Patents Assigned to Laboratoire Roger Bellon
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Patent number: 5556861Abstract: 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: GrantFiled: June 7, 1995Date of Patent: September 17, 1996Assignee: Laboratoire Roger BellonInventors: Eric Bacque, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Michel Kryvenko, Marc P. Lavergne, Jean-Marc Paris, Guy Picaut
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Patent number: 5484921Abstract: 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: GrantFiled: April 8, 1994Date of Patent: January 16, 1996Assignee: Laboratoire Roger BellonInventors: Christophe Daubie, Jean-Jacques Legrand, Clive Pemberton
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Patent number: 5442070Abstract: 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: GrantFiled: April 7, 1994Date of Patent: August 15, 1995Assignee: Laboratoire Roger BellonInventors: Christophe Daubie, Jean-Jacques Legrand, Clive Pemberton
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Patent number: 5403852Abstract: 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: GrantFiled: December 11, 1992Date of Patent: April 4, 1995Assignee: Laboratoire Roger BellonInventors: Michel Barreau, Michel Kryvenko, Marc-Pierre Lavergne, Auguste Techer
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Patent number: 5225207Abstract: 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: GrantFiled: October 15, 1991Date of Patent: July 6, 1993Assignee: Laboratoire Roger BellonInventors: Michel Barreau, Jean-Claude Chottard, Jean-Bernard Le Peco, Patrick Mailliet
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Patent number: 5053509Abstract: 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: GrantFiled: October 30, 1990Date of Patent: October 1, 1991Assignee: Laboratoire Roger BellonInventors: Michel Antoine, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Guy Picaut
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Patent number: 5004745Abstract: 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: GrantFiled: January 16, 1990Date of Patent: April 2, 1991Assignee: Laboratoire Roger BellonInventors: Michel Antoine, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Guy Picaut
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Patent number: 4918105Abstract: 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: GrantFiled: January 5, 1988Date of Patent: April 17, 1990Assignee: SA Laboratoire Roger BellonInventors: Terence Cartwright, Romaine Bouboutou-Tello, Yves Lelievre, Marie-Claude Fournier-Zaluski
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Patent number: 4513001Abstract: 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: GrantFiled: March 22, 1983Date of Patent: April 23, 1985Assignee: Laboratoire Roger BellonInventors: Michel Joannic, Francoise Roquet, Marcel Pesson
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Patent number: 4496566Abstract: 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: GrantFiled: December 21, 1981Date of Patent: January 29, 1985Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Shinichi Nakamura
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Patent number: 4442101Abstract: 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: GrantFiled: February 4, 1982Date of Patent: April 10, 1984Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Hitoshi Ichihashi, Terukazu Tanaka, Yu Imasato
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Patent number: 4382937Abstract: 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: GrantFiled: February 24, 1982Date of Patent: May 10, 1983Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Shinichi Nakamura
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Patent number: 4359578Abstract: 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: GrantFiled: August 23, 1979Date of Patent: November 16, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4352803Abstract: 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: GrantFiled: May 18, 1981Date of Patent: October 5, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4341784Abstract: 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: GrantFiled: September 15, 1980Date of Patent: July 27, 1982Assignees: Dainippon Pharmaceutical Co., Ltd., Laboratoire Roger BellonInventors: Jun-ichi Matsumoto, Yoshiyuki Takase, Yoshiro Nishimura
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Patent number: 4337263Abstract: 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: GrantFiled: June 30, 1980Date of Patent: June 29, 1982Assignee: Laboratoire Roger BellonInventors: Henri Techer, Gilles Monnier, Marcel Pesson
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Patent number: 4129737Abstract: 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: GrantFiled: August 17, 1976Date of Patent: December 12, 1978Assignee: Laboratoire Roger BellonInventor: Marcel Pesson
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Patent number: 4125720Abstract: Process for the preparation of a 4-chloro-5-alkoxycarbonyl-2-methoxy-pyrimidine of the formula: ##STR1## IN WHICH R.sub.Type: GrantFiled: April 12, 1977Date of Patent: November 14, 1978Assignee: Laboratoire Roger BellonInventors: Marcel E. Pesson, Suzanne W. Geiger
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Patent number: 4015002Abstract: 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: GrantFiled: August 1, 1975Date of Patent: March 29, 1977Assignee: Laboratoire Roger BellonInventors: Marcel Pesson, Henri Techer
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Patent number: 3950338Abstract: 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: GrantFiled: July 31, 1973Date of Patent: April 13, 1976Assignee: Laboratoire Roger BellonInventor: Marcel Pesson