Patents Assigned to Laboratoire Roger Bellon
  • Patent number: 5556861
    Abstract: This invention relates to a novel 1,8 benzo[b]naphythyridine derivative of general formula (I), ##STR1## wherein R is H or a hydroxy, amino or alkylamino radical optionally substituted by amino or hydroxy, or R is dialkylamino of which the alkyl portions may form, with the nitrogen atom, a 5- or 6-membered heterocyclic ring which optionally contains a further heteroatom chosen from nitrogen, oxygen or sulphur, or R is C.sub.3-6 cycloalkylamino or an alkanylamino, N-alkyl N-alkanylamino or aminoalkylphenylamino radical; R.sub.1 and R.sub.2, which are the same or different, are in positions 2 and 3 and represent H, alkyl, C.sub.2-4 alkenyl, phenyl, or substituted phenyl, or R.sub.1 and R.sub.2 are in position 2 and represent alkyl; R.sub.3 is H or alkyl, fluoroalkyl, carboxyalkyl, C.sub.3-6 cycloalkyl, fluorophenyl, difluorophenyl, alkyloxy or alkylamino; and R.sub.4 is H or F, wherein the C.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 17, 1996
    Assignee: Laboratoire Roger Bellon
    Inventors: Eric Bacque, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Michel Kryvenko, Marc P. Lavergne, Jean-Marc Paris, Guy Picaut
  • Patent number: 5484921
    Abstract: This invention relates to a method for the preparation of benzo[b]naphthyridines having the general formula (I) ##STR1## comprising: 1) condensation of an amine having the formula R'--NH--CH.sub.2 --CH.sub.2 --R" with a chlorofluoroquinoline of formula (II) ##STR2## 2) cyclization of the obtained fluoroquinoline of formula (IV) ##STR3## and; 3) oxidation of tetrahydro-1,2,3,4benzo[b]naphthyridine-1,8 of formula (V) ##STR4## is effected, and then, optionally, the ester obtained is transformed into an acid and optionally into a salt.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: January 16, 1996
    Assignee: Laboratoire Roger Bellon
    Inventors: Christophe Daubie, Jean-Jacques Legrand, Clive Pemberton
  • Patent number: 5442070
    Abstract: This invention relates to new derivatives of fluoro quinoline carboxylic-3 acid having general formula (I), ##STR1## wherein R is a hydrogen atom or an alkyl radical and Hal is a halogen atom, as well as salts thereof, when they exist, preparation thereof and utilization as synthesis intermediary.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: August 15, 1995
    Assignee: Laboratoire Roger Bellon
    Inventors: Christophe Daubie, Jean-Jacques Legrand, Clive Pemberton
  • Patent number: 5403852
    Abstract: Oxazole derivatives of the formula ##STR1## wherein R and R' are each hydrogen or alkyl containing 1 or 2 carbon atoms, R.sub.1 and R.sub.2 are the same or different and represent hydrogen, halogen or straight- or branched-chain (C.sub.1-4) alkyloxy radicals, and n is 3-6; their salts their isomers and mixtures and their preparation method, are method are described. These derivatives display anti-inflammatory activity.
    Type: Grant
    Filed: December 11, 1992
    Date of Patent: April 4, 1995
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Barreau, Michel Kryvenko, Marc-Pierre Lavergne, Auguste Techer
  • Patent number: 5225207
    Abstract: New complexes of general formula (I) in whichR.sub.1 and R.sub.2 together form a saturated or unsaturated polycyclic carbocyclic radical containing 7 to 12 carbon atoms, or a saturated or partially saturated mono-, bi- or tricyclic heterocyclic radical containing 5 to 11 chain members and a hetero-atom chosen from oxygen, sulphur or nitrogen, which latter atom can optionally be substituted by an alkoxycarbonyl radical, and,X.sub.1 and X.sub.2 represent chlorine atoms or together formeither a radical of structure: ##STR1## in which n is 0 to 2 and R.sub.6 and R.sub.7, which are identical or different, are hydrogen atoms or, when n=1, can be alkyl radicals or form, together with the carbon atom to which they are attached, a cyclobutyl radical,or a radical of structure: ##STR2## in which n, R.sub.6 and R.sub.7 are defined as above, or their salts where such exist, and their hydrates, their preparation and the pharmaceutical compositions which contain them.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Barreau, Jean-Claude Chottard, Jean-Bernard Le Peco, Patrick Mailliet
  • Patent number: 5053509
    Abstract: New benzo[b][1,8]naphthyridine derivatives of general formula (I), in which R.sub.1 is a hydrogen atom or a hydroxyl or alkyl radical, R.sub.2 is a hydrogen atom or an alkyl, fluoroalkyl, cycloalkyl (3 to 6 C), alkyloxy or alkylamino radical, R.sub.3 is a phenyl or phenylalkyl radical substituted with one or more halogen atoms or alkyl, cycloalkyl (3 to 6 C), alkyloxy, cyano, amino, alkylamino, dialkylamino, alkyloxyalkyl, hydroxyalkyl, hydroxyalkyloxy, methylenedioxy, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl radicals, or R.sub.3 is a heterocyclic radical, and R.sub.4 is a hydrogen atom or a fluorine atom, the alkyl radicals (1 to 4 C) being linear or branched, their salts, their preparation and compositions containing them.These new products are useful as antimicrobials, or in the treatment of AIDS.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: October 1, 1991
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Antoine, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Guy Picaut
  • Patent number: 5004745
    Abstract: New benzo[b][1,8]naphthyridine derivatives of general formula (I) in which R.sub.1 is a hydrogen atom or an alkyl or hydroxyalkyl radical, R.sub.2 is a hydrogen atom or an alkyl, fluoroalkyl, cycloalkyl (3 to 6 C), alkoxy or alkylamino radical and R.sub.3 is alkyl, R.sub.4 and R.sub.5 are different and are hydrogen or alkyl, or R.sub.3 is H, alkyl or cycloalkyl and R.sub.4 and R.sub.5 are hydrogen, R.sub.6 is hydrogen or fluorine and n is equal to 1 or 2, their salts, their preparation and the compositions which contain them.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: April 2, 1991
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Antoine, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Guy Picaut
  • Patent number: 4918105
    Abstract: The present invention relates to a novel family of chemical compounds possessing a pharmacological activity, in particular a collagenase-inhibiting activity, a process for the production of these compounds and pharmaceutical compositions in which they are present.According to the invention, these compounds correspond to the general formula: ##STR1## in which: W represents an amino acid residue selected from the group comprising valine, lysine, norleucine and methionine, andZ represents an amino radical or an alkylamino radical of which the alkyl part, which contains 1 or 2 carbon atoms, is substituted by a phenyl or trifluorophenyl radical,and also include their diastereoisomers and their addition salts with pharmaceutically acceptable acids.The invention is applicable especially in the pharmaceutical industry.
    Type: Grant
    Filed: January 5, 1988
    Date of Patent: April 17, 1990
    Assignee: SA Laboratoire Roger Bellon
    Inventors: Terence Cartwright, Romaine Bouboutou-Tello, Yves Lelievre, Marie-Claude Fournier-Zaluski
  • Patent number: 4513001
    Abstract: Novel compounds with .beta.-adrenergic properties comprising 1-[1-benzimidazolyl] N-[2-(4-hydroxy 3-methoxy phenyl) 2-hydroxy ethyl]3-amino butane, corresponding to the following formula ##STR1## as well as its addition salts with pharmaceutically acceptable non-toxic inorganic or organic acids, and the hydrates of said salts. These compounds are particularly useful for the treatment of asthma and in the case of premature labor.
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: April 23, 1985
    Assignee: Laboratoire Roger Bellon
    Inventors: Michel Joannic, Francoise Roquet, Marcel Pesson
  • Patent number: 4496566
    Abstract: A 1,8-naphthyridine compound of the formula ##STR1## wherein R.sub.1 is a lower alkyl group, and the esters and salts thereof. The 1,8-naphthyridine compound of the formula (I) in which R.sub.1 is a methyl group is useful as an antibacterial agent.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: January 29, 1985
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Shinichi Nakamura
  • Patent number: 4442101
    Abstract: Novel 1-ethyl-6-fluoro-1,4-dihyono-4-oxo -7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid.sesquihydrate (ATT-2266.sesquihydrate). The aforesaid compound can be prepared by heating 1-ethyl-6-fluoro-1,4-dihydro-4-oxo -7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid at a temperature above about 60.degree. C. in the presence of water in an amount sufficient to form the sesquihydrate. This sesquihydrate is much more stable than the anhydrate and the trihydrate and is superior to the anhydrate in the rate of dissolution and transference into the body through the intestines. Thus, it is especially useful as a pharmaceutical compound.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: April 10, 1984
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Hitoshi Ichihashi, Terukazu Tanaka, Yu Imasato
  • Patent number: 4382937
    Abstract: A 1,8-naphthyridine compound of the formula ##STR1## wherein R is a vinyl or 2-fluoroethyl group, andR.sub.1 and R.sub.2 are the same or different and each represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms,and the esters thereof and salts thereof. For example, 7-(3-amino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1-vinyl-1,8-naphthyr idine-3-carboxylic acid and nontoxic salts thereof, which are covered by the aforesaid compound, are useful as an antibacterial agent.
    Type: Grant
    Filed: February 24, 1982
    Date of Patent: May 10, 1983
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Shinichi Nakamura
  • Patent number: 4359578
    Abstract: This invention relates to 1,8-naphthyridine compounds of the formula ##STR1## wherein X is a halogen atom especially fluorine atom,R.sub.1 is an ethyl group or a vinyl group, andR.sub.2 is a hydrogen atom or a lower alkyl group, their salts and processes for the preparation of them.The 1,8-naphthyridine compounds and their salts are useful as antibacterial agents and intermediates thereof.
    Type: Grant
    Filed: August 23, 1979
    Date of Patent: November 16, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4352803
    Abstract: This invention relates to 1,8-naphthyridine compounds of the formula ##STR1## wherein X is a halogen atom especially fluorine atom,R.sub.1 is an ethyl group or a vinyl group, andR.sub.2 is a hydrogen atom or a lower alkyl group, their salts and processes for the preparation of them.The 1,8-naphthyridine compounds and their salts are useful as antibacterial agents and intermediates thereof.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: October 5, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4341784
    Abstract: The present invention provides a 1,8-naphthyridine compound of the formula ##STR1## wherein R is hydrogen, methyl, ethyl or propyl, and a nontoxic pharmaceutically acceptable salt thereof, and a process for preparing a 1,8-naphthyridine compound of the above formula which comprises(A) reacting a compound of the formula ##STR2## wherein Y is halogen, lower alkoxy, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower alkylsulfonyloxy or arylsulfonyloxy, and R.sub.1 is hydrogen or lower alkyl,with a compound of the formula ##STR3## wherein R.sub.2 is hydrogen or a protective group for the amino group, and R is as defined above,and when a reaction product in which R.sub.1 is lower alkyl and/or R.sub.2 is the amino protective group is obtained, treating it with an acid or base, and/or reductively cleaving it,(B) decomposing a compound of the formula ##STR4## wherein A .crclbar. is a fluorine-containing anion, and R.sub.1 and R.sub.2 are as defined above,and when a reaction product in which R.sub.
    Type: Grant
    Filed: September 15, 1980
    Date of Patent: July 27, 1982
    Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger Bellon
    Inventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
  • Patent number: 4337263
    Abstract: 1-Aryl-4-.gamma.-arylsulphonyl-3-aminopropoxy-1H-pyrazoles of the formula: ##STR1## and their acid addition salts. Application of these compounds as medicaments useful in particular as hypolipemiant or hypocholesterolemiant agents.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 29, 1982
    Assignee: Laboratoire Roger Bellon
    Inventors: Henri Techer, Gilles Monnier, Marcel Pesson
  • Patent number: 4129737
    Abstract: Valuable antibacterial 8-alkyl-5-oxo-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acids, some of which are new compounds, are made from corresponding pyrimidines by a process involving condensation with an amino-ester, cyclization, halogenation, dehydrohalogenation, and saponification.
    Type: Grant
    Filed: August 17, 1976
    Date of Patent: December 12, 1978
    Assignee: Laboratoire Roger Bellon
    Inventor: Marcel Pesson
  • Patent number: 4125720
    Abstract: Process for the preparation of a 4-chloro-5-alkoxycarbonyl-2-methoxy-pyrimidine of the formula: ##STR1## IN WHICH R.sub.
    Type: Grant
    Filed: April 12, 1977
    Date of Patent: November 14, 1978
    Assignee: Laboratoire Roger Bellon
    Inventors: Marcel E. Pesson, Suzanne W. Geiger
  • Patent number: 4015002
    Abstract: This invention relates to 1-aryl-2-oxo-2,4,5,6,7,7a-hexahydro-indoles, and acid addition salts thereof. In particular, the compounds have (.beta.-aminoethoxy- or .gamma.-amino-propoxy)-phenyl substituents, the amino groups in each case either being joined to two C.sub.1.sub.-5 alkyl groups or forming part of a heterocyclic group such as a pyrolidino, piperidino or morpholino group. Compounds in accordance with the invention have been found to exhibit interesting actions on the cardiovascular system in particular as vasodilators.
    Type: Grant
    Filed: August 1, 1975
    Date of Patent: March 29, 1977
    Assignee: Laboratoire Roger Bellon
    Inventors: Marcel Pesson, Henri Techer
  • Patent number: 3950338
    Abstract: Valuable antibacterial 8-alkyl-5-oxo-5,8-dihydro-pyrido(2,3-d)pyrimidine-6-carboxylic acids, some of which are new compounds, are made from corresponding pyrimidines by a process involving condensation with an amino-ester, cyclization, halogenation, dehydrohalogenation, and saponification.
    Type: Grant
    Filed: July 31, 1973
    Date of Patent: April 13, 1976
    Assignee: Laboratoire Roger Bellon
    Inventor: Marcel Pesson