IE46210B1 - Phosphorus containing guanine derivatives having antiviral activity - Google Patents

Phosphorus containing guanine derivatives having antiviral activity

Info

Publication number: IE46210B1
Authority: IE; Ireland
Prior art keywords: formula; compound; hydroxyethoxymethyl; pharmaceutically acceptable; derivative
Prior art date: 1977-02-24

Application number

IE397/78A

Other languages

English (en)

Other versions

IE780397L (en

Inventor

Howard John Raleigh Nc Us Schaeffer

Original Assignee

Wellcome Found

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.)

1977-02-24

Filing date

1978-02-24

Publication date

1983-03-23

1978-02-24 Application filed by Wellcome Found filed Critical Wellcome Found

1978-08-24 Publication of IE780397L publication Critical patent/IE780397L/xx

1983-03-23 Publication of IE46210B1 publication Critical patent/IE46210B1/en

Links

230000000840 anti-viral effect Effects 0.000 title claims abstract description 7
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
229910052698 phosphorus Inorganic materials 0.000 title 1
239000011574 phosphorus Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 29
150000001768 cations Chemical class 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
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 claims description 10
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
-1 methyl guanine derivative Chemical compound 0.000 claims description 7
239000011591 potassium Substances 0.000 claims description 7
229910052700 potassium Inorganic materials 0.000 claims description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
239000004411 aluminium Substances 0.000 claims description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
229910052782 aluminium Inorganic materials 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 6
229910052791 calcium Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000011777 magnesium Substances 0.000 claims description 6
229910052749 magnesium Inorganic materials 0.000 claims description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
238000005915 ammonolysis reaction Methods 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
230000000865 phosphorylative effect Effects 0.000 claims description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000006071 cream Substances 0.000 claims description 3
229940012356 eye drops Drugs 0.000 claims description 3
229940100662 nasal drops Drugs 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
239000002674 ointment Substances 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
238000007911 parenteral administration Methods 0.000 claims description 2
150000003016 phosphoric acids Chemical class 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
238000011200 topical administration Methods 0.000 claims 1
241000700605 Viruses Species 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 3
238000003786 synthesis reaction Methods 0.000 abstract 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 abstract 1
239000003814 drug Substances 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
229910019142 PO4 Inorganic materials 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
235000021317 phosphate Nutrition 0.000 description 12
239000010452 phosphate Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RWCYGLJSLQIGDH-UHFFFAOYSA-N 2-chloro-9-(2-hydroxyethoxymethyl)-3h-purin-6-one Chemical compound N1=C(Cl)NC(=O)C2=C1N(COCCO)C=N2 RWCYGLJSLQIGDH-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000001913 cellulose Substances 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000004712 monophosphates Chemical class 0.000 description 5
229910052788 barium Inorganic materials 0.000 description 4
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000001376 precipitating effect Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
BALXSYQWXWVVJJ-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;phosphoric acid Chemical compound OP(O)(O)=O.O=C1NC(N)=NC2=C1NC=N2 BALXSYQWXWVVJJ-UHFFFAOYSA-N 0.000 description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
102000002260 Alkaline Phosphatase Human genes 0.000 description 2
108020004774 Alkaline Phosphatase Proteins 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
150000003212 purines Chemical class 0.000 description 2
RDMGMZAMWLSHNS-UHFFFAOYSA-N 3,7-dihydropurin-6-one;phosphoric acid Chemical compound OP(O)(O)=O.O=C1NC=NC2=C1NC=N2 RDMGMZAMWLSHNS-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000450599 DNA viruses Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
240000001414 Eucalyptus viminalis Species 0.000 description 1
208000001860 Eye Infections Diseases 0.000 description 1
208000000903 Herpes simplex encephalitis Diseases 0.000 description 1
208000037018 Herpes simplex virus encephalitis Diseases 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
208000005100 Herpetic Keratitis Diseases 0.000 description 1
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
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 1
241000699670 Mus sp. Species 0.000 description 1
206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
YQLCZXVQEJBDPU-UHFFFAOYSA-N P(=O)([O-])([O-])[O-].OCCOCN1C=2N=C(NC(C2N=C1)=O)N.[NH4+].[NH4+].[NH4+] Chemical compound P(=O)([O-])([O-])[O-].OCCOCN1C=2N=C(NC(C2N=C1)=O)N.[NH4+].[NH4+].[NH4+] YQLCZXVQEJBDPU-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
241000700618 Vaccinia virus Species 0.000 description 1
206010046865 Vaccinia virus infection Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
WAKZZMMCDILMEF-UHFFFAOYSA-H barium(2+);diphosphate Chemical compound [Ba+2].[Ba+2].[Ba+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O WAKZZMMCDILMEF-UHFFFAOYSA-H 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000030609 dephosphorylation Effects 0.000 description 1
238000006209 dephosphorylation reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
208000011323 eye infectious disease Diseases 0.000 description 1
201000010884 herpes simplex virus keratitis Diseases 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229940054534 ophthalmic solution Drugs 0.000 description 1
239000002997 ophthalmic solution Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
INBGYHZFMWKMNX-UHFFFAOYSA-K trisodium 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one phosphate Chemical compound P(=O)([O-])([O-])[O-].OCCOCN1C=2N=C(NC(C2N=C1)=O)N.[Na+].[Na+].[Na+] INBGYHZFMWKMNX-UHFFFAOYSA-K 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
208000007089 vaccinia Diseases 0.000 description 1
238000005406 washing Methods 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Virology (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IE397/78A 1977-02-24 1978-02-24 Phosphorus containing guanine derivatives having antiviral activity IE46210B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US77177877A	1977-02-24	1977-02-24
GB5390577		1977-12-24

Publications (2)

Publication Number	Publication Date
IE780397L IE780397L (en)	1978-08-24
IE46210B1 true IE46210B1 (en)	1983-03-23

Family

ID=26267373

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE397/78A IE46210B1 (en)	1977-02-24	1978-02-24	Phosphorus containing guanine derivatives having antiviral activity

Country Status (27)

Country	Link
JP (1)	JPS53108999A (de)
AR (2)	AR219735A1 (de)
AT (1)	AT353286B (de)
AU (1)	AU521577B2 (de)
CA (1)	CA1094062A (de)
CH (1)	CH643858A5 (de)
DD (1)	DD134098A5 (de)
DE (1)	DE2808096A1 (de)
DK (1)	DK147198C (de)
ES (2)	ES467300A1 (de)
FI (1)	FI68402C (de)
FR (1)	FR2381781A1 (de)
GR (1)	GR64404B (de)
HU (1)	HU178808B (de)
IE (1)	IE46210B1 (de)
IL (1)	IL54130A0 (de)
IN (1)	IN149483B (de)
IT (1)	IT1105259B (de)
LU (1)	LU79126A1 (de)
MC (1)	MC1182A1 (de)
NL (1)	NL7802111A (de)
NO (1)	NO153260C (de)
NZ (1)	NZ186555A (de)
PH (1)	PH13996A (de)
PL (1)	PL114474B1 (de)
PT (1)	PT67706B (de)
SE (1)	SE430507B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0015584A3 (de) *	1979-03-12	1980-12-10	Kailash Kumar Dr. Prof. Gauri	Neue Nukleotide, Verfahren zu ihrer Herstellung und Arzneimittel
US5047533A (en) *	1983-05-24	1991-09-10	Sri International	Acyclic purine phosphonate nucleotide analogs
GB2150570B (en) *	1983-05-24	1987-04-08	Stanford Res Inst Int	Novel antiviral agents
US4579849A (en) *	1984-04-06	1986-04-01	Merck & Co., Inc.	N-alkylguanine acyclonucleosides as antiviral agents
CS264222B1 (en) *	1986-07-18	1989-06-13	Holy Antonin	N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them
FR2733234B1 (fr) *	1995-04-21	1997-07-04	Centre Nat Rech Scient	Derives de l'acyclovir comme agents antiviraux
AU5511196A (en) *	1995-04-21	1996-11-07	Centre National De La Recherche Scientifique (Cnrs)	Acyclovir derivatives as antiviral agents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1523865A (en) *	1974-09-02	1978-09-06	Wellcome Found	Purine compunds and salts thereof

1978
- 1978-02-23 AU AU33560/78A patent/AU521577B2/en not_active Expired
- 1978-02-24 NL NL7802111A patent/NL7802111A/xx not_active Application Discontinuation
- 1978-02-24 FR FR7805305A patent/FR2381781A1/fr active Granted
- 1978-02-24 DK DK85178A patent/DK147198C/da active
- 1978-02-24 IT IT48192/78A patent/IT1105259B/it active
- 1978-02-24 FI FI780626A patent/FI68402C/fi not_active IP Right Cessation
- 1978-02-24 MC MC781287A patent/MC1182A1/xx unknown
- 1978-02-24 PH PH20817A patent/PH13996A/en unknown
- 1978-02-24 PL PL1978204885A patent/PL114474B1/pl unknown
- 1978-02-24 IN IN205/CAL/78A patent/IN149483B/en unknown
- 1978-02-24 DE DE19782808096 patent/DE2808096A1/de active Granted
- 1978-02-24 SE SE7802140A patent/SE430507B/sv not_active IP Right Cessation
- 1978-02-24 PT PT67706A patent/PT67706B/pt unknown
- 1978-02-24 DD DD78203838A patent/DD134098A5/de unknown
- 1978-02-24 IE IE397/78A patent/IE46210B1/en not_active IP Right Cessation
- 1978-02-24 ES ES467300A patent/ES467300A1/es not_active Expired
- 1978-02-24 AT AT134678A patent/AT353286B/de not_active IP Right Cessation
- 1978-02-24 HU HU78WE571A patent/HU178808B/hu unknown
- 1978-02-24 CA CA297,833A patent/CA1094062A/en not_active Expired
- 1978-02-24 JP JP2077878A patent/JPS53108999A/ja active Pending
- 1978-02-24 CH CH204078A patent/CH643858A5/de not_active IP Right Cessation
- 1978-02-24 GR GR55543A patent/GR64404B/el unknown
- 1978-02-24 LU LU79126A patent/LU79126A1/xx unknown
- 1978-02-24 IL IL54130A patent/IL54130A0/xx not_active IP Right Cessation
- 1978-02-24 NZ NZ186555A patent/NZ186555A/xx unknown
- 1978-02-24 AR AR271214A patent/AR219735A1/es active
- 1978-02-24 NO NO780644A patent/NO153260C/no unknown
- 1978-05-31 ES ES470383A patent/ES470383A1/es not_active Expired
1979
- 1979-04-27 AR AR276336A patent/AR218718A1/es active

Also Published As

Publication number	Publication date
ES467300A1 (es)	1978-10-16
PT67706A (en)	1978-03-01
JPS53108999A (en)	1978-09-22
CH643858A5 (en)	1984-06-29
FI68402C (fi)	1985-09-10
FR2381781A1 (fr)	1978-09-22
ES470383A1 (es)	1979-09-16
HU178808B (en)	1982-06-28
FR2381781B1 (de)	1980-04-25
SE7802140L (sv)	1978-08-25
AR218718A1 (es)	1980-06-30
AT353286B (de)	1979-11-12
MC1182A1 (fr)	1978-12-22
DK147198C (da)	1984-11-12
NO153260C (no)	1986-02-12
PL204885A1 (pl)	1979-04-23
NO780644L (no)	1978-08-25
PL114474B1 (en)	1981-01-31
GR64404B (en)	1980-03-21
FI68402B (fi)	1985-05-31
NL7802111A (nl)	1978-08-28
SE430507B (sv)	1983-11-21
AU3356078A (en)	1979-08-30
PH13996A (en)	1980-11-28
DE2808096A1 (de)	1978-08-31
IN149483B (de)	1981-12-26
IT1105259B (it)	1985-10-28
DE2808096C2 (de)	1988-02-18
IE780397L (en)	1978-08-24
IT7848192A0 (it)	1978-02-24
DK85178A (da)	1978-08-25
ATA134678A (de)	1979-04-15
DK147198B (da)	1984-05-14
DD134098A5 (de)	1979-02-07
NO153260B (no)	1985-11-04
IL54130A0 (en)	1978-04-30
CA1094062A (en)	1981-01-20
AR219735A1 (es)	1980-09-15
LU79126A1 (fr)	1978-10-17
AU521577B2 (en)	1982-04-22
FI780626A (fi)	1978-08-25
NZ186555A (en)	1981-02-11
PT67706B (en)	1980-03-04

Legal Events

Date	Code	Title	Description
1995-05-03	MM4A	Patent lapsed

Publication	Publication Date	Title
US4287188A (en)	1981-09-01	Purine derivatives
US4579849A (en)	1986-04-01	N-alkylguanine acyclonucleosides as antiviral agents
CA2155673C (en)	2004-08-17	N-alkyl-2-substituted atp analogues
RU2043361C1 (ru)	1995-09-10	Способ получения производных 2'-дезокси-2'-фторрибонуклеозидов или их фармацевтически приемлемых солей
EP0074306B1 (de)	1988-06-01	Antivirale Guaninderivate
US4816447A (en)	1989-03-28	Anti-viral guanine compounds
WO2006091905A1 (en)	2006-08-31	Bicyclo (3.1.0) hexane derivatives as antiviral compounds
EP0138656B1 (de)	1989-09-27	Zyklische Purin- und Pyrimidin-Acyclonucleosiden, ihre Herstellung und ihre Anwendung in anti-viralen Zusammensetzungen
EP0074101B1 (de)	1985-04-03	1-Beta-D-Arabinofuranosyl-(E)-5-(2-halogensubstituiertes vinyl) uracil-5-Phosphate; ihre Herstellung und Verwendung
US3703507A (en)	1972-11-21	Process for the production of 9-(beta-d-arabinofuranosyl) adenine,5'-phosphate and salts thereof
US4590269A (en)	1986-05-20	Process for preparing the cyclic phosphate ester of substituted 9-(1,3-dihydroxy-2-propoxymethyl)purines
IE46210B1 (en)	1983-03-23	Phosphorus containing guanine derivatives having antiviral activity
GB1590500A (en)	1981-06-03	Phosphorus containing guanine derivatives having antiviral activity
EP0090405B1 (de)	1986-06-25	Azole Dinukleotide und Verfahren zu ihrer Herstellung
EP0226753B1 (de)	1991-04-10	Alpha-tocopherol(halo)uridin-Diester von Phosphorsäure, deren Salze und Verfahren zu deren Herstellung
NO880606L (no)	1988-08-15	Nukleotidanaloger og fremgangsmaate for deres fremstilling.
CS248003B2 (cs)	1987-01-15	Způsob výroby derivátů 9-hydroxyethoxymethylguaninu
NO784332L (no)	1979-06-25	Amidderivater, farmasoeytiske preparater og fremgangsmaate til bekjempelse av virusinfeksjoner
US4966895A (en)	1990-10-30	Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents
EP0381533A2 (de)	1990-08-08	Cyclische Monophosphate von Purin- und Pyrimidin-Acyclonucleosiden
CS248005B2 (cs)	1987-01-15	Způsob výroby derivátů 9-hydroxyethoxymethylguaninu
AT366055B (de)	1982-03-10	Verfahren zur herstellung von neuen 9-hydroxyaethoxymethylguaninderivaten
Baddiley et al.	1952	724. Coenzyme A. Part VI. The identification of pantothenic acid-4′ and-2′: 4′ phosphates from a hydrolysate