EP0741571A1 - Utilisation des derives de 2- 4-(azolylbutyl)piperazinyl(methyl)] benzimidazole pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme - Google Patents
Utilisation des derives de 2- 4-(azolylbutyl)piperazinyl(methyl)] benzimidazole pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthmeInfo
- Publication number
- EP0741571A1 EP0741571A1 EP95941089A EP95941089A EP0741571A1 EP 0741571 A1 EP0741571 A1 EP 0741571A1 EP 95941089 A EP95941089 A EP 95941089A EP 95941089 A EP95941089 A EP 95941089A EP 0741571 A1 EP0741571 A1 EP 0741571A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- benzimidazole
- ethoxyethyl
- butyl
- methyl
- piperazin
- 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.)
- Withdrawn
Links
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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to the use of the derivatives of 2. - [4- (azolylbutyl) piperazinyl (methyl)] benzimidazole and the like, and their physiologically acceptable salts for the manufacture of medicaments for the treatment or prophylaxis of asthma in mammals, including humans.
- compositions containing these derivatives and analogues or their salts and in the form of an aerosol intended for the treatment or prophylaxis of asthma in mammals, humans included.
- n can have the values 0 or 1
- n 2 or 3
- X, Y, Z and W equal or different, represent a nitrogen atom or a
- an sulphonic radical carbon atom linked to a hydrogen atom, a halogen atom, a methyl radical, an ethyl carboxylate radical, a carboxylic radical or a sulphonic radical.
- aerosol is meant in the sense of the present invention, all suspensions of solid or liquid particles in a propellant vehicle, in the form of gas, making it possible to accompany the suspension to its place of application.
- These may, for example, be devices commonly known as two-pockets, that is to say formed from a rigid outer container and an elastic inner container, the upper edge of which is fixed to the outer container. .
- the outer container is surmounted by a valve holder cover placed on the upper edge of the outer container and a flow valve which extends into the inner container, a propellant being placed in the free space separating the outer container of the inner container.
- the propellant gas discharges the product contained in the inner container to the outside by the flow valve which is then open.
- the propellant is supplied by the compression of a fluid, which is most often air, inside the container by means of the actuation of the piston of the pump chamber.
- an aerosol can that is to say a container containing the suspension to be vaporized under pressure.
- Examples 1 to 19 are obtained by the methods described in European patents EP 468 884 and EP 507 696, and their properties are set out in Tables 1 and 2. Following these Tables, the properties are illustrated of some derivatives falling within the scope of the present invention.
- Examples 1 to 19 particular compounds corresponding to formula I were used.
- Table 1 the column of the example is indicated, respectively, the number of the example, the values of n and of m and the nature of the radicals R and A; in the last column, the wavelength values (in cm -1 ) are indicated for which the characteristic peaks of each product appear, in infrared spectrometry.
- Table 2 the column number, respectively, is given the example number and the values for which the characteristic NMR peaks appear for each product.
- the U test was performed in different parts of the pulmonary system; it is representative of the vascular permeability at these locations.
- Example 1 decreases the increased permeability by the antigen in all the respiratory tracts, the decrease being statistically significant in the stem bronchi and distal and proximal intrapulmonary.
- the activity of this compound of Example 1 is demonstrated as an anti-asthmatic.
- Solutions in 0.9% NaCl of 0.1 mg / ml, 0.01 mg / ml, 0.001 mg / ml and 0.0003 mg / ml of the compound of Example 1 were used. This corresponds to estimated doses of 50, 5, 0.5 and 0.15 ⁇ g / kg.
- the solutions are placed in an automatic injection pump which feeds a nebulizer (no. 950, Hospitak, NY, USA) and are diluted with filtered air to give the desired concentrations.
- the guinea pigs were anesthetized with pentobarbital. After a tracheal cannulation, the animals were paralyzed with gallamine (10 mg / kg, im) and ventilated (60 strokes / minute, 8 ml / kg) with air supplemented with oxygen (60% v / v ). The jugular vein was cannulated to deliver histamine. Tracheal flow and transpulmonary pressure were measured with a pneumotacograph (Métabo, Switzerland) and a PLS 300 (Mumed, UK). We can immediately deduce the air resistance and the level of protection obtained.
- bronchospasm by intravenous injection of histamine (5.6 ⁇ g / kg) is caused.
- the bronchospasm reflects the increase in air resistance compared to that measured before administering histamine.
- an increase in resistance and an increase in protection compared to the reference group is observed.
- the administration dose is of course a function of the severity of the condition to be treated.
- the derivatives of the invention will, for example, be administered in the form of an aerosol.
- the present invention extends to the use of these compounds and their therapeutically acceptable salts for the manufacture of medicaments intended for the treatment or prophylaxis of asthmatic diseases in mammals, including humans, as well as pharmaceutical compositions containing these compounds or their therapeutically acceptable salts and in the form of an aerosol.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9414766A FR2727865B1 (fr) | 1994-12-08 | 1994-12-08 | Utilisation des derives de 2-(4-(azolybutyl)-piperazinyl- (methyl))-benzimidazole et analogues ainsi que de leurs sels, pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme |
FR9414766 | 1994-12-08 | ||
PCT/EP1995/004884 WO1996017609A1 (fr) | 1994-12-08 | 1995-12-06 | Utilisation des derives de 2-[4-(azolylbutyl)piperazinyl(methyl)] benzimidazole pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0741571A1 true EP0741571A1 (fr) | 1996-11-13 |
Family
ID=9469596
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95941089A Withdrawn EP0741571A1 (fr) | 1994-12-08 | 1995-12-06 | Utilisation des derives de 2- 4-(azolylbutyl)piperazinyl(methyl)] benzimidazole pour la preparation de medicaments destines au traitement ou a la prophylaxie de l'asthme |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0741571A1 (pt) |
JP (1) | JPH09508923A (pt) |
AU (1) | AU714581B2 (pt) |
BR (1) | BR1100852A (pt) |
CA (1) | CA2182904A1 (pt) |
ES (1) | ES2105986B1 (pt) |
FR (1) | FR2727865B1 (pt) |
WO (1) | WO1996017609A1 (pt) |
ZA (1) | ZA9510435B (pt) |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4200641A (en) * | 1976-12-21 | 1980-04-29 | Janssen Pharmaceutica, N.V. | 1-[(Heterocyclyl)-alkyl]-4-diarylmethoxy piperidine derivatives |
JPH0383924A (ja) * | 1989-08-28 | 1991-04-09 | Kanebo Ltd | 経皮投与用組成物 |
FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
FR2668150B1 (fr) * | 1990-10-17 | 1994-11-18 | Theramex | Nouveaux derives du terbutylphenyl 1-amino 4-hydroxybutane, leurs procedes de preparation et les compositions pharmaceutiques en renfermant. |
FR2674856B1 (fr) * | 1991-04-05 | 1993-07-30 | Esteve Labor Dr | Nouveaux antihistaminiques non sedatifs, derives de benzimidazole, leur procede de preparation et leur utilisation en tant que medicaments. |
-
1994
- 1994-12-08 FR FR9414766A patent/FR2727865B1/fr not_active Expired - Fee Related
-
1995
- 1995-12-06 AU AU42611/96A patent/AU714581B2/en not_active Ceased
- 1995-12-06 WO PCT/EP1995/004884 patent/WO1996017609A1/fr not_active Application Discontinuation
- 1995-12-06 JP JP8517338A patent/JPH09508923A/ja active Pending
- 1995-12-06 CA CA002182904A patent/CA2182904A1/fr not_active Abandoned
- 1995-12-06 EP EP95941089A patent/EP0741571A1/fr not_active Withdrawn
- 1995-12-07 ES ES09502465A patent/ES2105986B1/es not_active Expired - Lifetime
- 1995-12-08 ZA ZA9510435A patent/ZA9510435B/xx unknown
-
1997
- 1997-05-12 BR BR1100852-0A patent/BR1100852A/pt active IP Right Grant
Non-Patent Citations (1)
Title |
---|
See references of WO9617609A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2182904A1 (fr) | 1996-06-13 |
BR1100852A (pt) | 1999-10-13 |
ES2105986A1 (es) | 1997-10-16 |
AU4261196A (en) | 1996-06-26 |
AU714581B2 (en) | 2000-01-06 |
ES2105986B1 (es) | 1998-07-01 |
FR2727865B1 (fr) | 1997-07-18 |
WO1996017609A1 (fr) | 1996-06-13 |
JPH09508923A (ja) | 1997-09-09 |
FR2727865A1 (fr) | 1996-06-14 |
ZA9510435B (en) | 1996-06-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK FR GB GR IE IT LI LU MC NL PT SE |
|
17P | Request for examination filed |
Effective date: 19961209 |
|
17Q | First examination report despatched |
Effective date: 20000620 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20010306 |
|
RTI1 | Title (correction) |
Free format text: USE OF 2- 4-(AZOLYLBUTYL)PIPERAZINYL-(METHYL) BENZIMIDAZOLE DERIVATIVES FOR PREPARING DRUGS FOR TREATING OR PREVENTING ASTHMA |