WO1999032431A1 - A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL-[2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE - Google Patents

A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL-[2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE Download PDF

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Publication number
WO1999032431A1
WO1999032431A1 PCT/SE1998/002316 SE9802316W WO9932431A1 WO 1999032431 A1 WO1999032431 A1 WO 1999032431A1 SE 9802316 W SE9802316 W SE 9802316W WO 9932431 A1 WO9932431 A1 WO 9932431A1
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WO
WIPO (PCT)
Prior art keywords
isopropyl
methyl
ethyl
amine
propoxyphenoxy
Prior art date
Application number
PCT/SE1998/002316
Other languages
French (fr)
Inventor
Karol Horvath
Ulf Larsson
Rune Sandberg
Original Assignee
Astrazeneca Ab
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to JP2000525368A priority Critical patent/JP2001526254A/en
Priority to SK806-2000A priority patent/SK8062000A3/en
Priority to KR1020007006882A priority patent/KR20010033407A/en
Priority to PL98341525A priority patent/PL341525A1/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Priority to BR9814381-6A priority patent/BR9814381A/en
Priority to EEP200000384A priority patent/EE200000384A/en
Priority to CA002314989A priority patent/CA2314989A1/en
Priority to US09/254,420 priority patent/US6235792B1/en
Priority to AU19892/99A priority patent/AU1989299A/en
Priority to HU0004428A priority patent/HUP0004428A3/en
Priority to IL13682998A priority patent/IL136829A0/en
Priority to EP98964600A priority patent/EP1047663A1/en
Publication of WO1999032431A1 publication Critical patent/WO1999032431A1/en
Priority to IS5544A priority patent/IS5544A/en
Priority to NO20003216A priority patent/NO20003216D0/en

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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
    • C07C217/14—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 a carbon atom of a six-membered aromatic ring
    • C07C217/18—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 a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/20—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 a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A61P23/02—Local anaesthetics
    • 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

Definitions

  • the present invention relates to a novel phosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine. Additionally, the present invention also relates to a process for the preparation of a phosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine as well as a pharmaceutical formulation containing it and its use in medicine.
  • Isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine is a compound with anaesthetic properties. It is therefore useful as an anaesthetic compound for the treatment of pain, including localised pain.
  • WO 9715548 discloses isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amineas well as a process for its preparation. Said process comprises a couple of reaction steps starting with reacting 3-n-propoxyphenol with 1 ,2-dibromoethane resulting in l-(2-bromoethoxy)-3-n- propoxybenzene. Further, l-(2-bromoethoxy)-3-n-propoxybenzene is reacted with N- methylisopropylamine in an autoclave. The product, isopropyl-methyl- [2-(3-n-propoxy- phenoxy)ethyl]amine, was thereafter further purified by distillation in vacuo.
  • the object of the present invention is to provide a monophosphate salt of isopropyl-methyl- [2-(3 -n-propoxyphenoxy )ethy 1] amine .
  • a process for the preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine which comprises treating isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine with phosphoric acid in a solvent system.
  • the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine is a crystalline and stable salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine and therefore has advantageous properties.
  • the crystalline monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine can be used to introduce a crystalline intermediate in the process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine.
  • This introduces a simple and convenient purification step in a reaction sequence where all other intermediates are syrups. Thereby, the time and energy consuming distillation used in processes according to prior art is avoided.
  • the content of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine in ethyl acetate is preferably 7-9 ml ethyl acetate per gram of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine.
  • methanol and a solution of phosphoric acid in methanol are added to the assayed solution of isopropyl-methyl- [2-(3-n-propoxyphenoxy)ethyl]amine in ethyl acetate.
  • the amount of phosphoric acid should be around 0.9 to 1.0 molar equivalents, preferably 0.95 equivalents.
  • the total amount of methanol added to the assayed solution should be adjusted to the amount of phosphoric acid used.
  • concentration of phosphoric acid in the resulting solution of isopropyl- methyl- [2-(3-n-propoxyphenoxy)ethyl]amine in metanol/ ethyl acetate should be around 5- 15%, by volume, preferably 9-11%, by volume.
  • the precipitated salt is collected, for example by filtration or centrifugation, and thereafter washed with ethyl acetate.
  • the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine can thereafter be further processed by processes known in the art, e.g. converted back to its basic form, i.e. isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine, by treatment of aqueous base.
  • the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine is useful because it possesses pharmacological activity and especially for the use as an anaesthetic compound. It is therefore indicated as a pharmaceutical, especially in the treatment of pain, including localised pain.
  • the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine for use as a pharmaceutical, especially in the treatment of pain.
  • the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine will normally be administered parenterally, especially injected in the form of pharmaceutical formulations comprising the active ingredient in a pharmaceutically acceptable dosage form.
  • Compositions comprising the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine for parenteral administration may include other ingredients commonly used in the parenteral administration of pharmaceutically-active compounds.
  • a pharmaceutical formulation containing the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine in admixture with a pharmaceutically acceptable adjuvant, diluent or carrier.
  • Formulations including the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine may be prepared by techniques which are known per se. Usually the active substance will constitute between 0.5 and 10% by weight of the preparation, more specifically between 1 and 5% by weight.
  • a method for treatment of a pain which method comprises administration of a therapeutically effective amount of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)- ethyljamine to a person suffering from, or susceptible to pain.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Anesthesiology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a novel monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine. Moreover, the present invention also relates to a process for the preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine as well as a pharmaceutical formulation containing it and its use in medicine.

Description

A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL-[2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE
Field of the invention
The present invention relates to a novel phosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine. Additionally, the present invention also relates to a process for the preparation of a phosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine as well as a pharmaceutical formulation containing it and its use in medicine.
Background of the invention and prior art
Isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amineis a compound with anaesthetic properties. It is therefore useful as an anaesthetic compound for the treatment of pain, including localised pain.
WO 9715548 discloses isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amineas well as a process for its preparation. Said process comprises a couple of reaction steps starting with reacting 3-n-propoxyphenol with 1 ,2-dibromoethane resulting in l-(2-bromoethoxy)-3-n- propoxybenzene. Further, l-(2-bromoethoxy)-3-n-propoxybenzene is reacted with N- methylisopropylamine in an autoclave. The product, isopropyl-methyl- [2-(3-n-propoxy- phenoxy)ethyl]amine, was thereafter further purified by distillation in vacuo.
Summary of the Invention
The object of the present invention is to provide a monophosphate salt of isopropyl-methyl- [2-(3 -n-propoxyphenoxy )ethy 1] amine . According to the invention there is also provided a process for the preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine which comprises treating isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine with phosphoric acid in a solvent system.
The monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine is a crystalline and stable salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine and therefore has advantageous properties.
Additionally, the crystalline monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine can be used to introduce a crystalline intermediate in the process for the preparation of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine. This introduces a simple and convenient purification step in a reaction sequence where all other intermediates are syrups. Thereby, the time and energy consuming distillation used in processes according to prior art is avoided. The crystallization of the monophosphate salt of isopropyl-methyl-^2-(3-n-propoxyphenoxy)ethyl]amine results in an intermediate of a high purity that can be further converted to the corresponding isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine by a simple alkalization step.
Preparation
In the preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine the content of isopropyl-methyl-[2-(3-n-propoxyphenoxy)_.thyl]amine in ethyl acetate is first assayed and adjusted to 6-10 ml ethyl acetate per gram of isopropyl- methyl-[2-(3-n-propoxyphenoxy)ethyl]amine. The content of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine in ethyl acetate is preferably 7-9 ml ethyl acetate per gram of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine. To the assayed solution of isopropyl-methyl- [2-(3-n-propoxyphenoxy)ethyl]amine in ethyl acetate, methanol and a solution of phosphoric acid in methanol are added. The amount of phosphoric acid should be around 0.9 to 1.0 molar equivalents, preferably 0.95 equivalents. The total amount of methanol added to the assayed solution should be adjusted to the amount of phosphoric acid used. The concentration of phosphoric acid in the resulting solution of isopropyl- methyl- [2-(3-n-propoxyphenoxy)ethyl]amine in metanol/ ethyl acetate should be around 5- 15%, by volume, preferably 9-11%, by volume. The precipitated salt is collected, for example by filtration or centrifugation, and thereafter washed with ethyl acetate.
The monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine can thereafter be further processed by processes known in the art, e.g. converted back to its basic form, i.e. isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine, by treatment of aqueous base.
Medical and pharmaceutical use
The monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine is useful because it possesses pharmacological activity and especially for the use as an anaesthetic compound. It is therefore indicated as a pharmaceutical, especially in the treatment of pain, including localised pain.
According to a further aspect of the invention there is thus provided the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine for use as a pharmaceutical, especially in the treatment of pain.
Pharmaceutical Formulations
The monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine will normally be administered parenterally, especially injected in the form of pharmaceutical formulations comprising the active ingredient in a pharmaceutically acceptable dosage form. Compositions comprising the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine for parenteral administration may include other ingredients commonly used in the parenteral administration of pharmaceutically-active compounds.
According to a further aspect of the invention there is thus provided a pharmaceutical formulation containing the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine in admixture with a pharmaceutically acceptable adjuvant, diluent or carrier. Formulations including the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine may be prepared by techniques which are known per se. Usually the active substance will constitute between 0.5 and 10% by weight of the preparation, more specifically between 1 and 5% by weight.
According to a further aspect of the present invention, there is provided a method for treatment of a pain which method comprises administration of a therapeutically effective amount of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)- ethyljamine to a person suffering from, or susceptible to pain.
The present invention is described in more detail in the following non-limiting examples
Examples Example 1. Preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine
To an assayed solution of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine (19.0 kg, 75.7 mol) in ethyl acetate (8 ml EtOAc/g isopropyl-methyl- [2-(3-n-propoxyphenoxy> ethyl]amine) is added MeOH (9.6 L) followed by H3PO4 (4.85 L, 72.5 mol) dissolved in MeOH (19.2 L) over 3 hours at ambient temperature. The resulting slurry of the title compound is then isolated by filtration and the solid material is washed with EtOAc. Yield 89% (41.8 kg wet compound, corresponds to 67.6 mol dry compound); Mp: 131-134°C.

Claims

Claims
1. A phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine.
2. A monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine.
3. A process for the preparation of the monophosphate salt of isopropyl-methyl-[2-(3-n- propoxyphenoxy)ethyl]amine comprising the following steps: i) adding phosphoric acid to a solution of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine in an organic solvent system; ii) allowing the solution to crystallize; iii) isolating the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy phenoxy)ethyl]amine thus obtained.
4. A process according to claim 3, characterized in that the organic solvent system used in step i) is ethyl acetate.
5. A process according to claim 3, characterized in that the phosphoric acid added in step i) is added as an alcoholic solution of phosphoric acid.
6. A process according to claim 5, characterized in that the alcoholic solution is a methanolic solution.
7. A process according to claim 3, characterized in that 0.9-1.0 equivalents of phosphoric acid is used in step i)
8. A process according to claim 3, characterized in that 0.95 equivalents of phosphoric acid is used in step i)
. A process according to claim 3, characterized in that the concentration of phosphoric acid in the resultant solution after complete addition is between 5-15%, by weight.
10. A process according to claim 3, characterized in that the concentration of phosphoric acid in the resultant solution after addition should be between 9-11 , by weight.
11. A pharmaceutical formulation comprising the monophosphate salt of isopropyl-methyl- [2-(3-n-propoxyphenoxy)ethyl]amine and a pharmaceutically acceptable carrier or diluent.
12. Use of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)- ethyljamine in therapy.
13. Use of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)- ethyl]amine in the manufacture of a medicament for treatment of pain.
14. The phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine prepared by a process according to any of claims 3-10.
15. A method of treatment of pain which comprises administration of a therapeutically effective amount of the monophosphate salt of isopropyl-methyl-[2-(3-n-propoxy- phenoxy)ethyl]amine to a patient suffering from pain.
PCT/SE1998/002316 1997-12-22 1998-12-15 A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL-[2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE WO1999032431A1 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
EEP200000384A EE200000384A (en) 1997-12-22 1998-12-15 New phosphate salt of isopropylmethyl- [2- (3-n-propoxyphenoxy) ethyl] amine
KR1020007006882A KR20010033407A (en) 1997-12-22 1998-12-15 A Novel Phosphate Salt of Isopropyl-Methyl-[2-(3-n-Propoxyphenoxy)Ethyl]Amine
PL98341525A PL341525A1 (en) 1997-12-22 1998-12-15 Novel isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl] amine phosphate
US09/254,420 US6235792B1 (en) 1997-12-22 1998-12-15 Phosphate salt of isopropyl-methyl- [2-(3-n-propoxyphenoxy)ethyl]amine
BR9814381-6A BR9814381A (en) 1997-12-22 1998-12-15 Compound, process for preparation and use of the isopropyl-methyl- [2- (3-n-propoxyphenoxy) ethyl] amine monophosphate salt, pharmaceutical formulation, isopropyl-methyl- [2- [3-n-propoxyphenoxy) ethyl salt ] amine, and, pain treatment process
SK806-2000A SK8062000A3 (en) 1997-12-22 1998-12-15 A novel phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine
CA002314989A CA2314989A1 (en) 1997-12-22 1998-12-15 A novel phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine
JP2000525368A JP2001526254A (en) 1997-12-22 1998-12-15 Novel isopropyl-methyl- [2- (3-n-propoxyphenoxy) ethyl] amine phosphate
AU19892/99A AU1989299A (en) 1997-12-22 1998-12-15 A novel phosphate salt of isopropyl-methyl-{2-(3-n-propoxyphenoxy)ethyl}amine
HU0004428A HUP0004428A3 (en) 1997-12-22 1998-12-15 A novel phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphenoxy)ethyl]amine
IL13682998A IL136829A0 (en) 1997-12-22 1998-12-15 A novel phosphate salt of isopropyl-methyl-[2-(3-n-propoxyphe oxy) ethyl]amine
EP98964600A EP1047663A1 (en) 1997-12-22 1998-12-15 A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL- 2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE
IS5544A IS5544A (en) 1997-12-22 2000-06-21 New phosphate salt of isopropyl-methyl- [2- (3-n-propoxyphenoxy) ethyl] amine
NO20003216A NO20003216D0 (en) 1997-12-22 2000-06-21 Fresh phosphate salt of isopropylmethyl- (2- (3-n-propoxyphenoxy) ethyl) amine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9704835A SE9704835D0 (en) 1997-12-22 1997-12-22 New compound
SE9704835-9 1997-12-22

Publications (1)

Publication Number Publication Date
WO1999032431A1 true WO1999032431A1 (en) 1999-07-01

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PCT/SE1998/002316 WO1999032431A1 (en) 1997-12-22 1998-12-15 A NOVEL PHOSPHATE SALT OF ISOPROPYL-METHYL-[2-(3-n-PROPOXYPHENOXY)ETHYL]AMINE

Country Status (22)

Country Link
US (1) US6235792B1 (en)
EP (1) EP1047663A1 (en)
JP (1) JP2001526254A (en)
KR (1) KR20010033407A (en)
CN (1) CN1280559A (en)
AR (1) AR017199A1 (en)
AU (1) AU1989299A (en)
BR (1) BR9814381A (en)
CA (1) CA2314989A1 (en)
EE (1) EE200000384A (en)
HU (1) HUP0004428A3 (en)
ID (1) ID26940A (en)
IL (1) IL136829A0 (en)
IS (1) IS5544A (en)
NO (1) NO20003216D0 (en)
PL (1) PL341525A1 (en)
SE (1) SE9704835D0 (en)
SK (1) SK8062000A3 (en)
TR (1) TR200002012T2 (en)
TW (1) TW455590B (en)
WO (1) WO1999032431A1 (en)
ZA (1) ZA9811237B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3105854A (en) * 1958-11-06 1963-10-01 Ciba Geigy Corp Meta-substituted phenoxyethylamines
WO1997015548A1 (en) * 1995-10-27 1997-05-01 Astra Aktiebolag New [(3-alkoxy-phenoxy)-ethyl]-dialkylamine derivatives and their use as local anaesthetics

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3105854A (en) * 1958-11-06 1963-10-01 Ciba Geigy Corp Meta-substituted phenoxyethylamines
WO1997015548A1 (en) * 1995-10-27 1997-05-01 Astra Aktiebolag New [(3-alkoxy-phenoxy)-ethyl]-dialkylamine derivatives and their use as local anaesthetics

Also Published As

Publication number Publication date
JP2001526254A (en) 2001-12-18
ZA9811237B (en) 1999-07-19
SE9704835D0 (en) 1997-12-22
PL341525A1 (en) 2001-04-23
IS5544A (en) 2000-06-21
TR200002012T2 (en) 2000-10-23
CA2314989A1 (en) 1999-07-01
HUP0004428A3 (en) 2002-04-29
NO20003216L (en) 2000-06-21
EP1047663A1 (en) 2000-11-02
EE200000384A (en) 2001-12-17
US6235792B1 (en) 2001-05-22
TW455590B (en) 2001-09-21
SK8062000A3 (en) 2001-02-12
KR20010033407A (en) 2001-04-25
NO20003216D0 (en) 2000-06-21
BR9814381A (en) 2000-10-10
IL136829A0 (en) 2001-06-14
HUP0004428A2 (en) 2002-03-28
CN1280559A (en) 2001-01-17
ID26940A (en) 2001-02-22
AR017199A1 (en) 2001-08-22
AU1989299A (en) 1999-07-12

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