NO310721B1 - Benzotiazolonderivater, fremgangsmåter for deres fremstilling, mellomprodukter, farmasöytisk preparat inneholdendenevnte derivater, og anvendelse derav - Google Patents
Benzotiazolonderivater, fremgangsmåter for deres fremstilling, mellomprodukter, farmasöytisk preparat inneholdendenevnte derivater, og anvendelse derav Download PDFInfo
- Publication number
- NO310721B1 NO310721B1 NO19981104A NO981104A NO310721B1 NO 310721 B1 NO310721 B1 NO 310721B1 NO 19981104 A NO19981104 A NO 19981104A NO 981104 A NO981104 A NO 981104A NO 310721 B1 NO310721 B1 NO 310721B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- hydroxy
- oxo
- benzothiazol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 51
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 8
- 239000000543 intermediate Substances 0.000 title description 5
- BXQNSPXDWSNUKE-UHFFFAOYSA-N 1,3-benzothiazole 1-oxide Chemical class C1=CC=C2S(=O)C=NC2=C1 BXQNSPXDWSNUKE-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 144
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- -1 hemifumarate- Chemical compound 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 150000001408 amides Chemical class 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 239000003638 chemical reducing agent Substances 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 9
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 9
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- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 claims description 2
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- NEWRWHOKGIGNKK-UHFFFAOYSA-N 3-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]-n-[2-(2-phenylethoxy)ethyl]propane-1-sulfonamide Chemical group C1=2SC(=O)NC=2C(O)=CC=C1CCNCCCS(=O)(=O)NCCOCCC1=CC=CC=C1 NEWRWHOKGIGNKK-UHFFFAOYSA-N 0.000 claims description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 2
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- XRHGYUZYPHTUJZ-UHFFFAOYSA-M 4-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-M 0.000 claims 1
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
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- 238000003818 flash chromatography Methods 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 10
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- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 201000010659 intrinsic asthma Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940071648 metered dose inhaler Drugs 0.000 description 1
- VPQWANNFLPTRAN-UHFFFAOYSA-N methyl 2-[2-(2-phenylethoxy)ethylsulfonylamino]acetate Chemical compound COC(=O)CNS(=O)(=O)CCOCCC1=CC=CC=C1 VPQWANNFLPTRAN-UHFFFAOYSA-N 0.000 description 1
- KRMYTFGSRJIFRW-UHFFFAOYSA-N methyl 3-[2-(2-phenylethoxy)ethylsulfamoyl]propanoate Chemical compound COC(=O)CCS(=O)(=O)NCCOCCC1=CC=CC=C1 KRMYTFGSRJIFRW-UHFFFAOYSA-N 0.000 description 1
- JSJHDDLFSYQPMO-UHFFFAOYSA-N methyl 3-[2-(2-phenylsulfanylethoxy)ethylsulfamoyl]propanoate Chemical compound COC(=O)CCS(=O)(=O)NCCOCCSC1=CC=CC=C1 JSJHDDLFSYQPMO-UHFFFAOYSA-N 0.000 description 1
- JCCOIVGANVKHMN-UHFFFAOYSA-N methyl 3-[2-[2-(2-methylphenyl)ethoxy]ethylsulfamoyl]propanoate Chemical compound COC(=O)CCS(=O)(=O)NCCOCCC1=CC=CC=C1C JCCOIVGANVKHMN-UHFFFAOYSA-N 0.000 description 1
- ZWHSNXBZWUMKEL-UHFFFAOYSA-N methyl 3-[2-[2-(4-chlorophenyl)ethoxy]ethylsulfamoyl]propanoate Chemical compound COC(=O)CCS(=O)(=O)NCCOCCC1=CC=C(Cl)C=C1 ZWHSNXBZWUMKEL-UHFFFAOYSA-N 0.000 description 1
- WHWLDJMAHUVFJU-UHFFFAOYSA-N methyl n-[2-[2-(4-fluorophenyl)ethoxy]ethyl]carbamate Chemical compound COC(=O)NCCOCCC1=CC=C(F)C=C1 WHWLDJMAHUVFJU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- AGIOVOOODCXGPO-UHFFFAOYSA-N n-[2-[2-(4-chlorophenyl)ethoxy]ethyl]-3-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]propane-1-sulfonamide;hydrochloride Chemical compound Cl.C1=2SC(=O)NC=2C(O)=CC=C1CCNCCCS(=O)(=O)NCCOCCC1=CC=C(Cl)C=C1 AGIOVOOODCXGPO-UHFFFAOYSA-N 0.000 description 1
- PQQNPLOSZBKVJM-UHFFFAOYSA-N n-[2-[2-(4-fluorophenyl)ethoxy]ethyl]-3-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]propane-1-sulfonamide;hydrochloride Chemical compound Cl.C1=2SC(=O)NC=2C(O)=CC=C1CCNCCCS(=O)(=O)NCCOCCC1=CC=C(F)C=C1 PQQNPLOSZBKVJM-UHFFFAOYSA-N 0.000 description 1
- WNRJJIVXASHZPO-UHFFFAOYSA-N n-[2-[2-(4-hydroxy-2-oxo-3h-1,3-benzothiazol-7-yl)ethylamino]ethyl]-2-(2-phenylethoxy)ethanesulfonamide;hydrochloride Chemical compound Cl.C1=2SC(=O)NC=2C(O)=CC=C1CCNCCNS(=O)(=O)CCOCCC1=CC=CC=C1 WNRJJIVXASHZPO-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000003982 neuronal uptake Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- DSNJNSHPAJNKNH-UHFFFAOYSA-N tert-butyl 2-(2-phenylsulfanylethoxy)acetate Chemical compound CC(C)(C)OC(=O)COCCSC1=CC=CC=C1 DSNJNSHPAJNKNH-UHFFFAOYSA-N 0.000 description 1
- QXWBKQKRZNANCB-UHFFFAOYSA-N tert-butyl 3-[2-(4-fluorophenyl)ethoxy]propanoate Chemical compound CC(C)(C)OC(=O)CCOCCC1=CC=C(F)C=C1 QXWBKQKRZNANCB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229950000339 xinafoate Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
- C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9518952.8A GB9518952D0 (en) | 1995-09-15 | 1995-09-15 | Compounds |
| GBGB9614346.6A GB9614346D0 (en) | 1996-07-10 | 1996-07-10 | Benzothiazolone derivatives |
| PCT/GB1996/002247 WO1997010227A1 (en) | 1995-09-15 | 1996-09-12 | Benzothiazolone derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981104D0 NO981104D0 (no) | 1998-03-12 |
| NO981104L NO981104L (no) | 1998-05-14 |
| NO310721B1 true NO310721B1 (no) | 2001-08-20 |
Family
ID=26307771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981104A NO310721B1 (no) | 1995-09-15 | 1998-03-12 | Benzotiazolonderivater, fremgangsmåter for deres fremstilling, mellomprodukter, farmasöytisk preparat inneholdendenevnte derivater, og anvendelse derav |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US5846989A (is) |
| EP (1) | EP0850232B1 (is) |
| JP (1) | JP3213327B2 (is) |
| KR (1) | KR19990044674A (is) |
| CN (2) | CN1073098C (is) |
| AR (1) | AR004512A1 (is) |
| AT (1) | ATE190610T1 (is) |
| AU (1) | AU706094B2 (is) |
| BR (1) | BR9610316A (is) |
| CA (1) | CA2231003A1 (is) |
| CY (1) | CY2227B1 (is) |
| CZ (1) | CZ74098A3 (is) |
| DE (1) | DE69607183T2 (is) |
| EE (1) | EE03395B1 (is) |
| ES (1) | ES2146901T3 (is) |
| GR (1) | GR3033681T3 (is) |
| HK (1) | HK1008781A1 (is) |
| HU (1) | HUP9802393A3 (is) |
| IL (4) | IL141955A0 (is) |
| IS (1) | IS4679A (is) |
| MY (1) | MY113518A (is) |
| NO (1) | NO310721B1 (is) |
| NZ (4) | NZ318007A (is) |
| PL (1) | PL325517A1 (is) |
| PT (1) | PT850232E (is) |
| SK (1) | SK282394B6 (is) |
| TR (1) | TR199800457T2 (is) |
| TW (1) | TW356468B (is) |
| WO (1) | WO1997010227A1 (is) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5187991B2 (ja) * | 1997-10-17 | 2013-04-24 | アーク・セラピューティックス・リミテッド | レニン−アンジオテンシン系の阻害剤の使用 |
| SE0004750D0 (sv) * | 2000-12-19 | 2000-12-19 | Astrazeneca Ab | Novel formulation |
| GB0218629D0 (en) * | 2002-08-09 | 2002-09-18 | Novartis Ag | Organic compounds |
| AR040962A1 (es) * | 2002-08-09 | 2005-04-27 | Novartis Ag | Compuestos derivados de tiazol 1,3-2-ona, composicion farmaceutica y proceso de preparacion del compuesto |
| CN100569760C (zh) * | 2003-11-21 | 2009-12-16 | 施万制药 | 具有β2肾上腺素能受体激动剂和毒蕈碱性受体拮抗剂活性的化合物 |
| GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
| TW200738658A (en) * | 2005-08-09 | 2007-10-16 | Astrazeneca Ab | Novel compounds |
| CN101282950B (zh) * | 2005-08-09 | 2012-09-12 | 阿斯利康(瑞典)有限公司 | 新颖的苯并噻唑酮衍生物 |
| TW200740781A (en) * | 2005-08-29 | 2007-11-01 | Astrazeneca Ab | Novel compounds |
| TW200745067A (en) | 2006-03-14 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| TW200833670A (en) * | 2006-12-20 | 2008-08-16 | Astrazeneca Ab | Novel compounds 569 |
| US20100056508A1 (en) * | 2006-12-20 | 2010-03-04 | Astrazeneca Ab | Amine derivatives and their use in beta-2-adrenoreceptor mediated diseases |
| GB0702458D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | Salts 668 |
| UY31905A (es) | 2008-06-18 | 2010-01-29 | Astrazeneca Ab | Derivados de benzoxazinona, procesos de preparación, composiciones farmacéuticas conteniéndolos y aplicaciones. |
| WO2009154562A1 (en) * | 2008-06-20 | 2009-12-23 | Astrazeneca Ab | Pharmaceutical composition comprising a 4-hydroxy-2-oxo-2, 3- dihydro-1, 3-benzothiazol-7-yl compound for modulation of beta2-adrenoreceptor activity |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314944A (en) * | 1980-08-22 | 1982-02-09 | Smithkline Corporation | 4-Aminoalkyl-7-hydroxy-2(3H)-indolones |
| US4452808A (en) * | 1982-12-07 | 1984-06-05 | Smithkline Beckman Corporation | 4-Aminoalkyl-2(3H)-indolones |
| GB8426200D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
| US4554284A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | 7-(2-Aminoethyl)-1,3-benzthia- or oxa-zol-2(3H)-ones |
| US4554287A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
| DK514585A (da) * | 1984-11-08 | 1986-05-09 | Syntex Inc | Aminoethylanilinderivater |
| DE3728695A1 (de) * | 1987-08-25 | 1989-03-09 | Schering Ag | Neue benzimidazol-derivate |
| GB9024208D0 (en) * | 1990-11-07 | 1990-12-19 | Salutar Inc | Compounds |
| GB9211172D0 (en) * | 1992-05-27 | 1992-07-08 | Fisons Plc | Compounds |
| IE914003A1 (en) * | 1990-11-20 | 1992-05-20 | Astra Pharma Prod | Biologically Active Amines |
| GB9210632D0 (en) * | 1992-05-19 | 1992-07-01 | Fisons Plc | Compounds |
-
1996
- 1996-09-11 TW TW085111075A patent/TW356468B/zh active
- 1996-09-12 JP JP51175297A patent/JP3213327B2/ja not_active Expired - Fee Related
- 1996-09-12 SK SK295-98A patent/SK282394B6/sk unknown
- 1996-09-12 IL IL14195596A patent/IL141955A0/xx unknown
- 1996-09-12 BR BR9610316A patent/BR9610316A/pt not_active Application Discontinuation
- 1996-09-12 KR KR1019980701929A patent/KR19990044674A/ko not_active Application Discontinuation
- 1996-09-12 CN CN96198311A patent/CN1073098C/zh not_active Expired - Fee Related
- 1996-09-12 AU AU69371/96A patent/AU706094B2/en not_active Ceased
- 1996-09-12 NZ NZ318007A patent/NZ318007A/xx unknown
- 1996-09-12 US US08/776,770 patent/US5846989A/en not_active Expired - Lifetime
- 1996-09-12 IL IL141954??A patent/IL141954A0/xx unknown
- 1996-09-12 PL PL96325517A patent/PL325517A1/xx unknown
- 1996-09-12 ES ES96930256T patent/ES2146901T3/es not_active Expired - Lifetime
- 1996-09-12 HU HU9802393A patent/HUP9802393A3/hu unknown
- 1996-09-12 DE DE69607183T patent/DE69607183T2/de not_active Expired - Fee Related
- 1996-09-12 EP EP96930256A patent/EP0850232B1/en not_active Expired - Lifetime
- 1996-09-12 CA CA002231003A patent/CA2231003A1/en not_active Abandoned
- 1996-09-12 PT PT96930256T patent/PT850232E/pt unknown
- 1996-09-12 IL IL14195696A patent/IL141956A0/xx unknown
- 1996-09-12 EE EE9800069A patent/EE03395B1/xx not_active IP Right Cessation
- 1996-09-12 WO PCT/GB1996/002247 patent/WO1997010227A1/en not_active Application Discontinuation
- 1996-09-12 IL IL12363996A patent/IL123639A/en not_active IP Right Cessation
- 1996-09-12 AT AT96930256T patent/ATE190610T1/de not_active IP Right Cessation
- 1996-09-12 CZ CZ98740A patent/CZ74098A3/cs unknown
- 1996-09-12 TR TR1998/00457T patent/TR199800457T2/xx unknown
- 1996-09-13 MY MYPI96003788A patent/MY113518A/en unknown
- 1996-09-13 AR ARP960104355A patent/AR004512A1/es not_active Application Discontinuation
-
1998
- 1998-03-04 IS IS4679A patent/IS4679A/is unknown
- 1998-03-12 NO NO19981104A patent/NO310721B1/no unknown
- 1998-07-29 HK HK98109506A patent/HK1008781A1/xx not_active IP Right Cessation
- 1998-09-02 US US09/146,047 patent/US6008365A/en not_active Expired - Lifetime
- 1998-09-02 US US09/146,046 patent/US5977384A/en not_active Expired - Lifetime
- 1998-09-02 US US09/145,281 patent/US5973167A/en not_active Expired - Lifetime
- 1998-09-02 US US09/146,048 patent/US6080869A/en not_active Expired - Lifetime
- 1998-10-19 NZ NZ332396A patent/NZ332396A/xx unknown
- 1998-10-19 NZ NZ332397A patent/NZ332397A/xx unknown
- 1998-10-19 NZ NZ332395A patent/NZ332395A/xx unknown
-
2000
- 2000-06-14 GR GR20000401368T patent/GR3033681T3/el not_active IP Right Cessation
- 2000-12-30 CN CN00137051A patent/CN1356323A/zh active Pending
-
2001
- 2001-07-20 CY CY0100016A patent/CY2227B1/xx unknown
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