[go: up one dir, main page]

FI76072B - Foerfarande foer framstaellning av terapeutiskt verkande oktahydro-1-( -merkaptoalkanoyl)-1h-indol-2- karboxylsyrafoereningar. - Google Patents

Foerfarande foer framstaellning av terapeutiskt verkande oktahydro-1-( -merkaptoalkanoyl)-1h-indol-2- karboxylsyrafoereningar. Download PDF

Info

Publication number
FI76072B
FI76072B FI810971A FI810971A FI76072B FI 76072 B FI76072 B FI 76072B FI 810971 A FI810971 A FI 810971A FI 810971 A FI810971 A FI 810971A FI 76072 B FI76072 B FI 76072B
Authority
FI
Finland
Prior art keywords
octahydro
indole
carboxylic acid
formula
compounds
Prior art date
Application number
FI810971A
Other languages
English (en)
Finnish (fi)
Other versions
FI76072C (sv
FI810971L (fi
Inventor
Milton L Hoefle
George Bobowski
Original Assignee
Warner Lambert Co
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
Priority claimed from US06/233,940 external-priority patent/US4350704A/en
Application filed by Warner Lambert Co filed Critical Warner Lambert Co
Publication of FI810971L publication Critical patent/FI810971L/fi
Priority to FI854743A priority Critical patent/FI76560C/sv
Application granted granted Critical
Publication of FI76072B publication Critical patent/FI76072B/fi
Publication of FI76072C publication Critical patent/FI76072C/sv

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (8)

1. Förfarande för framställning av terapeutiskt verkan-de oktahydro-l-tco-merkaptoalkanoyl)-lH-indol-2-karboxylsyra-föreningar med formeln I 900ft RrS- CH, -CH-C-N^ * O (I) i vilken R är väte eller lagalkyl, är väte eller lagalkyl, 28 7 6 0 7 2 o VV R2 är väte eller en grupp 113-0-, väri R3 är lagalkyl, eller en fenylgrupp, som kan vara substituerad med en eller tv! fluor-, klor- eller bromatomer eller en eller tv! l!galkyl-eller lagalkoxigrupper, och l!galkyl- och l!galkoxigrupperna betecknar raka eller förgrenade grupper med 1-4 kolatomer; i racemisk form eller s!som optiska isomerer, samt farmaceu-tiskt godtagbara salter av s!dana föreningar, när R är väte, kännetecknat därav, att a) i ett basiskt medium acyleras oktahydro-lH-indol-2-karboxylsyra med formeln III COOR dii) & o VV med en halogenid av w-R3-c-merkaptoalkansyra med formeln IV O Rl Il f R3 - C - S - CH2 - CH - C - X (IV) o i vilka formler R, R^ och R3 betecknar detsamma som ovan och X är klor eller brom, och, om s! önskas, utförs hydrolyse-ring med en bas, s! att man erh!ller föreningar med formeln I, väri R och R2 är väteatomer, eller b) för framställning av föreningar med formeln I, väri 0 II R är väte och R2 * R3-O-, acyleras en trimetylsilylester av O n en fri syra med formeln III med en halogenid av u)-R3-0-mer-kaptoalkansyra med formeln IV, och omvandlas den erh!llna mellanprodukten tili en fri syra genom att behandla med vat-ten, eller c) för framställning av föreningar med formeln I, väri R och R2 är b!da väteatomer, ammonolyseras en förening med formeln 11 76072 n R COOH ft Τ' JL RpC-S- 0¾ -CH-9-r^ i vilken och R3 betecknar detsanuna som ovan, eller d) för framställning av föreningar med formeln I, väri O H r2 * R3-C-, en förening, väri R2 är väte, acyleras med en O 11 förening R3-C-X, väri X är en avgaende grupp, och, om sa önskas, den erhallna fria föreningen omvandlas tili ett sait och/eller det erhallna racematet atskiljs tili de enskilda stereoisomererna.
2. Förfarande enligt patentkravet 1, känneteck-n a t därav, att man framställer oktahydro-l-(3-merkaptopro-panoyl)-lH-indol-2-karboxylsyra eller ett farmaceutiskt god-tagbart bassalt därav.
3. Förfarande enligt patentkravet l,känneteck-n a t därav, att man framställer oktahydro-l-(3-merkapto-2-metylpropanoyl)-lH-indol-2-karboxylsyra eller ett farmaceutiskt godtagbart bassalt därav.
4. Förfarande enligt patentkravet 3, känneteck-n a t därav, att man framställer (2a,3a3,7a6)-oktahydro-l- (3-merkapto-2-metyl-propanoyl)-lH-indol-2-karboxylsyra eller ett farmaceutiskt godtagbart bassalt därav.
5. Förfarande enligt patentkravet 4, känneteck-n a t därav, att man framställer diastereomer A av (2a,3aB, 7a3)-oktahydro-l-(3-merkapto-2-metyl-propanoyl)-lH-indol-2-karboxylsyra eller ett farmaceutiskt godtagbart bassalt därav.
6. Förfarande enligt patentkravet 4, känneteck-n a t därav, att man framställer diastereomer A av (£)-(2a, 3a3,7a6)-oktahydro-l-(3-merkapto-2-metyl-propanoyl)-lH-indol- 2-karboxylsyra eller ett farmaceutiskt godtagbart bassalt
FI810971A 1980-04-02 1981-03-30 Förfarande för framställning av terapeutiskt verkande oktahydro-1-(ome ga-merkaptoalkanoyl)-1H-indol-2-karboxylsyraföreningar FI76072C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI854743A FI76560C (sv) 1980-04-02 1985-11-29 Förfarande för framställning av farmaceutiskt användbar 1-/2-/(1-karbe toxi-3-fenylpropyl)amino/-1-oxopropyl/-oktahydro-1H-indol-2-karboxylsy ra

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US13710680A 1980-04-02 1980-04-02
US13710680 1980-04-02
US19430780A 1980-10-06 1980-10-06
US19430780 1980-10-06
US23394081 1981-02-17
US06/233,940 US4350704A (en) 1980-10-06 1981-02-17 Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids

Publications (3)

Publication Number Publication Date
FI810971L FI810971L (fi) 1981-10-03
FI76072B true FI76072B (fi) 1988-05-31
FI76072C FI76072C (sv) 1988-09-09

Family

ID=27384960

Family Applications (1)

Application Number Title Priority Date Filing Date
FI810971A FI76072C (sv) 1980-04-02 1981-03-30 Förfarande för framställning av terapeutiskt verkande oktahydro-1-(ome ga-merkaptoalkanoyl)-1H-indol-2-karboxylsyraföreningar

Country Status (14)

Country Link
EP (1) EP0037231B1 (sv)
KR (2) KR850000302B1 (sv)
AU (1) AU543861B2 (sv)
CA (1) CA1205476A (sv)
DE (1) DE3175875D1 (sv)
DK (2) DK157851C (sv)
ES (2) ES500965A0 (sv)
FI (1) FI76072C (sv)
HK (1) HK30489A (sv)
IE (1) IE52663B1 (sv)
IL (1) IL62294A (sv)
NO (1) NO156609C (sv)
NZ (1) NZ196704A (sv)
SG (1) SG3889G (sv)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4599357A (en) * 1979-12-17 1986-07-08 Ciba-Geigy Corporation 1-mercaptoalkanoylindoline-2-carboxylic acids
DE3177130D1 (de) * 1980-08-30 1990-01-11 Hoechst Ag Aminosaeurederivate, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung.
FR2492381A1 (fr) * 1980-10-21 1982-04-23 Science Union & Cie Nouveaux acides aza bicyclo alcane carboxyliques substitues leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme
DE3174844D1 (en) * 1980-10-23 1986-07-24 Schering Corp Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them
US4374847A (en) * 1980-10-27 1983-02-22 Ciba-Geigy Corporation 1-Carboxyalkanoylindoline-2-carboxylic acids
GB2086390B (en) * 1980-11-03 1984-06-06 Ciba Geigy Ag 1-carboxy-azaalkanoylindoline-2-carboxylic acids process for their manufacture pharmaceutical preparations containing these compounds and their therapeutic application
US4479963A (en) * 1981-02-17 1984-10-30 Ciba-Geigy Corporation 1-Carboxyalkanoylindoline-2-carboxylic acids
DE3260423D1 (en) * 1981-02-17 1984-08-30 Warner Lambert Co Substituted acyl derivatives of octahydro-1h-isoindole-1-carboxylic acids and esters
DE3134933A1 (de) * 1981-09-03 1983-03-31 Hoechst Ag, 6230 Frankfurt "harnstoffderivate, verfahren zu ihrer herstellung und diese enthaltende medikamente sowie deren verwendung"
DE3226768A1 (de) * 1981-11-05 1983-05-26 Hoechst Ag, 6230 Frankfurt Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
IE55867B1 (en) * 1981-12-29 1991-02-14 Hoechst Ag New derivatives of bicyclic aminoacids,processes for their preparation,agents containing these compounds and their use,and new bicyclic aminoacids as intermediates and processes for their preparation
ATE25244T1 (de) * 1981-12-29 1987-02-15 Hoechst Ag Neue derivate bicyclischer aminosaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie neue bicyclische aminosaeuren als zwischenstufen und verfahren zu deren herstellung.
DE3210496A1 (de) * 1982-03-23 1983-10-06 Hoechst Ag Neue derivate bicyclischer aminsaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie neue bicyclische aminosaeuren als zwischenstufen und verfahren zu deren herstellung
DE3211397A1 (de) * 1982-03-27 1983-11-10 Hoechst Ag, 6230 Frankfurt Spiro (4.(3+n))-2-aza-3-carbonsaeure-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung
DE3246503A1 (de) * 1982-12-16 1984-06-20 Hoechst Ag, 6230 Frankfurt Derivate der cis, endo-2-azabicyclo-(5.3.0)-decan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
HU191120B (en) * 1983-01-31 1987-01-28 Hoechts Ag,De Process for raceme separation of optically active byciclic imino-alpha-carbonic acid esthers
US5175306A (en) * 1983-01-31 1992-12-29 Hoechst Aktiengesellschaft Process for the resolution of racemates of optically active bicyclic imino-α-carboxylic esters
DE3303344A1 (de) 1983-02-02 1984-08-02 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von n-alkylierten aminosaeuren und deren estern
DE3333454A1 (de) * 1983-09-16 1985-04-11 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von n-alkylierten dipeptiden und deren estern
DE3333455A1 (de) * 1983-09-16 1985-04-11 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung n-alkylierter dipeptide und deren estern
DE3413710A1 (de) * 1984-04-12 1985-10-24 Hoechst Ag, 6230 Frankfurt Verfahren zur behandlung der herzinsuffizienz
US5684016A (en) * 1984-04-12 1997-11-04 Hoechst Aktiengesellschaft Method of treating cardiac insufficiency
DE3431541A1 (de) * 1984-08-28 1986-03-06 Hoechst Ag, 6230 Frankfurt Cis,endo-2-azabicycloalkan-3-carbonsaeure-derivate, verfahren zu deren herstellung, deren verwendung sowie zwischenprodukte bei deren herstellung
US5231080A (en) * 1985-10-15 1993-07-27 Hoechst Aktiengesellschaft Method for the treatment of atherosclerosis, thrombosis, and peripheral vessel disease
US5231084A (en) * 1986-03-27 1993-07-27 Hoechst Aktiengesellschaft Compounds having a cognition adjuvant action, agents containing them, and the use thereof for the treatment and prophylaxis of cognitive dysfuncitons
EP0566157A1 (en) 1986-06-20 1993-10-20 Schering Corporation Neutral metalloendopeptidase inhibitors in the treatment of hypertension
US4749688A (en) * 1986-06-20 1988-06-07 Schering Corporation Use of neutral metalloendopeptidase inhibitors in the treatment of hypertension
EP0254032A3 (en) 1986-06-20 1990-09-05 Schering Corporation Neutral metalloendopeptidase inhibitors in the treatment of hypertension
DE3633496A1 (de) * 1986-10-02 1988-04-14 Hoechst Ag Kombination von angiotensin-converting-enzyme-hemmern mit calciumantagonisten sowie deren verwendung in arzneimitteln
FR2605630B1 (fr) * 1986-10-22 1989-06-30 Roussel Uclaf Procede de preparation de derives de l'octahydroindole et intermediaires de preparation
DE3639879A1 (de) * 1986-11-21 1988-06-01 Hoechst Ag Verfahren zur herstellung von mono-, bi- und tricyclischen aminosaeuren, zwischenprodukte dieses verfahrens sowie ein verfahren zu deren herstellung
DE3641451A1 (de) * 1986-12-04 1988-06-16 Hoechst Ag Derivate bicyclischer aminocarbonsaeuren, verfahren und zwischenprodukte zu deren herstellung sowie deren verwendung
DE3722007A1 (de) * 1987-07-03 1989-01-12 Hoechst Ag Verfahren zur herstellung bicyclischer aminocarbonsaeuren, zwischenprodukte dieses verfahrens und deren verwendung
FR2620703B1 (fr) * 1987-09-17 1991-10-04 Adir Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides
BRPI0409560A (pt) * 2003-04-15 2006-04-18 Warner Lambert Co derivados bicìclicos [b]-condensados de prolina e sua utilização para tratar condições artrìticas
SI21800A (sl) 2004-05-14 2005-12-31 Krka, Tovarna Zdravil, D.D., Novo Mesto Nov postopek sinteze perindoprila
EP1792896A1 (en) 2005-12-01 2007-06-06 KRKA, tovarna zdravil, d.d., Novo mesto Process for the preparation of perindopril and salts thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE608905R (fr) * 1960-12-19 1962-04-06 Bayer Ag Procédé de fabrication d'un composé agissant sur la tension sanguine.
DE1174781B (de) * 1960-12-24 1964-07-30 Bayer Ag Verfahren zur Herstellung von Salzen von 1-(Guanidinoalkyl)-pyrrolidinen
US4105776A (en) * 1976-06-21 1978-08-08 E. R. Squibb & Sons, Inc. Proline derivatives and related compounds
JPS5572169A (en) * 1978-11-27 1980-05-30 Tanabe Seiyaku Co Ltd Isoquinoline derivative and its preparation
IL58849A (en) * 1978-12-11 1983-03-31 Merck & Co Inc Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them
US4461896A (en) * 1979-02-07 1984-07-24 Norwich Eaton Pharmaceuticals, Inc. 1-[Acylthio) and (mercapto)-1-oxoalkyl]-1,2,3,4-tetrahydroquinoline-2-carboxylic acids
EP0018104B1 (en) * 1979-03-26 1983-05-25 Takeda Chemical Industries, Ltd. Tetrahydroisoquinolines, their production and the compounds and pharmaceutical compositions containing them for use in the prevention or treatment of hypertension
US4303583A (en) * 1979-08-13 1981-12-01 American Home Products Corporation 1H,5H-[1,4]Thiazepino[4,3-a]indole-1,5-diones
DE2937779A1 (de) * 1979-09-19 1981-04-09 Hoechst Ag, 6000 Frankfurt Aminosaeurederivate und verfahren zu ihrer herstellung
FR2487829A2 (fr) * 1979-12-07 1982-02-05 Science Union & Cie Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme

Also Published As

Publication number Publication date
DK159419B (da) 1990-10-15
NO156609B (no) 1987-07-13
DK157851C (da) 1990-07-30
KR850000303B1 (ko) 1985-03-18
NO811121L (no) 1981-10-05
DK148281A (da) 1981-10-03
IL62294A0 (en) 1981-05-20
SG3889G (en) 1989-06-02
ES8206474A1 (es) 1982-08-16
ES504189A0 (es) 1982-06-16
EP0037231A3 (en) 1982-04-28
IL62294A (en) 1986-07-31
DK91088A (da) 1988-02-22
DK91088D0 (da) 1988-02-22
HK30489A (en) 1989-04-21
DE3175875D1 (en) 1987-03-05
EP0037231B1 (en) 1987-01-28
EP0037231A2 (en) 1981-10-07
DK159419C (da) 1991-03-18
IE52663B1 (en) 1988-01-20
NO156609C (no) 1987-10-21
ES8205771A1 (es) 1982-06-16
FI76072C (sv) 1988-09-09
FI810971L (fi) 1981-10-03
DK157851B (da) 1990-02-26
NZ196704A (en) 1984-12-14
CA1205476A (en) 1986-06-03
KR850000302B1 (ko) 1985-03-18
AU6893981A (en) 1981-10-08
ES500965A0 (es) 1982-08-16
IE810463L (en) 1981-10-02
KR830005136A (ko) 1983-08-03
AU543861B2 (en) 1985-05-09

Similar Documents

Publication Publication Date Title
FI76072B (fi) Foerfarande foer framstaellning av terapeutiskt verkande oktahydro-1-( -merkaptoalkanoyl)-1h-indol-2- karboxylsyrafoereningar.
US4350704A (en) Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
US4310461A (en) Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4578474A (en) Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4390695A (en) Imido, amido and amino derivatives of mercaptoacyl prolines and pipecolic acids
US4404206A (en) Substituted iminoacid derivatives, process for preparing them and their use as enzyme inhibitors
US4508729A (en) Substituted iminodiacids, their preparation and pharmaceutical compositions containing them
US4086338A (en) N-carboxyalkanoyl derivatives of azetidine-2-carboxylic acid
US4154960A (en) Amino acid derivatives
FI78690B (fi) Foerfarande foer framstaellning av terapeutiskt verkande substituerade acylderivat av 1,2,3,4- tetrahydroisokinolin-3-karboxylsyror.
US4562202A (en) N-Acyl hexahydroindole-2-carboxylic acids and anti-hypertensive use thereof
JPH07300479A (ja) ベンゾ縮合ラクタム類
JPS604815B2 (ja) プロリン誘導体
EP0049658A1 (fr) Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant
CZ20014496A3 (cs) Indolové deriváty a jejich pouľití pro léčení osteoporózy
US4154937A (en) Hydroxycarbamoylalkylacylpipecolic acid compounds
HU185324B (en) Process for preparing 1-carboxy-azaalkanoyl-indoline-2-carboxylic acid derivatives
US4425355A (en) Substituted acyl derivatives of chair form of octahydro-1H-indole-2-carboxylic acids
US4564612A (en) Condensed, seven-membered ring compounds and their use
US4438031A (en) N-(Alkylsulfonyl)-L-proline amide and N-(alkylsulfonyl)-2-carboxylic acid amide-indoline derivatives
EP0500989B1 (en) N-(alpha-substituted-pyridinyl) carbonyl dipeptide antihypertensive agents
CZ280776B6 (cs) Derivát tripeptidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
EP0093805B1 (en) Octahydro-2-(omega-mercaptoalkanoyl)3-oxo-1h-isoindole-1-carboxylic acids and esters
US4555508A (en) Antihypertensive spiro-cyclic compounds
EP0053017A1 (en) Amide derivatives

Legal Events

Date Code Title Description
MM Patent lapsed

Owner name: WARNER-LAMBERT COMPANY