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WO2006006858A1 - Psychofarmaceutical preparation - Google Patents

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Publication number
WO2006006858A1
WO2006006858A1 PCT/NL2005/000502 NL2005000502W WO2006006858A1 WO 2006006858 A1 WO2006006858 A1 WO 2006006858A1 NL 2005000502 W NL2005000502 W NL 2005000502W WO 2006006858 A1 WO2006006858 A1 WO 2006006858A1
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group
preparation
psychopharmaceutical
active substance
benzene ring
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PCT/NL2005/000502
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French (fr)
Inventor
Willem Jacob Van Der Burg
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    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • 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
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/22—Anxiolytics

Definitions

  • the present invention relates to a psychopharmaceutical preparation comprising an aromatic, multi-cyclic compound as active substance, in which both a pyridine ring and a benzene ring are present and to which is bonded an N-alkyl piperidene group.
  • a psychopharmaceutical preparation is here understood to mean a preparation which is intended to be prescribed in the case of psychological complaints of diverse nature.
  • Psychopharmaceutical preparations therefore find application on a large scale in psychotherapeutic and psychiatric treatments.
  • An important role is set aside here for antidepressants which are utilized to positively influence the state of mind of the patient in the case of complaints of a depressive nature.
  • Known antidepressants in this respect are agents commercially available under the brand names of Tolvon® and Remeron®, which are based on respectively mianserin hydrochloride and mirtazapine as tetracyclic aromatic active substance.
  • the present invention has for its object, among others, to provide a psychopharmaceutical preparation which is able to effectively combat psychological disorders of diverse nature, and more particularly migraine and/or depression.
  • a psychopharmaceutical preparation of the type stated in the preamble has according to a first aspect of the invention the feature that the active substance is characterized by the following structural formula:
  • Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring;
  • R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group; and
  • R3 represents a single or a double bond.
  • This substitution is seen as being responsible for a strong action of the compound as a whole as an antidepressant, in addition to an effective anti-migraine action.
  • this substance can be synthesized relatively simply in that the pyridine group desired therein requires only a relatively simple substitution in the peripheral benzene ring thereof.
  • a psychopharmaceutical preparation of the type stated in the preamble has according to a second aspect of the invention the feature that the active substance is characterized by the following structural formula:
  • Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring;
  • R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group.
  • This tricyclic compound also comprises a pyridine group and has the intended action as antidepressant.
  • this preparation with the N-alkyl piperidene group bonded to the tricyclic group, provides a strong action against migraine.
  • the invention is herein based on the insight that these active substances have both a strong antidepressant action and an anti-migraine action.
  • the invention hereby provides a remedy which can be utilized for both symptoms, which may or may not occur simultaneously.
  • the psychopharmaceutical preparation according to the invention has the feature that Rl represents a hydrogen atom or an organic group substituted therefor in the benzene ring and having a chain of a maximum of four carbon atoms.
  • the invention relates to an antidepressant comprising the psychopharmaceutical preparation according to the invention as specified above.
  • the invention relates to a psychotherapeutic agent against depression and/or headache, in particular migraine, comprising the psychopharmaceutical preparation in accordance with the second aspect of the invention as specified above.
  • Rl represents hydrogen in the benzene ring or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl
  • R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group
  • R3 represents a single or a double bond.
  • This compound is mixed with suitable quantities of binder, filler, flavouring and the like for manufacturing tablets therefrom which each contain a fixed dosage of active substance lying typically between 10 and 50 milligrams.
  • the active substance is mixed with lactose and vegetable starch and pressed to form different tablets which each contain 30 mg respectively 50 mg of active substance per tablet.
  • the tablets are therein provided halfway along with a break line so that the user will be readily able to take a half-dose.
  • the relevant tablets are provided with visual markings such as a specific imprint or colour. Both types of tablet are then arranged per dozen in an air-tight blister pack and placed per two blister packs in a cardboard consumer packaging.
  • an initial choice is preferably made for a relatively low dosage of for instance 15 mg of active substance per day. If a disorder persists, this dosage can be gradually increased to an optimal level.
  • the agent must be used for 2 to 4 weeks and then evaluated in consultation with a doctor.
  • Exemplary embodiment 2 Use is made as an active substance of
  • Rl represents hydrogen in the benzene ring or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl
  • R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group.
  • the dihydrochloride of the compound of the first exemplary embodiment is used as active substance. This substance is dissolved in water at a dosage of 10 grams per litre. The liquid is packaged in 50 millilitre bottles which are equipped with a precise drop dispenser. The delivery of the dispenser is set here to 1 millilitre per droplet. A precise individual daily dosage is thus possible in consultation with a doctor.
  • the preparation according to the invention can thus be processed as desired into dosages and means of administering other than those described.
  • other substitutes can also be applied within the tricyclic compound in order to enhance the effective action and/or reduce possible side effects.
  • pharmaceutically acceptable acid addition salts of the intended tricyclic compound can in particular be applied in the preparation.
  • the invention generally provides a particularly effective agent against psychological disorders of varying nature.

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

Abstract

A psychopharmaceutical preparation comprises a tricyclic compound as active substance. This is an aromatic tricyclic compound in which both a pyridine group and a benzene ring are present and to which is bonded an N-alkyl piperidene group. The benzene group and the pyridine group are connected according to the invention to a shared cyclocarbon group, wherein the cyclocarbon group comprises six or seven carbon atoms. Diverse groups and atoms can be substituted on the tricyclic compound. The psychopharmaceutical preparation is particularly suitable as antidepressant and as remedy against headache, particularly migraine.

Description

Psychofarmaceutical preparation
The present invention relates to a psychopharmaceutical preparation comprising an aromatic, multi-cyclic compound as active substance, in which both a pyridine ring and a benzene ring are present and to which is bonded an N-alkyl piperidene group.
A psychopharmaceutical preparation is here understood to mean a preparation which is intended to be prescribed in the case of psychological complaints of diverse nature. Psychopharmaceutical preparations therefore find application on a large scale in psychotherapeutic and psychiatric treatments. An important role is set aside here for antidepressants which are utilized to positively influence the state of mind of the patient in the case of complaints of a depressive nature. Known antidepressants in this respect are agents commercially available under the brand names of Tolvon® and Remeron®, which are based on respectively mianserin hydrochloride and mirtazapine as tetracyclic aromatic active substance.
According to the World Health Organization (WHO) the number of people with psychological problems is increasing dramatically. The organization warns that one in four people have to contend at a certain point in their life with a psychological or neurological disorder , and that mental illnesses are one of the most important causes worldwide of illness and physical disorders. Depression is the most common of these. This disorder is the most destructive both mentally and physically and is treated effectively in only a relatively small number of cases. Depression is therefore one of the most important, if not the most important, causes worldwide of physical disorders in patients of five years and older. It is estimated that seven percent of adults in
Europe suffer from a serious form of depression, while another nine percent has to contend with less serious forms of this disorder. Without adequate countermeasures, this number will only increase as society becomes increasingly hectic. It therefore goes without saying that the demand for effective antidepressants will increase, wherein there will also be a need for a certain diversity thereof, partly with a view to possible side effects which can differ from person to person. In addition, a large part of the population suffers from headache disorders varying from incidental symptoms to possibly chronic migraine. These are also increasing in number.
The present invention has for its object, among others, to provide a psychopharmaceutical preparation which is able to effectively combat psychological disorders of diverse nature, and more particularly migraine and/or depression.
In order to achieve the intended objective, a psychopharmaceutical preparation of the type stated in the preamble has according to a first aspect of the invention the feature that the active substance is characterized by the following structural formula:
Figure imgf000003_0001
in which
Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring; R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group; and R3 represents a single or a double bond.
This is (optionally a derivative of) cyproheptadine in which a benzene ring is substituted with a pyridine ring. This substitution is seen as being responsible for a strong action of the compound as a whole as an antidepressant, in addition to an effective anti-migraine action. Using cyproheptadine this substance can be synthesized relatively simply in that the pyridine group desired therein requires only a relatively simple substitution in the peripheral benzene ring thereof.
In order to achieve the intended objective, a psychopharmaceutical preparation of the type stated in the preamble has according to a second aspect of the invention the feature that the active substance is characterized by the following structural formula:
Figure imgf000004_0001
in which
Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring; and
R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group.
This tricyclic compound also comprises a pyridine group and has the intended action as antidepressant. In addition, this preparation, with the N-alkyl piperidene group bonded to the tricyclic group, provides a strong action against migraine.
The invention is herein based on the insight that these active substances have both a strong antidepressant action and an anti-migraine action. The invention hereby provides a remedy which can be utilized for both symptoms, which may or may not occur simultaneously.
In a preferred embodiment the psychopharmaceutical preparation according to the invention has the feature that Rl represents a hydrogen atom or an organic group substituted therefor in the benzene ring and having a chain of a maximum of four carbon atoms.
In a particular embodiment, the invention relates to an antidepressant comprising the psychopharmaceutical preparation according to the invention as specified above.
In a further particular embodiment, the invention relates to a psychotherapeutic agent against depression and/or headache, in particular migraine, comprising the psychopharmaceutical preparation in accordance with the second aspect of the invention as specified above.
The invention will be further elucidated hereinbelow on the basis of several exemplary embodiments.
Exemplary embodiment 1
Use is made of 4-(5-benzo[a],pyridino[e]cycloheptatrienylidene)-methylpiperidine, generally designated with the following structural formula:
Figure imgf000005_0001
as active substance. In this structural formula Rl represents hydrogen in the benzene ring or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl, R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group, and R3 represents a single or a double bond. This compound is mixed with suitable quantities of binder, filler, flavouring and the like for manufacturing tablets therefrom which each contain a fixed dosage of active substance lying typically between 10 and 50 milligrams. In this example the active substance is mixed with lactose and vegetable starch and pressed to form different tablets which each contain 30 mg respectively 50 mg of active substance per tablet. The tablets are therein provided halfway along with a break line so that the user will be readily able to take a half-dose. In order to distinguish the different doses from each other, the relevant tablets are provided with visual markings such as a specific imprint or colour. Both types of tablet are then arranged per dozen in an air-tight blister pack and placed per two blister packs in a cardboard consumer packaging.
In respect of the agent, an initial choice is preferably made for a relatively low dosage of for instance 15 mg of active substance per day. If a disorder persists, this dosage can be gradually increased to an optimal level. The agent must be used for 2 to 4 weeks and then evaluated in consultation with a doctor.
Exemplary embodiment 2 Use is made as an active substance of
4-(5-benzo[a],pyridino[d]cyclohexadienylidene)-methylpiperidine, generally designated with the following structural formula:
Figure imgf000006_0001
In this structural formula Rl represents hydrogen in the benzene ring or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl, and R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group. This compound is processed into tablets of a dosage of 5 mg respectively 20 mg of active substance per tablet in the same manner as in the above described first exemplary embodiment. In addition to starch and lactose, other per se common substances such as for instance colloidal silicon dioxide, magnesium stearate, methylcellulose, calcium hydrogen phosphate dihydrate, hydroxypropylmethylcellulose and polyethylene glycol can herein also be admixed. The tablets are administered and applied as described in respect of the first example.
Exemplary embodiment 3
The dihydrochloride of the compound of the first exemplary embodiment is used as active substance. This substance is dissolved in water at a dosage of 10 grams per litre. The liquid is packaged in 50 millilitre bottles which are equipped with a precise drop dispenser. The delivery of the dispenser is set here to 1 millilitre per droplet. A precise individual daily dosage is thus possible in consultation with a doctor.
Although the invention has been further elucidated above with reference to only a few exemplary embodiments, it will be apparent that the invention is by no means limited thereto. On the contrary, many other variations and embodiments are possible within the scope of the invention for a person with ordinary skill in the art. The preparation according to the invention can thus be processed as desired into dosages and means of administering other than those described. Within the scope of the invention other substitutes can also be applied within the tricyclic compound in order to enhance the effective action and/or reduce possible side effects. Within the scope of the invention pharmaceutically acceptable acid addition salts of the intended tricyclic compound can in particular be applied in the preparation. The invention generally provides a particularly effective agent against psychological disorders of varying nature.

Claims

Claims
1. Psychopharmaceutical preparation comprising an aromatic, multi-cyclic compound as active substance, in which both a pyridine ring and a benzene ring are present and to which is bonded an N-alkyl piperidene group, characterized in that the active substance is characterized by the following structural formula:
Figure imgf000008_0001
in which
Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring;
R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group; and
R3 represents a single or a double bond.
2. Psychopharmaceutical preparation comprising an aromatic, tricyclic compound as active substance, in which both a pyridine ring and a benzene ring are present and to which is bonded an N-alkyl piperidene group, characterized in that the active substance is characterized by the following structural formula:
Figure imgf000009_0001
in which
Rl represents hydrogen or a group substituted therefor from a collection of an alkyl group, an alkoxy group, a halogen, a hydroxy group, an SH group and trifluoromethyl in the benzene ring; and
R2 represents hydrogen or a group substituted therefor from a collection of an alkyl group and an aralkyl group.
3. Psychopharmaceutical preparation as claimed in claim 1 or 2, characterized in that Rl represents a hydrogen atom or an organic group substituted therefor in the benzene ring and having a chain of a maximum of four carbon atoms.
4. Antidepressant comprising the psychopharmaceutical preparation as claimed in one or more of the foregoing claims.
5. Psychotherapeutic agent against depression and/or headache, in particular migraine, comprising the psychopharmaceutical preparation as claimed in claim 2 or 3.
PCT/NL2005/000502 2004-07-12 2005-07-12 Psychofarmaceutical preparation Ceased WO2006006858A1 (en)

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NL1026634A NL1026634C2 (en) 2004-07-12 2004-07-12 Psychopharmaceutical preparation and active ingredient.

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US12459965B2 (en) 2017-10-09 2025-11-04 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use

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US11629159B2 (en) 2017-10-09 2023-04-18 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US12312375B2 (en) 2017-10-09 2025-05-27 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10954259B1 (en) 2017-10-09 2021-03-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11149044B2 (en) 2017-10-09 2021-10-19 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11180517B2 (en) 2017-10-09 2021-11-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11447510B2 (en) 2017-10-09 2022-09-20 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11505564B2 (en) 2017-10-09 2022-11-22 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US12459965B2 (en) 2017-10-09 2025-11-04 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10947257B2 (en) 2017-10-09 2021-03-16 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11851451B2 (en) 2017-10-09 2023-12-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11939346B2 (en) 2017-10-09 2024-03-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11738035B2 (en) 2019-04-17 2023-08-29 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US12377112B2 (en) 2019-04-17 2025-08-05 Compass Pathfinder Limited Methods of treating neurocognitive disorders, chronic pain and reducing inflammation
US12433904B2 (en) 2019-04-17 2025-10-07 Compass Pathfinder Limited Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US12447164B2 (en) 2019-04-17 2025-10-21 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin

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