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WO1993013056A1 - Sels stables de l'acide (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylique, procede de preparation et compositions pharmaceutiques les contenant - Google Patents

Sels stables de l'acide (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylique, procede de preparation et compositions pharmaceutiques les contenant Download PDF

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Publication number
WO1993013056A1
WO1993013056A1 PCT/EP1992/002903 EP9202903W WO9313056A1 WO 1993013056 A1 WO1993013056 A1 WO 1993013056A1 EP 9202903 W EP9202903 W EP 9202903W WO 9313056 A1 WO9313056 A1 WO 9313056A1
Authority
WO
WIPO (PCT)
Prior art keywords
oxoethyl
carbonyl
carboxylic acid
salts
alkaline
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1992/002903
Other languages
English (en)
Inventor
Raffaello Giorgi
Alessandro Subissi
Luigi Turbanti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Laboratorio Guidotti SpA
Original Assignee
Laboratorio Guidotti SpA
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.)
Filing date
Publication date
Application filed by Laboratorio Guidotti SpA filed Critical Laboratorio Guidotti SpA
Priority to RU9293052414A priority Critical patent/RU2079489C1/ru
Priority to BR9205652A priority patent/BR9205652A/pt
Priority to FI933685A priority patent/FI933685A7/fi
Priority to JP5511398A priority patent/JPH06506002A/ja
Priority to AU30871/92A priority patent/AU657591B2/en
Publication of WO1993013056A1 publication Critical patent/WO1993013056A1/fr
Priority to BG98050A priority patent/BG98050A/bg
Priority to NO93932982A priority patent/NO932982L/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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

Definitions

  • This invention refers to novel salts of
  • (+)-(lS,2R)-2-[[N-(2-hydroxylamino-2-oxoethyl)-N-methyl-amino]carbonyl]cyclohexane- 1-carboxylic acid 1, (D.C.I. Idrapril) is a compound disclosed in the European Patent Application No. 89106304.2 as a novel ACE- inhibitory agent and therefore having antihypertensive activity.
  • This acid when kept exposed to the air in the normal environmental conditions of humidity and temperature, is subject to autodecomposition processes which give rise to impurities obviously incompatible with regard to a therapeutical use. Such degradation processes are also accelerated by a temperature increase of the acid kept in the above conditions.
  • novel salts according to this invention do not undergo to the autodecomposition and degradation processes previously mentioned.
  • the salts of the invention are stable compounds in the normal environmental conditions. Further the salts remain unchanged with time either kept as such or included (in a solid state) in a pharmaceutical preparation (tablets, pills, capsules, lyophilized compositions and the like) provided for their therapeutical use.
  • a pharmaceutical preparation tablettes, pills, capsules, lyophilized compositions and the like
  • the preparation of the compounds of the invention is based on a process characterized in that a compound, selected between
  • (+)-(1S,2R)-2-[[N-(2-hydroxyIamino-2-oxoethyl)-N-methylam ⁇ no]carbonyllcyclohexane-1 -carboxylic acid 1, is reacted with a compound selected among hydrates and carbonates or other suitable salts of alkaline and alkaline-earth metals, as defined in the present invention, as well as with organic bases, in an organic solvent or mixtures thereof with water, the reaction taking place, in the case of the starting product 2, contemporaneous hydrogenalysis of the protecting benzyl group with hydrogen at atmospheric pressure, in the presence of a suitable hydrogenation catalyst, the process being completed by isolating the desired salt of the acid.
  • Q is said hydroxide, or alkaline salt or calcium salt or an organic base.
  • the preferred hydrogenation catalyst is charcoal-supported Pd, but PtO 2 ,Rh/Al 2 O 3 and Ni-Raney can also be used.
  • propanol, tetrahydrofuran and dioxane are also suitable besides methanol and ethanol.
  • the catalyst was filtered and washed with awater/methanol (1/1) mixture (300 ml) and the filtrate, combined with the washings, concentrated under vacuum at 40°C until all the methanol has been removed.
  • the final suspension was cooled for 20 hours at 0-4°C and the precipitate was filtered and washed on the filter with 70 ml precooled water at 0-4°C.
  • (+)-(1S,2R)-2-[[N-(2-hydroxylamino-2-oxoethyI)-N-methylamino ⁇ carbonyl]cyclohexane-1 -carboxylic acid 1 were added and the mixture was further vigorously stirred for 60 minutes at 20°C.
  • the light suspension thus obtained was filtered (on paper) and the filtrate was concentrated under vacuum at 40°C to 200 mL.
  • the precipitated product was filtered and washed on filter with 50 mL of precooled water at 0-4°C.
  • Sample preparation Dissolve 20 mg of sample substance in 100 ml H 2 O/CH 3 CN 80/20
  • Table 1 shows the results, and in the first column, the data for the acid 1, tested in the same way, are reported.
  • the salts of the invention are also, within the suitable dosage ratios, practically comparable either for potency and for the activity lasting time to the acid 1.
  • the salts of this invention constitute the active ingredients for preparing pharmaceutical compositions both for oral and parenteral use.
  • compositions and preparations are made with the well-known pharmaceutical techniques and employing conventional excipients, carriers and solvents.

Landscapes

  • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Nouveaux sels de l'acide (+)-(1S,2R)-2-[[N-(2-hydroxylamino-2-oxoéhyl)-N-méthyl-amino]carbonyl]cyclohexane-1-carboxylique, présentant des bases organiques et métalliques, et représentés par la formule générale (I), dans laquelle R et R', lorsqu'ils sont réunis, représentent un cation bivalent choisi entre le calcium, la diamine d'éthylène et d'autres bases organiques ou cations pharmaceutiquement acceptables, ou, si R'=H+, R représente sodium, potassium, un groupe imidazole, lysine, choline, diéthanolamine, arginine ou hiotidine. Ces sels présentent une activité d'inhibition par rapport à l'enzyme de conversion d'angiotensine (ACE), et sont ainsi utiles comme principes actifs de médicaments anti-hypertensifs. Le procédé de préparation implique de préférence la mise en réaction de l'acide de départ, protégé par un groupe benzyle, avec l'hydrate, le carbonate ou la base organique appropriés, dans des conditions d'hydrogénation en présence d'un catalyseur d'hydrogénation.
PCT/EP1992/002903 1991-12-23 1992-12-12 Sels stables de l'acide (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylique, procede de preparation et compositions pharmaceutiques les contenant Ceased WO1993013056A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
RU9293052414A RU2079489C1 (ru) 1991-12-23 1992-12-12 Стабильные соли (+)-(1s,2r)-2[[n-(2-гидроксиамино-2-оксоэтил)-n-метиламино]-карбонил]циклогексан-1-карбоновой кислоты, способ их получения и фармацевтическая композиция
BR9205652A BR9205652A (pt) 1991-12-23 1992-12-12 Sais estáveis de (+) - (15,2R)-N- (2-hidroxilamina-2-oxoetil)N-metilamino carbonil ciclohexano-ácido carboxilico, processo de sua preparaçao, e composiçao farmaceutica
FI933685A FI933685A7 (fi) 1991-12-23 1992-12-12 (+)-(1S,2R)-2-((N-(2-hydroksyyliamino-2-oksoetyyli)-N-metyyliamino)kar bonyyli)sykloheksaani-1-karboksyylihapon stabiilit suolat, menetelmä n iiden valmistamiseksi ja farmaseuttiset koostumukset, jotka sisältävät niitä
JP5511398A JPH06506002A (ja) 1991-12-23 1992-12-12 （＋）−（１ｓ，２ｒ）−２−［［ｎ−（２−ヒドロキシルアミノ−２−オキソエチル）−ｎ−メチル−アミノ］カルボニル］シクロヘキサン−１−カルボン酸の安定な塩
AU30871/92A AU657591B2 (en) 1991-12-23 1992-12-12 Stable salts of (+)-(1S,2R)-2-((N-(2-hydroxylamino-2-oxoethyl)-N-methyl- amino)carbonyl)cyclohexane-1-carboxylic acid, process for their preparation and pharmaceutical compositions containing them
BG98050A BG98050A (bg) 1991-12-23 1993-08-18 Устойчиви соли на (+)-(1s,2r)-2-//n-(2-хидроксиламино-2- оксоетил)-n-метил-амино/карбонил/циклохексан-1-карбонова киселина, метод за получаването им и фармацевтични състави, в които те се съдържат
NO93932982A NO932982L (no) 1991-12-23 1993-08-20 Stabile salter av (+)-(1s,2r)-2-((n-(2-hydroksylamino-2-oksoetyl)-n-metylamino)karbonyl)cykloheksan-1-karboksylsyreog fremgangsmaate for fremstilling derav og farmasoeytiske sammensetninger som inneholder disse

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI91A003448 1991-12-23
ITMI913448A IT1252708B (it) 1991-12-23 1991-12-23 Sali stabili dell'acido (+)-(1r,2s)-2((n-(2-idrossilammino-2-ossoetil)-n-metilammino)carbonil)cicloesan-1-carbossilico,ad attivita' ace inibitrice, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono.

Publications (1)

Publication Number Publication Date
WO1993013056A1 true WO1993013056A1 (fr) 1993-07-08

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002903 Ceased WO1993013056A1 (fr) 1991-12-23 1992-12-12 Sels stables de l'acide (+)-(1s,2r)-2-[[n-(2-hydroxylamino-2-oxoethyl)-n-methyl-amino]carbonyl]cyclohexane-1-carboxylique, procede de preparation et compositions pharmaceutiques les contenant

Country Status (26)

Country Link
EP (1) EP0575572A1 (fr)
JP (1) JPH06506002A (fr)
CN (1) CN1079474A (fr)
AU (1) AU657591B2 (fr)
BG (1) BG98050A (fr)
BR (1) BR9205652A (fr)
CA (1) CA2104372A1 (fr)
CZ (1) CZ379692A3 (fr)
EE (1) EE9400006A (fr)
FI (1) FI933685A7 (fr)
HR (1) HRP921454A2 (fr)
HU (1) HUT69287A (fr)
IT (1) IT1252708B (fr)
LV (1) LV10426B (fr)
MA (1) MA22749A1 (fr)
MX (1) MX9207543A (fr)
NZ (1) NZ245547A (fr)
PL (1) PL169086B1 (fr)
PT (1) PT101156A (fr)
RU (1) RU2079489C1 (fr)
SI (1) SI9200409A (fr)
SK (1) SK379692A3 (fr)
TN (1) TNSN92117A1 (fr)
WO (1) WO1993013056A1 (fr)
YU (1) YU110892A (fr)
ZA (1) ZA9210004B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2279345A (en) * 1993-06-21 1995-01-04 Guidotti & C Spa Labor Cyclohexanecarboxylic acid derivatives
WO1996020918A1 (fr) * 1994-12-29 1996-07-11 The Procter & Gamble Company Composes a base d'acide hydroxamique inhibiteurs des metalloproteases matricielles
EP2079304A4 (fr) * 2006-09-28 2010-01-06 Merck & Co Inc Sels à base d'acide suberoylanilide-hydroxamique (saha) et des formes polymorphes de ceux-ci

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2817241B1 (fr) 2000-11-30 2003-03-07 Cebal Tube aluminium avec embout secable
EP4030978B1 (fr) * 2020-04-27 2024-11-06 Carter-Hoffmann, LLC Système de mouvement de porte pour une armoire

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337348A2 (fr) * 1988-04-12 1989-10-18 Laboratori Guidotti S.p.A. Amides d'acides cyclométhylène-1,2 bicarboxyliques ayant une activité thérapeutique, procédés pour leur préparation et compositions pharmaceutiques les contenant

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337348A2 (fr) * 1988-04-12 1989-10-18 Laboratori Guidotti S.p.A. Amides d'acides cyclométhylène-1,2 bicarboxyliques ayant une activité thérapeutique, procédés pour leur préparation et compositions pharmaceutiques les contenant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2279345A (en) * 1993-06-21 1995-01-04 Guidotti & C Spa Labor Cyclohexanecarboxylic acid derivatives
WO1996020918A1 (fr) * 1994-12-29 1996-07-11 The Procter & Gamble Company Composes a base d'acide hydroxamique inhibiteurs des metalloproteases matricielles
US5639746A (en) * 1994-12-29 1997-06-17 The Procter & Gamble Company Hydroxamic acid-containing inhibitors of matrix metalloproteases
AU706409B2 (en) * 1994-12-29 1999-06-17 Procter & Gamble Company, The Hydroxamic acid-containing inhibitors of matrix metalloproteases
EP2079304A4 (fr) * 2006-09-28 2010-01-06 Merck & Co Inc Sels à base d'acide suberoylanilide-hydroxamique (saha) et des formes polymorphes de ceux-ci

Also Published As

Publication number Publication date
SI9200409A (en) 1993-09-30
PL297118A1 (en) 1993-09-06
LV10426A (lv) 1995-02-20
ITMI913448A0 (it) 1991-12-23
HUT69287A (en) 1995-09-28
SK379692A3 (en) 1995-04-12
NZ245547A (en) 1995-12-21
CN1079474A (zh) 1993-12-15
PT101156A (pt) 1994-06-30
PL169086B1 (pl) 1996-05-31
YU110892A (sh) 1996-01-08
ITMI913448A1 (it) 1993-06-23
EE9400006A (et) 1995-12-15
HRP921454A2 (en) 1995-02-28
TNSN92117A1 (fr) 1993-06-08
RU2079489C1 (ru) 1997-05-20
MX9207543A (es) 1993-08-01
BR9205652A (pt) 1994-05-03
JPH06506002A (ja) 1994-07-07
CA2104372A1 (fr) 1993-06-24
LV10426B (en) 1995-08-20
EP0575572A1 (fr) 1993-12-29
AU657591B2 (en) 1995-03-16
FI933685L (fi) 1993-08-20
ZA9210004B (en) 1993-12-13
BG98050A (bg) 1994-04-29
HU9302389D0 (en) 1993-11-29
FI933685A0 (fi) 1993-08-20
MA22749A1 (fr) 1993-07-01
FI933685A7 (fi) 1993-08-20
CZ379692A3 (en) 1993-09-15
AU3087192A (en) 1993-07-28
IT1252708B (it) 1995-06-26

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