FI63027C - Nytt foerfarande foer framstaellning av som laekemedel anvaenda racematiska eller optiskt aktiva n-(furyl- eller tienyl-metyl)-bensomorfaner - Google Patents
Nytt foerfarande foer framstaellning av som laekemedel anvaenda racematiska eller optiskt aktiva n-(furyl- eller tienyl-metyl)-bensomorfaner Download PDFInfo
- Publication number
- FI63027C FI63027C FI274873A FI274873A FI63027C FI 63027 C FI63027 C FI 63027C FI 274873 A FI274873 A FI 274873A FI 274873 A FI274873 A FI 274873A FI 63027 C FI63027 C FI 63027C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- alkyl
- formula
- hydrogen
- eller
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 239000002253 acid Chemical group 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 3
- 230000000397 acetylating effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 230000001035 methylating effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- -1 lithium aluminum hydride Chemical group 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000007868 Raney catalyst Substances 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- AFFZVBHMMXZNKE-UHFFFAOYSA-N 2-methylfuran-3-carbonyl chloride Chemical compound CC=1OC=CC=1C(Cl)=O AFFZVBHMMXZNKE-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- 238000007280 thionation reaction Methods 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- DFXNZMRXFMWEGQ-UHFFFAOYSA-N 3-methylfuran-2-carbonyl chloride Chemical compound CC=1C=COC=1C(Cl)=O DFXNZMRXFMWEGQ-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NGPGDYLVALNKEG-OLXYHTOASA-N diammonium L-tartrate Chemical class [NH4+].[NH4+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O NGPGDYLVALNKEG-OLXYHTOASA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI792993A FI63028C (fi) | 1972-09-06 | 1979-09-26 | Nytt foerfarande foer framstaellning av som laekemedel anvaenda n-(furyl-metyl)-bentsomorfaner |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2243703 | 1972-09-06 | ||
| DE19722243703 DE2243703A1 (de) | 1972-09-06 | 1972-09-06 | Verfahren zur herstellung von n(heteroaryl-methyl)-benzomorphanen und -morphinanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI63027B FI63027B (fi) | 1982-12-31 |
| FI63027C true FI63027C (fi) | 1983-04-11 |
Family
ID=5855589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI274873A FI63027C (fi) | 1972-09-06 | 1973-09-04 | Nytt foerfarande foer framstaellning av som laekemedel anvaenda racematiska eller optiskt aktiva n-(furyl- eller tienyl-metyl)-bensomorfaner |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS578109B2 (en(2012)) |
| AT (1) | AT327408B (en(2012)) |
| BG (1) | BG22392A3 (en(2012)) |
| CH (2) | CH590270A5 (en(2012)) |
| CS (2) | CS168043B2 (en(2012)) |
| DD (1) | DD107035A5 (en(2012)) |
| DE (1) | DE2243703A1 (en(2012)) |
| DK (1) | DK140171C (en(2012)) |
| ES (2) | ES418488A1 (en(2012)) |
| FI (1) | FI63027C (en(2012)) |
| HU (1) | HU176927B (en(2012)) |
| NL (1) | NL7312177A (en(2012)) |
| PL (1) | PL86931B1 (en(2012)) |
| RO (1) | RO62924A (en(2012)) |
| SE (1) | SE417821B (en(2012)) |
| SU (1) | SU543347A3 (en(2012)) |
| YU (2) | YU36022B (en(2012)) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5769970B2 (ja) * | 2007-11-16 | 2015-08-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンゾモルファン及び関連骨格のアリール−及びヘテロアリールカルボニル誘導体、かかる化合物を含有する医薬及びこれらの使用 |
-
1972
- 1972-09-06 DE DE19722243703 patent/DE2243703A1/de active Pending
-
1973
- 1973-08-14 AT AT710973A patent/AT327408B/de not_active IP Right Cessation
- 1973-09-03 CH CH1260873A patent/CH590270A5/xx not_active IP Right Cessation
- 1973-09-03 CH CH24277A patent/CH599953A5/xx not_active IP Right Cessation
- 1973-09-04 CS CS615673A patent/CS168043B2/cs unknown
- 1973-09-04 FI FI274873A patent/FI63027C/fi active
- 1973-09-04 HU HU73BO1460A patent/HU176927B/hu unknown
- 1973-09-04 CS CS812174A patent/CS185228B2/cs unknown
- 1973-09-04 BG BG025597A patent/BG22392A3/xx unknown
- 1973-09-04 DD DD17326773A patent/DD107035A5/xx unknown
- 1973-09-04 NL NL7312177A patent/NL7312177A/xx not_active Application Discontinuation
- 1973-09-05 JP JP10010173A patent/JPS578109B2/ja not_active Expired
- 1973-09-05 YU YU236573A patent/YU36022B/xx unknown
- 1973-09-05 ES ES418488A patent/ES418488A1/es not_active Expired
- 1973-09-05 DK DK489973A patent/DK140171C/da not_active IP Right Cessation
- 1973-09-05 PL PL16504273A patent/PL86931B1/pl unknown
- 1973-09-05 SE SE7312111A patent/SE417821B/sv unknown
- 1973-09-05 RO RO7599273A patent/RO62924A/ro unknown
-
1974
- 1974-01-04 ES ES422006A patent/ES422006A1/es not_active Expired
- 1974-10-10 SU SU2065404A patent/SU543347A3/ru active
-
1979
- 1979-11-27 YU YU291379A patent/YU36023B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG22392A3 (bg) | 1977-02-20 |
| FI63027B (fi) | 1982-12-31 |
| CS185228B2 (en) | 1978-09-15 |
| ATA710973A (de) | 1975-04-15 |
| YU236573A (en) | 1981-04-30 |
| YU36023B (en) | 1981-11-13 |
| YU36022B (en) | 1981-11-13 |
| ES418488A1 (es) | 1976-04-01 |
| DK140171C (da) | 1979-11-26 |
| ES422006A1 (es) | 1976-06-16 |
| YU291379A (en) | 1981-04-30 |
| PL86931B1 (en(2012)) | 1976-06-30 |
| JPS578109B2 (en(2012)) | 1982-02-15 |
| CS168043B2 (en(2012)) | 1976-05-28 |
| DK140171B (da) | 1979-07-02 |
| SU543347A3 (ru) | 1977-01-15 |
| DE2243703A1 (de) | 1974-03-14 |
| CH599953A5 (en(2012)) | 1978-06-15 |
| AT327408B (de) | 1976-01-26 |
| CH590270A5 (en(2012)) | 1977-07-29 |
| DD107035A5 (en(2012)) | 1974-07-12 |
| JPS49100085A (en(2012)) | 1974-09-20 |
| SE417821B (sv) | 1981-04-13 |
| NL7312177A (en(2012)) | 1974-03-08 |
| HU176927B (hu) | 1981-06-28 |
| RO62924A (fr) | 1978-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Raap et al. | Tetrazolylacetic acids | |
| Rogers et al. | The α-Amino-ι-Hydroxamino Acids | |
| McKay et al. | Amino Acids. II. Synthesis of Cyclic Guanidino Acids1 | |
| JPH04230277A (ja) | ２−アミノアルキル−５−アリールアルキル−１，３−ジオキサン誘導体、その製造方法およびそれを含有する医薬 | |
| FI63027C (fi) | Nytt foerfarande foer framstaellning av som laekemedel anvaenda racematiska eller optiskt aktiva n-(furyl- eller tienyl-metyl)-bensomorfaner | |
| Toki | Studies on sarkomycin–optically active 2-methylenecyclopentanone-3-carboxylic acids | |
| HU181911B (en) | Process for preparing alpha-fluoromethyl-alpha-amino-alkane-carboxylic acids and esters thereof | |
| DK141875B (da) | Analogifremgangsmaade til fremstilling af normorphinonderivater eller syreadditionssalte deraf | |
| Gardner et al. | Synthesis of Compounds for Chemotherapy of Tuberculosis. VII. Pyridine N-Oxides with Sulfur-Containing Groups. | |
| EP0381628B1 (en) | Glycocyamidine derivatives | |
| McCoubrey et al. | 148. Contributions to the chemistry of iso quinolines. Part I. The synthesis of diamino-1-phenylisoquinoline methiodides in a search for new trypanocides, with some observations on the nitration of 1-phenylisoquinoline | |
| US2864822A (en) | 9-amino-7-methyl-belta10-ergolene and derivatives thereof | |
| Balenović et al. | SYNTHESIS OF L-β-AMINO-γ-BENZYLTHIOBUTYRIC ACID.[L-β-AMINO-S-(BENZYL) HOMOCYSTEINE.] AMINO ACIDS. VI. | |
| GB823068A (en) | Condensation products from glucosides | |
| KR830001838B1 (ko) | 페닐-퀴놀리지딘의 제조방법 | |
| US2571940A (en) | Oxazolines | |
| US4500708A (en) | Benzothiazine derivatives | |
| Zinnes et al. | Alternate precursors in biogenetic-type synthesis. IV. Selective conversion of 2-alkyl-1-(indol-3-ylmethyl)-1, 2-dihydroisoquinolines to either 2-alkyl-3-(indol-3-ylmethyl)-3, 4-dihydroisoquinolinium salts or indolopavine derivatives | |
| US2762804A (en) | 3-methyl-5-phenyl-2, 6-piperazinedione and derivatives thereof and method of preparing same | |
| Marion et al. | The Synthesis of l-Roemerine1 | |
| JPS59176234A (ja) | ｐ‐ニトロフエニル３−ブロモ−２，２−ジエトキシ−プロピオネート | |
| Gensler et al. | Assay and methylation of 2-methyl-1, 2-dihydroisoquinoline | |
| FI63028C (fi) | Nytt foerfarande foer framstaellning av som laekemedel anvaenda n-(furyl-metyl)-bentsomorfaner | |
| US2924600A (en) | Certificate of correction | |
| ARMSTRONG | A PREPARATION OF L-CYSTATHIONINE AND L-ALLOCYSTATHIONINE1 |