GB1451377A - Method for the synthesis of plus-minus glaziovine - Google Patents
Method for the synthesis of plus-minus glaziovineInfo
- Publication number
- GB1451377A GB1451377A GB5720573A GB5720573A GB1451377A GB 1451377 A GB1451377 A GB 1451377A GB 5720573 A GB5720573 A GB 5720573A GB 5720573 A GB5720573 A GB 5720573A GB 1451377 A GB1451377 A GB 1451377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- hydroxy
- glaziovine
- synthesis
- yield
- 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
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 229950005847 glaziovine Drugs 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- OLMDPVRISKOBIT-UHFFFAOYSA-N N-methylcrotsparine Natural products COc1cc2CCN(C)C3c2c(CC34C=CC(=O)C=C4)c1O OLMDPVRISKOBIT-UHFFFAOYSA-N 0.000 title 1
- PNJUPRNTSWJWAX-ZDUSSCGKSA-N glaziovine Chemical compound C([C@@H]1N(C)CCC=2C=C(C(=C3C=21)O)OC)C13C=CC(=O)C=C1 PNJUPRNTSWJWAX-ZDUSSCGKSA-N 0.000 title 1
- 229930004040 glaziovine Natural products 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- DIVQKHQLANKJQO-UHFFFAOYSA-N 3-methoxytyramine Chemical compound COC1=CC(CCN)=CC=C1O DIVQKHQLANKJQO-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- XJHGAJLIKDAOPE-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1 XJHGAJLIKDAOPE-UHFFFAOYSA-N 0.000 abstract 1
- AKAVYGZMOWPRHS-UHFFFAOYSA-N 6-methoxy-1-[(4-phenylmethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-7-ol Chemical compound C1=2C=C(O)C(OC)=CC=2CCNC1CC(C=C1)=CC=C1OCC1=CC=CC=C1 AKAVYGZMOWPRHS-UHFFFAOYSA-N 0.000 abstract 1
- PMOLYQFOCHANML-UHFFFAOYSA-N 6-methoxy-1-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydroisoquinolin-7-ol Chemical compound C(C1=CC=CC=C1)OC1=CC=C(CC2=NCCC3=CC(=C(C=C23)O)OC)C=C1 PMOLYQFOCHANML-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000049 anti-anxiety effect Effects 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- NEYHHNWLRYDUCA-UHFFFAOYSA-N n-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2-(4-phenylmethoxyphenyl)acetamide Chemical compound C1=C(O)C(OC)=CC(CCNC(=O)CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 NEYHHNWLRYDUCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1878472A CH575930A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-12-22 | 1972-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1451377A true GB1451377A (en) | 1976-09-29 |
Family
ID=4435263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5720573A Expired GB1451377A (en) | 1972-12-22 | 1973-12-10 | Method for the synthesis of plus-minus glaziovine |
Country Status (8)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2577216B2 (ja) * | 1987-01-16 | 1997-01-29 | 化研生薬株式会社 | ベンジルイソキノリン誘導体 |
| JPH0424277A (ja) * | 1990-05-18 | 1992-01-28 | Hirano Tecseed Co Ltd | 布目矯正ローラ |
-
1972
- 1972-12-22 CH CH1878472A patent/CH575930A5/xx not_active IP Right Cessation
-
1973
- 1973-12-10 GB GB5720573A patent/GB1451377A/en not_active Expired
- 1973-12-18 BE BE138998A patent/BE808781A/xx unknown
- 1973-12-18 ZA ZA739528A patent/ZA739528B/xx unknown
- 1973-12-20 DE DE2363530A patent/DE2363530A1/de active Pending
- 1973-12-21 FR FR7345942A patent/FR2211433A1/fr not_active Withdrawn
- 1973-12-22 JP JP744872A patent/JPS5310985B2/ja not_active Expired
- 1973-12-22 ES ES421744A patent/ES421744A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS504079A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-16 |
| BE808781A (fr) | 1974-04-16 |
| ZA739528B (en) | 1974-11-27 |
| DE2363530A1 (de) | 1974-06-27 |
| JPS5310985B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-18 |
| ES421744A1 (es) | 1976-04-16 |
| CH575930A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-31 |
| FR2211433A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |