DE2552868A1 - 1,4-benzodioxane, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
1,4-benzodioxane, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2552868A1 DE2552868A1 DE19752552868 DE2552868A DE2552868A1 DE 2552868 A1 DE2552868 A1 DE 2552868A1 DE 19752552868 DE19752552868 DE 19752552868 DE 2552868 A DE2552868 A DE 2552868A DE 2552868 A1 DE2552868 A1 DE 2552868A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- radical
- value
- compounds according
- piperidino
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- -1 alkyl radicals Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- 206010006482 Bronchospasm Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- FLTQFDOLIDLFQN-UHFFFAOYSA-N 1-(5-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)ethanone Chemical compound O1CCOC2=C(O)C(C(=O)C)=CC=C21 FLTQFDOLIDLFQN-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7533783A FR2330390A2 (fr) | 1975-11-05 | 1975-11-05 | Nouvelles benzodioxanes-1,4, leur procede de preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2552868A1 true DE2552868A1 (de) | 1977-05-18 |
Family
ID=9162052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752552868 Pending DE2552868A1 (de) | 1975-11-05 | 1975-11-25 | 1,4-benzodioxane, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (14)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2449088A1 (fr) * | 1979-02-14 | 1980-09-12 | Delalande Sa | Nouveaux derives du benzodioxanne portant en position 5 du noyau benzodioxanne un enchainement n-arylpiperazinopropyl (ou hydroxy-2 propyl) oxy, leurs procedes de preparation et leur application en therapeutique |
| FR2537970B1 (fr) * | 1982-12-15 | 1986-08-14 | Delalande Sa | Nouveaux derives aminoalkoxy aromatiques, leur procede de preparation et leur application en therapeutique |
| US6514996B2 (en) | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| EP0943613A4 (en) * | 1996-11-19 | 2002-07-10 | Kyowa Hakko Kogyo Kk | Oxygenic heterocyclic compounds |
-
1975
- 1975-11-05 FR FR7533783A patent/FR2330390A2/fr active Pending
- 1975-11-21 BE BE162085A patent/BE835828A/xx unknown
- 1975-11-24 CH CH1522575A patent/CH610322A5/xx not_active IP Right Cessation
- 1975-11-25 GB GB48302/75A patent/GB1486356A/en not_active Expired
- 1975-11-25 SE SE7513235A patent/SE7513235L/xx unknown
- 1975-11-25 DE DE19752552868 patent/DE2552868A1/de active Pending
- 1975-12-01 CA CA240,784A patent/CA1065321A/fr not_active Expired
- 1975-12-04 JP JP50144905A patent/JPS5259166A/ja active Pending
- 1975-12-04 LU LU73931A patent/LU73931A1/xx unknown
- 1975-12-05 AU AU87298/75A patent/AU499442B2/en not_active Expired
- 1975-12-10 NL NL7514416A patent/NL7514416A/xx not_active Application Discontinuation
- 1975-12-10 ES ES443357A patent/ES443357A1/es not_active Expired
- 1975-12-18 SU SU752199290A patent/SU586840A3/ru active
- 1975-12-31 IT IT70254/75A patent/IT1059875B/it active
-
1976
- 1976-01-08 JP JP51001832A patent/JPS5259167A/ja active Pending
- 1976-10-25 SU SU762414459A patent/SU645576A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5259167A (en) | 1977-05-16 |
| SE7513235L (sv) | 1977-05-06 |
| NL7514416A (nl) | 1977-05-09 |
| AU499442B2 (en) | 1979-04-12 |
| JPS5259166A (en) | 1977-05-16 |
| SU645576A3 (ru) | 1979-01-30 |
| BE835828A (fr) | 1976-05-21 |
| IT1059875B (it) | 1982-06-21 |
| SU586840A3 (ru) | 1977-12-30 |
| LU73931A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-11 |
| GB1486356A (en) | 1977-09-21 |
| CA1065321A (fr) | 1979-10-30 |
| CH610322A5 (en) | 1979-04-12 |
| FR2330390A2 (fr) | 1977-06-03 |
| ES443357A1 (es) | 1977-05-01 |
| AU8729875A (en) | 1977-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |