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 PREPARATORYInfo
- 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
- Authority
- RU
- Russia
- Prior art keywords
- pyridinyl
- triazole
- dihydro
- propyl
- formula
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 3
- 241000589989 Helicobacter Species 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical class O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- -1 6-methoxy -2-pyridinyl Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Claims (5)
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 представляет радикал формул
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 представляет радикал формулы (а-1).1. Substituted Azolone Derivatives of Formula I
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 represents the radical of formulas
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 represents a radical of formula (a-1).
[1(4-хлорбензоил)пропил] -2,4-дигидро-4-[6-[4-(4-метоксифенил)-1- пиперазинил]-3-пиридинил]-3 -1,2,4-триазол-3-он;
2-[1- [(4-хлорбензоил) пропил]-2,4-дигидро-4-[6-[4- (3-гидроксифенил)- 1-пиперазинил]-3-пиридинил]-3 -1,2,4-триазол-3-он;
2-[1- [(4-хлорфенил)гидроксиметил] пропил] -2,4-дигидро-4-[6-[4- (3-гидроксифенил)-1-пиперазинил]-3-пиридинил]-3-1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил) пропил)-2,4-дигидpo-4-[4-[4(6-метокси-3-пиридинид]-1-пиперазинил] фенил]-3-1,2,4-триазол-3-он;
2-[1-(4-хлорбензоил)пропил] -4-[6-[4-(3-метоксифенил)-1-пиперазинил] - 3-пиридинил]-2,4-дигидро-3 -1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил] пропил] -2,4-дигидро-4-[6-[4- (3-метоксифенил)-1-пиперазинил]-3-пиридинил]-3-1,2,4-триазол-3-он;
2-[1-(4-хлорбензоил)пропил]-4-[6-[4-(3,4-диметоксифенил)-1 -пиперидинил] -3-пиридинил]-2,4-дигидро-3-1,2,4-триазол-3-он;
2-[1- [(4-хлорфенил)гидроксиметил]пропил]-2,4-дигидро-4-[4-[4-(6-метокси -2-пиридинил) 3-1,2,4-триазол-3-он;
2-[1-[(4-хлорфенил)гидроксиметил] пропил] -4-[6-[4-(3,4 -диметоксифенил)-1-пиперазинил]-3-пиридинил]-2,4-дигидро-3 -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- 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 -1,2,4-triazole-3-one;
2- [1- [(4-chlorobenzoyl) propyl] -2,4-dihydro-4- [6- [4- (3-hydroxyphenyl) -1-piperazinyl] -3-pyridinyl] -3 -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 -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 -1,2,4-triazole-3-one;
2- [1- (4-chlorobenzoyl) propyl] -4- [6- [4- (3-methoxyphenyl) -1-piperazinyl] -3-pyridinyl] -2,4-dihydro-3 -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 -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 -1,2,4-triazole-3-one;
2- [1- [(4-chlorophenyl) hydroxymethyl] propyl] -2,4-dihydro-4- [4- [4- (6-methoxy -2-pyridinyl) 3 -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 -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 - 1,2,4-triazole-3-one
their pharmaceutically acceptable salts with acids or their stereochemical isomers.
где Аr, X, R1, R2, R3, R4, R5, Z и группа принимают значения по п. 1, отличающийся тем, что промежуточное соединение формулы (II) N -алкилируют реагентом формулы (III):
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:
where Ar, X, R 1 , R 2 , R 3 , R 4 , R 5 , Z and the group The values given in claim 1, wherein the intermediate compound of formula (II) is N-alkylated with a reagent of formula (III):
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.
его фармацевтически приемлемую соль с кислотой или его стереохимический изомер, где X, Y, R1-R5, Z, Ar и группа 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 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
its pharmaceutically acceptable salt with an acid or its stereochemical isomer, where X, Y, R 1 -R 5 , Z, Ar and group 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 represents a radical of formula (a-1).
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU95122796A true RU95122796A (en) | 1998-01-10 |
RU2128659C1 RU2128659C1 (en) | 1999-04-10 |
Family
ID=8213653
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU95122796A RU2128659C1 (en) | 1993-02-19 | 1994-02-09 | Substituted derivatives of azolone, method of their synthesis, pharmaceutical composition and method of its preparing |
Country Status (19)
Country | Link |
---|---|
US (1) | US5650411A (en) |
EP (1) | EP0684821A1 (en) |
JP (1) | JPH08506821A (en) |
CN (1) | CN1118138A (en) |
AP (1) | AP435A (en) |
AU (1) | AU675508B2 (en) |
CA (1) | CA2155830A1 (en) |
FI (1) | FI953899A (en) |
HU (1) | HUT73662A (en) |
IL (1) | IL108703A (en) |
LT (1) | LT3214B (en) |
MX (1) | MX9401294A (en) |
NO (1) | NO953254L (en) |
NZ (1) | NZ261854A (en) |
PL (1) | PL174836B1 (en) |
RU (1) | RU2128659C1 (en) |
TW (1) | TW279864B (en) |
WO (1) | WO1994018978A1 (en) |
ZA (1) | ZA941137B (en) |
Families Citing this family (20)
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)
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 |
-
1994
- 1994-02-02 TW TW083100854A patent/TW279864B/zh active
- 1994-02-09 CN CN94191221A patent/CN1118138A/en active Pending
- 1994-02-09 US US08/491,960 patent/US5650411A/en not_active Expired - Fee Related
- 1994-02-09 HU HU9501923A patent/HUT73662A/en unknown
- 1994-02-09 EP EP94907534A patent/EP0684821A1/en not_active Withdrawn
- 1994-02-09 CA CA002155830A patent/CA2155830A1/en not_active Abandoned
- 1994-02-09 AU AU61081/94A patent/AU675508B2/en not_active Ceased
- 1994-02-09 JP JP6518613A patent/JPH08506821A/en active Pending
- 1994-02-09 PL PL94310348A patent/PL174836B1/en unknown
- 1994-02-09 WO PCT/EP1994/000380 patent/WO1994018978A1/en not_active Application Discontinuation
- 1994-02-09 NZ NZ261854A patent/NZ261854A/en unknown
- 1994-02-09 RU RU95122796A patent/RU2128659C1/en active
- 1994-02-18 MX MX9401294A patent/MX9401294A/en unknown
- 1994-02-18 AP APAP/P/1994/000622A patent/AP435A/en active
- 1994-02-18 ZA ZA941137A patent/ZA941137B/en unknown
- 1994-02-18 LT LTIP1874A patent/LT3214B/en not_active IP Right Cessation
- 1994-02-18 IL IL108703A patent/IL108703A/en not_active IP Right Cessation
-
1995
- 1995-08-18 NO NO953254A patent/NO953254L/en unknown
- 1995-08-18 FI FI953899A patent/FI953899A/en unknown
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