LV10426B - STABLE SALTS OF (+)-(1S,2R)-2-{£N-(2-hydroxylamino-2-oxoethyl)-N-methylamino|carbonyl}-cyclohexane-1-carbocyclic acid, process for their preparation and pharmaceutical compositions containing them - Google Patents

STABLE SALTS OF (+)-(1S,2R)-2-{£N-(2-hydroxylamino-2-oxoethyl)-N-methylamino|carbonyl}-cyclohexane-1-carbocyclic acid, process for their preparation and pharmaceutical compositions containing them Download PDF

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Publication number
LV10426B
LV10426B LVP-92-358A LV920358A LV10426B LV 10426 B LV10426 B LV 10426B LV 920358 A LV920358 A LV 920358A LV 10426 B LV10426 B LV 10426B
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Prior art keywords
oxoethyl
carbonyl
cyclohexane
methylamino
hydroxylamino
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LVP-92-358A
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Latvian (lv)
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LV10426A (en
Inventor
Giorgi Raffaello
Subissi Alessandro
Turbanti Luigi
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Guidotti & C Spa Labor
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Publication of LV10426A publication Critical patent/LV10426A/en
Publication of LV10426B publication Critical patent/LV10426B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The novel salts of (+)-(1S,2R)-2-[[N-(2-hydroxylamino-2-oxoethyl)-N-methyl-amino]carbonyl ]cyclohexane-1-carboxylic acid with metals and organic bases, represented by general formula (I) wherein R and R' if taken together represent a bivalent cation selected from calcium, ethylene diamine and other pharmaceutically acceptable cations or organic bases, or if R' = H<+>, R represents sodium, potassium, an imidazole group, lysine, choline, diethanolamine, arginine, or histidine, possess ACE-inhibitory activity and are therefore useful as active ingredients of antihypertensive drugs. The process for their preparation preferably entails the reaction of the starting acid, protected with a benzyl group, with the suitable hydrate, carbonate or organic base in hydrogenation conditions in the presence of a hydrogenation catalyst.

Description

Kopsavilkums:Summary:

Jaunajiem (+)-(1 S,2R)-2-{[N-(2-hidroksilamino-2-oksoetil)-N-metil-amino]karbonii)cik(oheksān-1-karbonskābes sāļiem ar metāliem un organiskām bāzēm, kurus attēlo vispārīgā formula ^''-''^co—N—CHT—co—NH—O I 2 CH, + + RH'The new salts of (+) - (1S, 2R) -2 - {[N- (2-hydroxylamino-2-oxoethyl) -N-methylamino] carbonyl) -cyclohexane-1-carboxylic acid with metals and organic bases, represented by the general formula ^ '' - '' ^ co-N-CHT-co-NH-OI 2 CH, + + RH '

R un R’ ja tie ņemti kopā, apzīmē bivalentu katjonu, izvēlētu no kalcija, etilēndiamina un citiem farmaceitiski pieņemamiem katjoniem vai organiskām bāzēm, vai, jaR and R ', taken together, represent a bivalent cation selected from calcium, ethylenediamine and other pharmaceutically acceptable cations or organic bases, or

R’ ir H+, tadR 'is H + then

R apzīmē nātriju, kāliju, imidazola grupu, lizīnu, holīnu, dietilaminu, argininu vai histidinu, ir AKE-inhibējoša aktivitāte un tāpēc tie ir lietojami kā prethipertenzijas zāļu aktīvie ingredienti. Tos iegūst reaģējot izejas skābei, kas ir aizsargāta ar benzilgrupu, ar piemērotu hidrātu, karbonātu vai organisku bāzi hidrogenēšanas apstākļos un katalizatora klātbūtne.R represents sodium, potassium, imidazole group, lysine, choline, diethylamine, arginine or histidine, have ACE-inhibitory activity and are therefore useful as active ingredients in antihypertensive drugs. They are obtained by reacting the starting acid, which is protected with a benzyl group, with a suitable hydrate, carbonate or organic base under hydrogenation conditions and in the presence of a catalyst.

- 1 Stable salts of (+)-(lS,2R)-2-[[N-(2-hydroxyIamino-2-oxoethyl)-N-methyI-amino]carbonyl]cycIohexanel-carboxylic acid, process for their preparation and pharmaceutical compositions containing them- 1 Stable salts of (+) - (1S, 2R) -2 - [[N- (2-hydroxyamino-2-oxoethyl) -N-methyI-amino] carbonyl] cyclo-hexanel-carboxylic acid, process for their preparation and pharmaceutical compositions containing them

ABSTRACTABSTRACT

The novel salts of (+)-(lS,2R)-2-[[N-(2-hydroxylamino-2-oxoethyl)-N-methyI-amino]carbonyI]cyclohexanel-carboxylic acid vvith metāls and organic bases, represented by the general formulaThe novel salts of (+) - (1S, 2R) -2 - [[N- (2-hydroxylamino-2-oxoethyl) -N-methyI-amino] carbonyI] cyclohexanel-carboxylic acid vvith metal and organic bases represented by the general formula

CH3 ++CH 3 ++

R R* vvherein R and R’ if taken together represent a bivalent cation selected from calcium, ethylene diamine and other pharmaceutically acceptable cations or organic bases, or if R’ = H+, R represents sodium, potassium, an imidazole group, lysine, choline, diethanolamine, arginine, or histidine, possess ACE-inhibitory activity and are threfore useful as active ingredients of antihypertensive drugs.RR * vvherein R and R 'if taken together represent a bivalent cation selected from calcium, ethylene diamine and other acceptable bases or organic bases, or if R' = H + , R represents sodium, potassium, an imidazole group, lysine, choline , diethanolamine, arginine, or histidine, possess ACE-inhibitory activity and are useful as active ingredients of antihypertensive drugs.

The process for their preparation preferably entails the reaction of the starting acid, protected vvith a benzyl group, vvith the suitable hydrate, carbonate or organic base in hydrogenation conditions in the presence of a hydrogentation catalyst.The process for their preparation entails the reaction of the starting acid, protected vvith a benzyl group, vvith a suitable hydrate, carbonate or organic base in the presence of a hydrogentation catalyst.

Claims (10)

1. Stabili (+)-(lS, 2R)-2-[[N-(2-hidroksilamino-2-oksoetiI)-N-metil-amino] karbonil] cikloheksān-l-karbonskābes sāļi, attēloti ar vispārīgo formulu (I)Stable salts of (+) - (1S, 2R) -2 - [[N- (2-hydroxylamino-2-oxoethyl) -N-methylamino] carbonyl] cyclohexane-1-carboxylic acid represented by the general formula (I) ) CO - N - CH9- CO - NH - 0 I z CH, kur R un R', ja tie ņemti kopā, apzīmē bivalentu katjonu, izvēlētu no kalcija, etilēndiamīna un farmaceitiski pieņemamiem katjoniem vai organiskām bāzēm, vai, ja R-H+, R apzīmē nātriju, kāliju, imidazola grupu, lizīnu, holīnu, dietanolamīnu, arginīnu vai histidīnu.CO - N - CH 9 - CO - NH - 0 I z CH, wherein R and R ', taken together, represent a bivalent cation selected from calcium, ethylenediamine and pharmaceutically acceptable cations or organic bases, or when RH + , R represents sodium, potassium, imidazole, lysine, choline, diethanolamine, arginine or histidine. 2. Sāļi pēc 1. punkta, atšķiras ar t o, ka tiem ir AKE-inhibējoša aktivitāte.2. Salts according to claim 1, characterized in that they have ACE-inhibitory activity. 3. Paņēmiens sāļu izgatavošanai, atbilstoši 1. punkta formulai (I), atšķiras ar t o, ka savienojums, izvēlēts starp (+)-(lS, 2R)-2-[[N-(2benzilhidroksiamino-2-oksoetil)-N-metil-amino] karbonil] cikloheksān-l-karbonskābi 2 un (+)-(18, 2R)-2-[[N-(2-hidroksilamino-2-oksoetil)-N-metil-amino] karbonil] cikloheksān-l-karbonskābi 1, reaģē ar savienojumu, izvēlētu starp sārmu vai sārmzemju metālu hidrātiem un karbonātiem vai citiem piemērotiem sāļiem, kā noteikts šajā izgudrojumā, arī ar organiskām bāzēm, organiskā šķīdinātājā vai to maisījumos ar ūdeni, reakcija notiek, izejprodukta 2. gadījumā, ar aizsargājošās benzilgrupas vienlaicīgu hidrogenolīzi ar ūdeņradi atmosfēras spiedienā, piemērota hidrogenēšanas katalizatora klātbūtnē, paņēmiens tiek pabeigts ar izvēlētā skābes 1 sāļa izolēšanu.3. A process for the preparation of salts according to formula (I) according to claim 1, characterized in that the compound selected between (+) - (1S, 2R) -2 - [[N- (2-benzylhydroxyamino-2-oxoethyl) -N- methylamino] carbonyl] cyclohexane-1-carboxylic acid 2 and (+) - (18,2R) -2 - [[N- (2-hydroxylamino-2-oxoethyl) -N-methylamino] carbonyl] cyclohexane-1 -carboxylic acid 1, reacts with a compound selected between the hydrates and carbonates of the alkali or alkaline-earth metals or other suitable salts as defined in this invention, including organic bases, in an organic solvent or mixtures thereof with water, simultaneous hydrogenolysis of the benzyl group with hydrogen under atmospheric pressure in the presence of a suitable hydrogenation catalyst is accomplished by isolation of the selected acid 1 salt. 4. Paņēmiens pēc 3. punkta, a tšķira s ar to, ka skābes 2 maisījumu ar savienojumu, izvēlētu no sārmu vai sārmzemju metāla vai organiskas bāzes hidrātiem un karbonātiem, pakļauj reakcijai ar ūdeņradi atmosfēras spiedienā hidrogenēšanas katalizatora klātbūtnē.4. A process according to claim 3, wherein the mixture of acid 2 with a compound selected from an alkali or alkaline earth metal or organic base hydrates and carbonates is reacted with hydrogen at atmospheric pressure in the presence of a hydrogenation catalyst. 5. Paņēmiens pēc 3. punkta, atšķiras ar To, ka minētais sārmzemju metāls ir kalcijs.5. A process according to claim 3, wherein said alkaline earth metal is calcium. 6. Paņēmiens pēc 3. punkta, atšķiras ar to, Pa minētais sārmu metāls ir izvēlēts starp nātriju un kāliju.6. The process of claim 3, wherein said alkali metal is chosen between sodium and potassium. 7. Paņēmiens pēc 3. punkta, atšķiras ar to,Pa minētais hidrogenēšanas katalizators ir uz apdedzinātām oglēm uznests palādijs.7. The process of claim 3, wherein said hydrogenation catalyst is palladium on charcoal. 8. Paņēmiens pēc 3. punkta, atšķiras ar t o, ka minētais organiskais šķīdinātājs ir izvēlēts no propanola, tetrahidrofurāna un dioksāna.The process according to claim 3, wherein said organic solvent is selected from propanol, tetrahydrofuran and dioxane. 9. Farmaceitiska kompozīcija, atšķiras ar t o, ka tā satur kā aktīvo ingredientu sāli saskaņā ar 1. punktu, arī parastos saistvielas un nesējus.Pharmaceutical composition, characterized in that it contains as an active ingredient salt according to claim 1 also conventional binders and carriers. 10. Farmaceitiska kompozīcija pēc 9. punkta, atšķiras ar t o, ka tai ir prethipertensijas aktivitāte.The pharmaceutical composition according to claim 9, characterized in that it has antihypertensive activity.
LVP-92-358A 1991-12-23 1992-12-23 STABLE SALTS OF (+)-(1S,2R)-2-{£N-(2-hydroxylamino-2-oxoethyl)-N-methylamino|carbonyl}-cyclohexane-1-carbocyclic acid, process for their preparation and pharmaceutical compositions containing them LV10426B (en)

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Application Number Priority Date Filing Date Title
ITMI913448A IT1252708B (en) 1991-12-23 1991-12-23 STABLE SALTS OF (+) - (1R, 2S) -2 ((N- (2-HYDROXYLAMINE-2-OSSOETHL) -N-METHYLAMINE) CARBONYL) CYCLOHEXAN-1-CARBOXYL, ACE INHIBITIVE ACTIVITY, PROCEDURE FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.

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LV10426A LV10426A (en) 1995-02-20
LV10426B true LV10426B (en) 1995-08-20

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EP (1) EP0575572A1 (en)
JP (1) JPH06506002A (en)
CN (1) CN1079474A (en)
AU (1) AU657591B2 (en)
BG (1) BG98050A (en)
BR (1) BR9205652A (en)
CA (1) CA2104372A1 (en)
CZ (1) CZ379692A3 (en)
EE (1) EE9400006A (en)
FI (1) FI933685A (en)
HR (1) HRP921454A2 (en)
HU (1) HUT69287A (en)
IT (1) IT1252708B (en)
LV (1) LV10426B (en)
MA (1) MA22749A1 (en)
MX (1) MX9207543A (en)
NZ (1) NZ245547A (en)
PL (1) PL169086B1 (en)
PT (1) PT101156A (en)
RU (1) RU2079489C1 (en)
SI (1) SI9200409A (en)
SK (1) SK379692A3 (en)
TN (1) TNSN92117A1 (en)
WO (1) WO1993013056A1 (en)
YU (1) YU110892A (en)
ZA (1) ZA9210004B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1264860B1 (en) * 1993-06-21 1996-10-17 Guidotti & C Spa Labor DERIVATIVES OF CIS- AND TRANS-2(((2-(HYDROXYAMINO)-2-OXOETHYL)- ALKYLAMINO)CARBONYL)CYCLOHEXINECARBOXYLIC ACIDS
US5639746A (en) * 1994-12-29 1997-06-17 The Procter & Gamble Company Hydroxamic acid-containing inhibitors of matrix metalloproteases
FR2817241B1 (en) 2000-11-30 2003-03-07 Cebal ALUMINUM TUBE WITH SPLITABLE END
CN101516191A (en) * 2006-09-28 2009-08-26 默克公司 Amine base salts of SAHA and polymorphs thereof
EP4030978A1 (en) * 2020-04-27 2022-07-27 Carter-Hoffmann, LLC Door movement system for cabinet

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* Cited by examiner, † Cited by third party
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IT1224627B (en) * 1988-04-12 1990-10-04 Guidotti & C Spa Labor ACID STARCHES CYCLOMETHYLEN_1,2_DICARBOSSILS THERAPEUTIC ADAPTIVITY, PROCEDURES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.

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TNSN92117A1 (en) 1993-06-08
ITMI913448A0 (en) 1991-12-23
CA2104372A1 (en) 1993-06-24
WO1993013056A1 (en) 1993-07-08
CN1079474A (en) 1993-12-15
JPH06506002A (en) 1994-07-07
PL297118A1 (en) 1993-09-06
BR9205652A (en) 1994-05-03
MX9207543A (en) 1993-08-01
AU3087192A (en) 1993-07-28
EP0575572A1 (en) 1993-12-29
PL169086B1 (en) 1996-05-31
HUT69287A (en) 1995-09-28
IT1252708B (en) 1995-06-26
CZ379692A3 (en) 1993-09-15
SI9200409A (en) 1993-09-30
PT101156A (en) 1994-06-30
SK379692A3 (en) 1995-04-12
EE9400006A (en) 1995-12-15
HU9302389D0 (en) 1993-11-29
NZ245547A (en) 1995-12-21
AU657591B2 (en) 1995-03-16
ZA9210004B (en) 1993-12-13
YU110892A (en) 1996-01-08
FI933685A0 (en) 1993-08-20
FI933685A (en) 1993-08-20
ITMI913448A1 (en) 1993-06-23
HRP921454A2 (en) 1995-02-28
BG98050A (en) 1994-04-29
MA22749A1 (en) 1993-07-01
RU2079489C1 (en) 1997-05-20
LV10426A (en) 1995-02-20

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