DE2708827C2 - - Google Patents
Info
- Publication number
- DE2708827C2 DE2708827C2 DE2708827A DE2708827A DE2708827C2 DE 2708827 C2 DE2708827 C2 DE 2708827C2 DE 2708827 A DE2708827 A DE 2708827A DE 2708827 A DE2708827 A DE 2708827A DE 2708827 C2 DE2708827 C2 DE 2708827C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- guanine
- formyloxyethoxymethyl
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 10
- OFDJYPIEYXKRHP-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl formate Chemical compound O=C1NC(N)=NC2=C1N=CN2COCCOC=O OFDJYPIEYXKRHP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241001529453 unidentified herpesvirus Species 0.000 description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 5
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- -1 Alkali metal salts Chemical class 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000338 in vitro Methods 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
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 2
- 229960003962 trifluridine Drugs 0.000 description 2
- 210000003501 vero cell Anatomy 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PTXSLPXLYZHGEM-UHFFFAOYSA-N 2-(chloromethoxy)ethyl formate Chemical compound ClCOCCOC=O PTXSLPXLYZHGEM-UHFFFAOYSA-N 0.000 description 1
- IAFAXGYXSQSJIX-UHFFFAOYSA-N 2-formyloxyethoxymethyl acetate Chemical compound CC(=O)OCOCCOC=O IAFAXGYXSQSJIX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 208000005100 Herpetic Keratitis Diseases 0.000 description 1
- 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 1
- 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 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
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 241000124008 Mammalia Species 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 201000010884 herpes simplex virus keratitis Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7988/76A GB1561380A (en) | 1976-03-01 | 1976-03-01 | Esters of hydroxyalkoxyalkyl purines their preparation and pharmaceutical compositions containing them |
| US71810576A | 1976-08-27 | 1976-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2708827A1 DE2708827A1 (de) | 1977-09-08 |
| DE2708827C2 true DE2708827C2 (enrdf_load_stackoverflow) | 1989-01-12 |
Family
ID=26241801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772708827 Granted DE2708827A1 (de) | 1976-03-01 | 1977-03-01 | Substituierte purinverbindungen, verfahren zu ihrer herstellung und pharmazeutische zubereitungen |
Country Status (25)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8202626A (nl) * | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| ES520140A0 (es) * | 1983-02-25 | 1984-04-01 | Ind Farma Especial | Un procedimiento para la preparacion de acicloguanosina. |
| GB8816760D0 (en) * | 1988-07-14 | 1988-08-17 | Wellcome Found | Therapeutic compounds |
| US5994361A (en) * | 1994-06-22 | 1999-11-30 | Biochem Pharma | Substituted purinyl derivatives with immunomodulating activity |
| JP4704223B2 (ja) * | 2006-01-30 | 2011-06-15 | Ｈｏｙａ株式会社 | 送りねじ機構 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5122049A (ja) * | 1974-08-19 | 1976-02-21 | Sanwa Denki Kk | Kahenteikosochi |
-
1977
- 1977-02-28 AU AU22759/77A patent/AU515553B2/en not_active Expired
- 1977-03-01 AR AR266728A patent/AR228232A1/es active
- 1977-03-01 CH CH257177A patent/CH629806A5/de not_active IP Right Cessation
- 1977-03-01 ZA ZA00771220A patent/ZA771220B/xx unknown
- 1977-03-01 BG BG035556A patent/BG27750A3/xx unknown
- 1977-03-01 RO RO7796630A patent/RO76591A/ro unknown
- 1977-03-01 DD DD197619A patent/DD128611A5/xx unknown
- 1977-03-01 GR GR52881A patent/GR66070B/el unknown
- 1977-03-01 BE BE175383A patent/BE851972R/xx not_active IP Right Cessation
- 1977-03-01 CA CA272,888A patent/CA1086316A/en not_active Expired
- 1977-03-01 LU LU76869A patent/LU76869A1/xx unknown
- 1977-03-01 FI FI770655A patent/FI60710C/fi not_active IP Right Cessation
- 1977-03-01 BG BG036534A patent/BG28067A3/xx unknown
- 1977-03-01 SU SU772455681A patent/SU637086A3/ru active
- 1977-03-01 SE SE7702233A patent/SE433216B/xx not_active IP Right Cessation
- 1977-03-01 PL PL1977196356A patent/PL115267B1/pl not_active IP Right Cessation
- 1977-03-01 DE DE19772708827 patent/DE2708827A1/de active Granted
- 1977-03-01 AT AT134877A patent/AT361007B/de not_active IP Right Cessation
- 1977-03-01 DK DK88677A patent/DK147824C/da not_active IP Right Cessation
- 1977-03-01 ES ES456432A patent/ES456432A2/es not_active Expired
- 1977-03-01 NL NL7702175A patent/NL7702175A/xx active Search and Examination
- 1977-03-01 IE IE438/77A patent/IE44708B1/en unknown
- 1977-03-01 PL PL1977211568A patent/PL115242B1/pl unknown
- 1977-03-01 FR FR7705924A patent/FR2342972A2/fr active Granted
- 1977-03-01 JP JP2211377A patent/JPS52106896A/ja active Granted
- 1977-03-01 HU HU77WE550A patent/HU176907B/hu not_active IP Right Cessation
-
1980
- 1980-06-12 IT IT8048953A patent/IT8048953A0/it unknown
-
1981
- 1981-07-24 AR AR286218A patent/AR228281A1/es active
- 1981-07-24 AR AR286219A patent/AR228282A1/es active
- 1981-07-24 AR AR286220A patent/AR228283A1/es active
- 1981-08-31 CH CH558581A patent/CH631176A5/de not_active IP Right Cessation
- 1981-08-31 CH CH558781A patent/CH632758A5/de not_active IP Right Cessation
- 1981-08-31 CH CH558681A patent/CH632757A5/de not_active IP Right Cessation
-
1984
- 1984-03-21 NL NL8400896A patent/NL8400896A/nl not_active Application Discontinuation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2539963 Format of ref document f/p: P |
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| AF | Is addition to no. |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |