JPS54145650A - Novel tricyclic cage-like amine compound - Google Patents
Novel tricyclic cage-like amine compoundInfo
- Publication number
- JPS54145650A JPS54145650A JP4438678A JP4438678A JPS54145650A JP S54145650 A JPS54145650 A JP S54145650A JP 4438678 A JP4438678 A JP 4438678A JP 4438678 A JP4438678 A JP 4438678A JP S54145650 A JPS54145650 A JP S54145650A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- give
- reacted
- amine compound
- 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.)
- Granted
Links
- -1 amine compound Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- BQHDXNZNSPVVKB-UHFFFAOYSA-N diethyl 2-methylidenepropanedioate Chemical compound CCOC(=O)C(=C)C(=O)OCC BQHDXNZNSPVVKB-UHFFFAOYSA-N 0.000 abstract 1
- VCDYGFUYBTURLC-UHFFFAOYSA-N diethyl bicyclo[2.2.2]oct-2-ene-5,5-dicarboxylate Chemical compound C1CC2C(C(=O)OCC)(C(=O)OCC)CC1C=C2 VCDYGFUYBTURLC-UHFFFAOYSA-N 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 206010022000 influenza Diseases 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000012046 mixed solvent Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Epoxy Compounds (AREA)
Abstract
NEW MATERIAL:A tricyclic cage-like amino compound of formula I: (l is 0 or 1; m and n are 1 or 2) and its acid addition salt.
EXAMPLE: 2,2-Diethoxycarbonyl bicyclo [2.2.2] oct-5-ene.
USE: Medicines having antivirial actions against influenza virases, etc.
PROCESS: cyclopentadiene or cyclohexadiene of formula II is subjected to the Diels- Alder reaction with diethyl methylenemalonate to give a compound of formula IV, which is hydrolyzed with NaOH in a mixed solvent of water, methanol, and tetra- hydrofuran. The hydrolysis product is then converted to an iodolactone, which is changed into an acid chloride. The chloride is reacted with Na3N to form an acid azide, which is reacted with ethanol to give a compound of formula V. The compound of formula V is reduced with tri-n-butyltin hydride, and etherified. The ether is hydrolyzed under heat refluxing to give the compound of formula I wherein l is 0.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4438678A JPS5919545B2 (en) | 1978-04-14 | 1978-04-14 | New tricyclic cage-shaped amine compound |
| ES479572A ES479572A1 (en) | 1978-04-14 | 1979-04-11 | A PROCEDURE FOR THE PREPARATION OF NEW CAGE TRICYCLIC DERIVATIVES. |
| DK155079A DK155079A (en) | 1978-04-14 | 1979-04-11 | PROCEDURE FOR MAKING TRICYCLIC BRIDGE CONNECTIONS |
| HU79SU1013A HU182048B (en) | 1978-04-14 | 1979-04-11 | Process for preparing brendane derivatives and brendane analogues |
| EP79300617A EP0006283B1 (en) | 1978-04-14 | 1979-04-12 | Heterotricyclic compounds, processes for their production and pharmaceutical compositions containing them |
| DE7979300617T DE2964590D1 (en) | 1978-04-14 | 1979-04-12 | Heterotricyclic compounds, processes for their production and pharmaceutical compositions containing them |
| DD79212199A DD142880A5 (en) | 1978-04-14 | 1979-04-12 | METHOD FOR PRODUCING HETEROTRICYCLIC CHICKEN COMPOUNDS |
| AT0278279A AT370099B (en) | 1978-04-14 | 1979-04-13 | METHOD FOR PRODUCING NEW TRICYCLIC COMPOUNDS AND THEIR SALTS |
| CA000325626A CA1169430A (en) | 1978-04-14 | 1979-04-17 | Tricyclic cage compounds, and their production and use |
| AU46120/79A AU527245B2 (en) | 1978-04-14 | 1979-04-17 | Tricyclic cage compounds |
| ES487562A ES487562A0 (en) | 1978-04-14 | 1980-01-09 | A PROCEDURE FOR THE PREPARATION OF NEW TRICYCLIC DERIVATIVES CAGE. (AS DIVISIONAL OF PATENT NUMBER 479.572) |
| ES487566A ES487566A0 (en) | 1978-04-14 | 1980-01-09 | A PROCEDURE FOR THE PREPARATION OF NEW TRICYCLIC DERIVATIVES CAGE. (AS DIVISIONAL OF PATENT NUMBER 479.572) |
| ES487565A ES8100292A1 (en) | 1978-04-14 | 1980-01-09 | A PROCEDURE FOR THE PREPARATION OF NEW TRICYCLIC DERIVATIVES CAGE. (AS DIVISIONAL OF PATENT NUMBER 479.572) |
| ES487563A ES487563A0 (en) | 1978-04-14 | 1980-01-09 | A PROCEDURE FOR THE PREPARATION OF NEW TRICYCLIC DERIVATIVES CAGE. (AS DIVISIONAL OF PATENT NUMBER 479.572) |
| ES487564A ES8100291A1 (en) | 1978-04-14 | 1980-01-09 | A PROCEDURE FOR THE PREPARATION OF NEW TRICYCLIC DERIVATIVES CAGE. (AS DIVISIONAL OF PATENT NUMBER 479.572) |
| SU802932252A SU957767A3 (en) | 1978-04-14 | 1980-06-11 | Process for producing tricyclic compounds |
| SU802942903A SU991949A3 (en) | 1978-04-14 | 1980-07-01 | Process for preparing tricyclic compounds |
| US06/171,109 US4347254A (en) | 1978-04-14 | 1980-07-22 | Tricyclic cage compounds, their synthesis and use as antiviral agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4438678A JPS5919545B2 (en) | 1978-04-14 | 1978-04-14 | New tricyclic cage-shaped amine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54145650A true JPS54145650A (en) | 1979-11-14 |
| JPS5919545B2 JPS5919545B2 (en) | 1984-05-07 |
Family
ID=12690059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4438678A Expired JPS5919545B2 (en) | 1978-04-14 | 1978-04-14 | New tricyclic cage-shaped amine compound |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5919545B2 (en) |
| ES (1) | ES8100292A1 (en) |
| SU (1) | SU957767A3 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009209114A (en) * | 2008-03-06 | 2009-09-17 | Tosoh Corp | Method for producing alicyclic diamine |
| US7674499B2 (en) | 2004-12-15 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing novel aspartic amine compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62188454U (en) * | 1986-05-22 | 1987-12-01 | ||
| JPS63177260U (en) * | 1987-05-07 | 1988-11-16 |
-
1978
- 1978-04-14 JP JP4438678A patent/JPS5919545B2/en not_active Expired
-
1980
- 1980-01-09 ES ES487565A patent/ES8100292A1/en not_active Expired
- 1980-06-11 SU SU802932252A patent/SU957767A3/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7674499B2 (en) | 2004-12-15 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing novel aspartic amine compounds |
| JP2009209114A (en) * | 2008-03-06 | 2009-09-17 | Tosoh Corp | Method for producing alicyclic diamine |
Also Published As
| Publication number | Publication date |
|---|---|
| ES487565A0 (en) | 1980-11-01 |
| ES8100292A1 (en) | 1980-11-01 |
| SU957767A3 (en) | 1982-09-07 |
| JPS5919545B2 (en) | 1984-05-07 |
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