RU95122796A - SUBSTITUTED DERIVATIVES OF ASOLOLON FOR THE TREATMENT OF DISEASES, WHICH ARE CAUSED BY HELICOBACTER, METHOD OF THEIR RECEIVING, PHARMACEUTICAL PREPARATION AND METHOD OF OBTAINING THE PHARMACEUTICAL PREPARATORY - Google Patents

SUBSTITUTED DERIVATIVES OF ASOLOLON FOR THE TREATMENT OF DISEASES, WHICH ARE CAUSED BY HELICOBACTER, METHOD OF THEIR RECEIVING, PHARMACEUTICAL PREPARATION AND METHOD OF OBTAINING THE PHARMACEUTICAL PREPARATORY

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Publication number
RU95122796A
RU95122796A RU95122796/04A RU95122796A RU95122796A RU 95122796 A RU95122796 A RU 95122796A RU 95122796/04 A RU95122796/04 A RU 95122796/04A RU 95122796 A RU95122796 A RU 95122796A RU 95122796 A RU95122796 A RU 95122796A
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RU
Russia
Prior art keywords
pyridinyl
triazole
dihydro
propyl
formula
Prior art date
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RU95122796/04A
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Russian (ru)
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RU2128659C1 (en
Inventor
Хэрес Ян
Эктор Мостманс Жозеф
Альфонс Лео Ван Дер Эйкен Люк
Кристофер Оддс Франк
Антуан Стокбрукс Раймон
Йозеф Мария Ван Дер АА Марсель
Original Assignee
Жансен Фармасетика Н.В.
Priority date (The priority date 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 date listed.)
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Application filed by Жансен Фармасетика Н.В. filed Critical Жансен Фармасетика Н.В.
Priority claimed from PCT/EP1994/000380 external-priority patent/WO1994018978A1/en
Publication of RU95122796A publication Critical patent/RU95122796A/en
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Publication of RU2128659C1 publication Critical patent/RU2128659C1/en

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Claims (5)

1. Замещенные производные азолона формулы I
Figure 00000001

их фармацевтически приемлемые соли с кислотой или стереохимические изомеры,
где Х и Y каждый независимо представляет СН или N; R1, R2 и R3 каждый независимо представляет водород или С1 - С4-алкил;
R4 и R5 каждый независимо представляет водород, галоген, С1-С4-алкил, С1-С4-алкилоксигруппу, гидроксигруппу, трифторметил, трифторметилоксигруппу или дифторметилоксигруппу;
Z представляет С=O или СНОН;
Аr представляет фенил, возможно замещенный вплоть до трех заместителями, выбранными из гидроксигруппы, С1-С4-алкила, С1-С4-алкилоксигруппы, галогена, трифторметила, три(С1-С4-алкил)силилоксигруппы, нитрогруппы, аминогруппы и цианогруппы, или пиридинил, замещенный гидроксигруппой или С1-С4-алкилоксигруппой, и группа
Figure 00000002
представляет радикал формул
Figure 00000003

Figure 00000004

Figure 00000005

Figure 00000006

Figure 00000007

Figure 00000008

при условии, что А отличен от 4-гидроксифенила, три(С1-С4-алкил)-4-гидроксифенила, 3,5-ди(С1-С4-алкил)-4-гидроксифенила или 4-метоксифенила, когда Х = N и группа
Figure 00000009
представляет радикал формулы (а-1).1. Substituted Azolone Derivatives of Formula I
Figure 00000001

their pharmaceutically acceptable salts with an acid or stereochemical isomers,
where X and Y each independently represents CH or N; R 1 , R 2 and R 3 each independently represents hydrogen or C 1 - C 4 -alkyl;
R 4 and R 5 each independently represents hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy;
Z is C = O or CHOH;
Ar represents phenyl, optionally substituted with up to three substituents selected from the hydroxy group, C 1 -C 4 alkyl, C 1 -C 4 alkyloxy group, halogen, trifluoromethyl, tri (C 1 -C 4 alkyl) silyloxy group, nitro groups, amino groups and cyano, or pyridinyl, substituted by a hydroxy group or C 1 -C 4 -alkyloxy group, and
Figure 00000002
represents the radical of formulas
Figure 00000003

Figure 00000004

Figure 00000005

Figure 00000006

Figure 00000007

Figure 00000008

with the proviso that A is other than 4-hydroxyphenyl, tri (C 1 -C 4 alkyl) -4-hydroxyphenyl, 3,5-di (C 1 -C 4 alkyl) -4-hydroxyphenyl or 4-methoxyphenyl, when X = N and group
Figure 00000009
represents a radical of formula (a-1). 2. Соединение по п. 1, отличающееся тем, что оно представляет собой
[1(4-хлорбензоил)пропил] -2,4-дигидро-4-[6-[4-(4-метоксифенил)-1- пиперазинил]-3-пиридинил]-3
Figure 00000010
-1,2,4-триазол-3-он;
2-[1- [(4-хлорбензоил) пропил]-2,4-дигидро-4-[6-[4- (3-гидроксифенил)- 1-пиперазинил]-3-пиридинил]-3
Figure 00000011
-1,2,4-триазол-3-он;
2-[1- [(4-хлорфенил)гидроксиметил] пропил] -2,4-дигидро-4-[6-[4- (3-гидроксифенил)-1-пиперазинил]-3-пиридинил]-3
Figure 00000012
-1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил) пропил)-2,4-дигидpo-4-[4-[4(6-метокси-3-пиридинид]-1-пиперазинил] фенил]-3
Figure 00000013
-1,2,4-триазол-3-он;
2-[1-(4-хлорбензоил)пропил] -4-[6-[4-(3-метоксифенил)-1-пиперазинил] - 3-пиридинил]-2,4-дигидро-3
Figure 00000014
-1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил] пропил] -2,4-дигидро-4-[6-[4- (3-метоксифенил)-1-пиперазинил]-3-пиридинил]-3
Figure 00000015
-1,2,4-триазол-3-он;
2-[1-(4-хлорбензоил)пропил]-4-[6-[4-(3,4-диметоксифенил)-1 -пиперидинил] -3-пиридинил]-2,4-дигидро-3
Figure 00000016
-1,2,4-триазол-3-он;
2-[1- [(4-хлорфенил)гидроксиметил]пропил]-2,4-дигидро-4-[4-[4-(6-метокси -2-пиридинил) 3
Figure 00000017
-1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил] пропил] -4-[6-[4-(3,4 -диметоксифенил)-1-пиперазинил]-3-пиридинил]-2,4-дигидро-3
Figure 00000018
-1,2,4-триазол-3-он;
2-[1-(4-хлорбензоил)пропил]-4-[6-[4-(3,4-диметоксифенил)-1 -пиперазинил] -3-пиридинил] -2,4-дигидро-3
Figure 00000019
- 1,2,4-триазол- 3-он,
их фармацевтически приемлемые соли с кислотами или их стереохимические изомеры.2. The compound according to claim 1, characterized in that it represents
[1 (4-chlorobenzoyl) propyl] -2,4-dihydro-4- [6- [4- (4-methoxyphenyl) -1-piperazinyl] -3-pyridinyl] -3
Figure 00000010
-1,2,4-triazole-3-one;
2- [1- [(4-chlorobenzoyl) propyl] -2,4-dihydro-4- [6- [4- (3-hydroxyphenyl) -1-piperazinyl] -3-pyridinyl] -3
Figure 00000011
-1,2,4-triazole-3-one;
2- [1- [(4-chlorophenyl) hydroxymethyl] propyl] -2,4-dihydro-4- [6- [4- (3-hydroxyphenyl) -1-piperazinyl] -3-pyridinyl] -3
Figure 00000012
-1,2,4-triazole-3-one;
2- [1 - [(4-chlorophenyl) hydroxymethyl) propyl) -2,4-dihydro-4- [4- [4 (6-methoxy-3-pyridinide] -1-piperazinyl] phenyl] -3
Figure 00000013
-1,2,4-triazole-3-one;
2- [1- (4-chlorobenzoyl) propyl] -4- [6- [4- (3-methoxyphenyl) -1-piperazinyl] -3-pyridinyl] -2,4-dihydro-3
Figure 00000014
-1,2,4-triazole-3-one;
2- [1 - [(4-chlorophenyl) hydroxymethyl] propyl] -2,4-dihydro-4- [6- [4- (3-methoxyphenyl) -1-piperazinyl] -3-pyridinyl] -3
Figure 00000015
-1,2,4-triazole-3-one;
2- [1- (4-chlorobenzoyl) propyl] -4- [6- [4- (3,4-dimethoxyphenyl) -1 -piperidinyl] -3-pyridinyl] -2,4-dihydro-3
Figure 00000016
-1,2,4-triazole-3-one;
2- [1- [(4-chlorophenyl) hydroxymethyl] propyl] -2,4-dihydro-4- [4- [4- (6-methoxy -2-pyridinyl) 3
Figure 00000017
-1,2,4-triazole-3-one;
2- [1 - [(4-chlorophenyl) hydroxymethyl] propyl] -4- [6- [4- (3,4-dimethoxyphenyl) -1-piperazinyl] -3-pyridinyl] -2,4-dihydro-3
Figure 00000018
-1,2,4-triazole-3-one;
2- [1- (4-chlorobenzoyl) propyl] -4- [6- [4- (3,4-dimethoxyphenyl) -1 -piperazinyl] -3-pyridinyl] -2,4-dihydro-3
Figure 00000019
- 1,2,4-triazole-3-one
their pharmaceutically acceptable salts with acids or their stereochemical isomers. 3. Способ получения замещенных производных азолона формулы:
Figure 00000020

где Аr, X, R1, R2, R3, R4, R5, Z и группа
Figure 00000021
принимают значения по п. 1, отличающийся тем, что промежуточное соединение формулы (II) N -алкилируют реагентом формулы (III):
Figure 00000022

в инертном в условиях реакции растворителе и в присутствии основания, с последующим при желании превращением соединений формулы (I) друг в друга путем превращения функциональных групп, превращением соединений формулы (I) в их соли с кислотами обработкой фармацевтически приемлемыми кислотами или наоборот превращением солей в свободные основания обработкой щелочью, и/или получением стереохимических изомеров.3. The method of obtaining substituted azolone derivatives of the formula:
Figure 00000020

where Ar, X, R 1 , R 2 , R 3 , R 4 , R 5 , Z and the group
Figure 00000021
The values given in claim 1, wherein the intermediate compound of formula (II) is N-alkylated with a reagent of formula (III):
Figure 00000022

in an inert solvent under the reaction conditions and in the presence of a base, followed, if desired, by converting the compounds of formula (I) into each other by converting functional groups, by converting compounds of formula (I) into their salts with acids, by treatment with pharmaceutically acceptable acids, or vice versa bases by alkali treatment, and / or the production of stereochemical isomers. 4. Фармацевтический препарат, содержащий фармацевтически приемлемый носитель и активный компонент, отличающийся тем, что используют терапевтически эффективное количество соединения формулы I
Figure 00000023

его фармацевтически приемлемую соль с кислотой или его стереохимический изомер, где X, Y, R1-R5, Z, Ar и группа
Figure 00000024
принимают значения по п. 1, при условии, что А отличен от 4-гидроксифенила, три(С1-С4-алкил)-4-гидроксифенила или 3,5-ди(С1-С4-алкил)-4-гидроксифенила, когда Х = N и группа
Figure 00000025
представляет радикал формулы (а-1).4. A pharmaceutical preparation containing a pharmaceutically acceptable carrier and an active ingredient, characterized in that a therapeutically effective amount of the compound of formula I is used
Figure 00000023

its pharmaceutically acceptable salt with an acid or its stereochemical isomer, where X, Y, R 1 -R 5 , Z, Ar and group
Figure 00000024
take the values according to claim 1, provided that A is other than 4-hydroxyphenyl, tri (C 1 -C 4 -alkyl) -4-hydroxyphenyl or 3,5-di (C 1 -C 4 -alkyl) -4- hydroxyphenyl when X = N and a group
Figure 00000025
represents a radical of formula (a-1). 5. Способ получения фармацевтического препарата по п. 4, отличающийся тем, что терапевтически эффективное количество соединения по п. 1 равномерно смешивают с фармацевтически приемлемым носителем. 5. A method for producing a pharmaceutical preparation according to claim 4, wherein a therapeutically effective amount of the compound according to claim 1 is evenly mixed with a pharmaceutically acceptable carrier.
RU95122796A 1993-02-19 1994-02-09 Substituted derivatives of azolone, method of their synthesis, pharmaceutical composition and method of its preparing RU2128659C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP93200474.0 1993-02-19
EP93200474 1993-02-19
PCT/EP1994/000380 WO1994018978A1 (en) 1993-02-19 1994-02-09 Substituted azolone derivatives for treating diseases caused by helicobacter

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RU95122796A true RU95122796A (en) 1998-01-10
RU2128659C1 RU2128659C1 (en) 1999-04-10

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Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5703236A (en) * 1993-12-21 1997-12-30 Schering Corporation Tetrahydrofuran antifungals
AU685935B2 (en) * 1994-04-06 1998-01-29 Janssen Pharmaceutica N.V. Anti-helicobacter ester and carbamate derivatives of azolones
US5607932A (en) * 1994-07-12 1997-03-04 Janssen Pharmaceutica N.V. Heterocyclic derivatives of azolones
US5639754A (en) * 1994-07-12 1997-06-17 Janssen Pharmaceutica N.V. Urea and thiourea derivatives of azolones
US5637592A (en) * 1994-07-12 1997-06-10 Janssen Pharmaceutica N.V. Acyl derivatives of azolones
CA2160423A1 (en) * 1994-11-02 1996-05-03 Hemant N. Joshi Salts of nefazodone having improved dissolution rates
GB9524754D0 (en) * 1995-12-04 1996-04-24 Symmetricom Inc Mobile position determination
SK285198B6 (en) * 1997-10-27 2006-08-03 Neurosearch A/S Homopiperazine derivative, pharmaceutical composition containing this derivative and using of it
US6369087B1 (en) 1999-08-26 2002-04-09 Robert R. Whittle Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same
US6268385B1 (en) 1999-08-26 2001-07-31 Robert R. Whittle Dry blend pharmaceutical formulations
US6312712B1 (en) 1999-08-26 2001-11-06 Robert R. Whittle Method of improving bioavailability
US6262085B1 (en) 1999-08-26 2001-07-17 Robert R. Whittle Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same
US6312723B1 (en) 1999-08-26 2001-11-06 Robert R. Whittle Pharmaceutical unit dosage form
US6326384B1 (en) 1999-08-26 2001-12-04 Robert R. Whittle Dry blend pharmaceutical unit dosage form
US6316020B1 (en) 1999-08-26 2001-11-13 Robert R. Whittle Pharmaceutical formulations
US6262086B1 (en) 1999-08-26 2001-07-17 Robert R. Whittle Pharmaceutical unit dosage form
US6780880B1 (en) 1999-08-26 2004-08-24 Robert R. Whittle FT-Raman spectroscopic measurement
JP4960085B2 (en) * 2003-03-19 2012-06-27 エクセリクシス， インク． TIE-2 modulator and usage
PT2114873E (en) * 2006-12-26 2013-05-06 Lantheus Medical Imaging Inc N-[3-bromo-4-(3- [18f]fluoropropoxy)-benzyl]-guanidine for imaging cardiac innervation
CN102234267A (en) * 2010-04-21 2011-11-09 中国科学院上海药物研究所 Novel triazole antifungal compounds, and medicinal composition, preparation method and application thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4724239A (en) * 1985-09-16 1988-02-09 Morgan Lee R Method of treating chemical ulcers with N,N'-diacetylcystine, N-acetyl homocysteine and N-acetyl cysteine
CA1292472C (en) * 1985-12-03 1991-11-26 Alfonsus Guilielmus Knaeps Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles
US4791111A (en) * 1985-12-23 1988-12-13 Janssen Pharmaceutica, N.V. [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles having anti-microbial properties
CA1331757C (en) * 1988-02-29 1994-08-30 Janssen Pharmaceutica Naamloze Vennootschap 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols
CA2076257A1 (en) * 1991-09-13 1993-03-14 Jan Heeres 4-¬4-¬4-(4-hydroxyphenyl)-1- piperazinyl|phenyl|-5-methyl-3h -1,2,4-triazol-3-one derivatives

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