CA1052794A - Method of producing n-methyl-n-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadienamine - Google Patents
Method of producing n-methyl-n-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadienamineInfo
- Publication number
- CA1052794A CA1052794A CA226,057A CA226057A CA1052794A CA 1052794 A CA1052794 A CA 1052794A CA 226057 A CA226057 A CA 226057A CA 1052794 A CA1052794 A CA 1052794A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- trimethoxybenzyl
- pentadienamine
- trimethyl
- methyl
- 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 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 238000006731 degradation reaction Methods 0.000 claims abstract description 3
- 230000002035 prolonged effect Effects 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- MJFWGIGCSSZKIY-UHFFFAOYSA-N n,2,3-trimethyl-n-[(3,4,5-trimethoxyphenyl)methyl]penta-2,4-dien-1-amine Chemical compound COC1=CC(CN(C)CC(C)=C(C)C=C)=CC(OC)=C1OC MJFWGIGCSSZKIY-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000001816 cooling Methods 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- -1 (3,4,5-trimethoxybenzyl)-2, 3-dimethyl-2,4-pentadienamine Chemical compound 0.000 claims 1
- 239000002184 metal Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- HAKSOKWVNPZVNM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CNC=CC1 HAKSOKWVNPZVNM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- FJNLGRCWQZQBSR-UHFFFAOYSA-N penta-1,3-dien-1-amine Chemical compound CC=CC=CN FJNLGRCWQZQBSR-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- AFCYWWIZGOUXCF-UHFFFAOYSA-N 1,2,3,6-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CC=CCN1 AFCYWWIZGOUXCF-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GJQORMPCSCCIEQ-UHFFFAOYSA-N penta-1,3-dien-1-amine;hydrochloride Chemical compound Cl.CC=CC=CN GJQORMPCSCCIEQ-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES425970A ES425970A1 (es) | 1974-05-04 | 1974-05-04 | Un procedimiento para la obtencion de n - metil - n-(3,4,5-trimeboxibencil)-2,3-dimetil-2,4-pentadienamina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052794A true CA1052794A (en) | 1979-04-17 |
Family
ID=8466594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA226,057A Expired CA1052794A (en) | 1974-05-04 | 1975-05-01 | Method of producing n-methyl-n-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadienamine |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5337337B2 (enExample) |
| AR (1) | AR206623A1 (enExample) |
| AT (1) | AT337160B (enExample) |
| AU (1) | AU8050775A (enExample) |
| BE (1) | BE828240A (enExample) |
| CA (1) | CA1052794A (enExample) |
| CH (1) | CH615150A5 (enExample) |
| DE (1) | DE2518534A1 (enExample) |
| ES (1) | ES425970A1 (enExample) |
| FR (1) | FR2269336B1 (enExample) |
| GB (1) | GB1501153A (enExample) |
| NL (1) | NL7505254A (enExample) |
| SE (1) | SE412755B (enExample) |
| SU (1) | SU562192A3 (enExample) |
-
1974
- 1974-05-04 ES ES425970A patent/ES425970A1/es not_active Expired
-
1975
- 1975-01-01 AR AR257859A patent/AR206623A1/es active
- 1975-03-07 AT AT181075A patent/AT337160B/de not_active IP Right Cessation
- 1975-04-15 SE SE7504301A patent/SE412755B/xx unknown
- 1975-04-15 GB GB15514/75A patent/GB1501153A/en not_active Expired
- 1975-04-22 BE BE155654A patent/BE828240A/xx unknown
- 1975-04-24 AU AU80507/75A patent/AU8050775A/en not_active Expired
- 1975-04-25 DE DE19752518534 patent/DE2518534A1/de active Pending
- 1975-04-30 FR FR7513536A patent/FR2269336B1/fr not_active Expired
- 1975-05-01 CA CA226,057A patent/CA1052794A/en not_active Expired
- 1975-05-02 CH CH568075A patent/CH615150A5/de not_active IP Right Cessation
- 1975-05-02 NL NL7505254A patent/NL7505254A/xx not_active Application Discontinuation
- 1975-05-02 JP JP5380075A patent/JPS5337337B2/ja not_active Expired
- 1975-05-04 SU SU2129803A patent/SU562192A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2269336B1 (enExample) | 1977-09-09 |
| SU562192A3 (ru) | 1977-06-15 |
| JPS50151835A (enExample) | 1975-12-06 |
| FR2269336A1 (enExample) | 1975-11-28 |
| DE2518534A1 (de) | 1975-11-13 |
| ATA181075A (de) | 1976-10-15 |
| AU8050775A (en) | 1976-10-28 |
| BE828240A (fr) | 1975-10-22 |
| AT337160B (de) | 1977-06-10 |
| JPS5337337B2 (enExample) | 1978-10-07 |
| ES425970A1 (es) | 1976-09-16 |
| NL7505254A (nl) | 1975-11-06 |
| CH615150A5 (en) | 1980-01-15 |
| GB1501153A (en) | 1978-02-15 |
| SE7504301L (sv) | 1975-11-05 |
| SE412755B (sv) | 1980-03-17 |
| AR206623A1 (es) | 1976-08-06 |
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