JPS6479176A - Intermediate of acromelic acid - Google Patents
Intermediate of acromelic acidInfo
- Publication number
- JPS6479176A JPS6479176A JP62167548A JP16754887A JPS6479176A JP S6479176 A JPS6479176 A JP S6479176A JP 62167548 A JP62167548 A JP 62167548A JP 16754887 A JP16754887 A JP 16754887A JP S6479176 A JPS6479176 A JP S6479176A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- react
- allowed
- 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.)
- Pending
Links
- CWXNEBSQRIECMV-UHFFFAOYSA-N Acromelic acid A Natural products OC(=O)CC1C(NCC1C1=CC=C(NC1=O)C(O)=O)C(O)=O CWXNEBSQRIECMV-UHFFFAOYSA-N 0.000 title abstract 2
- 229930183027 acromelic acid Natural products 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 abstract 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 abstract 1
- 229910015845 BBr3 Inorganic materials 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000002596 lactones Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000028161 membrane depolarization Effects 0.000 abstract 1
- 210000000653 nervous system Anatomy 0.000 abstract 1
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- -1 t-butoxycarbonyl Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
NEW MATERIAL:A compound of formula I (R is H, lower alkyl; R<1> is benzyl, t-butoxycarbonyl; R<2> is 1-3C alkyl, R<3> is alpha-hydrogen atom, beta-hydrogen atom). USE:An intermediate of acromelic acid and its relating compounds which has nervous system depolarization action and anthelmintic action, and can give the acid from easily available chemicals through reduced steps. PREPARATION:The compound of formula 5 is prepared from a compound of formula II through 4 steps, and allowed to react with BBr3 into a compound of formula 6. The product is treated with sodium hydroxide to open the lactone ring, then oxidized with NaIO4, CrO3 into carboxylic acid, and the acid is esterified with methanol and sulfuric acid into the compound of formula 7 in formula I. The compound of formula 7 is allowed to react with NaH and 1,8-diazabicyclo[5.4.0]-7-undecene into the compound of formula 8 in formula I. The compound of formula 7 can be directly synthesized from the compound of formula 5, too.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62167548A JPS6479176A (en) | 1987-02-25 | 1987-07-03 | Intermediate of acromelic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4348087 | 1987-02-25 | ||
| JP62167548A JPS6479176A (en) | 1987-02-25 | 1987-07-03 | Intermediate of acromelic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6479176A true JPS6479176A (en) | 1989-03-24 |
Family
ID=26383252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62167548A Pending JPS6479176A (en) | 1987-02-25 | 1987-07-03 | Intermediate of acromelic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6479176A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5341195A (en) * | 1991-08-23 | 1994-08-23 | Fuji Xerox Co., Ltd. | Electrophotographic printer using electroluminescent imaging head |
| WO2012074012A1 (en) * | 2010-11-30 | 2012-06-07 | 独立行政法人科学技術振興機構 | Nucleoside analog or salt thereof, oligonucleotide analog, gene expression inhibitor, and nucleic-acid probe for detecting gene |
-
1987
- 1987-07-03 JP JP62167548A patent/JPS6479176A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5341195A (en) * | 1991-08-23 | 1994-08-23 | Fuji Xerox Co., Ltd. | Electrophotographic printer using electroluminescent imaging head |
| WO2012074012A1 (en) * | 2010-11-30 | 2012-06-07 | 独立行政法人科学技術振興機構 | Nucleoside analog or salt thereof, oligonucleotide analog, gene expression inhibitor, and nucleic-acid probe for detecting gene |
| JP5199519B2 (en) * | 2010-11-30 | 2013-05-15 | 独立行政法人科学技術振興機構 | Nucleoside analogs or salts thereof, oligonucleotide analogs, gene expression inhibitors, and nucleic acid probes for gene detection |
| CN103237780A (en) * | 2010-11-30 | 2013-08-07 | 独立行政法人科学技术振兴机构 | Nucleoside analog or salt thereof, oligonucleotide analog, gene expression inhibitor, and nucleic-cid probe for detecting gene |
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