GB884663A - New amines and processes for their manufacture - Google Patents
New amines and processes for their manufactureInfo
- Publication number
- GB884663A GB884663A GB37789/59A GB3778959A GB884663A GB 884663 A GB884663 A GB 884663A GB 37789/59 A GB37789/59 A GB 37789/59A GB 3778959 A GB3778959 A GB 3778959A GB 884663 A GB884663 A GB 884663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- carbon atoms
- resorcinol
- aliphatic hydrocarbon
- salts
- 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
Classifications
-
- 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
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- 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
- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/084—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises basic resorcinol ethers of the formula <FORM:0884663/IV (b)/1> wherein R1 represents an aliphatic hydrocarbon radical of 3-7 carbon atoms such as an alkyl, cycloalkyl, alkenyl or cycloalkenyl radical, R2 is an aliphatic hydrocarbon radical preferably of 1-10, more preferably 3-6, carbon atoms, such as an alkyl, alkenyl or cycloalkyl radical and n is a whole number of at least 2, and physiologically tolerable acid addition salts of these compounds. It comprises also the preparation of these compounds by reaction of an appropriate ether of the formula R1O.C6H4.O.(CH2)n.X, wherein X is a reactive esterified hydroxyl group, e.g. a halide, sulphate or organic sulphonate with an amine H2N.R2, or by hydrogenolysis of the corresponding N-benzyl-phenoxy-alkylamine. The products are used pharmaceutically as local anaesthetics (see Group VI), preferred compounds being m-pentyloxy-phenoxyethyl-methylamine and isobutylamine and m-butoxyphenoxyethyl-n-butylamine. Many other products are exemplified. Phenoxyalkyl-halides used as starting materials, i.e. m-propoxy-, m-isobutoxy-, m-n-pentyloxy- and m-alloxy-, phenoxyethyl bromide are made by reacting the appropriate m-substituted phenol with ethylene dibromide in the presence of sodium ethoxide. Resorcinol ethers, i.e. resorcinol monopropyl, mono-isobutyl, mono-amyl and mono allyl ethers are made by the reaction of the appropriate alkyl or alkenyl halide on resorcinol in the presence of sodium ethoxide. N - Methyl - N - benzyl - m - butoxyphenoxethylamine is made by the reaction of N-methylbenzylamine on m-n-butoxyphenoxyethyl bromide.ALSO:Pharmaceutical preparations comprise compounds of the formula <FORM:0884663/VI/1> or acid addition salts thereof, wherein R1 is an aliphatic hydrocarbon radical of 3-7 carbon atoms and R2 is an aliphatic hydrocarbon radical, preferably of 1-10 carbon atoms (see Group IV (b)) together with a pharmaceutical carrier. The preparations suitably take the form of tablets, dragees, solutions, suspensions and emulsions suitable for enteral, parenteral or topical administration and may contain in addition to conventional diluents, preserving, stabilizing, wetting or emulsifying agents, salts for varying osmotic pressure or buffers. The active compounds have local an sthetic properties. Specified salts are hydrohalides, sulphates, nitrates, phosphates, thiocyanates, acetates, propionates, oxalates, malonates, tartrates, succinate, malates, methane-, ethane-, hydroxyethane-, benzene- and toluene-sulphonates, and salts with therapeutically active acids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH884663X | 1958-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB884663A true GB884663A (en) | 1961-12-13 |
Family
ID=4545167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37789/59A Expired GB884663A (en) | 1958-11-06 | 1959-11-06 | New amines and processes for their manufacture |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB884663A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2454555A (en) * | 2007-10-05 | 2009-05-13 | Acucela Inc | (Cyclo)alkyloxyphenylalkyl- and (cyclo)alkyloxyphenylalkoxy-amines for use in the treatment of ophthalmic diseases |
| US8450527B2 (en) | 2007-11-01 | 2013-05-28 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
| US9447078B2 (en) | 2012-01-20 | 2016-09-20 | Acucela Inc. | Substituted heterocyclic compounds for disease treatment |
| US10471027B2 (en) | 2009-07-02 | 2019-11-12 | Acucela, Inc. | Pharmacology of visual cycle modulators |
| US12029708B2 (en) | 2022-08-05 | 2024-07-09 | Acucela Inc. | Alkoxy compounds for disease treatment |
-
1959
- 1959-11-06 GB GB37789/59A patent/GB884663A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9458088B2 (en) | 2007-10-05 | 2016-10-04 | Acucela Inc. | Alkoxy compounds for disease treatment |
| GB2454555B (en) * | 2007-10-05 | 2011-01-26 | Acucela Inc | Alkoxy compounds for disease treatment |
| US7982071B2 (en) | 2007-10-05 | 2011-07-19 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US11446261B2 (en) | 2007-10-05 | 2022-09-20 | Acucela Inc. | Alkoxy compounds for disease treatment |
| GB2454555A (en) * | 2007-10-05 | 2009-05-13 | Acucela Inc | (Cyclo)alkyloxyphenylalkyl- and (cyclo)alkyloxyphenylalkoxy-amines for use in the treatment of ophthalmic diseases |
| US8829244B2 (en) | 2007-10-05 | 2014-09-09 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US8981153B2 (en) | 2007-10-05 | 2015-03-17 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US8993807B2 (en) | 2007-10-05 | 2015-03-31 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US10639286B2 (en) | 2007-10-05 | 2020-05-05 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US9079825B2 (en) | 2007-10-05 | 2015-07-14 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US10188615B2 (en) | 2007-10-05 | 2019-01-29 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US9737496B2 (en) | 2007-10-05 | 2017-08-22 | Acucela Inc. | Alkoxy compounds for disease treatment |
| US8716529B2 (en) | 2007-11-01 | 2014-05-06 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
| US9452153B2 (en) | 2007-11-01 | 2016-09-27 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
| US9056849B2 (en) | 2007-11-01 | 2015-06-16 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
| US8450527B2 (en) | 2007-11-01 | 2013-05-28 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
| US10471027B2 (en) | 2009-07-02 | 2019-11-12 | Acucela, Inc. | Pharmacology of visual cycle modulators |
| US9447078B2 (en) | 2012-01-20 | 2016-09-20 | Acucela Inc. | Substituted heterocyclic compounds for disease treatment |
| US12029708B2 (en) | 2022-08-05 | 2024-07-09 | Acucela Inc. | Alkoxy compounds for disease treatment |
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