JPS5519225A - 1-dithienylmethyleneindolizidine derivative - Google Patents
1-dithienylmethyleneindolizidine derivativeInfo
- Publication number
- JPS5519225A JPS5519225A JP9145078A JP9145078A JPS5519225A JP S5519225 A JPS5519225 A JP S5519225A JP 9145078 A JP9145078 A JP 9145078A JP 9145078 A JP9145078 A JP 9145078A JP S5519225 A JPS5519225 A JP S5519225A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- methanol
- ammonium salt
- 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 1-dithienylmethyleneindolizidine derivative Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 230000000767 anti-ulcer Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- HAJKHJOABGFIGP-UHFFFAOYSA-N indolizidine Chemical compound C1CCCN2CCCC21 HAJKHJOABGFIGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:1-(Dithien-2-ylmethylene)indolizidine of formula I, its acid adduct and its quarternary ammonium salt.
USE: Spasmolytic and antiulcerative agent having antihistaminic and antiacetylcholine activities.
PREPARATION: A novel compound, α,α-dithienylindolizidine-1-methanol of formula II, is dehydrated with hydrochloric acid, phosphorus oxychloride, sulfuric acid, or p-toluenesulfonic acid in a solvent as water, ethanol, methanol, benzene, toluene to give readily the objective compound of formula I. When necessary, a compound of the formula: R-X (R is lower alkyl; X is acid residue) is made to act on the product to give the quaternary ammonium salt. The compound of formula II is obtained by reaction between a compound of formula IV and another compound of formula V.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9145078A JPS5519225A (en) | 1978-07-28 | 1978-07-28 | 1-dithienylmethyleneindolizidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9145078A JPS5519225A (en) | 1978-07-28 | 1978-07-28 | 1-dithienylmethyleneindolizidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5519225A true JPS5519225A (en) | 1980-02-09 |
| JPS5638156B2 JPS5638156B2 (en) | 1981-09-04 |
Family
ID=14026692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9145078A Granted JPS5519225A (en) | 1978-07-28 | 1978-07-28 | 1-dithienylmethyleneindolizidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5519225A (en) |
-
1978
- 1978-07-28 JP JP9145078A patent/JPS5519225A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5638156B2 (en) | 1981-09-04 |
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