SE454355B - Akrylsyraderivat innehallande en furyl-, pyranyl-, bensofuranyl-, oxazolyl- eller isoxazolylgrupp, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda derivat - Google Patents

Akrylsyraderivat innehallande en furyl-, pyranyl-, bensofuranyl-, oxazolyl- eller isoxazolylgrupp, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda derivat

Info

Publication number: SE454355B
Authority: SE; Sweden
Prior art keywords: formula; acid; product; compounds; oxo
Prior art date: 1983-01-24

Application number

SE8306884A

Other languages

English (en)

Swedish (sv)

Other versions

SE8306884L (sv

SE8306884D0 (sv

Inventor

M Bianchi

F Barzaghi

Original Assignee

Roussel Uclaf

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-01-24

Filing date

1983-12-13

Publication date

1988-04-25

1983-01-24 Priority claimed from IT19249/83A external-priority patent/IT1193615B/it

1983-08-25 Priority claimed from IT22647/83A external-priority patent/IT1169782B/it

1983-12-13 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1983-12-13 Publication of SE8306884D0 publication Critical patent/SE8306884D0/xx

1984-07-25 Publication of SE8306884L publication Critical patent/SE8306884L/xx

1988-04-25 Publication of SE454355B publication Critical patent/SE454355B/sv

Links

-1 PYRANYL Chemical class 0.000 title claims description 29
238000000034 method Methods 0.000 title claims description 15
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000001252 acrylic acid derivatives Chemical class 0.000 title 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 11
239000003513 alkali Substances 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000002585 base Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
238000009938 salting Methods 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims 3
125000000842 isoxazolyl group Chemical group 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000002971 oxazolyl group Chemical group 0.000 claims 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 80
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
231100000111 LD50 Toxicity 0.000 description 9
239000000546 pharmaceutical excipient Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000007903 gelatin capsule Substances 0.000 description 6
229920002472 Starch Polymers 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
230000002496 gastric effect Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
239000008107 starch Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
KEFJLCGVTHRGAH-UHFFFAOYSA-N 2-acetyl-5-methylfuran Chemical compound CC(=O)C1=CC=C(C)O1 KEFJLCGVTHRGAH-UHFFFAOYSA-N 0.000 description 2
229910002012 Aerosil® Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
206010020601 Hyperchlorhydria Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
229940100486 rice starch Drugs 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 description 2
YNIWOEDFKVNOJS-ONEGZZNKSA-N (e)-4-(2,5-dimethylfuran-3-yl)-4-oxobut-2-enoic acid Chemical compound CC1=CC(C(=O)\C=C\C(O)=O)=C(C)O1 YNIWOEDFKVNOJS-ONEGZZNKSA-N 0.000 description 1
WIBDTHYNPIUMKW-OWOJBTEDSA-N (e)-4-(furan-3-yl)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C=1C=COC=1 WIBDTHYNPIUMKW-OWOJBTEDSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YUTFQTAITWWGFH-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)ethanone Chemical compound C1=CC=C2OC(C(=O)C)=CC2=C1 YUTFQTAITWWGFH-UHFFFAOYSA-N 0.000 description 1
XWLBBTGITHATTI-UHFFFAOYSA-N 1-(2,5-dimethyl-1,3-oxazol-4-yl)ethanone Chemical compound CC(=O)C=1N=C(C)OC=1C XWLBBTGITHATTI-UHFFFAOYSA-N 0.000 description 1
GCCKHXWBNPBUOD-UHFFFAOYSA-N 1-(furan-3-yl)ethanone Chemical compound CC(=O)C=1C=COC=1 GCCKHXWBNPBUOD-UHFFFAOYSA-N 0.000 description 1
IYEVQBUAWBANLZ-UHFFFAOYSA-N 2-Acetyl-5-methylfuran Natural products CC(=O)C1=CC(C)=CO1 IYEVQBUAWBANLZ-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
KBSVBCHYXYXDAG-UHFFFAOYSA-N 3-acetyl-2,5-dimethylfuran Chemical compound CC(=O)C=1C=C(C)OC=1C KBSVBCHYXYXDAG-UHFFFAOYSA-N 0.000 description 1
QQVPBWWENYKAGU-UHFFFAOYSA-N 4-(5-methylfuran-2-yl)-4-oxobut-2-enoic acid Chemical compound CC1=CC=C(C(=O)C=CC(O)=O)O1 QQVPBWWENYKAGU-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
241000928106 Alain Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019909 Hernia Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000029087 digestion Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SE8306884A 1983-01-24 1983-12-13 Akrylsyraderivat innehallande en furyl-, pyranyl-, bensofuranyl-, oxazolyl- eller isoxazolylgrupp, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda derivat SE454355B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT19249/83A IT1193615B (it)	1983-01-24	1983-01-24	Derivati dell'acido acrilico che comprendono un eterociclo contenente ossigeno quali medicinali,prodotti industriali e procedimento di preparazione
IT22647/83A IT1169782B (it)	1983-08-25	1983-08-25	Derivati dell'acido acrilico che contengono un ciclo ossazolico oppure isossazolico, loro procedimento di preparazione e loro applicazione come farmaco

Publications (3)

Publication Number	Publication Date
SE8306884D0 SE8306884D0 (sv)	1983-12-13
SE8306884L SE8306884L (sv)	1984-07-25
SE454355B true SE454355B (sv)	1988-04-25

Family

ID=26327109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8306884A SE454355B (sv)	1983-01-24	1983-12-13	Akrylsyraderivat innehallande en furyl-, pyranyl-, bensofuranyl-, oxazolyl- eller isoxazolylgrupp, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda derivat

Country Status (12)

Country	Link
US (2)	US4694019A (fr)
CA (1)	CA1244040A (fr)
CH (1)	CH661510A5 (fr)
DE (1)	DE3402313A1 (fr)
ES (2)	ES529073A0 (fr)
FI (1)	FI81793C (fr)
FR (1)	FR2546888B1 (fr)
GB (1)	GB2139216B (fr)
HU (1)	HU187982B (fr)
LU (1)	LU85178A1 (fr)
NL (1)	NL8400217A (fr)
SE (1)	SE454355B (fr)

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB532822A (en) *	1939-08-11	1941-01-31	John David Kendall	Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters
GB588108A (en) *	1944-10-23	1947-05-14	Roche Products Ltd	Manufacture of bacteriostatic substances
US2532579A (en) *	1946-08-06	1950-12-05	Du Pont	Pest control compositions containing beta-acyl acrylates
US2562208A (en) *	1947-04-14	1951-07-31	Schering Corp	Fungistatic composition
DE1282644B (de) *	1962-09-08	1968-11-14	Hoechst Ag	Verfahren zur Herstellung von ungesaettigten ª€-Ketocarbonsaeureestern
GR37790B (el) *	1966-12-30	1969-07-15	F. Hoffmann - La Roche & Co. Aktiengesellschaft	Μεθοδος δια την παρασκευην παραγωγων του αρουλακρυλικου οξεος.
NL6717403A (fr) *	1966-12-30	1968-07-01
DE2047806A1 (en) *	1970-09-29	1972-04-06	Dr Karl Thomae GmbH, 7950 Biberach	3-aroyl-acrylic acids - pharmaceutical intermediates prepd from acetophenones and glyoxylic acid derivs
DE2103749A1 (en) *	1971-01-27	1972-08-10	Dr. Karl Thomae GmbH, 7951 Biberach	3-acyl-acrylic acids prepn - from a ketone and glyoxylic acid (deriv)
DE2116293A1 (de) *	1971-04-02	1972-10-19	Cassella Farbwerke Mainkur Ag, 6000 Frankfurt	Ketonderivate und Verfahren zu ihrer Herstellung
US3753997A (en) *	1971-06-07	1973-08-21	A Ash	Trifluoromethly substituted-2,6-diphenyl-4-pyridyl carbinolamine antimalarials
BE788749A (fr) *	1971-09-13	1973-03-13	Takeda Chemical Industries Ltd	Acide 3-(benzoyl trisubstitue)-propionique et son procede de preparation
US4017517A (en) *	1971-09-13	1977-04-12	Takeda Chemical Industries, Ltd.	2-(Trisubstituted benzoyl)-propionic acid and a method for the production thereof
BE795893A (fr) *	1972-02-28	1973-06-18	Unicler	Derives de (methylene dioxy-3,4 phenyl)-1 dimethyl-4,4 pentene-1, leur preparation et leur application en therrapeutique
GB1392100A (en) *	1972-09-13	1975-04-23	Beecham Group Ltd	Insecticides
CH591415A5 (en) *	1972-09-13	1977-09-15	Takeda Chemical Industries Ltd	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
FR2270856B1 (fr) *	1974-01-17	1978-07-21	Screen
US3953463A (en) *	1974-03-06	1976-04-27	The United States Of America As Represented By The Secretary Of The Army	2-Aryl-6-trifluoromethyl-4-pyridyl-carbinolamine antimalarials
US3940404A (en) *	1974-03-06	1976-02-24	The United States Of America As Represented By The Secretary Of The Army	2-Substituted phenyl-6-trifluoromethyl-4-pyridyl-carbinolamines
JPS5536434A (en) *	1978-09-07	1980-03-14	Sankyo Co Ltd	4-phenyl-4-oxo-2-butenoic acid derivative and its preparation
CA1156236A (fr) *	1979-10-25	1983-11-01	George C. Rovnyak	Derives de l'acide mercaptoacyldihydropyrazole carboxylique
FR2481118A1 (fr) *	1980-04-24	1981-10-30	Roussel Uclaf	Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique
IT1171604B (it) *	1981-10-22	1987-06-10	Roussel Maestretti Spa	Derivati di acido 4-fenil-4-ossobuten-2-oico dotati di proprieta' farmacologiche e loro procedimento di preparazione

1983
- 1983-12-13 SE SE8306884A patent/SE454355B/sv not_active IP Right Cessation
1984
- 1984-01-19 FR FR8400797A patent/FR2546888B1/fr not_active Expired
- 1984-01-23 CH CH285/84A patent/CH661510A5/fr not_active IP Right Cessation
- 1984-01-23 HU HU84267A patent/HU187982B/hu not_active IP Right Cessation
- 1984-01-23 ES ES529073A patent/ES529073A0/es active Granted
- 1984-01-23 CA CA000445823A patent/CA1244040A/fr not_active Expired
- 1984-01-23 LU LU85178A patent/LU85178A1/fr unknown
- 1984-01-23 FI FI840269A patent/FI81793C/fi not_active IP Right Cessation
- 1984-01-24 NL NL8400217A patent/NL8400217A/nl not_active Application Discontinuation
- 1984-01-24 GB GB08401739A patent/GB2139216B/en not_active Expired
- 1984-01-24 DE DE19843402313 patent/DE3402313A1/de not_active Ceased
- 1984-08-31 ES ES535566A patent/ES535566A0/es active Granted
1985
- 1985-08-14 US US06/765,539 patent/US4694019A/en not_active Expired - Fee Related
1987
- 1987-05-22 US US07/052,972 patent/US4814348A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES8505917A1 (es)	1985-06-16
NL8400217A (nl)	1984-08-16
GB2139216B (en)	1986-07-16
FR2546888A1 (fr)	1984-12-07
FI840269A0 (fi)	1984-01-23
ES535566A0 (es)	1985-06-16
FR2546888B1 (fr)	1987-01-23
DE3402313A1 (de)	1984-07-26
CH661510A5 (fr)	1987-07-31
FI81793C (fi)	1990-12-10
FI840269A7 (fi)	1984-07-25
CA1244040A (fr)	1988-11-01
ES8507560A1 (es)	1985-09-01
SE8306884L (sv)	1984-07-25
SE8306884D0 (sv)	1983-12-13
GB8401739D0 (en)	1984-02-29
ES529073A0 (es)	1985-09-01
HU187982B (en)	1986-03-28
GB2139216A (en)	1984-11-07
LU85178A1 (fr)	1984-10-24
US4694019A (en)	1987-09-15
US4814348A (en)	1989-03-21
FI81793B (fi)	1990-08-31

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

Ref document number: 8306884-1

Effective date: 19920704

Format of ref document f/p: F

Publication	Publication Date	Title
EP0013960B1 (fr)	1982-11-03	Acétophénones substituées, préparations les contenant et procédés pour leur préparation
SE451838B (sv)	1987-11-02	Substituerade 4-fenyl-4-oxo-2-butensyraderivat till anvendning som lekemedel samt farmaceutisk komposition innehallande dessa
SU1409130A3 (ru)	1988-07-07	Способ получени производных ароилбензофуран/тиофенил/уксусной или пропионовой кислоты или их сложных эфиров, или их фармацевтически приемлемых солей
CA1168255A (fr)	1984-05-29	Procede de preparation de nouveaux derives d'acides phenyl aliphatique carboxyliques
NO126859B (fr)	1973-04-02
US4594443A (en)	1986-06-10	Derivatives of 4-phenyl-4-oxo-buten-2-oic acid and therapeutic use thereof
SU923369A3 (ru)	1982-04-23	Способ получени производных 5-/2-окси-3-тиопропокси/-хромон-2-уксусной кислоты или их солей со щелочными или щелочноземельными металлами
SE454355B (sv)	1988-04-25	Akrylsyraderivat innehallande en furyl-, pyranyl-, bensofuranyl-, oxazolyl- eller isoxazolylgrupp, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda derivat
US4473583A (en)	1984-09-25	Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them
SE453831B (sv)	1988-03-07	Nya 4-fenyl-4-oxo-2-butensyraderivat, deras salter, framstellning derav samt farmaceutiska kompositioner innehallande dem
JPH0356473A (ja)	1991-03-12	シクロオキシゲナーゼと５―リポキシゲナーゼの二重阻害剤である新規な７―アローイル―４―ヒドロキシ―３―メチル―ベンゾフラン
SU1685936A1 (ru)	1991-10-23	N-(Галоидфенил)-2-[(бензо-2,1,3-тиадиазол-4-сульфонил)амино]-5-хлорбензамиды, обладающие активностью при экспериментальном трихоцефалезе
JPS6241689B2 (fr)	1987-09-04
GB2162519A (en)	1986-02-05	New 4-oxo-2-butenoic acid derivatives
KR820002296B1 (ko)	1982-12-15	모라노린의 n-치환 유도체의 제조방법
CH652386A5 (fr)	1985-11-15	Derives d'acides phenyl aliphatique carboxyliques comme medicaments.
CS201009B2 (cs)	1980-10-31	Způsob výroby derivátů 9-methoxy-7H-furo-(3,2-g)(1)-benzopyran-7-onu
KR820001123B1 (ko)	1982-06-26	N-치환 몰라노린 유도체의 제조방법
AT382869B (de)	1987-04-27	Verfahren zur herstellung von acrylsaeurederivaten, die einen ein sauerstoffatom enthaltenden heterocyclus enthalten
SU791228A3 (ru)	1980-12-23	Способ получени производных аминопропанола или их солей
SU1705292A1 (ru)	1992-01-15	N-(4-хлорфенил)-2-[(бензо-2,1,3-тиадиазол-4-сульфонил)амино]-5-хлорбензамид, обладающий антигельминтной активностью
JPH0776583A (ja)	1995-03-20	クマリン誘導体及びそれらの用途
JPH08151341A (ja)	1996-06-11	スーパーオキシド産生阻害剤および１−ナフトール誘導体
JPS596312B2 (ja)	1984-02-10	セスキテルペン誘導体及びその製造法
GB2108500A (en)	1983-05-18	Aminobenzene medicaments