WO1993013056A1 - 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 - Google Patents
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 Download PDFInfo
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
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 |
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 |
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 |
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 |
FI933685A FI933685A (fi) | 1991-12-23 | 1993-08-20 | Stabila salter av (+)-(1s,2r)-2-((n-(2-hydroxylamino-2-oxoetyl)-n-metylamino)karbonyl)cyklohexan-1-karboxylsyra, deras framstaellningsmetoderoch farmaceutiska sammansaettningar innehaollande dessa |
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 |
---|---|---|---|
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. |
ITMI91A003448 | 1991-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993013056A1 true WO1993013056A1 (en) | 1993-07-08 |
Family
ID=11361409
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1992/002903 WO1993013056A1 (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 |
Country Status (26)
Country | Link |
---|---|
EP (1) | EP0575572A1 (lv) |
JP (1) | JPH06506002A (lv) |
CN (1) | CN1079474A (lv) |
AU (1) | AU657591B2 (lv) |
BG (1) | BG98050A (lv) |
BR (1) | BR9205652A (lv) |
CA (1) | CA2104372A1 (lv) |
CZ (1) | CZ379692A3 (lv) |
EE (1) | EE9400006A (lv) |
FI (1) | FI933685A (lv) |
HR (1) | HRP921454A2 (lv) |
HU (1) | HUT69287A (lv) |
IT (1) | IT1252708B (lv) |
LV (1) | LV10426B (lv) |
MA (1) | MA22749A1 (lv) |
MX (1) | MX9207543A (lv) |
NZ (1) | NZ245547A (lv) |
PL (1) | PL169086B1 (lv) |
PT (1) | PT101156A (lv) |
RU (1) | RU2079489C1 (lv) |
SI (1) | SI9200409A (lv) |
SK (1) | SK379692A3 (lv) |
TN (1) | TNSN92117A1 (lv) |
WO (1) | WO1993013056A1 (lv) |
YU (1) | YU110892A (lv) |
ZA (1) | ZA9210004B (lv) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2279345A (en) * | 1993-06-21 | 1995-01-04 | Guidotti & C Spa Labor | Cyclohexanecarboxylic acid derivatives |
WO1996020918A1 (en) * | 1994-12-29 | 1996-07-11 | The Procter & Gamble Company | Hydroxamic acid-containing inhibitors of matrix metalloproteases |
EP2079304A1 (en) * | 2006-09-28 | 2009-07-22 | Merck & Co., Inc. | Amine base salts of saha and polymorphs thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2817241B1 (fr) | 2000-11-30 | 2003-03-07 | Cebal | Tube aluminium avec embout secable |
US20210332635A1 (en) * | 2020-04-27 | 2021-10-28 | Carter-Hoffmann LLC | Door movement system for cabinet |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0337348A2 (en) * | 1988-04-12 | 1989-10-18 | Laboratori Guidotti S.p.A. | Amides of cyclomethylen-1,2-bicarboxylic acids having therapeutical activity, processes for their preparation and pharmaceutical compositions containing them |
-
1991
- 1991-12-23 IT ITMI913448A patent/IT1252708B/it active IP Right Grant
-
1992
- 1992-12-12 WO PCT/EP1992/002903 patent/WO1993013056A1/en not_active Application Discontinuation
- 1992-12-12 AU AU30871/92A patent/AU657591B2/en not_active Ceased
- 1992-12-12 JP JP5511398A patent/JPH06506002A/ja active Pending
- 1992-12-12 HU HU9302389A patent/HUT69287A/hu unknown
- 1992-12-12 RU RU9293052414A patent/RU2079489C1/ru active
- 1992-12-12 BR BR9205652A patent/BR9205652A/pt not_active Application Discontinuation
- 1992-12-12 CA CA002104372A patent/CA2104372A1/en not_active Abandoned
- 1992-12-12 EP EP92924726A patent/EP0575572A1/en not_active Withdrawn
- 1992-12-21 CZ CS923796A patent/CZ379692A3/cs unknown
- 1992-12-21 SK SK3796-92A patent/SK379692A3/sk unknown
- 1992-12-21 NZ NZ245547A patent/NZ245547A/en unknown
- 1992-12-22 HR HR921454A patent/HRP921454A2/hr not_active Application Discontinuation
- 1992-12-22 MA MA23040A patent/MA22749A1/fr unknown
- 1992-12-22 SI SI9200409A patent/SI9200409A/sl unknown
- 1992-12-23 LV LVP-92-358A patent/LV10426B/lv unknown
- 1992-12-23 TN TNTNSN92117A patent/TNSN92117A1/fr unknown
- 1992-12-23 CN CN92113839A patent/CN1079474A/zh active Pending
- 1992-12-23 YU YU110892A patent/YU110892A/sh unknown
- 1992-12-23 PL PL92297118A patent/PL169086B1/pl unknown
- 1992-12-23 ZA ZA9210004A patent/ZA9210004B/xx unknown
- 1992-12-23 MX MX9207543A patent/MX9207543A/es unknown
- 1992-12-23 PT PT101156A patent/PT101156A/pt not_active Application Discontinuation
-
1993
- 1993-08-18 BG BG98050A patent/BG98050A/bg unknown
- 1993-08-20 FI FI933685A patent/FI933685A/fi not_active Application Discontinuation
-
1994
- 1994-05-23 EE EE9400006A patent/EE9400006A/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0337348A2 (en) * | 1988-04-12 | 1989-10-18 | Laboratori Guidotti S.p.A. | Amides of cyclomethylen-1,2-bicarboxylic acids having therapeutical activity, processes for their preparation and pharmaceutical compositions containing them |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2279345A (en) * | 1993-06-21 | 1995-01-04 | Guidotti & C Spa Labor | Cyclohexanecarboxylic acid derivatives |
WO1996020918A1 (en) * | 1994-12-29 | 1996-07-11 | The Procter & Gamble Company | Hydroxamic acid-containing inhibitors of matrix metalloproteases |
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 |
EP2079304A1 (en) * | 2006-09-28 | 2009-07-22 | Merck & Co., Inc. | Amine base salts of saha and polymorphs thereof |
EP2079304A4 (en) * | 2006-09-28 | 2010-01-06 | Merck & Co Inc | AMINBASE SALTS FROM SAHA AND POLYMORPHE DAVON |
Also Published As
Publication number | Publication date |
---|---|
HU9302389D0 (en) | 1993-11-29 |
ITMI913448A0 (it) | 1991-12-23 |
LV10426A (lv) | 1995-02-20 |
PL297118A1 (en) | 1993-09-06 |
NZ245547A (en) | 1995-12-21 |
LV10426B (en) | 1995-08-20 |
JPH06506002A (ja) | 1994-07-07 |
TNSN92117A1 (fr) | 1993-06-08 |
EE9400006A (et) | 1995-12-15 |
BG98050A (bg) | 1994-04-29 |
FI933685A0 (fi) | 1993-08-20 |
SK379692A3 (en) | 1995-04-12 |
FI933685A (fi) | 1993-08-20 |
HUT69287A (en) | 1995-09-28 |
BR9205652A (pt) | 1994-05-03 |
ZA9210004B (en) | 1993-12-13 |
CN1079474A (zh) | 1993-12-15 |
EP0575572A1 (en) | 1993-12-29 |
AU3087192A (en) | 1993-07-28 |
SI9200409A (en) | 1993-09-30 |
ITMI913448A1 (it) | 1993-06-23 |
HRP921454A2 (en) | 1995-02-28 |
MX9207543A (es) | 1993-08-01 |
RU2079489C1 (ru) | 1997-05-20 |
MA22749A1 (fr) | 1993-07-01 |
PT101156A (pt) | 1994-06-30 |
CA2104372A1 (en) | 1993-06-24 |
CZ379692A3 (en) | 1993-09-15 |
IT1252708B (it) | 1995-06-26 |
YU110892A (sh) | 1996-01-08 |
PL169086B1 (pl) | 1996-05-31 |
AU657591B2 (en) | 1995-03-16 |
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