FR2482101A1 - 2-methanol a-aminomethyl benzo (1,4) dioxines, leur procede de preparation et leur application en therapeutique - Google Patents
2-methanol a-aminomethyl benzo (1,4) dioxines, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2482101A1 FR2482101A1 FR8010223A FR8010223A FR2482101A1 FR 2482101 A1 FR2482101 A1 FR 2482101A1 FR 8010223 A FR8010223 A FR 8010223A FR 8010223 A FR8010223 A FR 8010223A FR 2482101 A1 FR2482101 A1 FR 2482101A1
- Authority
- FR
- France
- Prior art keywords
- benzo
- group
- ether
- dioxin
- compound according
- 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
- 150000002013 dioxins Chemical class 0.000 title claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 MORPHOLINO, PIPERIDINO Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 4
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims description 2
- LWSWMTDGNKVQHL-UHFFFAOYSA-N 1-(1,4-benzodioxin-3-yl)-2-chloroethanone Chemical compound C1=CC=C2OC(C(=O)CCl)=COC2=C1 LWSWMTDGNKVQHL-UHFFFAOYSA-N 0.000 claims description 2
- 229940030600 antihypertensive agent Drugs 0.000 claims description 2
- 239000002220 antihypertensive agent Substances 0.000 claims description 2
- 230000008034 disappearance Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002785 azepinyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 5
- 108060003345 Adrenergic Receptor Proteins 0.000 description 5
- 102000017910 Adrenergic receptor Human genes 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000008485 antagonism Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- MFWHQHDMODQVBP-UHFFFAOYSA-N 1,4-benzodioxine-3-carbonyl chloride Chemical compound C1=CC=C2OC(C(=O)Cl)=COC2=C1 MFWHQHDMODQVBP-UHFFFAOYSA-N 0.000 description 3
- NLNGLCPAWPBRHX-UHFFFAOYSA-N 3-methyl-1,4-benzodioxine Chemical compound C1=CC=C2OC(C)=COC2=C1 NLNGLCPAWPBRHX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HREDEBSWJGLBSZ-UHFFFAOYSA-N ethyl 2,3-dibromo-2h-1,4-benzodioxine-3-carboxylate Chemical compound C1=CC=C2OC(Br)C(C(=O)OCC)(Br)OC2=C1 HREDEBSWJGLBSZ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229960001317 isoprenaline Drugs 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AODSQYZYAGVROA-UHFFFAOYSA-N 1,4-benzodioxin-3-ylmethanamine Chemical compound C1=CC=C2OC(CN)=COC2=C1 AODSQYZYAGVROA-UHFFFAOYSA-N 0.000 description 1
- IUIIXCRKXKRQTK-UHFFFAOYSA-N 1,4-benzodioxine-3-carbaldehyde Chemical compound C1=CC=C2OC(C=O)=COC2=C1 IUIIXCRKXKRQTK-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
- JTEZWBJJSGPYFM-UHFFFAOYSA-N 3-(chloromethyl)-1,4-benzodioxine Chemical compound ClCC1=COC2=C(O1)C=CC=C2 JTEZWBJJSGPYFM-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HYAIFRZTFJBMMC-UHFFFAOYSA-N ethyl 1,4-benzodioxine-3-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=COC2=C1 HYAIFRZTFJBMMC-UHFFFAOYSA-N 0.000 description 1
- DDIGEMWIKJMEIU-UHFFFAOYSA-N ethyl 2,3-dihydro-1,4-benzodioxine-3-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)COC2=C1 DDIGEMWIKJMEIU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 210000001177 vas deferen Anatomy 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
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8010223A FR2482101A1 (fr) | 1980-05-07 | 1980-05-07 | 2-methanol a-aminomethyl benzo (1,4) dioxines, leur procede de preparation et leur application en therapeutique |
| JP56501462A JPS57500510A (enExample) | 1980-05-07 | 1981-05-04 | |
| PCT/EP1981/000039 WO1981003172A1 (fr) | 1980-05-07 | 1981-05-04 | Nouvelles benzo(1,4)dioxines, leurs procedes de preparation et leur utilisation dans des compositions pharmaceutiques |
| AU70767/81A AU7076781A (en) | 1980-05-07 | 1981-05-04 | Novel benzo (1,4) dioxins, methods for their preparation and their use in pharmaceutical compositions |
| ZA00812948A ZA812948B (en) | 1980-05-07 | 1981-05-04 | Novel benzo(1,4)dioxins,methods for their preparation and their use in pharmaceutical compositions |
| FI813264A FI813264A7 (fi) | 1980-05-07 | 1981-05-04 | Uusia bentso(1,4)dioksiineja, menetelmä niiden valmistamiseksi ja niid en käyttö farmaseuttisissa koostumuksiss |
| IE810992A IE810992L (en) | 1980-05-07 | 1981-05-06 | Benzodioxines |
| EP81400710A EP0039646A1 (fr) | 1980-05-07 | 1981-05-06 | Nouvelles benzo (1,4) dioxines, leurs méthodes de préparation et leur application en thérapeutique |
| ES502003A ES502003A0 (es) | 1980-05-07 | 1981-05-07 | Un procedimiento para la preparacion de derivados de benzo (1,4) dioxina |
| DK417481A DK417481A (da) | 1980-05-07 | 1981-09-21 | Hidtil ukendte benzo (1,4) dioxiner fremgangsmaader til deres fremstilling og anvendelse i farmaceutiske midler |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8010223A FR2482101A1 (fr) | 1980-05-07 | 1980-05-07 | 2-methanol a-aminomethyl benzo (1,4) dioxines, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2482101A1 true FR2482101A1 (fr) | 1981-11-13 |
| FR2482101B1 FR2482101B1 (enExample) | 1983-05-27 |
Family
ID=9241732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8010223A Granted FR2482101A1 (fr) | 1980-05-07 | 1980-05-07 | 2-methanol a-aminomethyl benzo (1,4) dioxines, leur procede de preparation et leur application en therapeutique |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0039646A1 (enExample) |
| JP (1) | JPS57500510A (enExample) |
| DK (1) | DK417481A (enExample) |
| ES (1) | ES502003A0 (enExample) |
| FR (1) | FR2482101A1 (enExample) |
| IE (1) | IE810992L (enExample) |
| WO (1) | WO1981003172A1 (enExample) |
| ZA (1) | ZA812948B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367888A1 (en) * | 1988-11-08 | 1990-05-16 | ISTITUTO LUSO FARMACO D'ITALIA S.p.A. | 2,2-Disubstituted 2,3-dihydro-1,4-benzodioxin derivatives having hypotensive activity |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5522498A (en) * | 1996-12-13 | 1998-07-03 | Merck & Co., Inc. | Substituted aryl piperazines as modulators of chemokine receptor activity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3579M (fr) * | 1963-02-13 | 1965-10-04 | Ici Ltd | Nouveau médicament a base de dérivés de 1,4-benzodioxanne. |
| FR2213059A1 (enExample) * | 1973-01-04 | 1974-08-02 | Janssen Pharmaceutica Nv |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325633A1 (de) * | 1973-05-21 | 1974-12-12 | Boehringer Sohn Ingelheim | Piperazinderivate |
-
1980
- 1980-05-07 FR FR8010223A patent/FR2482101A1/fr active Granted
-
1981
- 1981-05-04 ZA ZA00812948A patent/ZA812948B/xx unknown
- 1981-05-04 WO PCT/EP1981/000039 patent/WO1981003172A1/de not_active Ceased
- 1981-05-04 JP JP56501462A patent/JPS57500510A/ja active Pending
- 1981-05-06 IE IE810992A patent/IE810992L/xx unknown
- 1981-05-06 EP EP81400710A patent/EP0039646A1/fr not_active Withdrawn
- 1981-05-07 ES ES502003A patent/ES502003A0/es active Granted
- 1981-09-21 DK DK417481A patent/DK417481A/da not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3579M (fr) * | 1963-02-13 | 1965-10-04 | Ici Ltd | Nouveau médicament a base de dérivés de 1,4-benzodioxanne. |
| FR2213059A1 (enExample) * | 1973-01-04 | 1974-08-02 | Janssen Pharmaceutica Nv |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367888A1 (en) * | 1988-11-08 | 1990-05-16 | ISTITUTO LUSO FARMACO D'ITALIA S.p.A. | 2,2-Disubstituted 2,3-dihydro-1,4-benzodioxin derivatives having hypotensive activity |
Also Published As
| Publication number | Publication date |
|---|---|
| DK417481A (da) | 1982-01-08 |
| JPS57500510A (enExample) | 1982-03-25 |
| ES8202811A1 (es) | 1982-03-01 |
| IE810992L (en) | 1981-11-07 |
| ZA812948B (en) | 1982-05-26 |
| WO1981003172A1 (fr) | 1981-11-12 |
| FR2482101B1 (enExample) | 1983-05-27 |
| ES502003A0 (es) | 1982-03-01 |
| EP0039646A1 (fr) | 1981-11-11 |
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