DK166127B - Estere af pyridin-2,4- og -2,5-dicarboxylsyre til anvendelse som laegemidler, samt laegemidler indeholdende disse estere - Google Patents

Estere af pyridin-2,4- og -2,5-dicarboxylsyre til anvendelse som laegemidler, samt laegemidler indeholdende disse estere Download PDF

Info

Publication number
DK166127B
DK166127B DK397785A DK397785A DK166127B DK 166127 B DK166127 B DK 166127B DK 397785 A DK397785 A DK 397785A DK 397785 A DK397785 A DK 397785A DK 166127 B DK166127 B DK 166127B
Authority
DK
Denmark
Prior art keywords
esters
pyridine
collagen
dicarboxylic acid
pharmaceuticals
Prior art date
Application number
DK397785A
Other languages
English (en)
Other versions
DK166127C (da
DK397785D0 (da
DK397785A (da
Inventor
Volkmar Guenzler
Hartmut Hanauske-Abel
Juergen Mohr
Georg Tschank
Kari Kivirikko
Kari Majama
Dietrich Brocks
Original Assignee
Hoechst Ag
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 Hoechst Ag filed Critical Hoechst Ag
Publication of DK397785D0 publication Critical patent/DK397785D0/da
Publication of DK397785A publication Critical patent/DK397785A/da
Publication of DK166127B publication Critical patent/DK166127B/da
Application granted granted Critical
Publication of DK166127C publication Critical patent/DK166127C/da

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyridine Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Description

i
DK 166127 B
Opfindelsen angår pyridindicarboxylsyreestere med den almene formel
R2OCO
5 (I) ^N^COOR1 hvor R1 og R2, der er ens eller forskellige, betyder alkyl 10 med 1-6 carbonatomer, og hvor gruppen R2OCO er bundet i 4-eller 5-stilling i pyridinringen, til anvendelse som lægemidler, især til inhibering af prolin- og lysinhydroxylase eller til anvendelse som fibrosuppressivum og immunsuppres-sivum. Opfindelsen angår også lægemidler, der indeholder en 15 forbindelse med formlen (I) , evt. sammen med acceptable farmaceutiske bærestoffer.
Ifølge den foreliggende opfindelse foretrækkes der sådanne forbindelser med formlen (I), hvor begge grupperne R1 og R2 betyder alkylgrupper med 1-3 carbonatomer, især 20 ethyl.
Fra EP-B1 nr. 0033151 (US-patentskrift nr. 4.457.
936) er det kendt, at carboxylsyrer af hydroxyphenylthiazol og derivater deraf påvirker kollagenstofskiftet. Disse forbindelser virker som inhibitorer af prolin- og lysinhydroxy-25 laser og bevirker således en meget selektiv hæmning af kolla-genbiosyntesen ved at påvirke de kollagenspecifikke hydroxy-leringsreaktioner. Under dette forløb hydroxyleres proteinbundet prolin eller lysin af enzymerne prolin- og lysinhydro-xylase. Såfremt denne reaktion hindres af inhibitorer, opstår 30 der et ikke-funktionsdygtigt, underhydroxyleret kollagenmole-kyle, der kun i ringe mængde kan afgives af cellen i det ekstracellulære rum. Desuden kan det underhydroxylerede kollagen ikke indbygges i kollagenmatrixen og nedbrydes meget let proteolytisk. Som en følge af disse virkninger 35 forringes tilsammen mængden af det ekstracellulært af lej rede kollagen.
DK 166127 B
2
Det er desuden kendt, at inhiberingen af prolinhydro-xylasen med kendte inhibitorer som α,α'-dipyridyl fører til en hæmning af Clg-biosyntesen af makrophager (jfr. W. Muller et al., FEBS Lett. 90 (1978) 218? Immunobiology 155 5 (1978) 47) . Dette udelukker den klassiske komplementaktive ring. Inhibitorer af prolinhydroxylase virker derfor også som immunsuppressiva, f.eks. ved immunkomplekssygdomme.
Det er kendt, at prolinhydroxylase hæmmes effektivt af pyridin-2,4- og -2,5-dicarboxylsyre (jfr. K. Majamaa et 10 al., Eur. J. Biochem. 138 (1984) 239-245). Disse forbindelser er ganske vist kun virksomme som hæmningsstoffer i cellekulturen i meget høje koncentrationer (jfr. V. Gunzler et al., Collagen and Related Research 3 (1983) 71). Overraskende nok har det nu vist sig, at estrene af disse forbindelser 15 er væsentlig mere højaktive hæmningsstoffer af kollagen-biosyntesen i celle- og organkulturer.
Stoffernes hæmmende virkning på kollagenbiosyntesen kan påvises i cellekulturen med fibroblaster eller andre kollagen-syntetiserende celler eller i organkulturer fra 20 kalvarier (embryonale kyllingehjerneskaller) eller andre kollagen-producerende organer.
Den hæmmende virkning på Clg-biosyntesen kan i cellekulturer bestemmes med makrophager (jfr. Muller et al., FEBS Lett., jfr. ovenfor).
25 Forbindelserne med formlen (I) kan anvendes som medi kamenter i form af farmaceutiske præparater, der indeholder disse eventuelt sammen med acceptable farmaceutiske bærestoffer. Forbindelserne kan anvendes som lægemidler, f.eks. i form af farmaceutiske præparater, der indeholder disse for-30 bindeiser i blanding med et til en enteral, perkutan eller parenteral applikation egnet farmaceutisk, organisk eller uorganisk bæremateriale, såsom vand, gummi arabicum, gelatine, mælkesukker, stivelse, magnesiumstearat, talkum, vegetabilske olier, polyalkylenglycoler, vaseline osv.
35 De farmaceutiske præparater kan foreligge i fast form, f.eks. som tabletter, dragées, suppositorier eller
DK 166127 B
3 kapsler, i halvfast form, f.eks. som salver, eller i flydende form, f.eks. som opløsninger, suspensioner eller emulsioner.
De er eventuelt steriliseret og/eller indeholder hjælpestoffer, såsom konserveringsmidler, stabiliseringsmidler, fugte-5 midler eller emulgeringsmidler, salte til ændring af det osmotiske tryk eller puffere. De kan også indeholde andre terapeutisk virksomme stoffer.
Forbindelser med formlen (I) kan tjene som insektfor-svarsmidler (jfr. US-patentskrift nr. 2.852.519) eller ud-10 gangsmaterialer til baktericider (jfr. US-patentskrift nr. 2.809.146). Deres fremstilling kan ske ifølge litteraturkendte metoder, f.eks. ifølge fremgangsmåden beskrevet i US-patentskrift nr. 2.852.519.
I det følgende er beskrevet bestemmelsen af den hæra-15 mende virkning på reaktionen prolin -* hydroxyprolin, som katalyseres af enzymet prolinhydroxylase.
a) Væv af EHS-sarkom-tumor, der producerer en basal-membranagtig ekstracellulær matrix og specielt type IV-kol-lagen (jfr. Erkin et al., Exp. Med. 145 (1977) 204-220), 20 inkuberes analogt med metoden ifølge K. Tryggvason et al. (Biochemistry 19 (1989) 1248-1289) i nærværelse af 14C-prolin og af inhibitorer i forskellig koncentration. Efter at inkubationen er standset, homogeniseres vævet og ekstraheres med fortyndet eddikesyre. Efter NaCl-fældning hydrolyseres 25 det ekstraherede kollagen med 6 M HC1, og forholdet mellem 14C-prolin og 14C-hydroxyprolin bestemmes.
b) Isolerede kalvarier inkuberes analogt med fremgangsmåden beskrevet af B. Peterkovsky og R. DiBlasio (Anal. Biochem. 66 (1975) 279-286) i nærværelse af U-14C-prolin og 30 inhibitorer. Efter at inkubationen er standset, homogeniseres kalvarierne, og kollagenet ekstraheres med fortyndet eddikesyre. Efter hydrolyse af ekstrakten med 6 M HC1 bestemmes forholdet mellem ^-4C-prolin og -*-4C-hydroxyprolin.
DK 166127 B
4
Der fås følgende resultater bestemt ved metode b) som er et udtryk for hæmningen af kollagenbiosyntesen.
Inhibitor med formlen (I): 5 12 2 R = R COOR 's position Kone., μΜ Hæmning, % H 4 670 50 C2H5 4 3 50 H 5 2100 50 C2H5 5 90 50

Claims (5)

1. Pyridindicarboxylsyreestere med den almene formel R2OCO 5 iPi (1) ^^COOR1 hvor R1 og R2, der er ens eller forskellige, betyder alkyl med 1-6 carbonatomer, og hvor gruppen R2OCO er bundet i 4-10 eller 5-stilling i pyridinringen, til anvendelse som lægemidler.
2. Forbindelser ifølge krav 1, kendetegnet ved, at R1 og R2 betyder alkylgrupper med 1-3 carbonatomer.
3. Forbindelser ifølge krav 1 og 2, kendete g-15 net ved, at R1 og R2 betyder ethyl.
4. Lægemiddel, kendetegnet ved, at det indeholder en forbindelse ifølge krav 1.
5. Lægemiddel, kendetegnet ved, at det indeholder en forbindelse ifølge krav 1 sammen med acceptable 20 farmaceutiske bærestoffer.
DK397785A 1984-08-31 1985-08-30 Estere af pyridin-2,4- og -2,5-dicarboxylsyre til anvendelse som laegemidler, samt laegemidler indeholdende disse estere DK166127C (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843432094 DE3432094A1 (de) 1984-08-31 1984-08-31 Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase
DE3432094 1984-08-31

Publications (4)

Publication Number Publication Date
DK397785D0 DK397785D0 (da) 1985-08-30
DK397785A DK397785A (da) 1986-03-01
DK166127B true DK166127B (da) 1993-03-15
DK166127C DK166127C (da) 1993-08-09

Family

ID=6244394

Family Applications (1)

Application Number Title Priority Date Filing Date
DK397785A DK166127C (da) 1984-08-31 1985-08-30 Estere af pyridin-2,4- og -2,5-dicarboxylsyre til anvendelse som laegemidler, samt laegemidler indeholdende disse estere

Country Status (13)

Country Link
US (1) US4717727A (da)
EP (1) EP0176741B1 (da)
JP (1) JPH0641412B2 (da)
AT (1) ATE38222T1 (da)
AU (1) AU588826B2 (da)
CA (1) CA1246456A (da)
DE (2) DE3432094A1 (da)
DK (1) DK166127C (da)
ES (1) ES8609255A1 (da)
GR (1) GR852098B (da)
IE (1) IE58599B1 (da)
PT (1) PT81058B (da)
ZA (1) ZA856646B (da)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5512586A (en) * 1987-02-10 1996-04-30 Hoechst Aktiengesellschaft Medicaments based on pyridine-2,4- and 2,5-dicarboxylic acid amides
DE3703959A1 (de) * 1987-02-10 1988-08-18 Hoechst Ag Pyridin-2,4- und 2,5-dicarbonsaeureamide, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
DE3703962A1 (de) * 1987-02-10 1988-08-18 Hoechst Ag Pyridin-2,4- und 2,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
US5238948A (en) * 1987-02-10 1993-08-24 Hoechst Aktiengesellschaft Pyridine-2,4- and -2,5-dicarboxylic acid derivatives and medicaments based on these compounds
DE3703963A1 (de) * 1987-02-10 1988-08-18 Hoechst Ag Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen
GB8702890D0 (en) * 1987-02-10 1987-03-18 Zyma Sa Heterocyclic compounds
DE3707429A1 (de) * 1987-03-07 1988-09-15 Hoechst Ag Substituierte pyridin-2,4-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
US5271939A (en) * 1988-10-03 1993-12-21 Alcon Laboratories, Inc. Pharmaceutical compositions and methods of treatment to prevent and treat corneal scar formation produced by laser irradiation
US4939135A (en) * 1988-10-03 1990-07-03 Alcon Laboratories, Inc. Pharmaceutical compositions and methods of treatment to prevent and treat corneal scar formation produced by laser irradiation
US5124392A (en) * 1988-10-03 1992-06-23 Alcon Laboratories, Inc. Pharmaceutical compositions and methods of treatment to prevent and treat corneal scar formation produced by laser irradiation
US5360611A (en) * 1988-10-03 1994-11-01 Alcon Laboratories, Inc. Pharmaceutical compositions and methods of treatment of the cornea following ultraviolet laser irradiation
DE3924093A1 (de) 1989-07-20 1991-02-07 Hoechst Ag N,n'-bis(alkoxy-alkyl)-pyridin-2,4-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung
DE3930696A1 (de) * 1989-09-14 1991-03-28 Hoechst Ag Gallensaeurederivate, verfahren zu ihrer herstellung, verwendung als arzneimittel
DE3938805A1 (de) * 1989-11-23 1991-05-29 Hoechst Ag Pyridin-2,4- und 2,5-dicarbonsaeurediamide, verfahren zu deren herstellung sowie deren verwendung
ZA91291B (en) * 1990-01-16 1991-09-25 Hoechst Ag Di(nitroxyalkyl)amides of pyridine-2,4-and-2,5-dicarboxylic acids,a process for the preparation thereof,and the use thereof
DE4020570A1 (de) 1990-06-28 1992-01-02 Hoechst Ag 2,4- und 2,5-substituierte pyridin-n-oxide, verfahren zu deren herstellung sowie deren verwendung
DE4030999A1 (de) * 1990-10-01 1992-04-09 Hoechst Ag 4- oder 5-substituierte pyridin-2-carbonsaeuren, verfahren zu deren herstellung sowie deren verwendung als arzneimittel
YU9492A (sh) * 1991-02-05 1995-03-27 Hoechst Ag. 2,4- i 2,5-bis-tetrazolilni piridini i postupak za njihovo dobijanje
TW352384B (en) * 1992-03-24 1999-02-11 Hoechst Ag Sulfonamido- or sulfonamidocarbonylpyridine-2-carboxamides, process for their preparation and their use as pharmaceuticals
DE4233124A1 (de) * 1992-10-02 1994-04-07 Hoechst Ag Acylsulfonamido- und Sulfonamidopyridin-2-carbonsäureester sowie ihre Pyridin-N-oxide, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US5624893A (en) * 1993-10-14 1997-04-29 Alcon Laboratories, Inc. Pharmaceutical compositions and methods of treatment of the cornea following laser irradiation
EP0878480A1 (en) * 1997-05-14 1998-11-18 H.W. Prof. Dr. Müller A method for the improvement of neuronal regeneration
EP1268639A1 (en) * 2000-02-11 2003-01-02 Huntsman International Llc Fatty acid and polyolefin wax release agent
US7598278B2 (en) * 2002-04-11 2009-10-06 L'oreal Administration of pyridinedicarboxylic acid compounds for stimulating or inducing the growth of human keratinous fibers and/or arresting their loss
WO2005020977A1 (en) * 2003-08-21 2005-03-10 Wisconsin Alumni Research Foundation Alpha-ketoglutarate potentiators of insulin secretion
FR2987742B1 (fr) 2012-03-09 2014-09-26 Oreal Procede de traitement pour la protection et la reparation des fibres keratiniques mettant en œuvre des polysaccharides oxydes
FR3010309B1 (fr) 2013-09-12 2017-03-10 Oreal Procede de traitement des fibres keratiniques avec un polysaccharide et un compose de sphingosine
FR3010308B1 (fr) * 2013-09-12 2016-11-25 Oreal Procede de traitement des fibres keratiniques avec un compose d'acide pyridine dicarboxylique
FR3010312B1 (fr) * 2013-09-12 2015-09-11 Oreal Procede de traitement des fibres keratiniques avec un polysaccharide et un compose d'acide pyridine dicarboxylique
FR3030248B1 (fr) 2014-12-22 2018-03-23 L'oreal Association derive d'acide pyridine-dicarboxylique/agent anti-oxydant particulier
US10788201B2 (en) * 2018-10-03 2020-09-29 Samuel Harriat Solar powered boiler assembly

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2809146A (en) * 1954-09-21 1957-10-08 Phillips Petroleum Co Method of destroying bacteria employing mercuric-chloride complexes of pyridine
US2852519A (en) * 1954-12-27 1958-09-16 Phillips Petroleum Co Method for producing esters of heterocyclic nitrogen carboxylic acids
FR3795M (fr) * 1964-09-09 1965-12-27 Metabio Soc Médicaments a base d'acide quinoléique.
FR2123141A6 (en) * 1971-01-25 1972-09-08 Aries Robert Organophosphorus pesticidal compsns - stabilized by esters of pyridine dicarboxylic acids
DE3002989A1 (de) * 1980-01-29 1981-07-30 Hoechst Ag, 6000 Frankfurt Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels

Also Published As

Publication number Publication date
AU588826B2 (en) 1989-09-28
ES546527A0 (es) 1986-07-16
US4717727A (en) 1988-01-05
IE58599B1 (en) 1993-10-20
PT81058A (de) 1985-09-01
DK166127C (da) 1993-08-09
ZA856646B (en) 1986-05-28
DK397785D0 (da) 1985-08-30
JPH0641412B2 (ja) 1994-06-01
DE3565832D1 (en) 1988-12-01
JPS6160655A (ja) 1986-03-28
ATE38222T1 (de) 1988-11-15
PT81058B (pt) 1987-11-11
AU4692885A (en) 1986-03-06
DE3432094A1 (de) 1986-03-06
DK397785A (da) 1986-03-01
CA1246456A (en) 1988-12-13
IE852150L (en) 1986-02-28
EP0176741B1 (de) 1988-10-26
GR852098B (da) 1986-01-02
EP0176741A1 (de) 1986-04-09
ES8609255A1 (es) 1986-07-16

Similar Documents

Publication Publication Date Title
DK166127B (da) Estere af pyridin-2,4- og -2,5-dicarboxylsyre til anvendelse som laegemidler, samt laegemidler indeholdende disse estere
US5260323A (en) 2,4- and 2,5-substituted pyridine-N-oxides, processes for their preparation and their use
Monod et al. Allosteric proteins and cellular control systems
FI101070B (fi) Menetelmä terapeuttisesti aktiivisten 2,4-alkoksialkyyliaminokarbonyyl i-substituoitujen pyridiini-N-oksidien valmistamiseksi
PT956865E (pt) Medicamentos compreendendo inibidores da rho cinase.
US3244590A (en) Polyenic compounds and procedures related thereto
WO1996018617A1 (en) Substituted 2-acylamino-pyridines as inhibitors of nitric oxide synthase
CZ279784B6 (cs) Racemická nebo opticky aktivní sloučenina, způsob její přípravy a farmaceutický přípravek
KR20100015343A (ko) 이노시톨 니아시네이트의 이성질체 및 그 용도
US6034107A (en) 5-Substituted picolinic acid compounds and their production process
DK168008B1 (da) Pyridin-2,4- og -2,5-dicarboxylsyrediamid-derivater, deres fremstilling og laegemidler indeholdende dem
JPH07228529A (ja) コリンエステラーゼ賦活剤
NO801843L (no) Nye kinazolinderivater og farmasoeytiske preparater
FI63568C (fi) Foerfarande foer framstaellning av nya terapeutiskt anvaendbara i 7-staellning substituerade 8-aminometylisoflavonderivat
Suter et al. 2-Pyruvoylaminobenzamide, a metabolite of Penicillium chrysogenum and P. notatum
US5908842A (en) Substituted 2-acylamino-pyridines as inhibitors of nitric oxide synthase
JPH0267295A (ja) プリン誘導体
EP0301474A3 (en) New cysteine derivatives having expectorant activity
US3324140A (en) Pyridoxolyl-hydrocarbon and substituted hydrocarbon disulfides
CN100422161C (zh) 羟基吗啉酮衍生物及其医药用途
TW199147B (da)
US3142672A (en) Derivatives of nu-alpha-phenyl-and nu-alpha-biphenylylbutyric acids and amino sugars
CN110511178A (zh) 新型磺胺类化合物及其在治疗高血脂中的用途
JPH045240A (ja) 抗痴呆剤
CN115626894A (zh) 一种具有镇痛活性的高乌甲素衍生物及其制备方法和应用

Legal Events

Date Code Title Description
PBP Patent lapsed

Country of ref document: DK