Patents Assigned to Pliva Farmaceutska, Kemijska, Prehrambena I Kozmeticka
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Patent number: 6399637Abstract: The present invention relates to the characterization of a new crystal modification III of torasemide, to a process for the preparation thereof by the use of controlled acidifying of alkaline solutions of torasemide with inorganic or organic acids with or without addition of a crystal seed, to its use a raw material for the preparation of the crystal modification I of torasemide and of pharmaceutically acceptable salts of torasemide as well as to pharmaceutical forms containing this new crystal modification III of torasemide.Type: GrantFiled: November 5, 1999Date of Patent: June 4, 2002Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Darko Filić, Miljenko Dumić, Aleksandar Danilovski, Bo{haeck over (z)}ena Klepić, Ines Fistrić, Marina Ore{haeck over (s)}ić, Jasna Horvat Mikul{haeck over (c)}ić
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Patent number: 6291518Abstract: The present invention relates to novel hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids of the general formulae I, II, III and IV: wherein R1=R2=4-hydroxycoumarin; R1=R2=4,7-dihydroxycoumarin; R1=R2=4,5,7-trihydroxycoumarin; R1=4-hydroxycoumarin, R2=—CH(OH)CH3. An object of the invention are also processes for the preparation of hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids, and the antiviral action thereof. Novel hydroxy and polyhydroxy derivatives of coumarin according to the present invention exhibit antiviral action against HIV-1 virus.Type: GrantFiled: January 3, 2000Date of Patent: September 18, 2001Assignee: Pliva farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Mladen Trkovnik, Zrinka Ivezić
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Patent number: 6110965Abstract: The present invention relates to the new 15-membered ketoazalides from the class of 6-O-methyl-8a-aza-8a-homo-and 6-O-methyl-9a-aza-9a-homoerythromycin A with the general formula (I) ##STR1## wherein A represents NH group and B at the same time represents C.dbd.O group, orA represents C.dbd.O group and B at the same time represents NH group,R.sup.1 represents OH group, L-cladinosyl group of the formula (II) ##STR2## or together with R.sup.2 represents ketone, R.sup.2 represents hydrogen or together with R.sup.1 represents ketone,R.sup.3 represents hydrogen or C.sub.1 -C.sub.4 alkanoyl group,to intermediates and a process for their preparation, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to the process for the preparation of pharmaceutical compositions, as well as to the use of pharmaceutical compositions for treating bacterial infections.Type: GrantFiled: July 31, 1998Date of Patent: August 29, 2000Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Gorjana Lazarevski, Gabrijela Kobrehel, Zeljko Kelneric
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Patent number: 6100409Abstract: The present invention relates to novel hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids of the general formulae I, II, III and IV: ##STR1## wherein R.sup.1 =R.sup.2 =4-hydroxycoumarin;R.sup.1 =R.sup.2 =4,7-dihydroxycoumarin;R.sup.1 =R.sup.2 =4,5,7-trihydroxycoumarin;R.sup.1 =4-hydroxycoumarin, R.sup.2 =--CH(OH)CH.sub.3.An object of the invention are also processes for the preparation of hydroxy and polyhydroxy derivatives of coumarin fused with dialdehydes and aldehyde acids, and the antiviral action thereof.Novel hydroxy and polyhydroxy derivatives of coumarin according to the present invention exhibit antiviral action against HIV-1 virus.Type: GrantFiled: October 2, 1998Date of Patent: August 8, 2000Assignee: PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija dionicko drustvoInventors: Mladen Trkovnik, Zrinka Ivezic
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Patent number: 6077944Abstract: The invention relates to novel secomacrolides from the class of erythromycin A, potential intermediates for preparation of novel macrolide antibiotics general formula ##STR1## and its pharmaceuticaly acceptable addition salts with inorganic or organic acids, wherein R.sub.1 represents hydrogen, C.sub.1 -C.sub.4 alkanoyl group, arylcarbonyl group and together with R.sub.2 and carbon atoms to which they are bound, cyclic carbonyl or thiocarbonyl group, R.sub.2 represents hydrogen or together with R.sub.1 and carbon atoms to which they are bound, cyclic carbonyl or thiocarbonyl group, R.sub.3 represents hydrogen, C.sub.1 -C.sub.4 alkanoyl or arylcarbonyl group,Z is hydrogen or L-cladinosyl group represented by formula (i) ##STR2## wherein R.sub.4 represents hydrogen or C.sub.1 -C.sub.4 alkanoyl group, W is hydrogen or D-desosaminyl group represented by formula (ii) ##STR3## wherein R.sub.5 represents hydrogen or C.sub.1 -C.sub.4 alkanoyl or arylcarbonyl group,X and Y together represent a lactone, or X is CH.sub.Type: GrantFiled: March 12, 1998Date of Patent: June 20, 2000Assignee: Pliva Farmaceutska, Kemijska, Prehrambena i Kozmeticka Industrija, Dionicko DrustvoInventors: Gorjana Lazarevski, Gabrijela Kobrehel, Amalija Narandja, Zrinka Banic-Tomisic
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Patent number: 6071886Abstract: The present invention relates to .beta.,.beta.-disubstituted derivatives of 9-deoxo-9a-N-ethenyl-9a-aza-9a-homoerythromycin A, new semisynthetic antibiotics of macrolide class of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are mutually the same or different and represent nitrile, carboxy group of the formula COOR.sup.3, wherein R.sup.3 represents C.sub.1 -C.sub.4 alkyl group, or keto group of the formula COR.sup.4, wherein R.sup.4 represents C.sub.1 -C.sub.4 alkyl group, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to a process for the preparation thereof, to a process for the preparation of pharmaceutical compositions, as well as to the use of the obtained pharmaceutical compositions in the treatment of bacterial infections.Type: GrantFiled: December 31, 1998Date of Patent: June 6, 2000Assignee: Pliva Farmaceutska, Kemijska, Prehrambena I Kozmeticka Industrija, Dionicko DrustvoInventors: Nedjeljko Kujundzic, Dina Pavlovic, Gabrijela Kobrehel, Gorjana Lazarevski, Zeljko Kelneric
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Patent number: 5962661Abstract: Seco compounds from a class of tylosins represented by the formula I whereinR stands for H or CH.sub.3,R.sup.1 stands for H, CH.sub.3, C.sub.1 -C.sub.3 acyl or aryl sulfonyl,R.sup.2 stands for H and R.sup.3 stands for NH.sub.2 or OH, or R.sup.2 and R.sup.3 together stand for .dbd.O or .dbd.NOH,R.sup.4 stands for H or C.sub.1 -C.sub.3 acyl,and the line - - - stands for a double or a single bond,and to a process for their preparation are provided.Oximation of 4'-demicarosyl-8a-aza-8a-homorelymycin causes breaking of the lactam to obtain a seco compound. The seco compound can be subjected to reductive N-alkylation or to conversion of the hydroxyimino group into a keto group and then optionally to N- or N,O-acylation, a catalytical hydrogenation of the double bond or a reduction of the ketone or a reduction of the hydroxyimino group into an amino group.Type: GrantFiled: July 14, 1998Date of Patent: October 5, 1999Assignee: Pliva, Farmaceutska, Kemijska, Prehrambena i Kozmeticka Industrija, Dionicko DrustvoInventors: Nevenka Lopotar, Amalija Narandja, Zoran Mandic
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Patent number: 5908933Abstract: The present invention relates to novel coumarin quinolone carboxylic acids wherein the pyridone system is fused in 3,4-, 6,7- and 7,8-positions of the coumarin system, of the general formula I ##STR1## wherein R.sup.1 R.sup.2 =--NHCH=C(CO.sub.2 R.sup.6)CO, R.sup.3 =NO.sub.2 or NH.sub.2, R.sup.4 =R.sup.5 =H, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 R.sup.2 =--NHCH=C(CO.sub.2 R.sup.6)CO, R.sup.3 =R.sup.4 =H, R.sup.5 =F, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 R.sup.2 =--CO(CO.sub.2 R.sup.6)C=CHNH, R.sup.3 =R.sup.4 =R.sup.5 =H, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 R.sup.2 =R.sup.3 R.sup.4 =--NHCH=C(CO.sub.2 R.sup.6)CO, R.sup.5 =H, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 =H or OH, R.sup.2 =R.sup.5 =H, R.sup.3 R.sup.4 =--NHCH (CO.sub.2 R.sup.6)CO, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 =OH, R.sup.2 =R.sup.3 =H, R.sup.4 R.sup.5 =--CO(CO.sub.2 R.sup.6) C=CHNH, R.sup.6 =H or C.sub.2 H.sub.5 ;R.sup.1 =R.sup.5 =H, R.sup.2 =CH.sub.3 or CF.sub.3, R.sup.3 R.sup.4 =--CO(CO.sub.2 R.sup.6)C=CHNH, R.sup.6 =H or C.sub.2 H.sub.Type: GrantFiled: July 18, 1997Date of Patent: June 1, 1999Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Mladen Trkovnik, Zrinka Ivezic, Zeljko Kelneric, Ljerka Polak
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Patent number: 5854219Abstract: The invention relates to 9-N-ethenyl derivatives of 9 (S)-erythromycylamine, new semisynthetic antibiotics of the macrolide class of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxyl group of the formula COOR.sup.3, wherein R.sup.3 represents a C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents a C.sub.1 -C.sub.4 alkyl group, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to a process for their preparation, to a process for the preparation of the pharmaceutical compositions as well as to the use of the obtained pharmaceutical compositions in the treatment of bacterial infections.Type: GrantFiled: October 23, 1997Date of Patent: December 29, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Nedjeljko Kujundzic, Dina Pavlovic, Gabrijela Kobrehel, Gorjana Lazarevski, Zeljko Kelneric
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Patent number: 5847119Abstract: Novel 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3-dibromo-4-oxo-azetidines, to processes for the preparation thereof and to the use thereof are provided. The azetidines of the present invention have the formula I ##STR1## wherein R.sup.1 is hydrogen or bromine,R.sup.2 is hydrogen or bromine, wherein at least one of R.sup.1 or R.sup.2 is bromine,R.sup.3 is hydrogen; Me.sub.2 --C.dbd.C--COOR.sup.4 wherein R.sup.4 is hydrogen, methyl, benzyl or some other carboxy-protective group, andX is bromine or nitroxy group (--ONO.sub.2).According to the invention 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3-dibromo-4-oxo-azetidines are prepared by reacting derivatives of protected penicillanic acid 1,1-dioxides with DBN reactant (1,5-diazabicyclo/3.4.Type: GrantFiled: March 27, 1996Date of Patent: December 8, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventor: Irena Lukic
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Patent number: 5843939Abstract: 3-Bromo- and 3,3-dibromo-4-oxo-1-azetidines of the formula I ##STR1## wherein R.sub.1 is hydrogen or bromo,R.sub.2 is hydrogen or bromo,R.sub.3 is hydrogen, ##STR2## wherein R.sub.4 is hydrogen, methyl, benzyl or some other protective group,R.sub.5 is hydrogen, alkyl, alkylaryl, a heterocyclic ring,Y is a halo atom,X is a halo atom, alkoxy group, nitroxy group are provided along with processes for the preparation thereof and the use thereof.Type: GrantFiled: February 6, 1997Date of Patent: December 1, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventor: Irena Lukic
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Patent number: 5840922Abstract: The present invention relates to new coumarin derivatives represented by the general formula I ##STR1## wherein R.sup.1 =NH.sub.2 or --NHCH.dbd.C(CO.sub.2 C.sub.2 H.sub.5).sub.2, R.sup.2 =R.sup.3 =R.sup.4 =H, R.sup.5 =F,R.sup.1 =R.sup.3 =NHCH.dbd.C(CO.sub.2 C.sub.2 H.sub.5).sub.2, R.sup.2 =R.sup.4 =R.sup.5 =H,R.sup.1 =H or OH, R.sup.3 =NHCH.dbd.C(CO.sub.2 C.sub.2 H.sub.5).sub.2, R.sup.2 =R.sup.4 =R.sup.5 =H,R.sup.1 =OH, R.sup.2 =R.sup.3 =R.sup.4 =H, R.sup.5 =--NHCH.dbd.C(CO.sub.2 C.sub.2 H.sub.5).sub.2,R.sup.1 =R.sup.3 =R.sup.5 =H, R.sup.2 =CH.sub.3 or CF.sub.3, R.sup.4 =--NHCH.dbd.C(CO.sub.2 C.sub.2 H.sub.5).sub.2,processes for the preparation thereof and their use as intermediates for the synthesis of new coumarin derivatives with potential biological action.Type: GrantFiled: July 2, 1997Date of Patent: November 24, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Mladen Trkovnik, Zrinka Ivezic, Ljerka Polak
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Patent number: 5721346Abstract: The present invention refers to the new compounds of the secomacrolide and secoazalide class, a process for the preparation thereof as well as to new intermediates for the preparation of these seco derivatives.Type: GrantFiled: March 7, 1996Date of Patent: February 24, 1998Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Gorjana Lazarevski, Gabrijela Kobrehel
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Patent number: 5688924Abstract: The invention relates to derivatives of 12,13-epoxy-tylosin, the novel seynthetic antibiotics from tylosin group and the methods of their preparation. According to this invention hydrogenation followed by oximation of 12,13-epoxy-tylosin derivatives yields the following tylosin derivatives: 10,11-dihydro-12,13-epoxy, respectively 10,11-dihydro-12,13-epoxy oxime.Direct oximation of 12,13-epoxy tylosin derivative gives 12,13-epoxy oxime derivatives of tylosin.Type: GrantFiled: August 13, 1996Date of Patent: November 18, 1997Assignee: PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, d.d.Inventors: Amalija Narandja, Nevenka Lopotar
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Patent number: 5637581Abstract: Formulations exhibiting antibacterial inhibitory or antitumor action containing an effective amount of 2-bromo-and 2-nitroxy derivatives of 3-bromo and 3,3-dibromo-4-oxo-azetidine, and a method of use of the formulations are provided.Type: GrantFiled: July 10, 1995Date of Patent: June 10, 1997Assignee: PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo ZagrebInventor: Irena Lukic
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Patent number: 5635529Abstract: Novel O-substituted or O-unsubstituted 6-sulfonamido-1,3-dioxepane-5-ols having hypoglycemic activity are obtained from 6-amino-1,3-dioxepane-5-ol, tetrahydro-6H-[1,3]-dioxepino[5,6-d]oxazole, 5,6-epoxy-1,3-dioxepane or N-sulfonyl-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirine as starting materials.Type: GrantFiled: February 17, 1995Date of Patent: June 3, 1997Assignee: PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo ZagrebInventors: Miljenko Dumic, Darko Filic, Mladen Vinkovic, Blanka Jamnicky
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Patent number: 5618968Abstract: The invention provides the preparation procedure for N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine having the general formula (I), where R is hydrogen and the group of the general formula (II), in which R.sub.1 is aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, and n is 0 and 1, and also covers the compounds of the general formula (I), where R is the group of the formula (II), in which R.sub.1 is aryl and alkylaryl group, and n is 0 and 1.According to this invention by condensation of N-substituted derivatives of N-methyl-3-phenyl-3-hydroxypropylamine (XV), where R.sub.1 is benzyl and p-nitrobenzyl group and n is 0, and p-trifluoromethylchlorbenzene (XVI) prepared N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine (I), where R is the group of the formula (II), in which n and R are the same as in the compound (XV), which by the reaction with chloroformic acid esther (XVII), where R.sub.Type: GrantFiled: November 3, 1993Date of Patent: April 8, 1997Assignee: PLIVA Farmaceutska kemijska, Prehrambena i kozmeticka industrija, dionicko drustvoInventors: Zdravko Crnic, Srecko I. Kirin
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Patent number: 5610181Abstract: The invention relates to the process for the preparation of new derivatives of amino-ascorbic acid, their acid and alkali salts, processes for preparation and action.According to this invention derivatives of amino-ascorbic acid are prepared by three types of reactions: 1. reductive alkylation of amino-ascorbic acid; 2. alkylation of primary and secondary amines with halogen-ascorbic acid and 3. acylation of amino-ascorbic acid.Type: GrantFiled: September 18, 1995Date of Patent: March 11, 1997Assignee: Pliva, farmaceutska, kemijska, prehrambena i kozmeticka industrija dionicko drustvoInventors: Bo zidar Su skovi c, Vanja Vela, Mira Bun ci c
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Patent number: 5545659Abstract: Novel 1-(2-,3- or 4-hydroxylaminobenzensulfonyl-1a,2,6,6 a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirines with hypoglycemic activity are prepared by selective reduction of appropriate 1-(2-,3- or 4-nitrobenzenesulfonyl) derivatives.Type: GrantFiled: February 21, 1995Date of Patent: August 13, 1996Assignee: PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvoInventors: Miljenko Dumi c, Darko Fili c, Mladen Vinkovi c, Blanka Jamnicky, Mirela E skinja
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Patent number: 5498699Abstract: The invention relates to the use of complexes and chelates resp., of antitics with bivalent and/or trivalent metals in antiulcer drugs, to new complexes and chelates resp., of antibiotics with bivalent and/or trivalent metals and to processes for the obtaining thereof.Type: GrantFiled: March 6, 1991Date of Patent: March 12, 1996Assignee: PLIVA Farmaceutska kemijska, prehrambena i kozmeticka industrija s.p.o.Inventors: Slobodan Djokic, Zlatko Vajtner, Hrvoje Krnjevic, Nevenka Lopotar, Lidija Kolacny-Babic