GB1459210A - Method for the synthesis of plus-minus-glaziovine - Google Patents
Method for the synthesis of plus-minus-glaziovineInfo
- Publication number
- GB1459210A GB1459210A GB5866273A GB5866273A GB1459210A GB 1459210 A GB1459210 A GB 1459210A GB 5866273 A GB5866273 A GB 5866273A GB 5866273 A GB5866273 A GB 5866273A GB 1459210 A GB1459210 A GB 1459210A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- glaziovine
- ylide
- group
- dihydroglaziovine
- 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
- 229950005847 glaziovine Drugs 0.000 title abstract 5
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- OLMDPVRISKOBIT-UHFFFAOYSA-N N-methylcrotsparine Natural products COc1cc2CCN(C)C3c2c(CC34C=CC(=O)C=C4)c1O OLMDPVRISKOBIT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002084 enol ethers Chemical class 0.000 abstract 2
- 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 abstract 2
- 229930004040 glaziovine Natural products 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- -1 6,7-dimethoxy-2-methyl- 1,2,3,4 - tetrahydroisoquinolinyl Chemical group 0.000 abstract 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007239 Wittig reaction Methods 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 230000000049 anti-anxiety effect Effects 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 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
-
- 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
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1878372A CH588467A5 (enrdf_load_stackoverflow) | 1972-12-22 | 1972-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1459210A true GB1459210A (en) | 1976-12-22 |
Family
ID=4435260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5866273A Expired GB1459210A (en) | 1972-12-22 | 1973-12-18 | Method for the synthesis of plus-minus-glaziovine |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS539224B2 (enrdf_load_stackoverflow) |
| CH (1) | CH588467A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2363531A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2211459A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1459210A (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5885395U (ja) * | 1981-12-02 | 1983-06-09 | 三菱電線工業株式会社 | 遮「へい」体 |
| JPS593999A (ja) * | 1982-06-29 | 1984-01-10 | 日本電気株式会社 | ケ−ブル用シ−ルドカバ− |
| US4639545A (en) * | 1984-02-07 | 1987-01-27 | Raychem Limited | Recoverable article for screening |
| JPS63115297U (enrdf_load_stackoverflow) * | 1987-01-21 | 1988-07-25 | ||
| JPH0720955Y2 (ja) * | 1987-05-28 | 1995-05-15 | 横河・ヒユーレツト・パツカード株式会社 | フレキシブルシ−ルドチユ−ブ |
| JPH0215798U (enrdf_load_stackoverflow) * | 1988-07-15 | 1990-01-31 | ||
| JPH0320495U (enrdf_load_stackoverflow) * | 1989-07-10 | 1991-02-28 | ||
| JPH0443821U (enrdf_load_stackoverflow) * | 1990-08-17 | 1992-04-14 |
-
1972
- 1972-12-22 CH CH1878372A patent/CH588467A5/xx not_active IP Right Cessation
-
1973
- 1973-12-18 GB GB5866273A patent/GB1459210A/en not_active Expired
- 1973-12-20 DE DE19732363531 patent/DE2363531A1/de active Pending
- 1973-12-21 FR FR7345941A patent/FR2211459A1/fr not_active Withdrawn
- 1973-12-22 JP JP487374A patent/JPS539224B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH588467A5 (enrdf_load_stackoverflow) | 1977-06-15 |
| FR2211459A1 (enrdf_load_stackoverflow) | 1974-07-19 |
| DE2363531A1 (de) | 1974-06-27 |
| JPS539224B2 (enrdf_load_stackoverflow) | 1978-04-04 |
| JPS504080A (enrdf_load_stackoverflow) | 1975-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |