CS254349B2 - Method of new substituted isoxazole derivatives production - Google Patents
Method of new substituted isoxazole derivatives production Download PDFInfo
- Publication number
- CS254349B2 CS254349B2 CS863572A CS357286A CS254349B2 CS 254349 B2 CS254349 B2 CS 254349B2 CS 863572 A CS863572 A CS 863572A CS 357286 A CS357286 A CS 357286A CS 254349 B2 CS254349 B2 CS 254349B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- mixture
- cyclization
- mmol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 150000002545 isoxazoles Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002516 radical scavenger Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- -1 4,5-dihydro-2-oxazolyl Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- VHLNLJATUHVCJE-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxamide Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C(=O)NCCO)S1 VHLNLJATUHVCJE-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- FWHWSIDEKGSJBP-UHFFFAOYSA-N methyl 4-hydroxythiophene-2-carboxylate Chemical compound COC(=O)C1=CC(O)=CS1 FWHWSIDEKGSJBP-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- AINVMTPHDUDZJT-UHFFFAOYSA-N 5-(7-chloroheptyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CCCCCCCCl)ON=1 AINVMTPHDUDZJT-UHFFFAOYSA-N 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- GNADIFGDFHOHCW-UHFFFAOYSA-N 5-(7-iodoheptyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CCCCCCCI)ON=1 GNADIFGDFHOHCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- VKIHGEOLKYTUCP-UHFFFAOYSA-N methyl 5-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1OCCCCCCCC1=CC(C)=NO1 VKIHGEOLKYTUCP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000709661 Enterovirus Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IVSDAMUJGWUUJU-UHFFFAOYSA-N 4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxylic acid Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CSC(C(O)=O)=C1 IVSDAMUJGWUUJU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002924 anti-infective effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- LQOXZBKAAJDINZ-UHFFFAOYSA-N methyl 4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(OCCCCCCCC=2ON=C(C)C=2)=C1 LQOXZBKAAJDINZ-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTJHNJCILMMRIQ-UHFFFAOYSA-N 1-chloro-6-iodohexane Chemical compound ClCCCCCCI QTJHNJCILMMRIQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DWVVQCRRPWILHV-UHFFFAOYSA-N 3,5-dimethyl-2h-1,3-oxazole Chemical compound CN1COC(C)=C1 DWVVQCRRPWILHV-UHFFFAOYSA-N 0.000 description 1
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 1
- FFIUBSLJPHJUCZ-UHFFFAOYSA-N 4-hydroxythiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CS1 FFIUBSLJPHJUCZ-UHFFFAOYSA-N 0.000 description 1
- WBWVCVIGPNKPAT-UHFFFAOYSA-N 5-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxylic acid Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C(O)=O)S1 WBWVCVIGPNKPAT-UHFFFAOYSA-N 0.000 description 1
- BHHCDNFPBLNHAU-UHFFFAOYSA-N 5-hydroxythiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(O)S1 BHHCDNFPBLNHAU-UHFFFAOYSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001466953 Echovirus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000709704 Human poliovirus 2 Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 210000005098 blood-cerebrospinal fluid barrier Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- YWOCPLCLKUUPHB-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[7-(3-methyl-1,2-oxazol-5-yl)heptoxy]thiophene-2-carboxamide Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CSC(C(=O)NCCO)=C1 YWOCPLCLKUUPHB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT149385 | 1985-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS254349B2 true CS254349B2 (en) | 1988-01-15 |
Family
ID=3515076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS863572A CS254349B2 (en) | 1985-05-17 | 1986-05-16 | Method of new substituted isoxazole derivatives production |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4812472A (no) |
| EP (1) | EP0211157B1 (no) |
| JP (1) | JPH0680059B2 (no) |
| KR (1) | KR930006776B1 (no) |
| AT (1) | ATE59647T1 (no) |
| AU (1) | AU588315B2 (no) |
| CA (1) | CA1271481A (no) |
| CS (1) | CS254349B2 (no) |
| DD (1) | DD258812A1 (no) |
| DE (1) | DE3676378D1 (no) |
| DK (1) | DK167679B1 (no) |
| ES (1) | ES8801805A1 (no) |
| FI (1) | FI83782C (no) |
| HU (1) | HU197003B (no) |
| NO (1) | NO164352C (no) |
| NZ (1) | NZ216125A (no) |
| SG (1) | SG43191G (no) |
| SU (1) | SU1493106A3 (no) |
| UA (1) | UA5548A1 (no) |
| ZA (1) | ZA863652B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861791A (en) * | 1983-08-29 | 1989-08-29 | Sterling Drug Inc. | Dihydro-oxazolyl substituted-phenyl-aliphatic lower alkyl and their use as antiviral agents |
| MY102282A (en) * | 1987-01-28 | 1992-05-15 | Cl Pharma | Isoxazole derivatives with antiviral activities and pharmaceutical products containing these. |
| GB8911158D0 (en) * | 1989-05-16 | 1989-07-05 | Janssen Pharmaceutica Nv | Antiviral pyridazinamines |
| US5070090A (en) * | 1989-05-15 | 1991-12-03 | Janssen Pharmaceutica N.V. | Antipicorpaviral herterocyclic-substituted morpholinyl alkylphenol ethers |
| EP1028959B1 (en) * | 1997-11-07 | 2007-06-27 | Basf Aktiengesellschaft | Herbicidal furanyl- and thienyloxyazines |
| CN116196752A (zh) * | 2023-02-22 | 2023-06-02 | 吴桥县六合德利化工有限责任公司 | 一种利用氯化亚砜为原料生产ob酸的尾气处理工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714082A (en) * | 1955-07-26 | New oxazoline derivatives | ||
| US4451476A (en) * | 1982-12-13 | 1984-05-29 | Sterling Drug Inc. | Isoxazoles as antiviral agents |
| NZ209209A (en) * | 1983-08-29 | 1988-02-12 | Sterling Drug Inc | Substituted phenyl-aliphatic isoxazole derivatives and pharmaceutical compositions |
-
1986
- 1986-05-09 FI FI861934A patent/FI83782C/fi not_active IP Right Cessation
- 1986-05-12 NZ NZ216125A patent/NZ216125A/xx unknown
- 1986-05-13 DD DD86290190A patent/DD258812A1/de not_active IP Right Cessation
- 1986-05-13 CA CA000508965A patent/CA1271481A/en not_active Expired - Fee Related
- 1986-05-14 DE DE8686106529T patent/DE3676378D1/de not_active Expired - Fee Related
- 1986-05-14 NO NO861923A patent/NO164352C/no unknown
- 1986-05-14 EP EP86106529A patent/EP0211157B1/de not_active Expired - Lifetime
- 1986-05-14 AT AT86106529T patent/ATE59647T1/de not_active IP Right Cessation
- 1986-05-15 KR KR1019860003792A patent/KR930006776B1/ko not_active Expired - Fee Related
- 1986-05-16 HU HU862078A patent/HU197003B/hu not_active IP Right Cessation
- 1986-05-16 ES ES555030A patent/ES8801805A1/es not_active Expired
- 1986-05-16 SU SU864027501A patent/SU1493106A3/ru active
- 1986-05-16 JP JP61110975A patent/JPH0680059B2/ja not_active Expired - Lifetime
- 1986-05-16 AU AU57508/86A patent/AU588315B2/en not_active Ceased
- 1986-05-16 ZA ZA863652A patent/ZA863652B/xx unknown
- 1986-05-16 DK DK228086A patent/DK167679B1/da not_active Application Discontinuation
- 1986-05-16 CS CS863572A patent/CS254349B2/cs unknown
- 1986-05-16 UA UA4027501A patent/UA5548A1/uk unknown
-
1987
- 1987-11-12 US US07/120,264 patent/US4812472A/en not_active Expired - Fee Related
-
1991
- 1991-06-11 SG SG43191A patent/SG43191G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR930006776B1 (ko) | 1993-07-23 |
| EP0211157A1 (de) | 1987-02-25 |
| SU1493106A3 (ru) | 1989-07-07 |
| HU197003B (en) | 1989-02-28 |
| FI83782C (fi) | 1991-08-26 |
| DK228086A (da) | 1986-11-18 |
| HUT43594A (en) | 1987-11-30 |
| JPS61268680A (ja) | 1986-11-28 |
| NZ216125A (en) | 1988-10-28 |
| ES555030A0 (es) | 1987-07-16 |
| FI861934L (fi) | 1986-11-18 |
| EP0211157B1 (de) | 1991-01-02 |
| CA1271481A (en) | 1990-07-10 |
| US4812472A (en) | 1989-03-14 |
| DK228086D0 (da) | 1986-05-16 |
| DK167679B1 (da) | 1993-12-06 |
| UA5548A1 (uk) | 1994-12-28 |
| NO861923L (no) | 1986-11-18 |
| AU588315B2 (en) | 1989-09-14 |
| DE3676378D1 (de) | 1991-02-07 |
| ES8801805A1 (es) | 1987-07-16 |
| SG43191G (en) | 1991-08-23 |
| NO164352B (no) | 1990-06-18 |
| DD258812A1 (de) | 1988-08-03 |
| ZA863652B (en) | 1987-01-28 |
| NO164352C (no) | 1990-09-26 |
| KR860009011A (ko) | 1986-12-19 |
| FI861934A0 (fi) | 1986-05-09 |
| ATE59647T1 (de) | 1991-01-15 |
| JPH0680059B2 (ja) | 1994-10-12 |
| AU5750886A (en) | 1986-11-20 |
| FI83782B (fi) | 1991-05-15 |
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