FI106857B - Menetelmä uusien farmakologisesti aktiivisten salisyylihappojohdannaisten valmistamiseksi - Google Patents
Menetelmä uusien farmakologisesti aktiivisten salisyylihappojohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI106857B FI106857B FI942289A FI942289A FI106857B FI 106857 B FI106857 B FI 106857B FI 942289 A FI942289 A FI 942289A FI 942289 A FI942289 A FI 942289A FI 106857 B FI106857 B FI 106857B
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- Finland
- Prior art keywords
- het
- compound
- methyl
- eller
- hydrogen
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- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 20
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 title claims description 5
- 150000003872 salicylic acid derivatives Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 81
- -1 alkyl halogen Chemical class 0.000 claims description 39
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 15
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 8
- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004185 ester group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006555 catalytic reaction Methods 0.000 claims description 3
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- 150000007524 organic acids Chemical class 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
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- 230000003389 potentiating effect Effects 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
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- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
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- 235000007265 Myrrhis odorata Nutrition 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000009432 framing Methods 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 230000037431 insertion Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
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- 210000000653 nervous system Anatomy 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
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- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 42
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- 238000001914 filtration Methods 0.000 description 30
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 229960001860 salicylate Drugs 0.000 description 29
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- VTCABGNSRBFUEN-UHFFFAOYSA-N 2-hydroxy-5-[2-[4-[(3-methylpyridin-2-yl)sulfamoyl]phenyl]ethenyl]benzoic acid Chemical compound CC1=CC=CN=C1NS(=O)(=O)C(C=C1)=CC=C1C=CC1=CC=C(O)C(C(O)=O)=C1 VTCABGNSRBFUEN-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9103397A SE9103397D0 (sv) | 1991-11-18 | 1991-11-18 | Nya substituerade salicylsyror |
| SE9103397 | 1991-11-18 | ||
| SE9200758 | 1992-11-04 | ||
| PCT/SE1992/000758 WO1993010094A1 (en) | 1991-11-18 | 1992-11-04 | Novel substituted salicyclic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI942289L FI942289L (fi) | 1994-05-17 |
| FI942289A0 FI942289A0 (fi) | 1994-05-17 |
| FI106857B true FI106857B (fi) | 2001-04-30 |
Family
ID=20384352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI942289A FI106857B (fi) | 1991-11-18 | 1994-05-17 | Menetelmä uusien farmakologisesti aktiivisten salisyylihappojohdannaisten valmistamiseksi |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US5302718A (enExample) |
| EP (1) | EP0613468B1 (enExample) |
| JP (1) | JP3259915B2 (enExample) |
| KR (1) | KR100253748B1 (enExample) |
| AT (1) | ATE194597T1 (enExample) |
| AU (1) | AU668528B2 (enExample) |
| CA (1) | CA2123697C (enExample) |
| DE (1) | DE69231252T2 (enExample) |
| DK (1) | DK0613468T3 (enExample) |
| EE (1) | EE03026B1 (enExample) |
| ES (1) | ES2149780T3 (enExample) |
| FI (1) | FI106857B (enExample) |
| GR (1) | GR3034585T3 (enExample) |
| HU (2) | HU221476B (enExample) |
| IL (1) | IL103665A (enExample) |
| LT (1) | LT3182B (enExample) |
| LV (1) | LV10246B (enExample) |
| MX (1) | MX9206647A (enExample) |
| MY (1) | MY130169A (enExample) |
| NO (1) | NO300805B1 (enExample) |
| NZ (1) | NZ244998A (enExample) |
| PT (1) | PT101068B (enExample) |
| RU (1) | RU2124501C1 (enExample) |
| SE (1) | SE9103397D0 (enExample) |
| SK (1) | SK282080B6 (enExample) |
| TW (1) | TW304944B (enExample) |
| UA (1) | UA42869C2 (enExample) |
| WO (1) | WO1993010094A1 (enExample) |
| ZA (1) | ZA928864B (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5514696A (en) * | 1992-05-06 | 1996-05-07 | Bristol-Myers Squibb Co. | Phenyl sulfonamide endothelin antagonists |
| GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
| US5965732A (en) * | 1993-08-30 | 1999-10-12 | Bristol-Myers Squibb Co. | Sulfonamide endothelin antagonists |
| US5405842A (en) * | 1994-01-28 | 1995-04-11 | Silverman; Bernard A. | Treatment of steroid dependent asthmatics |
| GB9504854D0 (en) * | 1994-03-31 | 1995-04-26 | Zeneca Ltd | Nitrogen derivatives |
| US5612359A (en) * | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| US5846990A (en) * | 1995-07-24 | 1998-12-08 | Bristol-Myers Squibb Co. | Substituted biphenyl isoxazole sulfonamides |
| EP0788353A1 (en) | 1995-09-18 | 1997-08-13 | Ligand Pharmaceuticals, Inc. | Ppar gamma antagonists for treating obesity |
| JPH09124620A (ja) * | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| US5856507A (en) * | 1997-01-21 | 1999-01-05 | Bristol-Myers Squibb Co. | Methods for the preparation of biphenyl isoxazole sulfonamides |
| AU717230B2 (en) | 1996-02-20 | 2000-03-23 | Bristol-Myers Squibb Company | Methods for the preparation of biphenyl isoxazole sulfonamides |
| US5939446A (en) * | 1996-04-09 | 1999-08-17 | Bristol-Myers Squibb Co. | Heteroaryl substituted phenyl isoxazole sulfonamide endothelin antagonists |
| JP3814742B2 (ja) * | 1996-10-18 | 2006-08-30 | イハラケミカル工業株式会社 | ４−フルオロサリチル酸類 |
| WO1998033781A1 (en) * | 1997-01-30 | 1998-08-06 | Bristol-Myers Squibb Company | Method for preventing or treating low renin hypertension by administering an endothelin antagonist |
| TW536540B (en) * | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
| GB9805520D0 (en) | 1998-03-17 | 1998-05-13 | Zeneca Ltd | Chemical compounds |
| GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
| CA2334545A1 (en) | 1998-06-12 | 1999-12-16 | Ligand Pharmaceuticals Incorporated | Treatment of anti-estrogen resistant breast cancer using rxr modulators |
| CA2367916A1 (en) | 1999-03-19 | 2000-09-28 | Ambarish Singh | Methods for the preparation of biphenyl isoxazole sulfonamides |
| AU6715200A (en) | 1999-09-04 | 2001-04-10 | Astrazeneca Ab | Amides as inhibitors for pyruvate dehydrogenase |
| CZ2002773A3 (cs) | 1999-09-04 | 2002-06-12 | Astrazeneca Ab | Substituované deriváty N-fenyl-2-hydroxy-2-methyl-3,3,3-trifluorpropanamidu, které zvyąují aktivitu pyruvátdehydrogenázy |
| DE60031699T2 (de) | 1999-09-04 | 2007-08-30 | Astrazeneca Ab | Hydroxyacetamidobenzolsulfonamidderivate |
| CA2307278A1 (en) * | 2000-04-28 | 2001-10-28 | University Of British Columbia | Use of n-heterocyclic substituted salicylic acids for inhibition of cellular uptake of cystine |
| EP1278521B1 (en) * | 2000-04-28 | 2005-11-30 | The University of British Columbia | N-heterocyclic substituted salicylates for the treatment of cancer |
| US6639082B2 (en) | 2000-10-17 | 2003-10-28 | Bristol-Myers Squibb Company | Methods for the preparation of biphenyl isoxazole sulfonamides |
| KR100360342B1 (ko) * | 2002-04-19 | 2002-11-13 | 박계정 | 밸런스 머신의 언밸런스 수정위치 및 수정량의 자동 보상방법 |
| EP1661889A4 (en) * | 2003-09-05 | 2009-08-05 | Ono Pharmaceutical Co | ANTAGONIST OF THE CHEMOKINE RECEPTOR AND ITS USE FOR MEDICAL PURPOSES |
| BRPI0417687A (pt) * | 2003-12-19 | 2007-04-03 | Pfizer | derivados de benzenossulfonilamino-piridin-2-ila e compostos relacionados como inibidores de 11-beta-hidroxiesteróide desidrogenase tipo 1 (11-beta-hsd-1) para o tratamento de diabetes e obesidade |
| BRPI0512915A (pt) * | 2004-06-29 | 2008-04-15 | Warner Lambert Co | terapias de combinação utilizando inibidores benzamida do receptor p2x7 |
| GB2421947A (en) * | 2005-01-07 | 2006-07-12 | Univ Southampton | Sulphonamide compounds for use as inhibitors of NF-kB |
| MX2008010668A (es) * | 2006-02-21 | 2008-10-01 | Amgen Inc | Derivados de cinolina como inhibidores de fosfodiesterasa 10. |
| CN102076660B (zh) * | 2008-06-23 | 2014-01-08 | 安斯泰来制药有限公司 | 磺胺化合物或其盐 |
| EP2677865A4 (en) * | 2011-02-23 | 2015-04-22 | Icahn School Med Mount Sinai | BROMODOMAIN INHIBITORS AS MODULATORS OF GENE EXPRESSION |
| MA42145B1 (fr) | 2015-05-20 | 2020-05-29 | Amgen Inc | Triazoles agonistes du récepteur apj |
| WO2017123826A1 (en) | 2016-01-14 | 2017-07-20 | Beth Israel Deaconess Medical Center, Inc. | Mast-cell modulators and uses thereof |
| EP3452466B1 (en) | 2016-05-03 | 2020-08-12 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| EP3541802B1 (en) | 2016-11-16 | 2025-01-01 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| WO2019089335A1 (en) | 2017-11-03 | 2019-05-09 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| EP3788037A1 (en) | 2018-05-01 | 2021-03-10 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| CN111056978B (zh) * | 2019-12-13 | 2021-01-19 | 西安交通大学 | 一种磺酰胺类化合物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2396145A (en) | 1940-12-14 | 1946-03-05 | Pharmscia Ab | Heterocyclic sulphonamido azo compounds |
| BE791889A (fr) * | 1971-11-26 | 1973-05-24 | Pharmacia Ab | Nouveaux derives de la pyridine |
| AU567140B2 (en) * | 1984-01-06 | 1987-11-12 | Shionogi & Co., Ltd. | Sulphonamido-benzamide derivatives |
| US4663334A (en) * | 1985-12-11 | 1987-05-05 | Mcneilab, Inc. | Heteroaromatic acetylenes useful as antihypertensive agents |
| US4897397A (en) * | 1988-12-16 | 1990-01-30 | Schering Corporation | Aryl-alkynoic, alkenoic or alkanoic compounds and compositions useful as antiallergy and anti-inflammatory agents |
-
1991
- 1991-11-18 SE SE9103397A patent/SE9103397D0/xx unknown
-
1992
- 1992-11-03 NZ NZ244998A patent/NZ244998A/en not_active IP Right Cessation
- 1992-11-04 UA UA94005499A patent/UA42869C2/uk unknown
- 1992-11-04 DE DE69231252T patent/DE69231252T2/de not_active Expired - Fee Related
- 1992-11-04 JP JP50919193A patent/JP3259915B2/ja not_active Expired - Fee Related
- 1992-11-04 KR KR1019940701664A patent/KR100253748B1/ko not_active Expired - Fee Related
- 1992-11-04 WO PCT/SE1992/000758 patent/WO1993010094A1/en not_active Ceased
- 1992-11-04 DK DK92924067T patent/DK0613468T3/da active
- 1992-11-04 HU HU9401391A patent/HU221476B/hu not_active IP Right Cessation
- 1992-11-04 SK SK547-94A patent/SK282080B6/sk unknown
- 1992-11-04 ES ES92924067T patent/ES2149780T3/es not_active Expired - Lifetime
- 1992-11-04 CA CA002123697A patent/CA2123697C/en not_active Expired - Fee Related
- 1992-11-04 RU RU94028109A patent/RU2124501C1/ru not_active IP Right Cessation
- 1992-11-04 AU AU29589/92A patent/AU668528B2/en not_active Ceased
- 1992-11-04 EP EP92924067A patent/EP0613468B1/en not_active Expired - Lifetime
- 1992-11-04 AT AT92924067T patent/ATE194597T1/de not_active IP Right Cessation
- 1992-11-06 IL IL10366592A patent/IL103665A/xx not_active IP Right Cessation
- 1992-11-09 US US07/973,753 patent/US5302718A/en not_active Expired - Lifetime
- 1992-11-13 LV LVP-92-202A patent/LV10246B/xx unknown
- 1992-11-17 PT PT101068A patent/PT101068B/pt not_active IP Right Cessation
- 1992-11-17 MY MYPI92002100A patent/MY130169A/en unknown
- 1992-11-17 ZA ZA928864A patent/ZA928864B/xx unknown
- 1992-11-17 LT LTIP229A patent/LT3182B/lt not_active IP Right Cessation
- 1992-11-18 MX MX9206647A patent/MX9206647A/es not_active IP Right Cessation
- 1992-11-27 TW TW081109532A patent/TW304944B/zh active
-
1993
- 1993-10-07 US US08/132,874 patent/US5403930A/en not_active Expired - Fee Related
-
1994
- 1994-05-13 NO NO941799A patent/NO300805B1/no unknown
- 1994-05-17 FI FI942289A patent/FI106857B/fi not_active IP Right Cessation
- 1994-11-02 EE EE9400111A patent/EE03026B1/xx not_active IP Right Cessation
- 1994-12-29 US US08/365,869 patent/US5556855A/en not_active Expired - Fee Related
-
1995
- 1995-06-28 HU HU95P/P00492P patent/HU211163A9/hu unknown
-
2000
- 2000-10-09 GR GR20000402274T patent/GR3034585T3/el not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| GB | Transfer or assigment of application |
Owner name: PHARMACIA AB |
|
| MA | Patent expired |