DE2701629C2 - - Google Patents
Info
- Publication number
- DE2701629C2 DE2701629C2 DE2701629A DE2701629A DE2701629C2 DE 2701629 C2 DE2701629 C2 DE 2701629C2 DE 2701629 A DE2701629 A DE 2701629A DE 2701629 A DE2701629 A DE 2701629A DE 2701629 C2 DE2701629 C2 DE 2701629C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydrogenation
- groups
- protective groups
- phenolic hydroxyl
- 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
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 238000000034 method Methods 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 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- -1 substituted alkyl theophyllin derivatives Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 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
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-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
- PZUVSJJEOLUMIN-UHFFFAOYSA-N 7-[3-[benzyl-[2-(3,5-dihydroxyphenyl)-2-oxoethyl]amino]propyl]-1,3-dimethylpurine-2,6-dione;hydrochloride Chemical compound Cl.C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCCN(CC=1C=CC=CC=1)CC(=O)C1=CC(O)=CC(O)=C1 PZUVSJJEOLUMIN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 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
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 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
- 231100000614 poison Toxicity 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- WMCMJIGLYZDKRN-UHFFFAOYSA-N theodrenaline Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCNCC(O)C1=CC=C(O)C(O)=C1 WMCMJIGLYZDKRN-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical group C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-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
- C07D473/08—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)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772701629 DE2701629A1 (de) | 1977-01-17 | 1977-01-17 | Verfahren zur herstellung von basisch substituierten alkyltheophyllinderivaten |
| US05/862,977 US4150227A (en) | 1977-01-17 | 1977-12-21 | Process for the production of basic substituted alkyl theophylline |
| PT67531A PT67531B (de) | 1977-01-17 | 1978-01-13 | Verfahren zur herstellung von basich substituierten alkyltheophyllinderivaten |
| GR55156A GR66065B (en, 2012) | 1977-01-17 | 1978-01-13 | |
| SE7800500A SE425973B (sv) | 1977-01-17 | 1978-01-16 | Forfarande for framstellning av basiskt substituerade alkylteofyllinderivat |
| AT28678A AT356137B (de) | 1977-01-17 | 1978-01-16 | Verfahren zur herstellung von 7-aminoalkyl- theophyllinen |
| FI780137A FI64373C (fi) | 1977-01-17 | 1978-01-16 | Foerfarande foer framstaellning av basiskt substituerade alkylteofyllinderivat |
| CA295,031A CA1083571A (en) | 1977-01-17 | 1978-01-16 | Process for the production of basic substituted alkyl theophylline |
| EG23/78A EG12898A (en) | 1977-01-17 | 1978-01-16 | A process for the production of basically substituted alkyl theophilline derivatives |
| MX786777U MX5834E (es) | 1977-01-17 | 1978-01-16 | Procedimiento mejorado para la elaboracion de derivados de alquilteofilina |
| ES466032A ES466032A1 (es) | 1977-01-17 | 1978-01-16 | Procedimiento para la preparacion de derivados de alcohil- teofilina, sustituidos con radicales basicos. |
| AR270722A AR219732A1 (es) | 1977-01-17 | 1978-01-16 | Procedimiento para la elaboracion de 7- (3-(2-(3,5 o 3,4-dihidroxifenil)-2-hidroxi-etilamino)-alquil)-teofilina |
| CH42378A CH631984A5 (de) | 1977-01-17 | 1978-01-16 | Verfahren zur herstellung von basisch substituierten alkyltheophyllinderivaten. |
| DK19678A DK143753C (da) | 1977-01-17 | 1978-01-16 | Fremgangsmaade til fremstilling af basisk substituerede alkyltheophyllinderivater |
| NLAANVRAGE7800511,A NL179820C (nl) | 1977-01-17 | 1978-01-16 | Werkwijze voor het bereiden van basisch gesubstitueerde alkyltheofyllinederivaten. |
| ZA00780261A ZA78261B (en) | 1977-01-17 | 1978-01-16 | Process for the production of basic substituted alkyl theophylline derivatives |
| IT47656/78A IT1155770B (it) | 1977-01-17 | 1978-01-16 | Procedimento per la produzione di derivati di alchil-teofillina basicamente sostituiti |
| BE6046310A BE862964A (fr) | 1977-01-17 | 1978-01-16 | Procede de fabrication de derives d'alkyltheophylline a substition basique et produits obtenus suivant ce procede |
| AU32472/78A AU511128B2 (en) | 1977-01-17 | 1978-01-16 | Process forthe production of basic substituted alkyl theophylline |
| JP366378A JPS5390293A (en) | 1977-01-17 | 1978-01-17 | Process for preparing basically substituted alkyltheophiline derivative |
| GB1796/78A GB1565762A (en) | 1977-01-17 | 1978-01-17 | Process for the production of basically substituted alkyl theophylline derivatives |
| FR7801188A FR2377401A1 (fr) | 1977-01-17 | 1978-01-17 | Procede pour la preparation de derives alcoyl-theophylliniques a substitution basique |
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2701629A1 DE2701629A1 (de) | 1978-07-20 |
| DE2701629C2 true DE2701629C2 (en, 2012) | 1987-08-20 |
Family
ID=5998819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772701629 Granted DE2701629A1 (de) | 1977-01-17 | 1977-01-17 | Verfahren zur herstellung von basisch substituierten alkyltheophyllinderivaten |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4150227A (en, 2012) |
| JP (1) | JPS5390293A (en, 2012) |
| AR (1) | AR219732A1 (en, 2012) |
| AT (1) | AT356137B (en, 2012) |
| AU (1) | AU511128B2 (en, 2012) |
| BE (1) | BE862964A (en, 2012) |
| CA (1) | CA1083571A (en, 2012) |
| CH (1) | CH631984A5 (en, 2012) |
| DE (1) | DE2701629A1 (en, 2012) |
| DK (1) | DK143753C (en, 2012) |
| EG (1) | EG12898A (en, 2012) |
| ES (1) | ES466032A1 (en, 2012) |
| FI (1) | FI64373C (en, 2012) |
| FR (1) | FR2377401A1 (en, 2012) |
| GB (1) | GB1565762A (en, 2012) |
| GR (1) | GR66065B (en, 2012) |
| IT (1) | IT1155770B (en, 2012) |
| MX (1) | MX5834E (en, 2012) |
| NL (1) | NL179820C (en, 2012) |
| PT (1) | PT67531B (en, 2012) |
| SE (1) | SE425973B (en, 2012) |
| ZA (1) | ZA78261B (en, 2012) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1084152A (en, 2012) * | 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, 2012) | 1981-01-15 |
| FI64373C (fi) | 1983-11-10 |
| FR2377401B1 (en, 2012) | 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 |
| GB1565762A (en) | 1980-04-23 |
| EG12898A (en) | 1980-10-31 |
| US4150227A (en) | 1979-04-17 |
| SE425973B (sv) | 1982-11-29 |
| JPS625157B2 (en, 2012) | 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 |
| FI780137A7 (fi) | 1978-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |