BE829821A - Acides 1,4-benzopyrone-6-carboxyliques mono- et disubstitues et leurs derives - Google Patents

Acides 1,4-benzopyrone-6-carboxyliques mono- et disubstitues et leurs derives

Info

Publication number: BE829821A
Authority: BE; Belgium
Prior art keywords: emi; formula; halogen atom; lower alkoxy; compounds
Prior art date: 1974-06-05

Application number

BE156989A

Other languages

English (en)

French (fr)

Priority date (The priority date 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 date listed.)

1974-06-05

Filing date

1975-06-03

Publication date

1975-12-03

1975-06-03 Application filed filed Critical

1975-12-03 Publication of BE829821A publication Critical patent/BE829821A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 14
231100000252 nontoxic Toxicity 0.000 claims description 12
230000003000 nontoxic effect Effects 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 8
206010006482 Bronchospasm Diseases 0.000 claims description 7
230000007885 bronchoconstriction Effects 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
230000005494 condensation Effects 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
229910000027 potassium carbonate Inorganic materials 0.000 claims 1
231100000167 toxic agent Toxicity 0.000 claims 1
239000003440 toxic substance Substances 0.000 claims 1
230000009466 transformation Effects 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 8
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
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230000005764 inhibitory process Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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239000002585 base Substances 0.000 description 3
239000000168 bronchodilator agent Substances 0.000 description 3
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150000002314 glycerols Chemical class 0.000 description 3
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239000000047 product Substances 0.000 description 3
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PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
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241000700198 Cavia Species 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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229920002472 Starch Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000007883 bronchodilation Effects 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
DUVJMSPTZMCSTQ-UHFFFAOYSA-N 2-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC=C1C=O DUVJMSPTZMCSTQ-UHFFFAOYSA-N 0.000 description 1
GEFDYGOYVXEKBE-UHFFFAOYSA-N 2-oxochromene-6-carboxylic acid Chemical compound O1C(=O)C=CC2=CC(C(=O)O)=CC=C21 GEFDYGOYVXEKBE-UHFFFAOYSA-N 0.000 description 1
SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
UWMYLUKUURIJON-UHFFFAOYSA-N 4-oxochromene-6-carboxylic acid Chemical class O1C=CC(=O)C2=CC(C(=O)O)=CC=C21 UWMYLUKUURIJON-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
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GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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235000019483 Peanut oil Nutrition 0.000 description 1
206010036790 Productive cough Diseases 0.000 description 1
208000037656 Respiratory Sounds Diseases 0.000 description 1
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241000212342 Sium Species 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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150000001266 acyl halides Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 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
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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239000002775 capsule Substances 0.000 description 1
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239000000460 chlorine Substances 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000011565 manganese chloride Substances 0.000 description 1
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238000005259 measurement Methods 0.000 description 1
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
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230000003647 oxidation Effects 0.000 description 1
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239000000312 peanut oil Substances 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
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239000002504 physiological saline solution Substances 0.000 description 1
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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239000000741 silica gel Substances 0.000 description 1
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RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE156989A 1974-06-05 1975-06-03 Acides 1,4-benzopyrone-6-carboxyliques mono- et disubstitues et leurs derives BE829821A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US47675174A	1974-06-05	1974-06-05

Publications (1)

Publication Number	Publication Date
BE829821A true BE829821A (fr)	1975-12-03

Family

ID=23893112

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE156989A BE829821A (fr)	1974-06-05	1975-06-03	Acides 1,4-benzopyrone-6-carboxyliques mono- et disubstitues et leurs derives

Country Status (4)

Country	Link
AT (1)	ATA426575A (de)
BE (1)	BE829821A (de)
SE (1)	SE7506391L (de)
ZA (1)	ZA753569B (de)

1975
- 1975-06-03 ZA ZA3569A patent/ZA753569B/xx unknown
- 1975-06-03 BE BE156989A patent/BE829821A/fr unknown
- 1975-06-04 AT AT426575A patent/ATA426575A/de not_active Application Discontinuation
- 1975-06-04 SE SE7506391A patent/SE7506391L/xx unknown

Also Published As

Publication number	Publication date
ZA753569B (en)	1977-01-26
ATA426575A (de)	1977-10-15
SE7506391L (sv)	1975-12-08

Publication	Publication Date	Title
CH618431A5 (de)	1980-07-31
MC1817A1 (fr)	1988-03-18	Derives de tetrahydronaphtalene
EP0022118A1 (de)	1981-01-07	Sulfonyl-anilin-Derivate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0010460B1 (de)	1982-01-27	Pyrrolidine-2-methanol-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
EP0037778A1 (de)	1981-10-14	2-(1,4-Benzodioxanyl)-methoxy-propanolamine, Verfahren zu deren Herstellung und Verwendung als Arzneimittel
EP0624575A1 (de)	1994-11-17	Substituierte Indole und diese enthaltende Arzneimittel
US4325974A (en)	1982-04-20	β, γ-Dihydropolyprenyl alcohol and hypotensive pharmaceutical composition containing same
US4699928A (en)	1987-10-13	Fluoroallylamine derivatives
CA1095520A (fr)	1981-02-10	Procede de preparation de nouveaux derives de 20,21- dinoreburnamenine
JPS6340784B2 (de)	1988-08-12
EP0038784A2 (de)	1981-10-28	3,8-Dialkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Zusammensetzungen
EP0364350B1 (de)	1994-01-12	4-Methyl-5[2-(4-phenyl-1-piperazinyl)-ethyl]-Thiazolderivate, ihre Herstellung und Zusammenstellungen, die sie enthalten
EP0063084B1 (de)	1984-09-12	Phenethanolamin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
MC1357A1 (fr)	1981-08-10	Derives de 2,3-indoledione
FR2480286A1 (fr)	1981-10-16	Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique
BE829821A (fr)	1975-12-03	Acides 1,4-benzopyrone-6-carboxyliques mono- et disubstitues et leurs derives
EP0143016B1 (de)	1987-07-29	Derivate von 4-(3-Alkynyloxy-2-hydroxy-propyl)-piperazin-1-yl-N-phenylacetamid, ihre Herstellung und ihre therapeutische Verwendung
CH658053A5 (fr)	1986-10-15	Derive de la pyrazolo (1,5-a) pyridine sa preparation et les compositions pharmaceutiques qui le contiennent.
EP0005091B1 (de)	1981-11-25	Monosubstituierte Piperazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
FR2559771A1 (fr)	1985-08-23	Derives de la 3-pyrrolidinopropiophenone et procede pour leur preparation
FR2518537A1 (fr)	1983-06-24	Nouveaux derives de l'acide phenylacetique, leur preparation et compositions les contenant
EP0067769A1 (de)	1982-12-22	1,2,3,4,4a,9b-Hexahydro-4a-piperazinylmethyl-4-dibenzofuranone oder substituierte 4-dibenzofuranole, Verfahren zu ihrer Herstellung und ihre Anwendung in der Heilkunde
EP0275221B1 (de)	1991-04-17	N-(1H-indol-4-yl)-Benzamidderivate, ihre Salze und deren Anwendung als Heilmittel und Zusammenstellungen, die sie enthalten
EP0120770A1 (de)	1984-10-03	2-Aminoethyl-Pyridin oder Pyrazin-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
FR2558160A1 (fr)	1985-07-19	3-alkoxy 2-(n-pyrrolidino)-n-pyrimidinyl ou -pyrazinyl propylamines, leur preparation et leur application en therapeutique