CA1096863A - Improved process for preparing 9-substituted derivatives of guanine and adenine - Google Patents
Improved process for preparing 9-substituted derivatives of guanine and adenineInfo
- Publication number
- CA1096863A CA1096863A CA285,592A CA285592A CA1096863A CA 1096863 A CA1096863 A CA 1096863A CA 285592 A CA285592 A CA 285592A CA 1096863 A CA1096863 A CA 1096863A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- adenine
- formula
- guanine
- amino
- 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
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 title description 2
- 229930024421 Adenine Chemical class 0.000 title description 2
- 229960000643 adenine Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- ONSWVOSXVUHESJ-UHFFFAOYSA-N 2-(hydroxymethoxy)ethanol Chemical compound OCCOCO ONSWVOSXVUHESJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 150000005690 diesters Chemical class 0.000 claims abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 7
- 150000003212 purines Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- QNXFUWFRTWSSOK-UHFFFAOYSA-N n-acetyl-n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound O=C1NC(N(C(C)=O)C(=O)C)=NC2=C1NC=N2 QNXFUWFRTWSSOK-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- XFEQOLXBMLXKDE-UHFFFAOYSA-N 2-(acetyloxymethoxy)ethyl acetate Chemical compound CC(=O)OCCOCOC(C)=O XFEQOLXBMLXKDE-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- CSMCRCLIPQDIKB-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethanol Chemical compound NC1=NC(N)=C2N=CN(COCCO)C2=N1 CSMCRCLIPQDIKB-UHFFFAOYSA-N 0.000 description 2
- -1 2-hydroxy-ethoxymethyl Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KYCXTUXIIANKNP-UHFFFAOYSA-N 1-acetyloxybutyl acetate Chemical compound CCCC(OC(C)=O)OC(C)=O KYCXTUXIIANKNP-UHFFFAOYSA-N 0.000 description 1
- JXBPYDQBIDJOPX-UHFFFAOYSA-N 2-[(2,6-diacetamidopurin-9-yl)methoxy]ethyl acetate Chemical compound C(C)(=O)NC1=NC(=C2N=CN(C2=N1)COCCOC(C)=O)NC(C)=O JXBPYDQBIDJOPX-UHFFFAOYSA-N 0.000 description 1
- VBHLKZHSCMQLTI-UHFFFAOYSA-N 2-[(2-acetamido-6-oxo-3h-purin-9-yl)methoxy]ethyl acetate Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N(COCCOC(C)=O)C=N2 VBHLKZHSCMQLTI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241000709661 Enterovirus Species 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
- 241001135569 Human adenovirus 5 Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KLUTVBXWIFFOPM-UHFFFAOYSA-N N-(6-amino-7H-purin-2-yl)formamide Chemical compound C(=O)NC1=NC(=C2NC=NC2=N1)N KLUTVBXWIFFOPM-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000010884 herpes simplex virus keratitis Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71810576A | 1976-08-27 | 1976-08-27 | |
| US718,105 | 1976-08-27 | ||
| US05/773,135 US4146715A (en) | 1975-08-27 | 1977-02-28 | 2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines |
| US773,135 | 1977-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096863A true CA1096863A (en) | 1981-03-03 |
Family
ID=27109837
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA285,592A Expired CA1096863A (en) | 1976-08-27 | 1977-08-26 | Improved process for preparing 9-substituted derivatives of guanine and adenine |
| CA354,538A Expired CA1096864A (en) | 1976-08-27 | 1980-06-20 | Intermediates for the preparation of derivatives of guanine and adenine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA354,538A Expired CA1096864A (en) | 1976-08-27 | 1980-06-20 | Intermediates for the preparation of derivatives of guanine and adenine |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT357566B (cs) |
| CA (2) | CA1096863A (cs) |
| CH (1) | CH634843A5 (cs) |
| CS (1) | CS196384B2 (cs) |
| DD (1) | DD131856A6 (cs) |
| DK (1) | DK147857C (cs) |
| FI (1) | FI64160C (cs) |
| GB (1) | GB1567671A (cs) |
| NL (1) | NL7709458A (cs) |
| NO (2) | NO147186C (cs) |
| SE (2) | SE432764B (cs) |
| YU (1) | YU41079B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4880820A (en) * | 1983-06-24 | 1989-11-14 | Merck & Co., Inc. | Guanine derivatives |
| US4918219A (en) * | 1983-10-31 | 1990-04-17 | Warner-Lambert Company | Glycerine derivatives |
| IE842642L (en) * | 1983-10-31 | 1985-04-30 | Harvard College | Purine Derivatives |
| YU45690B (sh) * | 1984-12-22 | 1992-07-20 | Krka Tovarna Zdraviln.Sol.O. | Postopek za pripravo 9-(2-hidroksietoksimetil)-gvanina |
| DE3889248T2 (de) * | 1987-05-04 | 1994-11-17 | Kemijski Inst | Verfahren zu Herstellung von Purinverbindungen. |
| PL174765B1 (pl) * | 1993-09-10 | 1998-09-30 | Recordati Chem Pharm | Sposób wytwarzania 9-(2-hydroksy)etoksymetyloguaniny |
| DE19536164A1 (de) * | 1995-09-28 | 1997-04-03 | Boehringer Ingelheim Kg | Verbessertes Verfahren zur Herstellung von 9-[(2-Hyroxyethoxy)methyl]guanin (Acyclovir) |
| IT1276126B1 (it) * | 1995-11-14 | 1997-10-27 | Archimica Spa | Procedimento per la preparazine di 9-((2-idrossietossi)metil) guanina |
| WO1997024357A1 (en) * | 1995-12-28 | 1997-07-10 | Mallinckrodt Chemical, Inc. | Process for synthesis and purification of a compound useful in the preparation of acyclovir |
-
1977
- 1977-08-24 YU YU2022/77A patent/YU41079B/xx unknown
- 1977-08-26 DD DD7700200760A patent/DD131856A6/xx not_active IP Right Cessation
- 1977-08-26 GB GB35914/77A patent/GB1567671A/en not_active Expired
- 1977-08-26 AT AT620177A patent/AT357566B/de not_active IP Right Cessation
- 1977-08-26 CH CH1046677A patent/CH634843A5/de not_active IP Right Cessation
- 1977-08-26 SE SE7709606A patent/SE432764B/xx not_active IP Right Cessation
- 1977-08-26 NO NO772959A patent/NO147186C/no unknown
- 1977-08-26 CA CA285,592A patent/CA1096863A/en not_active Expired
- 1977-08-26 CS CS775615A patent/CS196384B2/cs unknown
- 1977-08-26 FI FI772548A patent/FI64160C/fi not_active IP Right Cessation
- 1977-08-26 DK DK380377A patent/DK147857C/da not_active IP Right Cessation
- 1977-08-26 NL NL7709458A patent/NL7709458A/xx active Search and Examination
-
1980
- 1980-06-20 CA CA354,538A patent/CA1096864A/en not_active Expired
-
1982
- 1982-07-20 NO NO822502A patent/NO150119C/no unknown
-
1983
- 1983-08-23 SE SE8304549A patent/SE447113B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1567671A (en) | 1980-05-21 |
| SE432764B (sv) | 1984-04-16 |
| FI64160C (fi) | 1983-10-10 |
| DD131856A6 (de) | 1978-07-26 |
| ATA620177A (de) | 1979-12-15 |
| SE447113B (sv) | 1986-10-27 |
| DK147857C (da) | 1985-06-10 |
| NO822502L (no) | 1978-02-28 |
| NO150119C (no) | 1984-08-22 |
| YU202277A (en) | 1983-02-28 |
| NO147186C (no) | 1983-02-16 |
| CS196384B2 (en) | 1980-03-31 |
| SE8304549D0 (sv) | 1983-08-23 |
| YU41079B (en) | 1986-12-31 |
| NO772959L (no) | 1978-02-28 |
| NO147186B (no) | 1982-11-08 |
| CA1096864A (en) | 1981-03-03 |
| DK147857B (da) | 1984-12-24 |
| FI772548A7 (fi) | 1978-02-28 |
| DK380377A (da) | 1978-02-28 |
| NL7709458A (nl) | 1978-03-01 |
| SE8304549L (sv) | 1983-08-23 |
| FI64160B (fi) | 1983-06-30 |
| SE7709606L (sv) | 1978-02-28 |
| AT357566B (de) | 1980-07-25 |
| NO150119B (no) | 1984-05-14 |
| CH634843A5 (en) | 1983-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |