NO176176B - Analogifremgangsmåte for fremstilling av terapeutisk aktive arylsulfonamider - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive arylsulfonamider Download PDFInfo
- Publication number
- NO176176B NO176176B NO902099A NO902099A NO176176B NO 176176 B NO176176 B NO 176176B NO 902099 A NO902099 A NO 902099A NO 902099 A NO902099 A NO 902099A NO 176176 B NO176176 B NO 176176B
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- compound
- constitutes
- carbon
- Prior art date
Links
- 125000004421 aryl sulphonamide group Chemical group 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 150000003839 salts Chemical class 0.000 claims abstract 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000007529 inorganic bases Chemical class 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 150000007530 organic bases Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- -1 trialkylphenyl Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- WMXQIJFLAQUQMT-UHFFFAOYSA-N 4-chloro-n-[2-[4-(1-pyridin-3-ylhex-1-enyl)phenyl]ethyl]benzenesulfonamide Chemical compound C=1C=CN=CC=1C(=CCCCC)C(C=C1)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 WMXQIJFLAQUQMT-UHFFFAOYSA-N 0.000 claims 1
- CVGMGVCODMCCTA-UHFFFAOYSA-N 6-[2-[(4-methylphenyl)sulfonylamino]-2,3-dihydro-1h-inden-5-yl]-6-pyridin-3-ylhex-5-enoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1CC2=CC(C(=CCCCC(O)=O)C=3C=NC=CC=3)=CC=C2C1 CVGMGVCODMCCTA-UHFFFAOYSA-N 0.000 claims 1
- LGHLGTHRJNIRCA-UHFFFAOYSA-N 6-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]-6-pyridin-3-ylhex-5-enoic acid Chemical compound C=1C=CN=CC=1C(=CCCCC(=O)O)C(C=C1)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 LGHLGTHRJNIRCA-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 2
- 239000005557 antagonist Substances 0.000 abstract 1
- 230000002785 anti-thrombosis Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 abstract 1
- 229960002986 dinoprostone Drugs 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/06—Heterocyclic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- A61P9/10—Drugs 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
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic 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 (3)
1. Analogifremgangsmåte for fremstilling av terapeutisk aktive arylsulfonamider med formel
hvor
Rx betyr en fenylalkyl-, trialkylfenyl-, tetrametylfenyl- eller pentametylfenylgruppe, en tienylgruppe som eventuelt er substituert med et halogenatom eller en alkylgruppe, eller en fenylgruppe som er monosubstituert med en nitrogruppe eller mono- eller disubstituert med et halogenatom,.en alkyl-, trifluormetyl- eller alkoksygruppe hvor substituentene kan være like eller forskjellige,
R2, R4 og R5 som kan være like eller forskjellige, hver utgjør et hydrogenatom eller en alkylgruppe eller
R2 er et hydrogenatom eller en alkylgruppe og R4 og R5 sammen utgjør en karbon-karbon-binding,
R3 er en pyridylgruppe,
R6 er en hydroksy-, alkoksy-, benzylamino- eller dialkylaminogruppe,
A er en gruppe med formel
hvor
R7 er et hydrogenatom eller en alkylgruppe,
R8 er et hydrogenatom eller
R7 og R8 sammen utgjør en metylen- eller etylengruppe og X utgjør en iminogruppe som er substituert med en alkylgruppe, eller et svovel atom, hvor -CHR7-gruppen er forbundet med -NR2-gruppen, og
B er en karbon-karbon-binding eller en rettkjedet alkylengruppe med 1 til 4 karbonatomer som eventuelt er substituert med én eller to alkylgrupper, hvor samtlige tidligere nevnte alkyl- og alkoksydeler kan inneholde 1 til 3 karbonatomer, deres enantiomerer, deres cis- og trans-isomerer, dersom RA og R5 sammen utgjør en karbon-karbon-binding, og deres addisjonssalter,
karakterisert ved at a.) en forbindelse med formel
hvor
R2 til R5, A og B er som ovenfor definert, acyleres med et sulfonsyre-derivat med formel
hvor
R-l er som ovenfor definert, og
X utgjør en nukleofil utgående gruppe så som et halogenatom eller en alkoksygruppe, f.eks. et klor- eller bromatom, en metoksy- eller etoksygruppe, eller b.) for fremstilling av forbindelser med formel I hvor R6 utgjør en hydroksygruppe: ■
det fra en forbindelse med den generelle formel
hvor
Rx til R5, A og B er som ovenfor definert og
Z utgjør en hydrolytisk, termolytisk eller hydrogenolytisk avspaltbar beskyttelsesgruppe for en karboksygruppe, eller et funksjonelt derivat av karboksygruppen, avspaltes en beskyttelsesrest, eller c.) for fremstilling av forbindelser med formel I, hvor R4 og R5 hver utgjør et hydrogenatom:
en forbindelse med formel
hvor
Rx til R3, R6, A og B er som ovenfor definert, hydreres, eller d.) for fremstilling av forbindelser med formel I, hvor R4 og R5 sammen utgjør en karbon-karbon-binding:
en forbindelse med formel
hvor
Rx til R3 og A er som ovenfor definert, omsettes med en forbindelse med formel
hvor
B og R6 er som ovenfor definert,
R5'betyr et hydrogenatom eller en alkylgruppe med 1 til 3 karbonatomer og
W utgjør en trifenylfosfoniumhalogenid-, dialkylfosfonsyre-eller magnesiumhalogenidrest, og eventuelt deretter dehydratiseres, og
en således oppnådd forbindelse med formel I, hvor R2 utgjør et hydrogenatom, ved alkylering overføres i en tilsvarende forbindelse med formel I, hvori R2 utgjør en alkylgruppe, eller
en således oppnådd forbindelse med formel I, hvori R6 utgjør en hydroksygruppe, ved forestring eller amidering, overføres i en tilsvarende forbindelse med formel I, hvori R6 utgjør en alkoksy-, benzylamino- eller dialkylaminogruppe, eller
en således oppnådd forbindelse med formel I, hvori RA og R5 sammen utgjør en karbon-karbon-binding, spaltes i dens cis- og trans-isomerer, eller
en således oppnådd forbindelse med formel I spaltes i dens enantiomerer, eller
en således oppnådd forbindelse med formel I overføres i dens addisjonssalter, spesielt i dens fysiologisk akseptable addisjonssalter med dens uorganiske eller organiske baser.
2. Fremgangsmåte ifølge krav 1 for fremstilling av forbindelsene 6-(2-(4-toluensulfonylamino)indan-5-yl)-6-(3-pyridyl)heks-5-en-syre,
6-(4-(2-(4-klorbenzensulfonylamino)etyl)fenyl)-6-(3-pyridyl)-heks-5-en-syre, eller 6-(4-(2-(4-trifluormetylbenzensulfonylamino)etyl)fenyl)-6-(3-pyridyl)heks-5-en-syre og deres syreaddisjonssalter, karakterisert ved at tilsvarende utgangsforbindelser benyttes.
3. Fremgangsmåte ifølge krav 1 for fremstilling av 6-(4-(2-(4-klorbenzensulfonylamino)etyl)fenyl)-6-(3-pyridyl)-heks-5-en-syre og dens syreaddisjonssalter, karakterisert ved at tilsvarende utgangsforbindelser benyttes.
Applications Claiming Priority (2)
| 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 |
| DE3932403A DE3932403A1 (de) | 1989-05-12 | 1989-09-28 | Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO902099D0 NO902099D0 (no) | 1990-05-11 |
| NO902099L NO902099L (no) | 1990-11-13 |
| NO176176B true NO176176B (no) | 1994-11-07 |
| NO176176C NO176176C (no) | 1995-02-15 |
Family
ID=25880794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO902099A NO176176C (no) | 1989-05-12 | 1990-05-11 | Analogifremgangsmåte for fremstilling av terapeutisk aktive arylsulfonamider |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5294626A (no) |
| EP (1) | EP0397044B1 (no) |
| JP (1) | JP2868283B2 (no) |
| KR (1) | KR0153527B1 (no) |
| AT (1) | ATE132138T1 (no) |
| AU (1) | AU627024B2 (no) |
| CA (1) | CA2016646C (no) |
| DE (2) | DE3932403A1 (no) |
| DK (1) | DK0397044T3 (no) |
| ES (1) | ES2083394T3 (no) |
| FI (1) | FI95372C (no) |
| GR (1) | GR3019044T3 (no) |
| HU (1) | HU214586B (no) |
| IE (1) | IE74207B1 (no) |
| IL (1) | IL94347A0 (no) |
| MX (1) | MX9202816A (no) |
| NO (1) | NO176176C (no) |
| NZ (1) | NZ233638A (no) |
| PT (1) | PT93994B (no) |
| RU (1) | RU2096405C1 (no) |
| UA (1) | UA26136C2 (no) |
Families Citing this family (14)
| 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 |
| US5286736A (en) * | 1990-11-22 | 1994-02-15 | Dr. Karl Thomae Gmbh | Pyridyl compounds and pharmaceutical compositions containing these compounds |
| DE4037112A1 (de) * | 1990-11-22 | 1992-05-27 | Thomae Gmbh Dr K | Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| 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 |
| CN1148190C (zh) | 1998-10-23 | 2004-05-05 | 东丽株式会社 | 用于免疫调节的药物组合物 |
| YU78601A (sh) * | 1999-05-05 | 2005-07-19 | Aventis Pharma Deutschland Gmbh. | 1-(p-tienilbenzil)-imidazoli kao agonisti angiotenzin-(1-7)- receptora, postupak za njihovu proizvodnju, njihova primena i farmaceutski preparati koji ih sadrže |
| WO2010115952A1 (en) * | 2009-04-09 | 2010-10-14 | N.V. Organon | Indane derivatives |
| KR101701943B1 (ko) | 2009-11-13 | 2017-02-02 | 도레이 카부시키가이샤 | 당뇨병의 치료 또는 예방약 |
| US9955802B2 (en) | 2015-04-08 | 2018-05-01 | Fasteners For Retail, Inc. | Divider with selectively securable track assembly |
Family Cites Families (8)
| 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 |
| EP0219756B1 (de) * | 1985-10-09 | 1994-01-05 | Shell Internationale Researchmaatschappij B.V. | Neue Acrylsäureamide |
| 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 |
| WO1989001330A2 (en) * | 1987-08-20 | 1989-02-23 | Smith Kline & French Laboratories Limited | W-arylsulphonamidoalkanoic acids for treatment of thromboxane mediated diseases |
-
1989
- 1989-09-28 DE DE3932403A patent/DE3932403A1/de not_active Withdrawn
-
1990
- 1990-05-04 AT AT90108433T patent/ATE132138T1/de not_active IP Right Cessation
- 1990-05-04 ES ES90108433T patent/ES2083394T3/es not_active Expired - Lifetime
- 1990-05-04 EP EP90108433A patent/EP0397044B1/de not_active Expired - Lifetime
- 1990-05-04 DK DK90108433.5T patent/DK0397044T3/da active
- 1990-05-04 DE DE59009994T patent/DE59009994D1/de not_active Expired - Fee Related
- 1990-05-10 PT PT93994A patent/PT93994B/pt not_active IP Right Cessation
- 1990-05-10 IL IL94347A patent/IL94347A0/xx not_active IP Right Cessation
- 1990-05-10 KR KR1019900006587A patent/KR0153527B1/ko not_active Expired - Fee Related
- 1990-05-10 NZ NZ233638A patent/NZ233638A/en unknown
- 1990-05-11 FI FI902358A patent/FI95372C/fi not_active IP Right Cessation
- 1990-05-11 HU HU903013A patent/HU214586B/hu not_active IP Right Cessation
- 1990-05-11 NO NO902099A patent/NO176176C/no not_active IP Right Cessation
- 1990-05-11 AU AU54924/90A patent/AU627024B2/en not_active Ceased
- 1990-05-11 JP JP2122825A patent/JP2868283B2/ja not_active Expired - Lifetime
- 1990-05-11 CA CA002016646A patent/CA2016646C/en not_active Expired - Fee Related
- 1990-05-11 IE IE170890A patent/IE74207B1/en not_active IP Right Cessation
- 1990-05-14 US US07/523,167 patent/US5294626A/en not_active Expired - Fee Related
-
1992
- 1992-01-08 RU SU925010477A patent/RU2096405C1/ru active
- 1992-06-12 MX MX9202816A patent/MX9202816A/es unknown
-
1993
- 1993-05-12 UA UA93002789A patent/UA26136C2/uk unknown
- 1993-11-18 US US08/154,647 patent/US5426119A/en not_active Expired - Fee Related
-
1995
- 1995-03-21 US US08/407,180 patent/US5681961A/en not_active Expired - Fee Related
-
1996
- 1996-02-21 GR GR960400447T patent/GR3019044T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO176176B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive arylsulfonamider | |
| SK285433B6 (sk) | Spôsob prípravy bifenylových derivátov vhodných na prípravu 4-aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridínov | |
| NO941101L (no) | Quinazolin-derivater | |
| US4994460A (en) | Agents for treatment of brain ischemia | |
| HRP20050944A2 (en) | Novel heterocyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them | |
| CA2369103A1 (en) | Nitrogen-containing heterocyclic compounds and benamide compounds and drugs containing the same | |
| EP0372657A1 (en) | Anxiolytically active piperazine derivatives | |
| HUP0004006A2 (hu) | Új benzotiofén-, benzofurán- és indolszármazékok, eljárás előállításukra és ilyen vegyületeket tartalmazó gyógyászati készítmények | |
| WO2002034754A3 (en) | Benzoxazinone derivatives, their preparation and use | |
| WO2009015485A1 (en) | Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer | |
| US4904663A (en) | N-(2-oxpyrrolidin-1-yl-)acetyl)piperazine derivatives and drug for senile dementia | |
| NO313196B1 (no) | Pyrimidinylpyrazol-derivat, og antitumormiddel inneholdende dette | |
| CZ265994A3 (en) | Derivatives of 1-/2h-1-benzopyran-2-on-8-yl/piperazine, process of their preparation pharmaceutical compositions containing thereof as active components and their use | |
| EP0612730B1 (en) | O-aryl ethers of morphinans | |
| NO20082226L (no) | 6-heteroarylpyridoindolonderivater, deres fremstilling og terapeutisk anvendelse derav | |
| MXPA06013953A (es) | Productos de biaril aromaticos, composiciones que contienen los mismos y uso como medicamentos. | |
| MX2009010243A (es) | Compuestos de quinolina apropiados para tratar trastornos que responden a la modulacion del receptor de serotonina 5-ht6. | |
| NO20002351D0 (no) | Nye substituerte pyridin- eller piperidinforbindelser, fremgangsmÕte ved deres fremstilling og farmasøytiske sammensetninger inneholdende dem | |
| US5180746A (en) | Aralkylamine compounds | |
| MX2023008250A (es) | Compuestos de derivados sustituidos en 4,6 de ip4. | |
| CH663616A5 (de) | 1,4-dihydropyridin-derivate und sie enthaltende pharmazeutische zubereitungen. | |
| HUP9900679A2 (hu) | Simaizom sejtburjánzást gátló benzimidazolszármazékok, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| AU627339B2 (en) | Novel cyclic vinylogous n-hydroxy-n-methylureas useful as 5-lipoxygenase inhibitors | |
| DK0944618T3 (da) | Nye N-benzensulfonyl-L-prolin-derivater, fremgangsmåde til deres fremstilling og deres anvendelse til terapeutiske formål | |
| AU636192B2 (en) | Indolylpropanols and preparations containing them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN NOVEMBER 2000 |