CA1212944A - Phenyl-(3-aminopropyl)-ketone derivatives - Google Patents
Phenyl-(3-aminopropyl)-ketone derivativesInfo
- Publication number
- CA1212944A CA1212944A CA000439563A CA439563A CA1212944A CA 1212944 A CA1212944 A CA 1212944A CA 000439563 A CA000439563 A CA 000439563A CA 439563 A CA439563 A CA 439563A CA 1212944 A CA1212944 A CA 1212944A
- Authority
- CA
- Canada
- Prior art keywords
- ketone
- trimethoxyphenyl
- group
- reacting
- hexamethyleneiminopropyl
- 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
- YVZLEAGJRDBABM-UHFFFAOYSA-N 4-amino-1-phenylbutan-1-one Chemical class NCCCC(=O)C1=CC=CC=C1 YVZLEAGJRDBABM-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- SOKKYQNPGLERHO-UHFFFAOYSA-N 4-(azepan-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCCCC1 SOKKYQNPGLERHO-UHFFFAOYSA-N 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- LKUDPHPHKOZXCD-UHFFFAOYSA-N 1,3,5-trimethoxybenzene Chemical compound COC1=CC(OC)=CC(OC)=C1 LKUDPHPHKOZXCD-UHFFFAOYSA-N 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- -1 1,3,5-trimenthoxybenzene Chemical compound 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000004658 ketimines Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- OQPSAQBHEQYYMJ-UHFFFAOYSA-N 4-(azepan-1-yl)butanenitrile Chemical compound N#CCCCN1CCCCCC1 OQPSAQBHEQYYMJ-UHFFFAOYSA-N 0.000 claims description 5
- ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 claims description 5
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 5
- VUKSFISGFOJLPO-UHFFFAOYSA-N 4-(azepan-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCCCC1 VUKSFISGFOJLPO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 229940124549 vasodilator Drugs 0.000 abstract description 9
- 239000003071 vasodilator agent Substances 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 3
- 230000036471 bradycardia Effects 0.000 abstract description 2
- 208000006218 bradycardia Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 210000000748 cardiovascular system Anatomy 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 12
- 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 9
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 230000002921 anti-spasmodic effect Effects 0.000 description 4
- 239000000810 peripheral vasodilating agent Substances 0.000 description 4
- 229960002116 peripheral vasodilator Drugs 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 3
- 230000000059 bradycardiac effect Effects 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 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 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- POLIOTNRLQFNRU-UHFFFAOYSA-N 4-piperidin-1-yl-1-(2,4,6-trimethoxyphenyl)butan-1-one;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(OC)=C1C(=O)CCCN1CCCCC1 POLIOTNRLQFNRU-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000146 antalgic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000003556 assay Methods 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
- 230000017531 blood circulation Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8217937A FR2534916B1 (fr) | 1982-10-26 | 1982-10-26 | Nouveaux derives de phenyl-(3-aminopropyl)-cetone, utilisation en therapeutique et procede de preparation |
| FR82.17.937 | 1982-10-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212944A true CA1212944A (en) | 1986-10-21 |
Family
ID=9278617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000439563A Expired CA1212944A (en) | 1982-10-26 | 1983-10-24 | Phenyl-(3-aminopropyl)-ketone derivatives |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2584715B1 (fr) * | 1985-07-10 | 1987-10-09 | Lafon Labor | Phenyl-(3-hexamethyleneiminopropyl)-cetone, procede de preparation et utilisation en therapeutique |
| ES2121210T3 (es) * | 1993-05-26 | 1998-11-16 | Syntex Inc | Nuevos ligandos de receptores 5-ht4 a base de 1-fenilalcan-1-onas. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6945M (enrdf_load_stackoverflow) * | 1967-12-22 | 1969-05-12 | ||
| FR2092133B1 (enrdf_load_stackoverflow) * | 1970-05-06 | 1974-03-22 | Orsymonde | |
| FR2101045A1 (en) * | 1970-08-12 | 1972-03-31 | Penciolelli Madeleine | Omega-dialkylamino-1-(2,4,6-trialkoxy phenyl) alkan-1-ones - with vasodilator and spasmolytic activity |
| FR2134218A1 (en) * | 1971-04-27 | 1972-12-08 | Penciolelli Madeleine | Phloroglucinol aminoketones - vasodilators and antispasmodics |
-
1982
- 1982-10-26 FR FR8217937A patent/FR2534916B1/fr not_active Expired
-
1983
- 1983-10-18 GR GR72730A patent/GR79617B/el unknown
- 1983-10-24 IE IE2488/83A patent/IE56129B1/en not_active IP Right Cessation
- 1983-10-24 CA CA000439563A patent/CA1212944A/en not_active Expired
- 1983-10-25 AU AU20568/83A patent/AU556589B2/en not_active Ceased
- 1983-10-25 AT AT83402070T patent/ATE26712T1/de not_active IP Right Cessation
- 1983-10-25 ES ES526736A patent/ES526736A0/es active Granted
- 1983-10-25 DK DK489283A patent/DK156003C/da not_active IP Right Cessation
- 1983-10-25 EP EP83402070A patent/EP0110748B1/fr not_active Expired
- 1983-10-25 DE DE8383402070T patent/DE3371077D1/de not_active Expired
- 1983-10-26 JP JP58199310A patent/JPS5995283A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK156003B (da) | 1989-06-12 |
| ES8406069A1 (es) | 1984-07-01 |
| GR79617B (enrdf_load_stackoverflow) | 1984-10-31 |
| DK156003C (da) | 1989-11-13 |
| DE3371077D1 (en) | 1987-05-27 |
| IE832488L (en) | 1984-04-26 |
| FR2534916B1 (fr) | 1985-11-22 |
| JPS5995283A (ja) | 1984-06-01 |
| DK489283A (da) | 1984-04-27 |
| DK489283D0 (da) | 1983-10-25 |
| EP0110748A1 (fr) | 1984-06-13 |
| IE56129B1 (en) | 1991-04-24 |
| ES526736A0 (es) | 1984-07-01 |
| EP0110748B1 (fr) | 1987-04-22 |
| ATE26712T1 (de) | 1987-05-15 |
| AU2056883A (en) | 1984-05-03 |
| FR2534916A1 (fr) | 1984-04-27 |
| AU556589B2 (en) | 1986-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |