GB1565762A - Process for the production of basically substituted alkyl theophylline derivatives - Google Patents
Process for the production of basically substituted alkyl theophylline derivatives Download PDFInfo
- Publication number
- GB1565762A GB1565762A GB1796/78A GB179678A GB1565762A GB 1565762 A GB1565762 A GB 1565762A GB 1796/78 A GB1796/78 A GB 1796/78A GB 179678 A GB179678 A GB 179678A GB 1565762 A GB1565762 A GB 1565762A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- group
- substituted alkyl
- alk
- production
- 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
- 238000000034 method Methods 0.000 title claims description 26
- -1 substituted alkyl theophylline derivatives Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000002904 solvent Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229940113088 dimethylacetamide Drugs 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 241000605281 Anaplasma phagocytophilum Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 229960000278 theophylline Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical class O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OQFMNXMRKPNXOY-UHFFFAOYSA-N 1,3-dimethyl-7h-purine-2,6-dione;hydrochloride Chemical compound Cl.O=C1N(C)C(=O)N(C)C2=C1NC=N2 OQFMNXMRKPNXOY-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- VUQMOERHEHTWPE-UHFFFAOYSA-N 1-ethylpiperidin-2-one Chemical compound CCN1CCCCC1=O VUQMOERHEHTWPE-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D473/08—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772701629 DE2701629A1 (de) | 1977-01-17 | 1977-01-17 | Verfahren zur herstellung von basisch substituierten alkyltheophyllinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1565762A true GB1565762A (en) | 1980-04-23 |
Family
ID=5998819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1796/78A Expired GB1565762A (en) | 1977-01-17 | 1978-01-17 | Process for the production of basically substituted alkyl theophylline derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4150227A (en:Method) |
| JP (1) | JPS5390293A (en:Method) |
| AR (1) | AR219732A1 (en:Method) |
| AT (1) | AT356137B (en:Method) |
| AU (1) | AU511128B2 (en:Method) |
| BE (1) | BE862964A (en:Method) |
| CA (1) | CA1083571A (en:Method) |
| CH (1) | CH631984A5 (en:Method) |
| DE (1) | DE2701629A1 (en:Method) |
| DK (1) | DK143753C (en:Method) |
| EG (1) | EG12898A (en:Method) |
| ES (1) | ES466032A1 (en:Method) |
| FI (1) | FI64373C (en:Method) |
| FR (1) | FR2377401A1 (en:Method) |
| GB (1) | GB1565762A (en:Method) |
| GR (1) | GR66065B (en:Method) |
| IT (1) | IT1155770B (en:Method) |
| MX (1) | MX5834E (en:Method) |
| NL (1) | NL179820C (en:Method) |
| PT (1) | PT67531B (en:Method) |
| SE (1) | SE425973B (en:Method) |
| ZA (1) | ZA78261B (en:Method) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1084152A (en:Method) * | 1965-11-16 | |||
| AT308139B (de) | 1970-07-27 | 1973-06-25 | Degussa | Verfahren zur Herstellung von neuen basisch substituierten Alkyltheophyllinen, ihren Isomeren und Säureadditionssalzen |
| US3728346A (en) * | 1971-07-16 | 1973-04-17 | Degussa | Hydroxyphenylhydroxyalkylaminoalkyltheophyllines |
-
1977
- 1977-01-17 DE DE19772701629 patent/DE2701629A1/de active Granted
- 1977-12-21 US US05/862,977 patent/US4150227A/en not_active Expired - Lifetime
-
1978
- 1978-01-13 GR GR55156A patent/GR66065B/el unknown
- 1978-01-13 PT PT67531A patent/PT67531B/pt unknown
- 1978-01-16 FI FI780137A patent/FI64373C/fi not_active IP Right Cessation
- 1978-01-16 DK DK19678A patent/DK143753C/da not_active IP Right Cessation
- 1978-01-16 AT AT28678A patent/AT356137B/de not_active IP Right Cessation
- 1978-01-16 AR AR270722A patent/AR219732A1/es active
- 1978-01-16 ES ES466032A patent/ES466032A1/es not_active Expired
- 1978-01-16 IT IT47656/78A patent/IT1155770B/it active
- 1978-01-16 ZA ZA00780261A patent/ZA78261B/xx unknown
- 1978-01-16 NL NLAANVRAGE7800511,A patent/NL179820C/xx not_active IP Right Cessation
- 1978-01-16 MX MX786777U patent/MX5834E/es unknown
- 1978-01-16 AU AU32472/78A patent/AU511128B2/en not_active Expired
- 1978-01-16 CA CA295,031A patent/CA1083571A/en not_active Expired
- 1978-01-16 EG EG23/78A patent/EG12898A/xx active
- 1978-01-16 BE BE6046310A patent/BE862964A/xx not_active IP Right Cessation
- 1978-01-16 SE SE7800500A patent/SE425973B/sv not_active IP Right Cessation
- 1978-01-16 CH CH42378A patent/CH631984A5/de not_active IP Right Cessation
- 1978-01-17 FR FR7801188A patent/FR2377401A1/fr active Granted
- 1978-01-17 JP JP366378A patent/JPS5390293A/ja active Granted
- 1978-01-17 GB GB1796/78A patent/GB1565762A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK143753B (da) | 1981-10-05 |
| ES466032A1 (es) | 1978-10-01 |
| NL179820B (nl) | 1986-06-16 |
| ATA28678A (de) | 1979-09-15 |
| ZA78261B (en) | 1978-12-27 |
| CH631984A5 (de) | 1982-09-15 |
| GR66065B (en:Method) | 1981-01-15 |
| FI64373C (fi) | 1983-11-10 |
| FR2377401B1 (en:Method) | 1980-02-22 |
| DK19678A (da) | 1978-07-18 |
| PT67531B (de) | 1979-06-12 |
| DE2701629A1 (de) | 1978-07-20 |
| CA1083571A (en) | 1980-08-12 |
| AT356137B (de) | 1980-04-10 |
| JPS5390293A (en) | 1978-08-08 |
| NL7800511A (nl) | 1978-07-19 |
| AR219732A1 (es) | 1980-09-15 |
| SE7800500L (sv) | 1978-07-18 |
| BE862964A (fr) | 1978-07-17 |
| PT67531A (de) | 1978-02-01 |
| FR2377401A1 (fr) | 1978-08-11 |
| AU511128B2 (en) | 1980-07-31 |
| IT7847656A0 (it) | 1978-01-16 |
| EG12898A (en) | 1980-10-31 |
| US4150227A (en) | 1979-04-17 |
| SE425973B (sv) | 1982-11-29 |
| JPS625157B2 (en:Method) | 1987-02-03 |
| MX5834E (es) | 1984-08-01 |
| AU3247278A (en) | 1979-07-26 |
| FI64373B (fi) | 1983-07-29 |
| IT1155770B (it) | 1987-01-28 |
| NL179820C (nl) | 1986-11-17 |
| DK143753C (da) | 1982-03-22 |
| DE2701629C2 (en:Method) | 1987-08-20 |
| FI780137A7 (fi) | 1978-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL163884B1 (pl) | Sposób wytwarzania fluoksetyny PL PL PL | |
| Gates et al. | The Synthesis and Resolution of 3-Hydroxy-N-methylisomorphinan1 | |
| CH558362A (de) | Verfahren zur herstellung von endoaethano-tetrahydrothebainen bzw. -oripavinen. | |
| DE2413102B2 (de) | Verfahren zur Herstellung von t-(33-Dihydroxyphenyl)-)-hydroxy-2- eckige Klammer auf l-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan | |
| Lahey et al. | Alkaloids of the Australian Rutaceae. The Structure and Reactions of Acronycidine | |
| DE1493976C3 (de) | Substituierte Flavandenvate sowie Verfahren zu ihrer Herstellung | |
| GB1565762A (en) | Process for the production of basically substituted alkyl theophylline derivatives | |
| DE1695943A1 (de) | Verfahren zur Herstellung von neuen 1,2,3,4,5,6-Hexahydroazepino(4,5-b)indolen und deren Saeureanlagerungssalzen | |
| FI85010C (fi) | Foerfarande foer framstaellning av rimantadin. | |
| US3288848A (en) | Alpha-amino dibasic acid hydrazides | |
| DE2024049C3 (de) | a-(3,4-Dihydroxyphenyl)-a- (2-piperidinyl)methanol | |
| EP0017727A1 (de) | Polysubstituierte Diazatricyclen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen | |
| HU176214B (en) | Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives | |
| US2983736A (en) | Process for the preparation of 20-alkylamino steroid derivatives and novel 20-alkylamino steroid derivatives prepared thereby | |
| US3547998A (en) | Intermediate and process for the preparation of nortriptyline | |
| US3274232A (en) | Arylhydrazides | |
| DE3048318A1 (de) | 4-alkoxyalkyl substituierte (beta)-carbolin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| SMALL et al. | Acetomorphine and acetocodeine | |
| Mueller et al. | Some Derivatives of 7-Methoxy-and 10-Methoxybenzo (f) quinoline | |
| DE1695381B2 (de) | Phthalazino eckige klammer auf 2,3-b eckige klammer zu phthalazine und ein verfahren zu ihrer herstellung | |
| DE834246C (de) | Verfahren zur Darstellung von substituierten Piperidooctahydrophenanthrenen | |
| HU191693B (en) | Process for production of derivatives of 9-or-11 substituated apovincamin acid | |
| DE1545749C (de) | Basisch substituierte Alkyltheophyllin derivate und ein Verfahren zu deren Her stellung | |
| RAPOPORT et al. | The Mannich reaction with dihydrocodeinone | |
| AT165073B (de) | Verfahren zur Darstellung substituierten Piperido-octahydrophenanthrenen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |