IE47367B1 - New phloroglucinol derivatives,their method of preparation and their use as pharmaceuticals - Google Patents
New phloroglucinol derivatives,their method of preparation and their use as pharmaceuticalsInfo
- Publication number
- IE47367B1 IE47367B1 IE1883/78A IE188378A IE47367B1 IE 47367 B1 IE47367 B1 IE 47367B1 IE 1883/78 A IE1883/78 A IE 1883/78A IE 188378 A IE188378 A IE 188378A IE 47367 B1 IE47367 B1 IE 47367B1
- Authority
- IE
- Ireland
- Prior art keywords
- crl
- pyrrolidinopropyl
- ketone
- salts
- pyrrolidino
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000002444 phloroglucinyl group Chemical class [H]OC1=C([H])C(O[H])=C(*)C(O[H])=C1[H] 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 8
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 7
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 7
- 150000003000 phloroglucinols Chemical class 0.000 claims description 6
- OSDDDHPYSNZBPF-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutanenitrile Chemical compound N#CCCCN1CCCC1 OSDDDHPYSNZBPF-UHFFFAOYSA-N 0.000 claims description 5
- 230000024883 vasodilation Effects 0.000 claims description 5
- BAWROKQOTBLQSB-UHFFFAOYSA-N 4-pyrrolidin-1-yl-1-(2,4,6-trihydroxyphenyl)butan-1-one Chemical compound OC1=CC(O)=CC(O)=C1C(=O)CCCN1CCCC1 BAWROKQOTBLQSB-UHFFFAOYSA-N 0.000 claims description 3
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000810 peripheral vasodilating agent Substances 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 23
- 230000000694 effects Effects 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 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 12
- 239000003071 vasodilator agent Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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 7
- 239000000203 mixture Substances 0.000 description 7
- 229960002116 peripheral vasodilator Drugs 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
- 241001465754 Metazoa Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000282472 Canis lupus familiaris Species 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 230000004872 arterial blood pressure Effects 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229940095064 tartrate Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229960004132 diethyl ether Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 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
- 238000011282 treatment Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- -1 (2,4-dimethoxy-6-hydroxy5 phenyl)-(3-pyrrolidino-propyl)-ketone Chemical compound 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002585 base Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 3
- 229960001553 phloroglucinol Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229940124549 vasodilator Drugs 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- RCUKXZJPJKYJEL-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(O)=C1C(=O)CCCN1CCCC1 RCUKXZJPJKYJEL-UHFFFAOYSA-N 0.000 description 2
- XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 208000004210 Pressure Ulcer Diseases 0.000 description 2
- 208000003782 Raynaud disease Diseases 0.000 description 2
- 208000012322 Raynaud phenomenon Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- VDDWLCYXYJTMJF-UHFFFAOYSA-N 1-(2,6-dihydroxy-4-methoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical compound COC1=CC(O)=C(C(=O)CCCN2CCCC2)C(O)=C1 VDDWLCYXYJTMJF-UHFFFAOYSA-N 0.000 description 1
- CSRSHQICCMIBML-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCCN1CCCC1 CSRSHQICCMIBML-UHFFFAOYSA-N 0.000 description 1
- 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
- NUVVGLXJJPTXRJ-UHFFFAOYSA-N 4-(diethylamino)butanenitrile Chemical compound CCN(CC)CCCC#N NUVVGLXJJPTXRJ-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- DCGGGRHMMWQNJI-UHFFFAOYSA-N Cl.OC1=C(C(=CC(=C1)O)O)C(=O)CCCN(CC)CC Chemical compound Cl.OC1=C(C(=CC(=C1)O)O)C(=O)CCCN(CC)CC DCGGGRHMMWQNJI-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 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
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 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
- 150000004658 ketimines Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3998277 | 1977-09-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE781883L IE781883L (en) | 1979-03-26 |
| IE47367B1 true IE47367B1 (en) | 1984-03-07 |
Family
ID=10412559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1883/78A IE47367B1 (en) | 1977-09-26 | 1978-09-18 | New phloroglucinol derivatives,their method of preparation and their use as pharmaceuticals |
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 |
| CA1126738A (fr) | 1982-06-29 |
| DK156395C (da) | 1990-01-08 |
| SE436277B (sv) | 1984-11-26 |
| 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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