CH615150A5 - Process for the preparation of N-methyl-N-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadiene- amine - Google Patents
Process for the preparation of N-methyl-N-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadiene- amine Download PDFInfo
- Publication number
- CH615150A5 CH615150A5 CH568075A CH568075A CH615150A5 CH 615150 A5 CH615150 A5 CH 615150A5 CH 568075 A CH568075 A CH 568075A CH 568075 A CH568075 A CH 568075A CH 615150 A5 CH615150 A5 CH 615150A5
- Authority
- CH
- Switzerland
- Prior art keywords
- trimethoxybenzyl
- formula
- trimethyl
- chloride
- tetrahydropyridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 9
- 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 title claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 7
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- UMVJFCZSLLVFMI-UHFFFAOYSA-N 1,4,5-trimethyl-3,6-dihydro-2h-pyridine Chemical compound CN1CCC(C)=C(C)C1 UMVJFCZSLLVFMI-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 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
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 4
- 229940035676 analgesics Drugs 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical class C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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 |
|---|---|
| CH615150A5 true CH615150A5 (en) | 1980-01-15 |
Family
ID=8466594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH568075A CH615150A5 (en) | 1974-05-04 | 1975-05-02 | Process for the preparation of N-methyl-N-(3,4,5-trimethoxybenzyl)-2,3-dimethyl-2,4-pentadiene- amine |
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 |
| CA1052794A (en) | 1979-04-17 |
| 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 |
| GB1501153A (en) | 1978-02-15 |
| SE7504301L (sv) | 1975-11-05 |
| SE412755B (sv) | 1980-03-17 |
| AR206623A1 (es) | 1976-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |