163287B (de)	1973-07-28
DK133149C (da)	1976-08-30
CH568280A5 (de)	1975-10-31
AR192969A1 (es)	1973-03-21
FR2121621A1 (de)	1972-08-25
NO136358B (de)	1977-05-16
SE374107B (de)	1975-02-24
BR7200100D0 (pt)	1973-12-18
ES398676A1 (es)	1975-05-16
IE35903B1 (en)	1976-06-23
IE35903L (en)	1972-07-07
ES444526A1 (es)	1977-06-16
IL38451A0 (en)	1972-03-28
SU486508A3 (ru)	1975-09-30
AU452832B2 (en)	1974-09-12
GB1311432A (en)	1973-03-28
NO136358C (no)	1977-08-24

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US4014934A (en)	1977-03-29	Substituted 4'-hydroxyphenyl guanidines and methods of using the same
US4109014A (en)	1978-08-22	Pharmaceutical, compositions containing substituted 4'-hydroxyphenyl guanidines and methods of using same
GB2084993A (en)	1982-04-21	N-lower-alkyl 3-phenoxy-1-azetidinecarboxamides
IL38451A (en)	1974-12-31	Antiviral ureidophenyl-guanidine compounds
US3849574A (en)	1974-11-19	Alpha-substituted-beta-arylthioalkyl amino-acids,for increasing heart rate
CZ196494A3 (en)	1995-10-18	N,n'-substituted imidocarbonimidediamides derived from hydroxylamines
JPS5933270A (ja)	1984-02-23	抗潰瘍剤
JPS63297364A (ja)	1988-12-05	抗腫瘍化合物
US3086910A (en)	1963-04-23	Central nervous system depressants 3-(2'-pyridyl)-4-quinazolones
US3546234A (en)	1970-12-08	Benzene-sulfonyl-semicarbazides
US4131678A (en)	1978-12-26	Urapidil/furosemide compounds, compositions and use
DE2236876C3 (de)	1981-02-12	N-Substituierte Aminocarbonsäuren und diese Verbindungen enthaltende Arzneimittel
US3714363A (en)	1973-01-30	Substituted amino guanidine as anti-diabetic agents
US3355355A (en)	1967-11-28	Antiviral cycloalkylamine compositions and method
JPS6396123A (ja)	1988-04-27	ビタミンａ酸亜鉛塩を含有する抗炎症剤
US5489609A (en)	1996-02-06	2-aminoethanesulfonic acid zinc complex compound
US5475028A (en)	1995-12-12	2-aminoethanesulfonic acid zinc complex
DE2637281A1 (de)	1977-03-10	Substituierte n-benzyl-alkandiamine und pharmazeutische zubereitungen, die diese verbindungen enthalten
PL91733B1 (de)	1977-03-31
IE43488B1 (en)	1981-03-11	Guanidine derivatives
GB2051801A (en)	1981-01-21	New compound with laxative activity, pharmaceutical compositions which contain it, and a process for its preparation
EP0275207A2 (de)	1988-07-20	Pharmazeutische und tierärztliche Zusammensetzungen
RU2021260C1 (ru)	1994-10-15	Соли акриловой кислоты, проявляющие цитопротекторную и противоязвенную активность, и состав, обладающий цитопротекторной и противоязвенной активностью
PL88932B1 (de)	1976-10-30