CH622519A5 - Process for the preparation of hydroxyalkylxanthines - Google Patents
Process for the preparation of hydroxyalkylxanthines Download PDFInfo
- Publication number
- CH622519A5 CH622519A5 CH859275A CH859275A CH622519A5 CH 622519 A5 CH622519 A5 CH 622519A5 CH 859275 A CH859275 A CH 859275A CH 859275 A CH859275 A CH 859275A CH 622519 A5 CH622519 A5 CH 622519A5
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- xanthine
- acid
- compounds
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract 2
- 239000012433 hydrogen halide Substances 0.000 claims abstract 2
- -1 alkenyl xanthines Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000006043 5-hexenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 229960004559 theobromine Drugs 0.000 claims 2
- ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 1,3-dimethyl-7-prop-2-enylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC=C)C=N2 ZGIBYCLLIMGXEZ-UHFFFAOYSA-N 0.000 claims 1
- BTFHIKZOEZREBX-UHFFFAOYSA-N 3,7-dimethyl-1-prop-2-enylpurine-2,6-dione Chemical compound CN1C(=O)N(CC=C)C(=O)C2=C1N=CN2C BTFHIKZOEZREBX-UHFFFAOYSA-N 0.000 claims 1
- GEPVMDINFCTKRV-UHFFFAOYSA-N 8,8-dimethyl-3H-purine-2,6-dione Chemical class CC1(N=C2NC(NC(C2=N1)=O)=O)C GEPVMDINFCTKRV-UHFFFAOYSA-N 0.000 claims 1
- 241000143437 Aciculosporium take Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims 1
- MXRGZXBFSKSZPH-UHFFFAOYSA-N protheobromine Chemical compound O=C1N(CC(O)C)C(=O)N(C)C2=C1N(C)C=N2 MXRGZXBFSKSZPH-UHFFFAOYSA-N 0.000 claims 1
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229940075420 xanthine Drugs 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LECGBNCYRJCWJJ-UHFFFAOYSA-N 1-(3-hydroxybutyl)-3,7-dimethylpurine-2,6-dione Chemical compound OC(CCN1C(=O)N(C=2N=CN(C2C1=O)C)C)C LECGBNCYRJCWJJ-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
- NSMXQKNUPPXBRG-UHFFFAOYSA-N 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione Chemical compound O=C1N(CCCCC(O)C)C(=O)N(C)C2=C1N(C)C=N2 NSMXQKNUPPXBRG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 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
- 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 description 1
- PESRCCQMYJSHAV-UHFFFAOYSA-N 7-(3-hydroxybutyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCC(O)C PESRCCQMYJSHAV-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
- LFUJRHXPQUKRTL-UHFFFAOYSA-N 7-(6-hydroxyheptyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCCC(O)C LFUJRHXPQUKRTL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- COCPIYBVBNOICS-UHFFFAOYSA-N 7-hex-5-enyl-3-methylpurine-2,6-dione Chemical compound O=C1NC(=O)N(C)C2=C1N(CCCCC=C)C=N2 COCPIYBVBNOICS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008030 superplasticizer Substances 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 |
|---|---|
| CH622519A5 true CH622519A5 (en) | 1981-04-15 |
Family
ID=27048497
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH859275A CH622519A5 (en) | 1974-07-05 | 1975-07-02 | Process for the preparation of hydroxyalkylxanthines |
| CH331680A CH622018A5 (en) | 1974-07-05 | 1980-04-29 | Process for the preparation of novel monoalkenyldialkylxanthines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH331680A CH622018A5 (en) | 1974-07-05 | 1980-04-29 | Process for the preparation of novel monoalkenyldialkylxanthines |
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 |
|---|---|---|---|---|
| US5077298A (en) * | 1984-01-12 | 1991-12-31 | Sandoz Ltd. | Novel 8α-acylaminoergolines |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3525801A1 (de) * | 1985-07-19 | 1987-01-22 | Hoechst Ag | Tertiaere hydroxyalkylxanthine, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung |
| 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 |
|---|---|---|---|---|
| US5077298A (en) * | 1984-01-12 | 1991-12-31 | Sandoz Ltd. | Novel 8α-acylaminoergolines |
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 |
| CA1062710A (en) | 1979-09-18 |
| SE7807853L (sv) | 1978-07-14 |
| NO143224B (no) | 1980-09-22 |
| 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 |
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