GB1453606A - Method for synthesis of plus-minus-glaziovine - Google Patents
Method for synthesis of plus-minus-glaziovineInfo
- Publication number
- GB1453606A GB1453606A GB5720473A GB5720473A GB1453606A GB 1453606 A GB1453606 A GB 1453606A GB 5720473 A GB5720473 A GB 5720473A GB 5720473 A GB5720473 A GB 5720473A GB 1453606 A GB1453606 A GB 1453606A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- group
- glaziovine
- ester
- 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 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- OLMDPVRISKOBIT-UHFFFAOYSA-N N-methylcrotsparine Natural products COc1cc2CCN(C)C3c2c(CC34C=CC(=O)C=C4)c1O OLMDPVRISKOBIT-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- BOKVLBSSPUTWLV-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1h-isoquinolin-7-ol Chemical compound C1=2C=C(O)C(OC)=CC=2CCN(C)C1CC1=CC=C(O)C=C1 BOKVLBSSPUTWLV-UHFFFAOYSA-N 0.000 abstract 1
- 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
- DIVQKHQLANKJQO-UHFFFAOYSA-N 3-methoxytyramine Chemical compound COC1=CC(CCN)=CC=C1O DIVQKHQLANKJQO-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229940125713 antianxiety drug Drugs 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 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 abstract 1
- 229930004040 glaziovine Natural products 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000001035 methylating effect Effects 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
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 230000009935 nitrosation Effects 0.000 abstract 1
- 238000007034 nitrosation reaction Methods 0.000 abstract 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1878472A CH575930A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-12-22 | 1972-12-22 | |
| CH277473A CH618971A5 (en) | 1973-02-26 | 1973-02-26 | Process for the synthesis of (+)-glaziovine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1453606A true GB1453606A (en) | 1976-10-27 |
Family
ID=25691363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5720473A Expired GB1453606A (en) | 1972-12-22 | 1973-12-10 | Method for synthesis of plus-minus-glaziovine |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH19604A (en) * | 1982-06-04 | 1986-05-27 | Egyt Gyogyszervegyeszeti Gyar | Isoquinoline derivatives and pharmaceutical compositions containing the same |
| JPH0616066B2 (ja) * | 1986-09-26 | 1994-03-02 | 日立電線株式会社 | 電力ケ−ブルの絶縁欠陥検出方法 |
| US4956371A (en) * | 1989-09-19 | 1990-09-11 | Euroceltique, S.A. | Substituted isoquinolines and methods of using same |
| KR20140020829A (ko) * | 2010-10-13 | 2014-02-19 | 유니버시티 오브 윈저 | 고 알칼리성 도금 욕을 이용하는 금속의 무전해 증착 방법 |
| CN103214381A (zh) * | 2013-05-14 | 2013-07-24 | 张家港威胜生物医药有限公司 | 一种制备2-羟基-2-(4-甲氧基苯基)乙胺盐酸盐的方法 |
-
1973
- 1973-12-10 GB GB5720473A patent/GB1453606A/en not_active Expired
- 1973-12-19 US US426185A patent/US3886166A/en not_active Expired - Lifetime
- 1973-12-20 DE DE2363529A patent/DE2363529A1/de not_active Withdrawn
- 1973-12-20 AU AU63820/73A patent/AU6382073A/en not_active Expired
- 1973-12-21 HU HUSI1369A patent/HU168113B/hu unknown
- 1973-12-21 NL NL7317561A patent/NL7317561A/xx not_active Application Discontinuation
- 1973-12-21 FR FR7345943A patent/FR2211460B1/fr not_active Expired
- 1973-12-21 AR AR251662A patent/AR200040A1/es active
- 1973-12-22 JP JP744871A patent/JPS5233640B2/ja not_active Expired
- 1973-12-22 OA OA55087A patent/OA04654A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3886166A (en) | 1975-05-27 |
| AR200040A1 (es) | 1974-10-15 |
| NL7317561A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-25 |
| AU6382073A (en) | 1975-06-26 |
| JPS504078A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-16 |
| OA04654A (fr) | 1980-07-31 |
| JPS5233640B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-30 |
| DE2363529A1 (de) | 1974-06-27 |
| HU168113B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-02-28 |
| FR2211460B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-12 |
| FR2211460A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |