IE52871B1 - (2,6-dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl)-ketone and its acid addition salts, use thereof in therapeutics and method for preparing same - Google Patents
(2,6-dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl)-ketone and its acid addition salts, use thereof in therapeutics and method for preparing sameInfo
- Publication number
- IE52871B1 IE52871B1 IE742/82A IE74282A IE52871B1 IE 52871 B1 IE52871 B1 IE 52871B1 IE 742/82 A IE742/82 A IE 742/82A IE 74282 A IE74282 A IE 74282A IE 52871 B1 IE52871 B1 IE 52871B1
- Authority
- IE
- Ireland
- Prior art keywords
- ketone
- dimethoxy
- piperidinopropyl
- hydroxyphenyl
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 15
- MVDBGZOSRSXNHU-UHFFFAOYSA-N 1-(4-hydroxy-2,6-dimethoxyphenyl)-4-piperidin-1-ylbutan-1-one Chemical compound COC1=CC(O)=CC(OC)=C1C(=O)CCCN1CCCCC1 MVDBGZOSRSXNHU-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 3
- 239000012429 reaction media Substances 0.000 claims abstract description 6
- ZNDKGZTXFLTQKE-UHFFFAOYSA-N 2-piperidin-1-ylbutanenitrile Chemical compound CCC(C#N)N1CCCCC1 ZNDKGZTXFLTQKE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000004658 ketimines Chemical class 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 239000000810 peripheral vasodilating agent Substances 0.000 claims description 10
- 229960002116 peripheral vasodilator Drugs 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- -1 2,6-dimethoxy-4-hydroxyphenyl Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UYCYOYFXVACSII-UHFFFAOYSA-N 1,7-di(piperidin-1-yl)heptan-4-one Chemical compound C1CCCCN1CCCC(=O)CCCN1CCCCC1 UYCYOYFXVACSII-UHFFFAOYSA-N 0.000 claims 1
- WKUHFAPIBUQVHU-UHFFFAOYSA-N 1-(4-hydroxy-2,6-dimethoxyphenyl)-4-piperidin-1-ylbutan-1-one;hydrochloride Chemical compound Cl.COC1=CC(O)=CC(OC)=C1C(=O)CCCN1CCCCC1 WKUHFAPIBUQVHU-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 4
- XQDNFAMOIPNVES-UHFFFAOYSA-N 3,5-Dimethoxyphenol Chemical compound COC1=CC(O)=CC(OC)=C1 XQDNFAMOIPNVES-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 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 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 5
- 230000004872 arterial blood pressure Effects 0.000 description 5
- 210000001105 femoral artery Anatomy 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010051814 Eschar Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 231100000333 eschar Toxicity 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- LXWYSZYNUKJMSC-UHFFFAOYSA-N 1,7-dipyrrolidin-1-yl-1,7-bis(2,4,6-trihydroxyphenyl)heptan-4-one Chemical compound OC1=C(C(=CC(=C1)O)O)C(CCC(=O)CCC(C1=C(C=C(C=C1O)O)O)N1CCCC1)N1CCCC1 LXWYSZYNUKJMSC-UHFFFAOYSA-N 0.000 description 1
- XZICCHYGIANPTF-UHFFFAOYSA-N 1-(2,4-dihydroxy-6-methoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical class COC1=CC(O)=CC(O)=C1C(=O)CCCN1CCCC1 XZICCHYGIANPTF-UHFFFAOYSA-N 0.000 description 1
- KBESRIYQCAEQGK-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-2-piperidin-1-ylethanone Chemical compound COC1=CC(OC)=CC=C1C(=O)CN1CCCCC1 KBESRIYQCAEQGK-UHFFFAOYSA-N 0.000 description 1
- IERUXOQELMHKNO-UHFFFAOYSA-N 1-(2-hydroxy-4,6-dimethoxyphenyl)-4-piperidin-1-ylbutan-1-one Chemical compound COC1=CC(OC)=CC(O)=C1C(=O)CCCN1CCCCC1 IERUXOQELMHKNO-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
- BJXQAMLBAONSIX-UHFFFAOYSA-N 1-(4-hydroxy-2,6-dimethoxyphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical class COC1=CC(O)=CC(OC)=C1C(=O)CCCN1CCCC1 BJXQAMLBAONSIX-UHFFFAOYSA-N 0.000 description 1
- YYQLYLIMEUROLG-UHFFFAOYSA-N 3-piperidin-1-yl-1-(2,4,6-trimethoxyphenyl)propan-1-one Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)CCN1CCCCC1 YYQLYLIMEUROLG-UHFFFAOYSA-N 0.000 description 1
- NNCONKQAAJWZFZ-UHFFFAOYSA-N 4-piperidin-1-yl-1-(2,4,6-trihydroxyphenyl)butan-1-one Chemical compound Oc1cc(O)c(C(=O)CCCN2CCCCC2)c(O)c1 NNCONKQAAJWZFZ-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010038419 Renal colic Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000146 antalgic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002585 base Substances 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
- 229960001415 buflomedil Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 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
- 230000010412 perfusion Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000024883 vasodilation 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8107597A FR2504136A1 (fr) | 1981-04-15 | 1981-04-15 | (2,6-dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl)-cetone et ses sels d'addition, utilisation en therapeutique et procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820742L IE820742L (en) | 1982-10-15 |
| IE52871B1 true IE52871B1 (en) | 1988-03-30 |
Family
ID=9257449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE742/82A IE52871B1 (en) | 1981-04-15 | 1982-03-29 | (2,6-dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl)-ketone and its acid addition salts, use thereof in therapeutics and method for preparing same |
Country Status (10)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534912B1 (fr) * | 1982-10-26 | 1985-06-28 | Lafon Labor | Nouveaux derives de (2,4,6-trimethoxyphenyl) - (3-piperidinopropyl) -cetone, utilisation en therapeutique et procede de preparation |
| FR2597864B1 (fr) * | 1986-04-28 | 1990-11-16 | Lafon Labor | Nouveaux derives de la n-((trimethoxy-2,4,6-benzoyl)-3 propyl) piperidine, leurs procedes de preparation et leur application en therapeutique |
| JP2569940Y2 (ja) * | 1992-02-14 | 1998-04-28 | 株式会社ヨシコー | 摩擦クラッチ |
| CZ289752B6 (cs) * | 1993-05-26 | 2002-03-13 | Syntex (U.S.A.) Inc. | 1-Fenylalkanonové ligandy 5-HT4 receptoru, farmaceutický prostředek, který je obsahuje, způsob jejich přípravy a pouľití |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2092133B1 (enrdf_load_stackoverflow) * | 1970-05-06 | 1974-03-22 | Orsymonde | |
| FR2134218A1 (en) * | 1971-04-27 | 1972-12-08 | Penciolelli Madeleine | Phloroglucinol aminoketones - vasodilators and antispasmodics |
| FR2404003A1 (fr) * | 1977-09-26 | 1979-04-20 | Lafon Labor | Nouveaux derives de phloroglucinol, leur procede de preparation et leur application en therapeutique |
| GB2004883B (en) * | 1977-09-26 | 1982-03-17 | Lafon Labor | Phloroglucinol derivatives their method of preparation and their use as pharmaceuticals |
-
1981
- 1981-04-15 FR FR8107597A patent/FR2504136A1/fr active Granted
-
1982
- 1982-03-29 IE IE742/82A patent/IE52871B1/en unknown
- 1982-03-30 DE DE8282400577T patent/DE3260320D1/de not_active Expired
- 1982-03-30 AT AT82400577T patent/ATE8258T1/de not_active IP Right Cessation
- 1982-03-30 EP EP82400577A patent/EP0063075B1/fr not_active Expired
- 1982-04-05 CA CA000400489A patent/CA1183853A/en not_active Expired
- 1982-04-06 GR GR67826A patent/GR75918B/el unknown
- 1982-04-14 ES ES511431A patent/ES8304105A1/es not_active Expired
- 1982-04-14 DK DK167782A patent/DK156002C/da not_active IP Right Cessation
- 1982-04-14 JP JP57063198A patent/JPS57181073A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3260320D1 (en) | 1984-08-09 |
| EP0063075B1 (fr) | 1984-07-04 |
| CA1183853A (en) | 1985-03-12 |
| ES511431A0 (es) | 1983-02-16 |
| DK156002C (da) | 1989-11-06 |
| JPS57181073A (en) | 1982-11-08 |
| DK156002B (da) | 1989-06-12 |
| ATE8258T1 (de) | 1984-07-15 |
| JPH039112B2 (enrdf_load_stackoverflow) | 1991-02-07 |
| ES8304105A1 (es) | 1983-02-16 |
| IE820742L (en) | 1982-10-15 |
| EP0063075A1 (fr) | 1982-10-20 |
| FR2504136A1 (fr) | 1982-10-22 |
| GR75918B (enrdf_load_stackoverflow) | 1984-08-02 |
| FR2504136B1 (enrdf_load_stackoverflow) | 1984-02-10 |
| DK167782A (da) | 1982-10-16 |
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