CA1062710A - Process for preparing hydroxyalkylxanthines - Google Patents
Process for preparing hydroxyalkylxanthinesInfo
- Publication number
- CA1062710A CA1062710A CA230,790A CA230790A CA1062710A CA 1062710 A CA1062710 A CA 1062710A CA 230790 A CA230790 A CA 230790A CA 1062710 A CA1062710 A CA 1062710A
- Authority
- CA
- Canada
- Prior art keywords
- xanthine
- methyl
- hydroxyhexyl
- omega
- groups
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 230000000887 hydrating effect Effects 0.000 claims abstract description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 3
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 3
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- GIHUMBWJDVZRRG-UHFFFAOYSA-N 1-(3-hydroxy-2-methylbutyl)-3,7-dimethylpurine-2,6-dione Chemical compound O=C1N(CC(C)C(O)C)C(=O)N(C)C2=C1N(C)C=N2 GIHUMBWJDVZRRG-UHFFFAOYSA-N 0.000 claims description 3
- QIAYXEJPDSASPC-UHFFFAOYSA-N 1-(5-hydroxyhexyl)-3-methyl-7-(2-methylpropyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)O)C(=O)C2=C1N=CN2CC(C)C QIAYXEJPDSASPC-UHFFFAOYSA-N 0.000 claims description 3
- CERFGCPAKWKZEK-UHFFFAOYSA-N 1-(5-hydroxyhexyl)-3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)O)C(=O)C2=C1N=CN2CCC CERFGCPAKWKZEK-UHFFFAOYSA-N 0.000 claims description 3
- NBXBTNZUOPMZAB-UHFFFAOYSA-N 7-butyl-1-(5-hydroxyhexyl)-3-methylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)O)C(=O)C2=C1N=CN2CCCC NBXBTNZUOPMZAB-UHFFFAOYSA-N 0.000 claims description 3
- RMGVVFDJVCGEPN-UHFFFAOYSA-N 7-decyl-1-(5-hydroxyhexyl)-3-methylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)O)C(=O)C2=C1N=CN2CCCCCCCCCC RMGVVFDJVCGEPN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- YVJPMXPSIMGRCD-UHFFFAOYSA-N 1-hexyl-7-(5-hydroxyhexyl)-3-methylpurine-2,6-dione Chemical compound O=C1N(CCCCCC)C(=O)N(C)C2=C1N(CCCCC(C)O)C=N2 YVJPMXPSIMGRCD-UHFFFAOYSA-N 0.000 claims 2
- NGCAQWOWNNVVSY-UHFFFAOYSA-N 7-(3-hydroxy-2-methylbutyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(C)C(O)C NGCAQWOWNNVVSY-UHFFFAOYSA-N 0.000 claims 2
- IUHVEMNMQVLXDE-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-3-methyl-1-(2-methylpropyl)purine-2,6-dione Chemical compound O=C1N(CC(C)C)C(=O)N(C)C2=C1N(CCCCC(C)O)C=N2 IUHVEMNMQVLXDE-UHFFFAOYSA-N 0.000 claims 2
- ZJEDKNDYTBFTMD-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-3-methyl-1-pentylpurine-2,6-dione Chemical compound O=C1N(CCCCC)C(=O)N(C)C2=C1N(CCCCC(C)O)C=N2 ZJEDKNDYTBFTMD-UHFFFAOYSA-N 0.000 claims 2
- IRZCBLPIFWYWRG-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-3-methyl-1-propylpurine-2,6-dione Chemical compound O=C1N(CCC)C(=O)N(C)C2=C1N(CCCCC(C)O)C=N2 IRZCBLPIFWYWRG-UHFFFAOYSA-N 0.000 claims 2
- RUNBVKCZPOHXJI-UHFFFAOYSA-N 7-ethyl-1-(5-hydroxyhexyl)-3-methylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)O)C(=O)C2=C1N=CN2CC RUNBVKCZPOHXJI-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- 230000017531 blood circulation Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 229940075420 xanthine Drugs 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229960004559 theobromine Drugs 0.000 description 5
- -1 hydroxypropyl Chemical group 0.000 description 4
- 125000006043 5-hexenyl group Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- LZRTZRBKFZHHQT-UHFFFAOYSA-N 1-hex-5-enyl-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCC=C)C(=O)C2=C1N=CN2C LZRTZRBKFZHHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CYCCBWAHGKLLTR-UHFFFAOYSA-N 1-(4-hydroxypentyl)-3,7-dimethylpurine-2,6-dione Chemical compound O=C1N(CCCC(O)C)C(=O)N(C)C2=C1N(C)C=N2 CYCCBWAHGKLLTR-UHFFFAOYSA-N 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- YOBYAKWFGPDGHG-UHFFFAOYSA-N 3,7-dimethyl-1-pent-4-enylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCC=C)C(=O)C2=C1N=CN2C YOBYAKWFGPDGHG-UHFFFAOYSA-N 0.000 description 1
- NHAXKHSVJBVINX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione;sodium Chemical compound [Na].CN1C(=O)NC(=O)C2=C1N=CN2C NHAXKHSVJBVINX-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- HSUAWWZANQUYQS-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCC(O)C HSUAWWZANQUYQS-UHFFFAOYSA-N 0.000 description 1
- JRUPQQAQYJPGJU-UHFFFAOYSA-N 7-hex-5-enyl-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCCCC=C)C=N2 JRUPQQAQYJPGJU-UHFFFAOYSA-N 0.000 description 1
- 238000010471 Markovnikov's rule Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
- 229960000278 theophylline Drugs 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
Classifications
-
- 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine
-
- 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48587074A | 1974-07-05 | 1974-07-05 | |
| US05/485,869 US4108995A (en) | 1973-07-11 | 1974-07-05 | Hydroxyhexyl-alkylxanthines and pharmaceutical compositions containing hydroxyhexyl-alkylxanthines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062710A true CA1062710A (en) | 1979-09-18 |
Family
ID=27048497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,790A Expired CA1062710A (en) | 1974-07-05 | 1975-07-04 | Process for preparing hydroxyalkylxanthines |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5250800B2 (en, 2012) |
| AR (1) | AR210330A1 (en, 2012) |
| AT (1) | AT339917B (en, 2012) |
| CA (1) | CA1062710A (en, 2012) |
| CH (2) | CH622519A5 (en, 2012) |
| DK (1) | DK140214B (en, 2012) |
| ES (1) | ES439141A1 (en, 2012) |
| FI (1) | FI59249C (en, 2012) |
| FR (1) | FR2277089A1 (en, 2012) |
| GB (1) | GB1500039A (en, 2012) |
| LU (1) | LU72897A1 (en, 2012) |
| NL (1) | NL166476C (en, 2012) |
| NO (1) | NO143224C (en, 2012) |
| SE (2) | SE420097B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4833146A (en) * | 1985-07-19 | 1989-05-23 | Hoechst Aktiengesellschaft | Tertiary hydroxyalkylxanthines, medicaments containing them and their use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU197569B (en) * | 1984-01-12 | 1989-04-28 | Sandoz Ag | Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds |
| EP0570831A2 (de) * | 1992-05-20 | 1993-11-24 | Hoechst Aktiengesellschaft | Verwendung von Xanthinderivaten zur Behandlung von Nervenschädigungen nach Unterbrechung der Blutzirkulation |
-
1975
- 1975-07-02 CH CH859275A patent/CH622519A5/de not_active IP Right Cessation
- 1975-07-03 DK DK301775AA patent/DK140214B/da not_active IP Right Cessation
- 1975-07-03 LU LU72897A patent/LU72897A1/xx unknown
- 1975-07-03 JP JP50081475A patent/JPS5250800B2/ja not_active Expired
- 1975-07-04 NL NL7507976.A patent/NL166476C/xx not_active IP Right Cessation
- 1975-07-04 ES ES439141A patent/ES439141A1/es not_active Expired
- 1975-07-04 SE SE7507726A patent/SE420097B/xx not_active IP Right Cessation
- 1975-07-04 AR AR258487A patent/AR210330A1/es active
- 1975-07-04 GB GB28341/75A patent/GB1500039A/en not_active Expired
- 1975-07-04 NO NO752423A patent/NO143224C/no unknown
- 1975-07-04 AT AT517275A patent/AT339917B/de not_active IP Right Cessation
- 1975-07-04 FI FI751958A patent/FI59249C/fi not_active IP Right Cessation
- 1975-07-04 CA CA230,790A patent/CA1062710A/en not_active Expired
- 1975-07-04 FR FR7521043A patent/FR2277089A1/fr active Granted
-
1978
- 1978-07-14 SE SE7807853A patent/SE427183B/sv not_active IP Right Cessation
-
1980
- 1980-04-29 CH CH331680A patent/CH622018A5/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4833146A (en) * | 1985-07-19 | 1989-05-23 | Hoechst Aktiengesellschaft | Tertiary hydroxyalkylxanthines, medicaments containing them and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| SE427183B (sv) | 1983-03-14 |
| AR210330A1 (es) | 1977-07-29 |
| NL166476C (nl) | 1981-08-17 |
| ES439141A1 (es) | 1977-02-16 |
| ATA517275A (de) | 1977-03-15 |
| DK140214C (en, 2012) | 1979-12-03 |
| AT339917B (de) | 1977-11-10 |
| FR2277089B1 (en, 2012) | 1978-03-17 |
| JPS5134194A (en, 2012) | 1976-03-23 |
| DK140214B (da) | 1979-07-09 |
| GB1500039A (en) | 1978-02-08 |
| SE7507726L (sv) | 1976-01-07 |
| NO143224C (no) | 1981-01-02 |
| AU8275575A (en) | 1977-01-06 |
| NO752423L (en, 2012) | 1976-01-06 |
| FI59249C (fi) | 1981-07-10 |
| NL166476B (nl) | 1981-03-16 |
| CH622018A5 (en) | 1981-03-13 |
| FI59249B (fi) | 1981-03-31 |
| NL7507976A (nl) | 1976-01-07 |
| FI751958A7 (en, 2012) | 1976-01-06 |
| SE7807853L (sv) | 1978-07-14 |
| NO143224B (no) | 1980-09-22 |
| CH622519A5 (en) | 1981-04-15 |
| DK301775A (en, 2012) | 1976-01-06 |
| SE420097B (sv) | 1981-09-14 |
| FR2277089A1 (fr) | 1976-01-30 |
| JPS5250800B2 (en, 2012) | 1977-12-27 |
| LU72897A1 (en, 2012) | 1976-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1062710A (en) | Process for preparing hydroxyalkylxanthines | |
| EP0704445B1 (en) | Preparation of N-9 substituted guanine compounds | |
| CA1062709A (en) | Hydroxyalkyl substituted xanthine derivatives | |
| US2756229A (en) | Xanthine derivatives | |
| US20080154038A1 (en) | Process for the manufacture of famciclovir using phase-transfer catalysts | |
| CN113501758B (zh) | 一种联苯化合物的制备方法 | |
| EP0031388B1 (en) | Process for preparing imidazole derivatives | |
| PL92088B1 (en, 2012) | ||
| US3475459A (en) | Hordatine compounds and synthesis | |
| CA1274513A (en) | Process for preparing substituted anthra [1,9- cd]pyrazol-6(1h)-ones | |
| US7223871B2 (en) | Process for preparing substituted imidazole derivatives and intermediates used in the process | |
| US5821367A (en) | Regiospecific process for synthesis of acyclic nucleosides | |
| DK151030B (da) | Fremgangsmaade til fremstilling af auranofin | |
| US3268530A (en) | 5-ethyl-5-(6-purinyl) thiobarbituric acid | |
| DK142790B (da) | Monoalken-1-yl-alkylxanthiner til anvendelse som mellemprodukter ved fremstilling af hydroxyalkyl-alkylxanthiner. | |
| US6022980A (en) | Preparation of 4-halo and 6-halomelatonins | |
| JPS5982366A (ja) | ケト中間体ならびにその用法および製造方法 | |
| KR810000271B1 (ko) | 1-(2'-퓨라니딜)-5-플루오로 우라실의 제조방법 | |
| IE45046B1 (en) | Method of producing 5-fluorouracil derivatives | |
| CN120230089A (zh) | 一种喹啉酮中间体的制备方法 | |
| EP0709385A1 (en) | Preparation of acyclovir | |
| CA1076566A (en) | Processes for the preparation of 3',4'-dideoxykanamycin b | |
| WO1989005805A1 (en) | Novel 2,3-thiomorpholinedione-2-oxime derivatives, pharmaceutical compositions containing them and process for preparing same | |
| NL8800484A (nl) | Piperazinederivaten en werkwijze voor de bereiding ervan. | |
| McKay et al. | A NEW SYNTHESIS OF 1-SUBSTITUTED-2, 3, 5, 6-TETRAHYDRO-1-IMIDAZ (1, 2-a) IMIDAZOLES |