FI95372B - Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider - Google Patents

Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider Download PDF

Info

Publication number
FI95372B
FI95372B FI902358A FI902358A FI95372B FI 95372 B FI95372 B FI 95372B FI 902358 A FI902358 A FI 902358A FI 902358 A FI902358 A FI 902358A FI 95372 B FI95372 B FI 95372B
Authority
FI
Finland
Prior art keywords
group
pyridyl
formula
acid
compound
Prior art date
Application number
FI902358A
Other languages
English (en)
Finnish (fi)
Other versions
FI902358A0 (sv
FI95372C (sv
Inventor
Josef Nickl
Armin Heckel
Gojko Muacevic
Thomas Mueller
Wolfgang Eisert
Rainer Soyka
Hans Weisenberger
Christopher Meade
Original Assignee
Thomae Gmbh Dr K
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 DE3915506A external-priority patent/DE3915506A1/de
Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K
Publication of FI902358A0 publication Critical patent/FI902358A0/sv
Publication of FI95372B publication Critical patent/FI95372B/sv
Application granted granted Critical
Publication of FI95372C publication Critical patent/FI95372C/sv

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55Acids; Esters
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56Amides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Claims (2)

1. Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider med formeln Ri R4 R= I I I R1 - S02 -N-A-C-CH-B-CO-R6 (I) ^3 där R^ avser en fenylalkyl-, trialkylfenyl-, tetrametylfenyl-eller pentametylfenylgrupp, eventuellt med en halogenatom eller alkylgruppe substituerad tienylgrupp eller fenylgrupp, som med en nitrogruppe kan vara monosubstituerad eller med en halogenatom, alkyl-, trifluormetyl- eller alkoxigrupp mono-eli er disubstituerad, varvid substituenterna kan vara lika eller olika, R2, R4 och Rg, som kan vara lika eller olika, avser repektive en väteatom eller alkylgrupp eller R2 avser en väteatom eller alkylgrupp och R4 och Rg tillsammans en kol-kol-bindning, r3 är en 3-pyridylgrupp, Rg är en hydroxi-, alkoxi-, amino-, alkylamino- eller dialkyl-aminogrupp, A är en grupp med formeln ... OfV tai lii' n8 joissa R7 avser en väteatom eller alkylgrupp, Rg en väteatom tai r7 och Rg tillsammans avser en metylen- eller etylengrupp och 70 9537? t X en med en alkylgrupp substituerad iminogrupp, syre- eller svavelatom, varvid en -CHR^-grupp är ansluten till -NR2-grup-pen, och B avser en koi-kol-bindning eller eventuellt med en eller tva alkylgrupper substituerad rakkedig alkylengrupp med 1-4 kolatomer, varvid alla ovan nämnda alkyl- och alkoxidelar respektive kan innehälla 1-3 kolatomer, deras enantiomerer, deras cis- och trans-isomerer, savida R^ och Rg tillsammans bildar en kol-kol-bindning, och deras additionssalter, kännetecknat därav, att a. ) en förening med formeln R4 R5 H-N-A-i-CH-B-CO-Ri· (II) A I K2 K3 där R2 ~ R5' A och B avser det samma som ovan, acyl eras med ett sulfonsyraderivat med formeln Rx - S02Y (III) där R^ avser det samma som ovan och Y avser en nukleofil avgäende grupp, säsom en halogenatom eller alkoxigrupp, t.ex. klor- eller bromatom, metoxi- eller etoxigrupp, eller b. ) för framställning av en förening med formeln I, där Rg avser en hydroxigrupp, en förening med formeln * Ro R^ Κς I I I R-i - SO, - N- A- C-CH-B-CO-Z (IV) R3 där R1 - R5, A och B avser det samma som ovan och 71 95372 Z är en hydrolytiskt, termolytiskt eller hydrogenolytiskt avspjälkbar karboxigrupp eller karboxigruppens funktionella derivats skyddsgrupp, avspjälks skyddsgruppen, eller c. ) för framställning av en förening med formeln I, där R4 och R5 resspektive avser väteatomer, en förening med formeln I2 Hi - S02 - N - A - C = CH - B - CO - Rg (V) där Rl - R3, Rg/ A och B avser det samma som ovan, hydreras eller d. ) för framställning av en förening med formeln I, där R4 och R5 tillsammans bildar en koi-koi-bindning, en förening med formeln I2 R1 - S02 - N - A - CO - R3 (VI) där Rl - R3 och A avser det samma som ovan, omsätts med en förening med formeln ' r W - CH - B - CO - Rg (VII) där B och Rg avser det samma som ovan, . R51 avser en väteatom eller alkylgrupp med 1-3 kolatomer och W avser en trifenylfosfoniumhalogenid-, dialkylfosfonsyra-eller magnesiumhalogenidrest och eventuellt därefter avspjälks vatten och vid behov därefter en sä erhällen förening med formeln I, där R2 avser en väteatom, omvandlas genom alkylering tili motsva-rande förening med formeln I, där R2 avser en alkylgrupp tai * 72 95372 en si erhillen förening med formeln I, där Rg avser en hydro-xigrupp, omvandlas genom forestring eller amidbildningsreakti-on till motsvarande förening med formeln I, där Rg avser en alkoxi-, amino-, alkylamino- eller dialkylaminogrupp eller en si erhillen förening med formeln I, där R^ och Rg tillsam-mans avser en koi-koi-bindning, separeras i sina cis- och trans-isomerer eller en si erhillen förening med formeln I separeras i sin enantiomerer eller en si erhillen förening med formeln I omvandlas till sina additionssalter, särskilt fysio-logiskt lämpliga additionssaalter med ooganiska eller organis-ka baser.
2. Förfarande enligt patentkravef 1, kännetecknat därav, att en förening, som är 6-(2-(4-toluensulfonylamino)indan-5-yl)-6-(3-pyridyl)-hex-5-ensyra, 6-(4-(2-(4-klorbensensulfonylamino)etyl)fenyl)-6-(3-pyridyl)-hex-5-ensyra och 6-(4-(2-(4-trifluormetylbensensulfonylamino)etyl)feny1)-6-(3-pyridyl)-hex-5-ensyra och deras syraadditionssalter, frams-tälIs. !l Ht-h
FI902358A 1989-05-12 1990-05-11 Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider FI95372C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3915506A DE3915506A1 (de) 1989-05-12 1989-05-12 Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3915506 1989-05-12
DE3932403 1989-09-28
DE3932403A DE3932403A1 (de) 1989-05-12 1989-09-28 Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (3)

Publication Number Publication Date
FI902358A0 FI902358A0 (sv) 1990-05-11
FI95372B true FI95372B (sv) 1995-10-13
FI95372C FI95372C (sv) 1996-01-25

Family

ID=25880794

Family Applications (1)

Application Number Title Priority Date Filing Date
FI902358A FI95372C (sv) 1989-05-12 1990-05-11 Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider

Country Status (21)

Country Link
US (3) US5294626A (sv)
EP (1) EP0397044B1 (sv)
JP (1) JP2868283B2 (sv)
KR (1) KR0153527B1 (sv)
AT (1) ATE132138T1 (sv)
AU (1) AU627024B2 (sv)
CA (1) CA2016646C (sv)
DE (2) DE3932403A1 (sv)
DK (1) DK0397044T3 (sv)
ES (1) ES2083394T3 (sv)
FI (1) FI95372C (sv)
GR (1) GR3019044T3 (sv)
HU (1) HU214586B (sv)
IE (1) IE74207B1 (sv)
IL (1) IL94347A0 (sv)
MX (1) MX9202816A (sv)
NO (1) NO176176C (sv)
NZ (1) NZ233638A (sv)
PT (1) PT93994B (sv)
RU (1) RU2096405C1 (sv)
UA (1) UA26136C2 (sv)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5153214A (en) * 1989-06-28 1992-10-06 Ciba-Geigy Corporation Certain (arylsulfonamido- and imidazolyl-)-substituted carboxylic acids and derivatives thereof and use for suppressing thromboxane activity
DE4025818A1 (de) * 1990-08-16 1992-02-20 Bayer Ag Phenylsulfonamid substituierte pyridinalken- und -aminooxyalkancarbonsaeure-derivate
DE4037112A1 (de) * 1990-11-22 1992-05-27 Thomae Gmbh Dr K Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
US5286736A (en) * 1990-11-22 1994-02-15 Dr. Karl Thomae Gmbh Pyridyl compounds and pharmaceutical compositions containing these compounds
US5374641A (en) * 1991-02-25 1994-12-20 Terumo Kabushiki Kaisha N-(3-pyridylalkyl)sulfonamide compounds which have useful pharmaceutical activity
GB9107043D0 (en) * 1991-04-04 1991-05-22 Pfizer Ltd Therapeutic agents
DE4216364A1 (de) * 1991-12-14 1993-11-25 Thomae Gmbh Dr K Neue Pyridylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
FR2686339B1 (fr) * 1992-01-22 1994-03-11 Adir Cie Nouveaux amides et sulfonamides naphtaleniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
DE4213919A1 (de) * 1992-04-28 1993-11-04 Thomae Gmbh Dr K Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CA2347939C (en) 1998-10-23 2006-10-10 Akira Matsumori Composition for the treatment of rheumatism, hepatitis or pancreatitis
EP2417101B1 (en) * 2009-04-09 2013-10-23 Merck Sharp & Dohme B.V. Indane derivatives
US9492422B2 (en) 2009-11-13 2016-11-15 Toray Industries, Inc. Therapeutic or prophylactic agent for diabetes
US9955802B2 (en) 2015-04-08 2018-05-01 Fasteners For Retail, Inc. Divider with selectively securable track assembly

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1134828A (en) * 1978-12-28 1982-11-02 Tadao Tanouchi Pyridine derivatives
EP0098690B1 (en) * 1982-06-14 1987-09-09 Takeda Chemical Industries, Ltd. Vinyl carboxylic acid derivatives, their production and use
US4518602A (en) * 1982-10-07 1985-05-21 Takeda Chemical Industries, Ltd. Vinyl carboxylic acid derivatives, their production and use as inhibitors of thromboxane synthetase
US4563446A (en) * 1983-07-27 1986-01-07 Takeda Chemical Industries, Ltd. Thromboxane synthetase inhibiting 3-(1-alkenyl) pyridines
ES2061432T3 (es) * 1985-10-09 1994-12-16 Shell Int Research Nuevas amidas de acido acrilico.
DE3623944A1 (de) * 1986-07-16 1988-02-11 Thomae Gmbh Dr K Neue benzolsulfonamido-indanylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
GB8708233D0 (en) * 1987-04-07 1987-05-13 Smith Kline French Lab Pharmaceutically active compounds
EP0304271A3 (en) * 1987-08-20 1992-09-02 Smith Kline & French Laboratories Limited Omega-arylsulphonamidoalkanoic acids for treatment of thromboxane medited diseases

Also Published As

Publication number Publication date
IE901708L (en) 1990-11-12
PT93994A (pt) 1991-01-08
DK0397044T3 (da) 1996-05-13
IE901708A1 (en) 1991-06-19
ES2083394T3 (es) 1996-04-16
US5294626A (en) 1994-03-15
EP0397044B1 (de) 1995-12-27
EP0397044A3 (de) 1991-10-16
HU903013D0 (en) 1990-09-28
HUT54649A (en) 1991-03-28
HU214586B (hu) 1998-04-28
KR0153527B1 (ko) 1998-11-16
EP0397044A2 (de) 1990-11-14
PT93994B (pt) 1997-04-30
MX9202816A (es) 1992-06-30
ATE132138T1 (de) 1996-01-15
JP2868283B2 (ja) 1999-03-10
FI902358A0 (sv) 1990-05-11
NO902099L (no) 1990-11-13
NZ233638A (en) 1992-03-26
IL94347A0 (en) 1991-03-10
DE59009994D1 (de) 1996-02-08
US5426119A (en) 1995-06-20
US5681961A (en) 1997-10-28
GR3019044T3 (en) 1996-05-31
CA2016646A1 (en) 1990-11-12
AU5492490A (en) 1990-11-15
RU2096405C1 (ru) 1997-11-20
IE74207B1 (en) 1997-07-16
UA26136C2 (uk) 1999-06-07
KR900018031A (ko) 1990-12-20
NO176176C (no) 1995-02-15
DE3932403A1 (de) 1991-04-11
NO176176B (no) 1994-11-07
FI95372C (sv) 1996-01-25
NO902099D0 (no) 1990-05-11
AU627024B2 (en) 1992-08-13
JPH035457A (ja) 1991-01-11
CA2016646C (en) 1999-09-07

Similar Documents

Publication Publication Date Title
FI95372B (sv) Förfarande för framställning av terapeutiskt värdefulla arylsulfonamider
SK22099A3 (en) Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides
NZ570528A (en) Indole-3-carboxylic acid amide, ester, thioamide and thiol ester compounds bearing aryl or heteroaryl groups having sphingosine-1-phosphate (s1p) receptor antagonist biological activity
JP2010504286A (ja) スフィンゴシン−1−リン酸(s1p)受容体アゴニスト及び/又はアンタゴニスト生物活性を有するヘテロ芳香族化合物
NO310719B1 (no) Substituerte N-[(Aminoiminometyl eller aminometyl)fenyl]- propylamider
EP2138482A1 (en) Bicyclic heterocyclic compound
FI100882B (sv) Förfarande för framställning av farmakologiskt värdefulla mätade eller omättade -fenyl- -(3-pyridyl)-karboxylsyraderivat och deras tetrazol ylanaloger
FI92190C (sv) Förfarande för framställning av farmakologiskt värdefull indanderivat
JPH0383979A (ja) 新規ベンゾピランおよびベンゾチオピラン誘導体
JPH072770A (ja) 新規な置換インドール類、その製造法及びそのインドール類を含有する製剤組成物
JPH0390064A (ja) 環式置換基を含む(キノリン―2―イル―メトキシ)フエニル酢酸誘導体
US6166020A (en) Aryl and heteroaryl alkoxynaphthalene derivatives
US5187188A (en) Oxazole carboxylic acid derivatives
JP2010502728A (ja) スフィンゴシン−1−リン酸(s1p)受容体アゴニスト生物活性を有するヘテロ芳香族化合物
PL184060B1 (pl) Podstawione związki fenylowe do zastosowania jako środki antagonistyczne endoteliny
JPH04243856A (ja) 置換されたフエニルアセチレン、これを含有する薬剤、この化合物及び薬剤を製造する方法
HUT56340A (en) Process for producing tetrahydronaphthalene derivatives and pharmaceutical compositions comprising such compounds
TW200306195A (en) A phosphodiestrase IV inhibitor containing pyridylacrylic acid derivatives
CN112457265A (zh) 四氮唑类衍生物、制备、含其的药物组合物及其应用
US5155130A (en) Certain benzopyran and benzothiopyran derivatives
JPH07233072A (ja) 医薬組成物
RU2329262C2 (ru) Производные фталазина в качестве ингибиторов фосфодиэстеразы 4
JPH04247077A (ja) トロポロン誘導体およびそれを有効成分とする虚血性疾患の予防・治療剤
JPH0912571A (ja) (ピリジルアルキル)(フェニルスルホンアミド)ピロール誘導体およびそれを含有する医薬製剤

Legal Events

Date Code Title Description
BB Publication of examined application
MM Patent lapsed

Owner name: DR. KARL THOMAE GESELLSCHAFT MIT