RU98108553A - PHARMACEUTICAL COMPOSITIONS CONTAINING HYDROXYMIC ACID DERIVATIVES - Google Patents
PHARMACEUTICAL COMPOSITIONS CONTAINING HYDROXYMIC ACID DERIVATIVESInfo
- Publication number
- RU98108553A RU98108553A RU98108553/14A RU98108553A RU98108553A RU 98108553 A RU98108553 A RU 98108553A RU 98108553/14 A RU98108553/14 A RU 98108553/14A RU 98108553 A RU98108553 A RU 98108553A RU 98108553 A RU98108553 A RU 98108553A
- Authority
- RU
- Russia
- Prior art keywords
- group
- formula
- use according
- pharmaceutically acceptable
- hydroxymycoic
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 150000003839 salts Chemical class 0.000 claims 16
- 239000011780 sodium chloride Substances 0.000 claims 16
- 150000007513 acids Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229940079593 drugs Drugs 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- -1 3-piperidino-2-hydroxy-1-propyl Chemical group 0.000 claims 2
- 210000003470 Mitochondria Anatomy 0.000 claims 2
- MQCKJEXXPCMUMU-UHFFFAOYSA-N N-[amino-[4-[5-[4-[amino(nitroso)methylidene]cyclohexa-2,5-dien-1-ylidene]furan-2-ylidene]cyclohexa-2,5-dien-1-ylidene]methyl]hydroxylamine Chemical compound C1=CC(=C(NO)N)C=CC1=C(C=C1)OC1=C1C=CC(=C(N)N=O)C=C1 MQCKJEXXPCMUMU-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 230000002438 mitochondrial Effects 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000005846 Cardiomyopathy Diseases 0.000 claims 1
- 201000001971 Huntington's disease Diseases 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N Isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- 206010028640 Myopathy Diseases 0.000 claims 1
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 201000008031 cardiomyopathy Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 201000010770 muscular disease Diseases 0.000 claims 1
- 201000009623 myopathy Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N oxygen atom Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004434 sulfur atoms Chemical group 0.000 claims 1
- 0 BC(*)(*C)N(*)OC Chemical compound BC(*)(*C)N(*)OC 0.000 description 1
Claims (18)
где R1 представляет собой водород или C1-5 алкильную группу;
R2 представляет собой водород, C1-5 алкильную группу, C3-8 циклоалкильную группу или фенильную группу, выборочно замещенные гидрокси или фенильной группами, или R1 и R2, совместно с атомом азота, к которому они присоединены, формируют 5 - 8-членное кольцо, выборочно содержащее один или более соседний атом водорода, кислорода или серы, и вышеупомянутое кольцо может быть конденсировано с другим ацикличным или гетероцикличным кольцом, предпочтительно, бензольным, нафталиновым, хинолиновым, изо-хинолиновым, пиридиновым или пиразолиновым кольцом, далее, если желательно и химически возможно, гетероатомы водорода и/или серы представлены в виде оксида или диоксида;
R3 означает водород, фенильную группу, нафтильную группу или пиридильную группу, где вышеупомянутые группы могут быть замещены одним или более атомами галогена или C1-4 алкокси группой (группами);
Y является водородом, гидрокси группой, C1-24 алкокси группой, выборочно замещенными амино группой, C2-24 полиалкенилокси группой, содержащей от 1 до 6 двойных связей, C1-25 алканоил группой, C3-9 алкеноил группой или группой формулы R7-COO-, где R7 представляет собой C2-30 полиалкенил группу, содержащую от 1 до 6 двойных связей;
X является галогеном, амино группой, C1-4 алкокси группой, или X и B формируют атом кислорода, или X и Y, совместно с атомами углерода, к которым они присоединены, и с группой -NR-O-CH2, находящейся между вышеупомянутыми атомами углерода, формируют кольцо формулы
где Z представляет собой кислород или водород;
R является водородом или R и B формируют химическую связь;
A является C1-4 алкиленовой группой или химической связью, или группой формулы
где R4 представляет собой водород, C1-5 алкильную группу, C3-8 циклоалкильную группу или фенильную группу, выборочно замещенные галогеном, C1-4 алкокси группой или C1-5 алкильной группой;
R5 является водородом, C1-4 алкильной группой или фенильной группой;
m имеет значение 0, 1 или 2;
n имеет значение 0, 1 или 2,
или его фармацевтически приемлемые соли добавленных кислот, выборочно в смеси с одним или более носителем (носителями), широко используемыми в фармацевтических композициях для приготовления лекарств, имеющих активность для защиты митохондриального генома и/или митохондрий от повреждений.1. The use of a derivative of hydroxymycoic acid of the formula I
where R 1 represents hydrogen or a C 1-5 alkyl group;
R 2 represents hydrogen, a C 1-5 alkyl group, a C 3-8 cycloalkyl group or a phenyl group, optionally substituted with hydroxy or phenyl groups, or R 1 and R 2 , together with the nitrogen atom to which they are attached, form 5 - An 8-membered ring optionally containing one or more adjacent hydrogen, oxygen or sulfur atoms, and the aforementioned ring can be fused to another acyclic or heterocyclic ring, preferably a benzene, naphthalene, quinoline, iso-quinoline, pyridine or pyrazoline ring, d further, if desired and chemically possible, the heteroatoms of hydrogen and / or sulfur are represented as oxide or dioxide;
R 3 means hydrogen, a phenyl group, a naphthyl group or a pyridyl group, where the above groups may be substituted with one or more halogen atoms or a C 1-4 alkoxy group (s);
Y is hydrogen, a hydroxy group, a C 1-24 alkoxy group selectively substituted with an amino group, a C 2-24 polyalkenyloxy group containing from 1 to 6 double bonds, a C 1-25 alkanoyl group, a C 3-9 alkenoyl group or a group of the formula R 7 -COO-, where R 7 represents a C 2-30 polyalkenyl group containing from 1 to 6 double bonds;
X is a halogen, amino group, C 1-4 alkoxy group, or X and B form an oxygen atom, or X and Y, together with the carbon atoms to which they are attached, and with the group -NR-O-CH 2 located between the aforementioned carbon atoms form a ring of the formula
where Z represents oxygen or hydrogen;
R is hydrogen or R and B form a chemical bond;
A is a C 1-4 alkylene group or a chemical bond, or a group of the formula
where R 4 represents hydrogen, a C 1-5 alkyl group, a C 3-8 cycloalkyl group or a phenyl group optionally substituted with halogen, a C 1-4 alkoxy group or a C 1-5 alkyl group;
R 5 is hydrogen, a C 1-4 alkyl group or a phenyl group;
m is 0, 1 or 2;
n is 0, 1 or 2,
or its pharmaceutically acceptable salts of added acids, optionally in admixture with one or more carrier (s), widely used in pharmaceutical compositions for the preparation of drugs having activity to protect the mitochondrial genome and / or mitochondria from damage.
где R1, R2, R3, R4, R5, m и n таковы, как обозначено в пункте 1, X представляет собой атом галогена или амино группу, Y означает гидроксигруппу или его фармацевтически приемлемые соли добавленных кислот.2. The use according to claim 1, in which a derivative of hydroxymycoic acid of the formula II is used
where R 1 , R 2 , R 3 , R 4 , R 5 , m and n are as indicated in paragraph 1, X represents a halogen atom or an amino group, Y denotes a hydroxy group or its pharmaceutically acceptable salts of added acids.
где R1, R2, R3 и A таковы, как обозначено в п.1, или его фармацевтически приемлемые соли добавленных кислот.3. The use according to claim 1, in which a derivative of hydroxymycoic acid of formula III is used
where R 1 , R 2 , R 3 and A are as defined in claim 1, or its pharmaceutically acceptable salts of added acids.
где R1, R2, R3 и A таковы, как обозначено в пункте 1, Z представляет собой атом кислорода или водорода, или его фармацевтически приемлемые соли добавленных кислот.4. The use according to claim 1, in which a derivative of hydroxymycoic acid of formula IV is used,
where R 1 , R 2 , R 3 and A are as indicated in paragraph 1, Z represents an oxygen or hydrogen atom, or its pharmaceutically acceptable salts of added acids.
где R1, R2, R3 и A таковы, как обозначено в п.1, R6 представляет собой C1-4 алкильную группу, или его фармацевтически приемлемые соли добавленных кислот.5. The use according to claim 1, in which a derivative of hydroxymycoic acid of formula V is used
where R 1 , R 2 , R 3 and A are as defined in claim 1, R 6 represents a C 1-4 alkyl group, or its pharmaceutically acceptable salts of added acids.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUP9502843 | 1995-09-29 | ||
HU9502843A HU9502843D0 (en) | 1995-09-29 | 1995-09-29 | Pharmaceutical composition |
Publications (2)
Publication Number | Publication Date |
---|---|
RU98108553A true RU98108553A (en) | 2000-02-27 |
RU2191005C2 RU2191005C2 (en) | 2002-10-20 |
Family
ID=10987259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU98108553/14A RU2191005C2 (en) | 1995-09-29 | 1996-09-26 | Pharmaceutical compositions comprising derivatives of hydroxamic acid |
Country Status (14)
Country | Link |
---|---|
US (1) | US6306878B1 (en) |
EP (2) | EP0852495B1 (en) |
JP (2) | JP3932559B2 (en) |
KR (1) | KR100363069B1 (en) |
CN (2) | CN1104894C (en) |
AT (1) | ATE321543T1 (en) |
AU (1) | AU7092296A (en) |
CA (1) | CA2233315C (en) |
DE (1) | DE69635996T2 (en) |
HU (1) | HU9502843D0 (en) |
IL (1) | IL123805A (en) |
RU (1) | RU2191005C2 (en) |
UA (1) | UA57712C2 (en) |
WO (1) | WO1997013504A1 (en) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU222994B1 (en) * | 1995-11-02 | 2004-01-28 | BIOREX Kutató és Fejlesztő Rt. | Hydroxylamine derivatives and use thereof in the preparation of a pharmaceutical compositions for enhancing of molecular chaperon production of cells |
HU9701081D0 (en) | 1997-06-23 | 1997-08-28 | Gene Research Lab Inc N | Pharmaceutical composition of antitumoral activity |
HUP9701080A3 (en) | 1997-06-23 | 1999-05-28 | Gene Res Lab Inc New York N | Pharmaceutical composition containing a compound of antiviral activity and a hydroximic acid ester derivative |
AU2474399A (en) * | 1998-01-26 | 1999-08-09 | Mitokor | Mitochondria protecting agents for treating mitochondria associated diseases |
US6268398B1 (en) | 1998-04-24 | 2001-07-31 | Mitokor | Compounds and methods for treating mitochondria-associated diseases |
WO2000007580A2 (en) * | 1998-08-03 | 2000-02-17 | N-Gene Kutató Kft. | Pharmaceutical compositions against autoimmune diseases |
HUP0001583A2 (en) | 2000-04-18 | 2002-11-28 | BIOREX Kutató és Fejlesztő Rt. | A pyridine-1-oxide derivative and process for its transformation into pharmaceutically effective compounds |
HU228783B1 (en) * | 2001-07-26 | 2013-05-28 | Greenearth Cleaning | Dry cleaning apparatus and method capable of utilizing a siloxane solvent |
WO2003057664A1 (en) | 2002-01-11 | 2003-07-17 | Biorex Kutató És Fejlesztö Rt. | Carboxamidine derivatives and their use in the treatment of vascular diseases |
RU2313339C2 (en) | 2003-09-09 | 2007-12-27 | Фумафарм Аг | Using derivatives of fumaric acid in treatment of cardiac insufficiency and asthma |
HUP0303584A3 (en) * | 2003-10-30 | 2009-12-28 | Cytrx Corp | Use of a hydroximic acid halide derivative in the treatment of neurodegenerative diseases |
HUP0401177A2 (en) * | 2004-06-14 | 2007-09-28 | N Gene Res Lab Inc | Pharmaceutical composition for increasing the mitochondrial genesis |
HUP0500145A2 (en) * | 2005-01-28 | 2006-11-28 | Gene Res Lab N | Use of o-(3-piperidino-2-hydroxy-1-propyl)-nicotinic amidoxime for preparation of medicaments against oral diseases |
US7763601B2 (en) * | 2006-11-02 | 2010-07-27 | N-Gene Research Laboratories, Inc. | Prevention and treatment of obesity |
US20080108602A1 (en) * | 2006-11-02 | 2008-05-08 | N-Gene Research Laboratories, Inc. | Prevention of obesity in antipsychotic, antidepressant and antiepileptic medication |
US20110112196A1 (en) | 2007-02-08 | 2011-05-12 | Matvey E Lukashev | Nrf2 screening assays and related methods and compositions |
US20090281143A1 (en) * | 2007-12-10 | 2009-11-12 | N-Gene Research Laboratories, Inc. | Dose Reduction of a Cannabinoid CB1 Receptor Antagonist in the Treatment of Overweight or Obesity |
HUP1100444A2 (en) | 2011-08-17 | 2013-02-28 | Pharma Gene Sa | Pharmaceutical composition |
HUP1100445A2 (en) * | 2011-08-17 | 2013-02-28 | Pharma Gene Sa | Pharmaceutical composition |
CN102408411B (en) * | 2011-09-19 | 2014-10-22 | 北京康辰药业股份有限公司 | Hydroximic acid compound containing quinolyl and preparation method thereof, and drug composition containing the compound and use thereof |
EP3263105A1 (en) | 2016-07-01 | 2018-01-03 | Montana State University | Use of bgp15 to treat familial dysautonomia |
EP3263104A1 (en) * | 2016-07-01 | 2018-01-03 | N-Gene Research Laboratories Inc. | Use of bgp15 to stimulate mitochondrial fusion |
JP7270979B2 (en) | 2017-06-08 | 2023-05-11 | エヌ-ジーン リサーチ ラボラトリーズ,アイエヌシー. | Methods of treating NASH and preventing NASH-induced HCC |
HUP1800298A1 (en) | 2018-08-30 | 2020-05-28 | N Gene Res Laboratories Inc | Combination of beta blocker and hydroximic acid derivative with reduced side effects |
KR20230128462A (en) | 2020-11-19 | 2023-09-05 | 제브라 덴마크 에이/에스 | Process for preparing arimoclomol citrate and intermediates thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4308399A (en) * | 1977-08-30 | 1981-12-29 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | O-(3-Amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same |
HU207988B (en) * | 1988-10-20 | 1993-07-28 | Biorex Kutato Fejlesztoe Kft | Process for producing halogenides of o-/3-amino-2-hydroxy-propyl/hydroximic acid and pharmaceutical compositions containing them as active components |
WO1995030649A1 (en) * | 1994-05-06 | 1995-11-16 | Biorex Kutató És Fejleszto^' Rt. | Novel hydroximic acid derivatives, pharmaceutical compositions containing them and process for preparing same |
-
1995
- 1995-09-29 HU HU9502843A patent/HU9502843D0/en unknown
-
1996
- 1996-09-26 IL IL12380596A patent/IL123805A/en not_active IP Right Cessation
- 1996-09-26 DE DE69635996T patent/DE69635996T2/en not_active Expired - Fee Related
- 1996-09-26 WO PCT/HU1996/000053 patent/WO1997013504A1/en active IP Right Grant
- 1996-09-26 JP JP51484497A patent/JP3932559B2/en not_active Expired - Fee Related
- 1996-09-26 AT AT96931924T patent/ATE321543T1/en not_active IP Right Cessation
- 1996-09-26 RU RU98108553/14A patent/RU2191005C2/en not_active IP Right Cessation
- 1996-09-26 CA CA002233315A patent/CA2233315C/en not_active Expired - Fee Related
- 1996-09-26 AU AU70922/96A patent/AU7092296A/en not_active Abandoned
- 1996-09-26 EP EP96931924A patent/EP0852495B1/en not_active Expired - Lifetime
- 1996-09-26 UA UA98041714A patent/UA57712C2/en unknown
- 1996-09-26 CN CN96197805A patent/CN1104894C/en not_active Expired - Fee Related
- 1996-09-26 EP EP99122692A patent/EP1020187A1/en not_active Withdrawn
- 1996-09-26 KR KR10-1998-0702380A patent/KR100363069B1/en not_active IP Right Cessation
- 1996-09-27 US US08/722,499 patent/US6306878B1/en not_active Expired - Fee Related
-
1999
- 1999-11-12 CN CN99124308A patent/CN1263763A/en active Pending
- 1999-12-03 JP JP11344653A patent/JP2000302676A/en active Pending
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