NO784332L - Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner - Google Patents

Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner

Info

Publication number: NO784332L
Authority: NO; Norway
Prior art keywords: same meaning; stated above; acid; cycloalkyl; compounds
Prior art date: 1977-12-22

Application number

NO784332A

Other languages

English (en)

Norwegian (no)

Inventor

Aake J E Helgstrand

Karl Nils-Gunnar Johansson

Alfons Misiorny

Jan-Olof Noren

Goeran Bertil Stening

Original Assignee

Astra Laekemedel Ab

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.)

1977-12-22

Filing date

1978-12-21

Publication date

1979-06-25

1978-12-21 Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab

1979-06-25 Publication of NO784332L publication Critical patent/NO784332L/no

Links

238000000034 method Methods 0.000 title claims description 65
241000700605 Viruses Species 0.000 title description 56
208000015181 infectious disease Diseases 0.000 title description 6
239000003814 drug Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 122
-1 hydroxycarbonylphosphonic acid triester Chemical class 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 53
238000006243 chemical reaction Methods 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 29
VNVRRNRPVIZREH-UHFFFAOYSA-N carbamoylphosphonic acid Chemical compound NC(=O)P(O)(O)=O VNVRRNRPVIZREH-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 19
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
ZJAOAACCNHFJAH-UHFFFAOYSA-N hydroxycarbonylphosphonic acid Natural products OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 11
150000001768 cations Chemical class 0.000 claims description 10
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
229910052744 lithium Inorganic materials 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 3
150000004703 alkoxides Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
241001465754 Metazoa Species 0.000 description 28
206010028980 Neoplasm Diseases 0.000 description 27
239000000243 solution Substances 0.000 description 22
238000011282 treatment Methods 0.000 description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 17
230000000694 effects Effects 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
230000003612 virological effect Effects 0.000 description 15
201000010099 disease Diseases 0.000 description 14
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
241001529453 unidentified herpesvirus Species 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
201000011510 cancer Diseases 0.000 description 12
230000002401 inhibitory effect Effects 0.000 description 12
229920002477 rna polymer Polymers 0.000 description 12
239000000126 substance Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
239000000825 pharmaceutical preparation Substances 0.000 description 10
230000009385 viral infection Effects 0.000 description 10
102000053602 DNA Human genes 0.000 description 9
108020004414 DNA Proteins 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
102100034343 Integrase Human genes 0.000 description 9
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 9
208000036142 Viral infection Diseases 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
230000001613 neoplastic effect Effects 0.000 description 9
241000712461 unidentified influenza virus Species 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000011734 sodium Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
229920002873 Polyethylenimine Polymers 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
102000039446 nucleic acids Human genes 0.000 description 6
108020004707 nucleic acids Proteins 0.000 description 6
150000007523 nucleic acids Chemical class 0.000 description 6
235000011007 phosphoric acid Nutrition 0.000 description 6
230000000840 anti-viral effect Effects 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000002512 chemotherapy Methods 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
238000002844 melting Methods 0.000 description 5
229930014626 natural product Natural products 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
230000026731 phosphorylation Effects 0.000 description 5
238000006366 phosphorylation reaction Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 5
210000002700 urine Anatomy 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
206010039491 Sarcoma Diseases 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
230000002068 genetic effect Effects 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
206010022000 influenza Diseases 0.000 description 4
208000032839 leukemia Diseases 0.000 description 4
230000008018 melting Effects 0.000 description 4
230000004060 metabolic process Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000523 sample Substances 0.000 description 4
230000009466 transformation Effects 0.000 description 4
241001430294 unidentified retrovirus Species 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010006187 Breast cancer Diseases 0.000 description 3
208000026310 Breast neoplasm Diseases 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
208000029433 Herpesviridae infectious disease Diseases 0.000 description 3
241000700588 Human alphaherpesvirus 1 Species 0.000 description 3
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000872 buffer Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000002775 capsule Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
229960005102 foscarnet Drugs 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
208000006454 hepatitis Diseases 0.000 description 3
231100000283 hepatitis Toxicity 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000001668 nucleic acid synthesis Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
150000003242 quaternary ammonium salts Chemical class 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
208000011691 Burkitt lymphomas Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
206010008342 Cervix carcinoma Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
241000450599 DNA viruses Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000700721 Hepatitis B virus Species 0.000 description 2
208000001688 Herpes Genitalis Diseases 0.000 description 2
208000004898 Herpes Labialis Diseases 0.000 description 2
206010062639 Herpes dermatitis Diseases 0.000 description 2
208000000903 Herpes simplex encephalitis Diseases 0.000 description 2
208000007514 Herpes zoster Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 2
206010061306 Nasopharyngeal cancer Diseases 0.000 description 2
206010067152 Oral herpes Diseases 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
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 2
229930006000 Sucrose Natural products 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052788 barium Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
201000008275 breast carcinoma Diseases 0.000 description 2
230000000711 cancerogenic effect Effects 0.000 description 2
231100000315 carcinogenic Toxicity 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000010307 cell transformation Effects 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
201000010881 cervical cancer Diseases 0.000 description 2
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
ZOSUESMUNBCBIF-UHFFFAOYSA-L disodium;n,n-diethyl-1-phosphonatoformamide Chemical compound [Na+].[Na+].CCN(CC)C(=O)P([O-])([O-])=O ZOSUESMUNBCBIF-UHFFFAOYSA-L 0.000 description 2
229940079593 drug Drugs 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
IZWWUWVUAGTWGV-UHFFFAOYSA-N ethylcarbamoylphosphonic acid Chemical compound CCNC(=O)P(O)(O)=O IZWWUWVUAGTWGV-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
201000004946 genital herpes Diseases 0.000 description 2
208000002672 hepatitis B Diseases 0.000 description 2
201000006747 infectious mononucleosis Diseases 0.000 description 2
208000037797 influenza A Diseases 0.000 description 2
208000037798 influenza B Diseases 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000010354 integration Effects 0.000 description 2
230000003993 interaction Effects 0.000 description 2
206010023332 keratitis Diseases 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
210000000214 mouth Anatomy 0.000 description 2
OESSYCYJMBTCNP-UHFFFAOYSA-N n-benzyl-1-diphenoxyphosphorylformamide Chemical compound C=1C=CC=CC=1OP(=O)(OC=1C=CC=CC=1)C(=O)NCC1=CC=CC=C1 OESSYCYJMBTCNP-UHFFFAOYSA-N 0.000 description 2
201000011216 nasopharynx carcinoma Diseases 0.000 description 2
230000002276 neurotropic effect Effects 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
210000001331 nose Anatomy 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
125000000962 organic group Chemical group 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
150000003009 phosphonic acids Chemical class 0.000 description 2
150000003016 phosphoric acids Chemical class 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000012088 reference solution Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000013112 stability test Methods 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
XUIXGKWPABGYBC-UHFFFAOYSA-N trisilyl phosphite Chemical compound [SiH3]OP(O[SiH3])O[SiH3] XUIXGKWPABGYBC-UHFFFAOYSA-N 0.000 description 2
239000001993 wax Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
IDCSCRMSZXLSAE-UHFFFAOYSA-N 1-diethoxyphosphoryl-n,n-diethylformamide Chemical compound CCOP(=O)(OCC)C(=O)N(CC)CC IDCSCRMSZXLSAE-UHFFFAOYSA-N 0.000 description 1
ARQYLCXWTZBKOV-UHFFFAOYSA-N 1-diethoxyphosphoryl-n-ethylformamide Chemical compound CCNC(=O)P(=O)(OCC)OCC ARQYLCXWTZBKOV-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000712891 Arenavirus Species 0.000 description 1
241000212384 Bifora Species 0.000 description 1
DPEZMZLOBGTORZ-UHFFFAOYSA-N C(C1=CC=CC=C1)NC(=O)P(O)(O)=O.C(C)[Na] Chemical compound C(C1=CC=CC=C1)NC(=O)P(O)(O)=O.C(C)[Na] DPEZMZLOBGTORZ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
241000867607 Chlorocebus sabaeus Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
241000711573 Coronaviridae Species 0.000 description 1
241000701022 Cytomegalovirus Species 0.000 description 1
206010011831 Cytomegalovirus infection Diseases 0.000 description 1
102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
229920003137 Eudragit® S polymer Polymers 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019799 Hepatitis viral Diseases 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
208000017604 Hodgkin disease Diseases 0.000 description 1
208000010747 Hodgkins lymphoma Diseases 0.000 description 1
241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
241000701372 Iridovirus Species 0.000 description 1
241001466453 Laminaria Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
208000034578 Multiple myelomas Diseases 0.000 description 1
RHUODGTXEYJWLD-UHFFFAOYSA-N NC(=O)OP(O)=O Chemical class NC(=O)OP(O)=O RHUODGTXEYJWLD-UHFFFAOYSA-N 0.000 description 1
NBHYIYZHIRRBAA-UHFFFAOYSA-N OP(C(OCC(C1=CC=CC=C1)C1=CC=CC=C1)=O)(O)=O Chemical compound OP(C(OCC(C1=CC=CC=C1)C1=CC=CC=C1)=O)(O)=O NBHYIYZHIRRBAA-UHFFFAOYSA-N 0.000 description 1
241000713112 Orthobunyavirus Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001631646 Papillomaviridae Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000709664 Picornaviridae Species 0.000 description 1
206010035226 Plasma cell myeloma Diseases 0.000 description 1
241000125945 Protoparvovirus Species 0.000 description 1
230000006819 RNA synthesis Effects 0.000 description 1
241000702263 Reovirus sp. Species 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
208000000453 Skin Neoplasms Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000519995 Stachys sylvatica Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
208000010094 Visna Diseases 0.000 description 1
CXHHBMRYVJHQAM-UHFFFAOYSA-N [SiH3]OP(=O)O[SiH3] Chemical class [SiH3]OP(=O)O[SiH3] CXHHBMRYVJHQAM-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
ZQPCSYKQYDZVKF-UHFFFAOYSA-N benzylcarbamoylphosphonic acid Chemical compound OP(O)(=O)C(=O)NCC1=CC=CC=C1 ZQPCSYKQYDZVKF-UHFFFAOYSA-N 0.000 description 1
210000000013 bile duct Anatomy 0.000 description 1
239000012472 biological sample Substances 0.000 description 1
GKRAALFEJXXZCF-UHFFFAOYSA-N bis(phenylmethoxy)phosphorylformamide Chemical class C=1C=CC=CC=1COP(=O)(C(=O)N)OCC1=CC=CC=C1 GKRAALFEJXXZCF-UHFFFAOYSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
210000003679 cervix uteri Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
150000003946 cyclohexylamines Chemical class 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
208000037765 diseases and disorders Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000007911 effervescent powder Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000000232 gallbladder Anatomy 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 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
210000000867 larynx Anatomy 0.000 description 1
210000000088 lip Anatomy 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000002502 liposome Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
210000002418 meninge Anatomy 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
IFXCMWFFSQBGPD-UHFFFAOYSA-N n-benzyl-1-diethoxyphosphorylformamide Chemical compound CCOP(=O)(OCC)C(=O)NCC1=CC=CC=C1 IFXCMWFFSQBGPD-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
210000003079 salivary gland Anatomy 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
201000000849 skin cancer Diseases 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
210000002105 tongue Anatomy 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
WZCZNEGTXVXAAS-UHFFFAOYSA-N trifluoromethanol Chemical compound OC(F)(F)F WZCZNEGTXVXAAS-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
241000701161 unidentified adenovirus Species 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3886—Acids containing the structure -C(=X)-P(=X)(XH)2 or NC-P(=X)(XH)2, (X = O, S, Se)
- C07F9/3891—Acids containing the structure -C(=X)-P(=X)(XH)2, (X = O, S, Se)

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Virology (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO784332A 1977-12-22 1978-12-21 Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner NO784332L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB5357877		1977-12-22
GB5357977		1977-12-22

Publications (1)

Publication Number	Publication Date
NO784332L true NO784332L (no)	1979-06-25

Family

ID=26267292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO784332A NO784332L (no)	1977-12-22	1978-12-21	Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner

Country Status (6)

Country	Link
EP (1)	EP0003008A1 (fi)
JP (1)	JPS54106432A (fi)
AU (1)	AU4268378A (fi)
DK (1)	DK564378A (fi)
FI (1)	FI783933A (fi)
NO (1)	NO784332L (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2926799A1 (de) *	1979-07-03	1981-01-15	Bayer Ag	Phosphonoameisensaeurehydrazide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2937509A1 (de) *	1979-09-17	1981-04-02	Bayer Ag, 5090 Leverkusen	Dialkoxy-phosphonyl-n-alkyl-ameisensaeureamide und ihre verwendung als zusatzmittel bei der herstellung von flammkaschierbaren und hochfrequenzverschweissbaren polyurethanschaumstoffen
GB8501374D0 (en) *	1985-01-18	1985-02-20	Wellcome Found	Treatment of aids
AU5722694A (en) *	1993-11-05	1995-05-23	Astra Aktiebolag	Novel amino acid derivatives
IL132315A0 (en)	1999-10-11	2001-03-19	Yissum Res Dev Co	Compositions comprising oxophosphonate-based metalloproteinase inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3005010A (en) *	1959-08-10	1961-10-17	Monsanto Chemicals	Method for preparing dihydrocarbyloxyphosphinyl formamides
SE7607496L (sv) *	1976-07-01	1978-01-02	Astra Laekemedel Ab	Sett for bekempning av virusinfektioner

1978
- 1978-12-15 DK DK564378A patent/DK564378A/da unknown
- 1978-12-19 AU AU42683/78A patent/AU4268378A/en active Pending
- 1978-12-19 EP EP78850029A patent/EP0003008A1/en not_active Withdrawn
- 1978-12-20 FI FI783933A patent/FI783933A/fi unknown
- 1978-12-21 NO NO784332A patent/NO784332L/no unknown
- 1978-12-22 JP JP15840078A patent/JPS54106432A/ja active Pending

Also Published As

Publication number	Publication date
FI783933A (fi)	1979-06-23
DK564378A (da)	1979-06-23
EP0003008A1 (en)	1979-07-11
JPS54106432A (en)	1979-08-21
AU4268378A (en)	1979-06-28

Publication	Publication Date	Title
NO154751B (no)	1986-09-08	Analogifremgangsmaate for fremstilling av terapeutisk virksomme hydroksykarbonylfosfonsyreestere.
US4665062A (en)	1987-05-12	Method for combating virus infection
KR102057751B1 (ko)	2019-12-19	테노포비르 전구약물 및 그의 약학적 용도
US20060046981A1 (en)	2006-03-02	Anti-nonmelanoma carcinoma compounds, compositions, and methods of use thereof
JP2002511406A (ja)	2002-04-16	感染症の治療および予防処置のための有機リン化合物の使用
EA026523B1 (ru)	2017-04-28	2'-фторзамещенные карбануклеозидные аналоги для противовирусного лечения
EP0165164A1 (en)	1985-12-18	Anti-viral compounds, their preparation and anti-viral compositions
EA036391B1 (ru)	2020-11-05	Нуклеотидные аналоги
Roux et al.	2013	Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: synthesis, antiviral activity and decomposition study
US8884011B2 (en)	2014-11-11	Nucleotide analogues as precursor molecules for antivirals
JPH11507642A (ja)	1999-07-06	局所使用のためのアシクロビル誘導体
US5254706A (en)	1993-10-19	Process of making phosphite-borane compounds
US20130324495A1 (en)	2013-12-05	Uridine di- or tri-phosphate derivatives and uses thereof
NO784332L (no)	1979-06-25	Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner
US6479472B1 (en)	2002-11-12	Methods of using therapeutic phospholipid derivatives
CA1094062A (en)	1981-01-20	9-(2-hydroxyethoxymethyl) guanine monophosphate derivatives
KR840002464B1 (ko)	1984-12-29	지방족 포스포노포름산 모노에스테르의 제조방법
NO860624L (no)	1986-08-21	Acylerte heksosederivater og fremgangsmaater til fremstilling derav.
GB1590500A (en)	1981-06-03	Phosphorus containing guanine derivatives having antiviral activity
CN117343052B (zh)	2024-02-06	蛋白酪氨酸磷酸酶抑制剂及其应用
AU2011222551A1 (en)	2012-09-27	Arylfluorophosphate inhibitors of intestinal apical membrane sodium/phosphate co-transport
NO860625L (no)	1986-08-21	Acylerte heksosederivater og fremgangsmaater til fremstilling derav.
CA1156651A (en)	1983-11-08	Derivatives of hydroxycarbonylphosphonic acid
RU2239638C2 (ru)	2004-11-10	Фосфонатные производные ацикловира и способ их получения
CA2421067A1 (en)	2003-02-28	Adenosine derivatives and use thereof