NO300805B1 - Nye substituerte salicylsyrer - Google Patents
Nye substituerte salicylsyrer Download PDFInfo
- Publication number
- NO300805B1 NO300805B1 NO941799A NO941799A NO300805B1 NO 300805 B1 NO300805 B1 NO 300805B1 NO 941799 A NO941799 A NO 941799A NO 941799 A NO941799 A NO 941799A NO 300805 B1 NO300805 B1 NO 300805B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- spin system
- hydroxy
- added
- solution
- Prior art date
Links
- 150000003870 salicylic acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 67
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 32
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical class C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- -1 for oral use Chemical class 0.000 description 67
- 239000000047 product Substances 0.000 description 60
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- 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 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical group OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 31
- 229960001860 salicylate Drugs 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 29
- 239000002253 acid Substances 0.000 description 27
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
- 238000001816 cooling Methods 0.000 description 25
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- 238000003756 stirring Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 238000001914 filtration Methods 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 238000009835 boiling Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 13
- 235000019253 formic acid Nutrition 0.000 description 13
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical group C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000005711 Benzoic acid Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
- 229960001940 sulfasalazine Drugs 0.000 description 12
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 9
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
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- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 7
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
- 210000003714 granulocyte Anatomy 0.000 description 7
- QOIIQYGCRPHBQJ-UHFFFAOYSA-N 2-methylpropyl 2-hydroxy-5-iodobenzoate Chemical compound CC(C)COC(=O)C1=CC(I)=CC=C1O QOIIQYGCRPHBQJ-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
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- 201000010099 disease Diseases 0.000 description 6
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- 238000000034 method Methods 0.000 description 6
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- CDBVOMLNZNWSGH-UHFFFAOYSA-N 4-iodo-n-pyridin-2-ylbenzenesulfonamide Chemical compound C1=CC(I)=CC=C1S(=O)(=O)NC1=CC=CC=N1 CDBVOMLNZNWSGH-UHFFFAOYSA-N 0.000 description 5
- 206010009900 Colitis ulcerative Diseases 0.000 description 5
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- 201000006704 Ulcerative Colitis Diseases 0.000 description 5
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- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 5
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- MBOOOFATVCDAHC-UHFFFAOYSA-M potassium;4-[2-(4-hydroxy-3-methoxycarbonylphenyl)ethenyl]benzenesulfonate Chemical compound [K+].C1=C(O)C(C(=O)OC)=CC(C=CC=2C=CC(=CC=2)S([O-])(=O)=O)=C1 MBOOOFATVCDAHC-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- RBOQHPLFKLNTKX-UHFFFAOYSA-N propan-2-yl 2-hydroxy-5-iodobenzoate Chemical compound CC(C)OC(=O)C1=CC(I)=CC=C1O RBOQHPLFKLNTKX-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 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
- C07D213/60—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
-
- 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]
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9103397A SE9103397D0 (sv) | 1991-11-18 | 1991-11-18 | Nya substituerade salicylsyror |
| PCT/SE1992/000758 WO1993010094A1 (en) | 1991-11-18 | 1992-11-04 | Novel substituted salicyclic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO941799D0 NO941799D0 (no) | 1994-05-13 |
| NO941799L NO941799L (el) | 1994-06-22 |
| NO300805B1 true NO300805B1 (no) | 1997-07-28 |
Family
ID=20384352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO941799A NO300805B1 (no) | 1991-11-18 | 1994-05-13 | Nye substituerte salicylsyrer |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US5302718A (el) |
| EP (1) | EP0613468B1 (el) |
| JP (1) | JP3259915B2 (el) |
| KR (1) | KR100253748B1 (el) |
| AT (1) | ATE194597T1 (el) |
| AU (1) | AU668528B2 (el) |
| CA (1) | CA2123697C (el) |
| DE (1) | DE69231252T2 (el) |
| DK (1) | DK0613468T3 (el) |
| EE (1) | EE03026B1 (el) |
| ES (1) | ES2149780T3 (el) |
| FI (1) | FI106857B (el) |
| GR (1) | GR3034585T3 (el) |
| HU (2) | HU221476B (el) |
| IL (1) | IL103665A (el) |
| LT (1) | LT3182B (el) |
| LV (1) | LV10246B (el) |
| MX (1) | MX9206647A (el) |
| MY (1) | MY130169A (el) |
| NO (1) | NO300805B1 (el) |
| NZ (1) | NZ244998A (el) |
| PT (1) | PT101068B (el) |
| RU (1) | RU2124501C1 (el) |
| SE (1) | SE9103397D0 (el) |
| SK (1) | SK282080B6 (el) |
| TW (1) | TW304944B (el) |
| UA (1) | UA42869C2 (el) |
| WO (1) | WO1993010094A1 (el) |
| ZA (1) | ZA928864B (el) |
Families Citing this family (45)
| 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 |
| AU7074496A (en) | 1995-09-18 | 1997-04-09 | Ligand Pharmaceuticals Incorporated | 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 |
| WO1997029747A1 (en) | 1996-02-20 | 1997-08-21 | 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 |
| EP1093362A1 (en) | 1998-06-12 | 2001-04-25 | Ligand Pharmaceuticals Incorporated | Treatment of anti-estrogen resistant breast cancer using rxr modulators |
| EP1165472A4 (en) | 1999-03-19 | 2002-11-20 | Bristol Myers Squibb Co | METHOD FOR PRODUCING BIPHENYL ISOXAZOLE |
| US6878712B1 (en) | 1999-09-04 | 2005-04-12 | Astrazeneca Ab | Amides as inhibitors for pyruvate dehydrogenase |
| SK286774B6 (sk) | 1999-09-04 | 2009-05-07 | Astrazeneca Ab | Substituované N-fenyl-2-hydroxy-2-metyl-3,3,3- trifluórpropánamidové deriváty, spôsob ich prípravy a farmaceutický prostriedok, ktorý ich obsahuje |
| WO2001017955A2 (en) | 1999-09-04 | 2001-03-15 | Astrazeneca Ab | Hydroxyacetamidobenzenesulphonamide derivatives |
| EP1278521B1 (en) * | 2000-04-28 | 2005-11-30 | The University of British Columbia | N-heterocyclic substituted salicylates for the treatment of cancer |
| 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 |
| US6639082B2 (en) | 2000-10-17 | 2003-10-28 | Bristol-Myers Squibb Company | Methods for the preparation of biphenyl isoxazole sulfonamides |
| WO2005023771A1 (ja) * | 2003-09-05 | 2005-03-17 | Ono Pharmaceutical Co., Ltd. | ケモカインレセプターアンタゴニストおよびその医薬用途 |
| JP2007514731A (ja) * | 2003-12-19 | 2007-06-07 | ファイザー インコーポレイテッド | 糖尿病及び肥満症の治療のための１１−ベータ−ヒドロキシステロイドデヒドロゲナーゼ１型（１１−β−ｈｓｄ−１）の阻害剤としてのベンゼンスルホニルアミノ−ピリジン−２−イル誘導体及び関連化合物 |
| EP1763353A1 (en) * | 2004-06-29 | 2007-03-21 | Warner-Lambert Company LLC | COMBINATION THERAPIES UTILIZING BENZAMIDE INHIBITORS OF THE P2X<sb>7</sb> RECEPTOR |
| GB2421947A (en) * | 2005-01-07 | 2006-07-12 | Univ Southampton | Sulphonamide compounds for use as inhibitors of NF-kB |
| JP2009527560A (ja) * | 2006-02-21 | 2009-07-30 | アムゲン インコーポレイティッド | ホスホジエステラーゼ１０阻害剤としてのシンノリン誘導体 |
| RU2481329C2 (ru) * | 2008-06-23 | 2013-05-10 | Астеллас Фарма Инк. | Сульфонамидные соединения или их соли |
| EP2677865A4 (en) * | 2011-02-23 | 2015-04-22 | Icahn School Med Mount Sinai | BROMODOMAIN INHIBITORS AS MODULATORS OF GENE EXPRESSION |
| KR102653667B1 (ko) | 2015-05-20 | 2024-04-03 | 암젠 인크 | Apj 수용체의 트라이아졸 작용제 |
| CN108602775B (zh) | 2016-01-14 | 2022-04-29 | 贝思以色列女会吏医学中心公司 | 肥大细胞调节剂及其用途 |
| US9988369B2 (en) | 2016-05-03 | 2018-06-05 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the APJ receptor |
| US10736883B2 (en) | 2016-11-16 | 2020-08-11 | Amgen Inc. | Triazole furan compounds as agonists of the APJ receptor |
| EP3541802A1 (en) | 2016-11-16 | 2019-09-25 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| EP3541804A1 (en) | 2016-11-16 | 2019-09-25 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| WO2018093580A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole pyridyl 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 |
| WO2018097945A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| EP3704122B1 (en) | 2017-11-03 | 2021-09-01 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | 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 (4)
| 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 |
| 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 DK DK92924067T patent/DK0613468T3/da active
- 1992-11-04 HU HU9401391A patent/HU221476B/hu not_active IP Right Cessation
- 1992-11-04 JP JP50919193A patent/JP3259915B2/ja not_active Expired - Fee Related
- 1992-11-04 KR KR1019940701664A patent/KR100253748B1/ko not_active IP Right Cessation
- 1992-11-04 SK SK547-94A patent/SK282080B6/sk unknown
- 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 ES ES92924067T patent/ES2149780T3/es not_active Expired - Lifetime
- 1992-11-04 AT AT92924067T patent/ATE194597T1/de not_active IP Right Cessation
- 1992-11-04 EP EP92924067A patent/EP0613468B1/en not_active Expired - Lifetime
- 1992-11-04 WO PCT/SE1992/000758 patent/WO1993010094A1/en active IP Right Grant
- 1992-11-04 CA CA002123697A patent/CA2123697C/en not_active Expired - Fee Related
- 1992-11-04 DE DE69231252T patent/DE69231252T2/de not_active Expired - Fee Related
- 1992-11-04 UA UA94005499A patent/UA42869C2/uk unknown
- 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 MY MYPI92002100A patent/MY130169A/en unknown
- 1992-11-17 PT PT101068A patent/PT101068B/pt not_active IP Right Cessation
- 1992-11-17 LT LTIP229A patent/LT3182B/lt not_active IP Right Cessation
- 1992-11-17 ZA ZA928864A patent/ZA928864B/xx unknown
- 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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