CH556354A - Verfahren zur herstellung von benzodioxan-derivaten. - Google Patents
Verfahren zur herstellung von benzodioxan-derivaten.Info
- Publication number
- CH556354A CH556354A CH164974A CH164974A CH556354A CH 556354 A CH556354 A CH 556354A CH 164974 A CH164974 A CH 164974A CH 164974 A CH164974 A CH 164974A CH 556354 A CH556354 A CH 556354A
- Authority
- CH
- Switzerland
- Prior art keywords
- ylmethyl
- benzodioxan
- preparation
- oxa
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 12
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title claims description 4
- -1 methylsulfonyloxy Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000000689 upper leg Anatomy 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YPLPUMJCHCMETL-UHFFFAOYSA-N (6-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC2=CC=C(C)C=C2OC1 YPLPUMJCHCMETL-UHFFFAOYSA-N 0.000 description 1
- DUMMLBFJPQGNSA-BTJKTKAUSA-N (z)-but-2-enedioic acid;decane Chemical compound OC(=O)\C=C/C(O)=O.CCCCCCCCCC DUMMLBFJPQGNSA-BTJKTKAUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SOGGTLCIHHUVEW-UHFFFAOYSA-N 1-oxa-4,8-diazaspiro[4.5]decane Chemical compound N1CCOC11CCNCC1 SOGGTLCIHHUVEW-UHFFFAOYSA-N 0.000 description 1
- 241001262617 Japonica Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45017513A JPS4920592B1 (enExample) | 1970-02-27 | 1970-02-27 | |
| JP45126833A JPS4946625B1 (enExample) | 1970-12-24 | 1970-12-24 | |
| JP45126834A JPS4946626B1 (enExample) | 1970-12-24 | 1970-12-24 | |
| JP45126832A JPS4946624B1 (enExample) | 1970-12-24 | 1970-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH556354A true CH556354A (de) | 1974-11-29 |
Family
ID=27456792
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH164974A CH556354A (de) | 1970-02-27 | 1971-02-26 | Verfahren zur herstellung von benzodioxan-derivaten. |
| CH283171A CH552615A (de) | 1970-02-27 | 1971-02-26 | Verfahren zur herstellung von benzodioxan-derivaten. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH283171A CH552615A (de) | 1970-02-27 | 1971-02-26 | Verfahren zur herstellung von benzodioxan-derivaten. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3720670A (enExample) |
| AT (1) | AT307419B (enExample) |
| CA (1) | CA952908A (enExample) |
| CH (2) | CH556354A (enExample) |
| DE (1) | DE2109333A1 (enExample) |
| FR (1) | FR2081550B1 (enExample) |
| GB (1) | GB1292787A (enExample) |
| SE (1) | SE366995B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3856797A (en) * | 1972-12-29 | 1974-12-24 | Yoshitomi Pharmaceutical | 8-aminoalkyl-3-oxo-1-thia-4,8-diazaspiro(4.5)decanes and analogs thereof |
| US4107139A (en) * | 1977-08-09 | 1978-08-15 | Hoechst Aktiengesellschaft | 1-Oxa-4,8-diazaspiro[4,5]decanes and polymers stabilized against UV light with these compounds |
| FR2420536A1 (fr) * | 1978-03-22 | 1979-10-19 | Roussel Uclaf | Nouveaux derives de 1,3-dihydro 3-/1-/2-(2,3-dihydro 1,4-benzodioxin-2-yl)2-hydroxyethyl/piperidin-4-yl/2h-indol-2-one, procede pour leur preparation et application comme medicaments |
| US4332804A (en) * | 1981-03-23 | 1982-06-01 | Syntex (U.S.A.) Inc. | 9-[2-(3-Indolyl)ethyl]-1oxa-4,9-diazaspiro[5.5]undecan-3-ones |
| US4349549A (en) * | 1981-05-18 | 1982-09-14 | Syntex (U.S.A.) Inc. | Anti-hypertensive 1-substituted spiro(piperidine-oxobenzoxazine)s |
| US4353901A (en) * | 1981-10-19 | 1982-10-12 | Syntex (U.S.A.) Inc. | 9-(1,4-Benzodioxan-2-ylalkyl and hydroxyalkyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-ones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1812768A1 (de) * | 1967-12-11 | 1969-07-03 | Yoshitomi Pharmaceutical | Neue Benzodioxanderivate |
| US3481942A (en) * | 1968-09-06 | 1969-12-02 | Smithkline Corp | Oxa-diazaspiro(4.5)decane compounds |
-
1971
- 1971-02-25 CA CA106,234A patent/CA952908A/en not_active Expired
- 1971-02-26 AT AT398172A patent/AT307419B/de not_active IP Right Cessation
- 1971-02-26 CH CH164974A patent/CH556354A/de not_active IP Right Cessation
- 1971-02-26 SE SE02494/71A patent/SE366995B/xx unknown
- 1971-02-26 DE DE19712109333 patent/DE2109333A1/de active Pending
- 1971-02-26 CH CH283171A patent/CH552615A/xx not_active IP Right Cessation
- 1971-02-26 FR FR7106771A patent/FR2081550B1/fr not_active Expired
- 1971-03-01 US US00119916A patent/US3720670A/en not_active Expired - Lifetime
- 1971-04-19 GB GB22985/71D patent/GB1292787A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2109333A1 (de) | 1971-09-09 |
| FR2081550B1 (enExample) | 1974-09-06 |
| CH552615A (de) | 1974-08-15 |
| SE366995B (enExample) | 1974-05-13 |
| AT307419B (de) | 1973-05-25 |
| US3720670A (en) | 1973-03-13 |
| FR2081550A1 (enExample) | 1971-12-03 |
| GB1292787A (en) | 1972-10-11 |
| CA952908A (en) | 1974-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH616676A5 (enExample) | ||
| CH556354A (de) | Verfahren zur herstellung von benzodioxan-derivaten. | |
| DE2726754A1 (de) | Substituierte (3-niedrigalkylamino- 2-acyl-0-propoxy)-pyridine, verfahren zu ihrer herstellung und ihre verwendung | |
| CH615151A5 (enExample) | ||
| CH616935A5 (en) | Process for the preparation of chromone derivatives | |
| DE68905363T2 (de) | Heterotetracyclische laktamderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten. | |
| DE2707135A1 (de) | Pyridoxinderivate, verfahren zu deren herstellung und dieselben enthaltendes mittel | |
| DE1038047B (de) | Verfahren zur Herstellung von N-aminoalkylierten Iminodibenzylen und deren Salzen | |
| DE2552868A1 (de) | 1,4-benzodioxane, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparate | |
| CH469736A (de) | Verfahren zur Herstellung von neuen Heterospiroalkanen | |
| DE2157299A1 (de) | Anthrachinonverbindungen, deren phar makologisch vertragliche Salze, Verfahren zu ihrer Herstellung und diese Verbindun gen enthaltende Arzneipraparate | |
| AT221495B (de) | Verfahren zur Herstellung von neuen Dibenzocycloheptanderivaten und deren Salzen bzw. quaternären Ammoniumverbindungen | |
| DE1795828A1 (de) | Adenosinderivate | |
| CH615181A5 (en) | Process for the preparation of novel ergolene derivatives | |
| AT276381B (de) | Verfahren zur Herstellung von neuen Phenylisoindolderivaten und deren Salzen | |
| AT361493B (de) | Verfahren zur herstellung von neuen 5,11- -dihydro-6h-pyrido(2,3-b)(1,4)-benzodiazepin-6- -on-derivaten und ihren salzen | |
| DE1595875C (de) | Phenothiazine und Verfahren zu deren Herstellung | |
| DE1470157C (de) | 2 Dimethylsulfat!^ 9 eckige Klammer auf 3 (4 methylpiperazino)-propyliden ecki ge Klammer zu thioxanthen, dessen eis/ trans Isomere, deren Salze und Verfahren zur Herstellung dieser Verbindungen | |
| AT358042B (de) | Verfahren zur herstellung neuer 1-amino-2- -hydroxy-3-heterocyclyloxy-propane und ihrer salze | |
| AT284133B (de) | Verfahren zur Herstellung eines neuen Thiepinderivates sowie seiner Säureadditionssalze | |
| AT265273B (de) | Verfahren zur Herstellung von neuen 2-Oxo-7-phenyl-1,2,3,4,6,7-hexahydro-11bH-benzo[a]-chinolizinen sowie von deren Säureadditions- und quartären Ammoniumsalzen | |
| AT294072B (de) | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen | |
| AT359072B (de) | Verfahren zur herstellung von neuen disubstituierten piperazinen sowie deren additionssalzen | |
| DE1445638C (de) | 9 geschweifte Klammer auf gamma eckige Klammer auf N* (beta hydroxyaryl) piperazino eckige Klammer zu propyl geschweifte Klam mer zu 9,10 dihydro 9,10 athano (1,2) anthra zen und seme Salze, Verfahren zu deren Her stellung und pharmazeutisches Mittel | |
| DE2039694B2 (de) | Imidazolidinonderivate, Verfahren zu ihrer Herstellung sowie Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |