JPS6287568A - ２，６−ジメチル−４−（２−ジフルオロメトキシフエニル）−１，４−ジヒドロピリジン−３，５−ジカルボン酸のアルコキシおよびフエノキシ−アルキルエステル - Google Patents
２，６−ジメチル−４−（２−ジフルオロメトキシフエニル）−１，４−ジヒドロピリジン−３，５−ジカルボン酸のアルコキシおよびフエノキシ−アルキルエステルInfo
- Publication number
- JPS6287568A JPS6287568A JP22461085A JP22461085A JPS6287568A JP S6287568 A JPS6287568 A JP S6287568A JP 22461085 A JP22461085 A JP 22461085A JP 22461085 A JP22461085 A JP 22461085A JP S6287568 A JPS6287568 A JP S6287568A
- Authority
- JP
- Japan
- Prior art keywords
- dihydropyridine
- difluoromethoxyphenyl
- dimethyl
- compounds
- alkoxy
- 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
- 125000005359 phenoxyalkyl group Chemical group 0.000 title claims description 4
- 125000003545 alkoxy group Chemical group 0.000 title description 3
- DBRDRIVCVOXDHT-UHFFFAOYSA-N 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1OC(F)F DBRDRIVCVOXDHT-UHFFFAOYSA-N 0.000 title 1
- -1 (difluoromethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 9
- 230000000304 vasodilatating effect Effects 0.000 description 6
- 230000004872 arterial blood pressure Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000002211 ultraviolet spectrum Methods 0.000 description 5
- 229940099259 vaseline Drugs 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 208000001871 Tachycardia Diseases 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000006794 tachycardia Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000036581 peripheral resistance Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004873 systolic arterial blood pressure Effects 0.000 description 2
- UWKZAPXRQCPUDZ-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]-4h-pyridine Chemical compound FC(F)OC1=CC=CC=C1N1C=CCC=C1 UWKZAPXRQCPUDZ-UHFFFAOYSA-N 0.000 description 1
- QPBNHDFPMRENBC-UHFFFAOYSA-N 2-(difluoromethoxy)benzaldehyde Chemical compound FC(F)OC1=CC=CC=C1C=O QPBNHDFPMRENBC-UHFFFAOYSA-N 0.000 description 1
- JKUOURUUCRHADD-UHFFFAOYSA-N 2-ethoxyethyl 3-oxobutanoate Chemical compound CCOCCOC(=O)CC(C)=O JKUOURUUCRHADD-UHFFFAOYSA-N 0.000 description 1
- PLHCSZRZWOWUBW-UHFFFAOYSA-N 2-methoxyethyl 3-oxobutanoate Chemical compound COCCOC(=O)CC(C)=O PLHCSZRZWOWUBW-UHFFFAOYSA-N 0.000 description 1
- BBBJXPCSKOPGLI-UHFFFAOYSA-N 2-propoxyethyl 3-oxobutanoate Chemical compound CCCOCCOC(=O)CC(C)=O BBBJXPCSKOPGLI-UHFFFAOYSA-N 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 210000002385 vertebral artery Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22461085A JPS6287568A (ja) | 1985-10-08 | 1985-10-08 | ２，６−ジメチル−４−（２−ジフルオロメトキシフエニル）−１，４−ジヒドロピリジン−３，５−ジカルボン酸のアルコキシおよびフエノキシ−アルキルエステル |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22461085A JPS6287568A (ja) | 1985-10-08 | 1985-10-08 | ２，６−ジメチル−４−（２−ジフルオロメトキシフエニル）−１，４−ジヒドロピリジン−３，５−ジカルボン酸のアルコキシおよびフエノキシ−アルキルエステル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6287568A true JPS6287568A (ja) | 1987-04-22 |
| JPH0478630B2 JPH0478630B2 (enrdf_load_stackoverflow) | 1992-12-11 |
Family
ID=16816420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22461085A Granted JPS6287568A (ja) | 1985-10-08 | 1985-10-08 | ２，６−ジメチル−４−（２−ジフルオロメトキシフエニル）−１，４−ジヒドロピリジン−３，５−ジカルボン酸のアルコキシおよびフエノキシ−アルキルエステル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6287568A (enrdf_load_stackoverflow) |
-
1985
- 1985-10-08 JP JP22461085A patent/JPS6287568A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0478630B2 (enrdf_load_stackoverflow) | 1992-12-11 |
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