CA1126738A - Derives du phloroglucinol, leur procede de preparation et leur application en therapeutique - Google Patents
Derives du phloroglucinol, leur procede de preparation et leur application en therapeutiqueInfo
- Publication number
- CA1126738A CA1126738A CA312,144A CA312144A CA1126738A CA 1126738 A CA1126738 A CA 1126738A CA 312144 A CA312144 A CA 312144A CA 1126738 A CA1126738 A CA 1126738A
- Authority
- CA
- Canada
- Prior art keywords
- crl
- ketone
- pyrrolidino
- salts
- pyrrolidinopropyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 125000002444 phloroglucinyl group Chemical class [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 title 1
- 239000000047 product Substances 0.000 description 22
- ZDPACSAHMZADFZ-UHFFFAOYSA-N 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride Chemical compound [Cl-].COC1=CC(OC)=CC(OC)=C1C(=O)CCC[NH+]1CCCC1 ZDPACSAHMZADFZ-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- -1 2,4,6-trihydroxyphenyl Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- HQQAGNPSTHHDOI-UHFFFAOYSA-N 4-pyrrolidin-1-yl-1-(2,4,6-trihydroxyphenyl)butan-1-one;hydrochloride Chemical compound Cl.OC1=CC(O)=CC(O)=C1C(=O)CCCN1CCCC1 HQQAGNPSTHHDOI-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000810 peripheral vasodilating agent Substances 0.000 description 6
- 229960002116 peripheral vasodilator Drugs 0.000 description 6
- 229940124549 vasodilator Drugs 0.000 description 6
- 239000003071 vasodilator agent Substances 0.000 description 6
- FUYNGWCGSJHNDN-UHFFFAOYSA-N 1-(4-hydroxy-2,6-dimethoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one;hydrochloride Chemical compound Cl.COC1=CC(O)=CC(OC)=C1C(=O)CCCN1CCCC1 FUYNGWCGSJHNDN-UHFFFAOYSA-N 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- OSDDDHPYSNZBPF-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutanenitrile Chemical compound N#CCCCN1CCCC1 OSDDDHPYSNZBPF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 4
- 229960001553 phloroglucinol Drugs 0.000 description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229940095064 tartrate Drugs 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 206010011985 Decubitus ulcer Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000012322 Raynaud phenomenon Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YRVLYKYZPPSUBM-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical class N1(CCCC1)CCCC(=O)C1=C(C=CC=C1)O YRVLYKYZPPSUBM-UHFFFAOYSA-N 0.000 description 1
- BJYDDRCDAFUVNY-UHFFFAOYSA-N 2-chloro-5-methoxybenzene-1,3-diol Chemical compound ClC1=C(O)C=C(C=C1O)OC BJYDDRCDAFUVNY-UHFFFAOYSA-N 0.000 description 1
- XHGZCXPDKIEKNY-UHFFFAOYSA-N 2-chlorobenzene-1,3,5-triol Chemical compound OC1=CC(O)=C(Cl)C(O)=C1 XHGZCXPDKIEKNY-UHFFFAOYSA-N 0.000 description 1
- OWYLAEYXIQKAOL-UHFFFAOYSA-N 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCC1 OWYLAEYXIQKAOL-UHFFFAOYSA-N 0.000 description 1
- CFHYJXOWVPBOHR-UHFFFAOYSA-N 4-(diethylamino)-1-(2,4,6-trihydroxyphenyl)butan-1-one Chemical compound OC1=C(C(=CC(=C1)O)O)C(=O)CCCN(CC)CC CFHYJXOWVPBOHR-UHFFFAOYSA-N 0.000 description 1
- NUVVGLXJJPTXRJ-UHFFFAOYSA-N 4-(diethylamino)butanenitrile Chemical compound CCN(CC)CCCC#N NUVVGLXJJPTXRJ-UHFFFAOYSA-N 0.000 description 1
- FMHHCUBLAXNVHV-UHFFFAOYSA-N 4-chloro-3,5-dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1Cl FMHHCUBLAXNVHV-UHFFFAOYSA-N 0.000 description 1
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 101000941450 Lasioglossum laticeps Lasioglossin-1 Proteins 0.000 description 1
- 241000408529 Libra Species 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 241001538234 Nala Species 0.000 description 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical compound O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 208000004210 Pressure Ulcer Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229960001415 buflomedil Drugs 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- HDVRLUFGYQYLFJ-UHFFFAOYSA-N flamenol Chemical compound COC1=CC(O)=CC(O)=C1 HDVRLUFGYQYLFJ-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3998277 | 1977-09-26 | ||
| GB39982/77 | 1977-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126738A true CA1126738A (fr) | 1982-06-29 |
Family
ID=10412559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA312,144A Expired CA1126738A (fr) | 1977-09-26 | 1978-09-26 | Derives du phloroglucinol, leur procede de preparation et leur application en therapeutique |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5495562A (en)) |
| AU (1) | AU523963B2 (en)) |
| BE (1) | BE870717A (en)) |
| CA (1) | CA1126738A (en)) |
| CH (1) | CH633774A5 (en)) |
| DE (1) | DE2858813C2 (en)) |
| DK (1) | DK156395C (en)) |
| ES (1) | ES473689A1 (en)) |
| FR (1) | FR2404003A1 (en)) |
| IE (1) | IE47367B1 (en)) |
| IT (1) | IT1108172B (en)) |
| LU (1) | LU80277A1 (en)) |
| NL (1) | NL190720C (en)) |
| SE (1) | SE436277B (en)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4273776A (en) | 1980-01-30 | 1981-06-16 | E. R. Squibb & Sons, Inc. | Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones |
| FR2504136A1 (fr) * | 1981-04-15 | 1982-10-22 | Lafon Labor | (2,6-dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl)-cetone et ses sels d'addition, utilisation en therapeutique et procede de preparation |
| ES8706598A1 (es) * | 1985-04-11 | 1987-07-01 | Nippon Kayaku Kk | Un procedimiento para preparar nuevos derivados de aminocetona |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2092133B1 (en)) * | 1970-05-06 | 1974-03-22 | Orsymonde | |
| FR2134218A1 (en) * | 1971-04-27 | 1972-12-08 | Penciolelli Madeleine | Phloroglucinol aminoketones - vasodilators and antispasmodics |
-
1978
- 1978-09-14 FR FR7826464A patent/FR2404003A1/fr active Granted
- 1978-09-18 IE IE1883/78A patent/IE47367B1/en not_active IP Right Cessation
- 1978-09-21 SE SE7809916A patent/SE436277B/sv not_active IP Right Cessation
- 1978-09-21 DK DK419178A patent/DK156395C/da not_active IP Right Cessation
- 1978-09-25 CH CH997678A patent/CH633774A5/fr not_active IP Right Cessation
- 1978-09-25 BE BE2057301A patent/BE870717A/xx not_active IP Right Cessation
- 1978-09-25 IT IT69202/78A patent/IT1108172B/it active
- 1978-09-25 LU LU80277A patent/LU80277A1/xx unknown
- 1978-09-25 DE DE2858813A patent/DE2858813C2/de not_active Expired - Fee Related
- 1978-09-26 AU AU40195/78A patent/AU523963B2/en not_active Expired
- 1978-09-26 CA CA312,144A patent/CA1126738A/fr not_active Expired
- 1978-09-26 ES ES473689A patent/ES473689A1/es not_active Expired
- 1978-09-26 NL NL7809754A patent/NL190720C/xx not_active IP Right Cessation
- 1978-09-26 JP JP11756078A patent/JPS5495562A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7809754A (nl) | 1979-03-28 |
| AU4019578A (en) | 1980-04-03 |
| NL190720B (nl) | 1994-02-16 |
| FR2404003B1 (en)) | 1981-07-31 |
| IT7869202A0 (it) | 1978-09-25 |
| JPS5495562A (en) | 1979-07-28 |
| CH633774A5 (en) | 1982-12-31 |
| AU523963B2 (en) | 1982-08-26 |
| DK419178A (da) | 1979-03-27 |
| DK156395C (da) | 1990-01-08 |
| SE436277B (sv) | 1984-11-26 |
| IE47367B1 (en) | 1984-03-07 |
| ES473689A1 (es) | 1979-05-01 |
| BE870717A (fr) | 1979-03-26 |
| NL190720C (nl) | 1994-07-18 |
| SE7809916L (sv) | 1979-03-27 |
| IE781883L (en) | 1979-03-26 |
| LU80277A1 (fr) | 1979-06-01 |
| DE2858813C2 (en)) | 1993-07-01 |
| FR2404003A1 (fr) | 1979-04-20 |
| DK156395B (da) | 1989-08-14 |
| IT1108172B (it) | 1985-12-02 |
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