CA1202309A - Derives d'aurone - Google Patents

Derives d'aurone

Info

Publication number: CA1202309A
Authority: CA; Canada
Prior art keywords: hydrogen; carboxyl; halogen; nitro; chcooh
Prior art date: 1978-09-13
Legal status (The legal status 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 status listed.): Expired

Application number

CA000335522A

Other languages

English (en)

Inventor

Stephen R. Baker

William J. Ross

William B. Jamieson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lilly Industries Ltd

Original Assignee

Lilly Industries Ltd

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.)

1978-09-13

Filing date

1979-09-12

Publication date

1986-03-25

1979-09-12 Application filed by Lilly Industries Ltd filed Critical Lilly Industries Ltd

1986-03-25 Application granted granted Critical

1986-03-25 Publication of CA1202309A publication Critical patent/CA1202309A/fr

Status Expired legal-status Critical Current

Links

229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 34
229910052736 halogen Inorganic materials 0.000 claims abstract description 25
150000002367 halogens Chemical class 0.000 claims abstract description 25
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
150000002431 hydrogen Chemical class 0.000 claims abstract description 22
-1 cyano, hydroxy Chemical group 0.000 claims abstract description 21
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
125000003368 amide group Chemical group 0.000 claims abstract description 11
150000002148 esters Chemical class 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 7
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 5
150000001875 compounds Chemical class 0.000 claims description 44
238000000034 method Methods 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 7
ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 4
150000001540 azides Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
239000000126 substance Substances 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 1
150000008062 acetophenones Chemical class 0.000 claims 1
229930015036 aurone Natural products 0.000 abstract description 9
150000001530 aurones Chemical class 0.000 abstract description 5
150000001529 aurone derivatives Chemical class 0.000 abstract description 4
125000001188 haloalkyl group Chemical group 0.000 abstract description 4
208000006673 asthma Diseases 0.000 abstract description 3
206010027654 Allergic conditions Diseases 0.000 abstract 1
238000002512 chemotherapy Methods 0.000 abstract 1
208000030603 inherited susceptibility to asthma Diseases 0.000 abstract 1
230000000069 prophylactic effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000002253 acid Substances 0.000 description 8
239000003921 oil Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
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 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000005605 benzo group Chemical group 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
OMUOMODZGKSORV-UVTDQMKNSA-N aurone Chemical compound O1C2=CC=CC=C2C(=O)\C1=C\C1=CC=CC=C1 OMUOMODZGKSORV-UVTDQMKNSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000010902 straw Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 2
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
229910000000 metal hydroxide Inorganic materials 0.000 description 2
150000004692 metal hydroxides Chemical class 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003380 propellant Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical compound C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
229940018563 3-aminophenol Drugs 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
206010002198 Anaphylactic reaction Diseases 0.000 description 1
101100190618 Arabidopsis thaliana PLC3 gene Proteins 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
101000768061 Escherichia phage P1 Antirepressor protein 1 Proteins 0.000 description 1
UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
240000003550 Eusideroxylon zwageri Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
206010020751 Hypersensitivity Diseases 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
241000282887 Suidae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241001558496 Talpa caeca Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000036783 anaphylactic response Effects 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
LNENVNGQOUBOIX-UHFFFAOYSA-N azidosilane Chemical compound [SiH3]N=[N+]=[N-] LNENVNGQOUBOIX-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
235000012241 calcium silicate Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
PMOWTIHVNWZYFI-WAYWQWQTSA-N cis-2-coumaric acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1O PMOWTIHVNWZYFI-WAYWQWQTSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
229940116333 ethyl lactate Drugs 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000004907 flux Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229920000591 gum Polymers 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 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
FPYAQSSSRQZXMS-UHFFFAOYSA-N methyl 3-acetyl-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(C(C)=O)=C1 FPYAQSSSRQZXMS-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 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
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)

CA000335522A 1978-09-13 1979-09-12 Derives d'aurone Expired CA1202309A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7836705		1978-09-13
GB36705/78		1978-09-13

Publications (1)

Publication Number	Publication Date
CA1202309A true CA1202309A (fr)	1986-03-25

Family

ID=10499649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000335522A Expired CA1202309A (fr)	1978-09-13	1979-09-12	Derives d'aurone

Country Status (29)

Country	Link
US (1)	USRE32196E (fr)
JP (1)	JPS5540692A (fr)
KR (1)	KR830001919B1 (fr)
AR (2)	AR228020A1 (fr)
AT (1)	AT376968B (fr)
AU (1)	AU535369B2 (fr)
BG (2)	BG43187A3 (fr)
CA (1)	CA1202309A (fr)
CH (1)	CH644603A5 (fr)
CS (1)	CS214806B2 (fr)
DD (1)	DD146046A5 (fr)
DK (1)	DK382579A (fr)
EG (1)	EG14105A (fr)
ES (1)	ES484115A1 (fr)
FI (1)	FI792850A7 (fr)
GR (1)	GR71200B (fr)
HU (1)	HU181450B (fr)
IE (1)	IE48824B1 (fr)
IL (1)	IL58229A (fr)
IT (1)	IT1162395B (fr)
MX (1)	MX6232E (fr)
NZ (1)	NZ191556A (fr)
PH (1)	PH15712A (fr)
PL (1)	PL124296B1 (fr)
PT (1)	PT70170A (fr)
SE (1)	SE447382B (fr)
SU (1)	SU1138027A3 (fr)
YU (1)	YU222079A (fr)
ZA (1)	ZA794836B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6307070B1 (en)	1996-01-26	2001-10-23	Phytera, Inc.	Substituted aurone derivatives
ID15918A (id) *	1996-01-26	1997-08-21	Phytera Inc	Turunan auron anti mikroba
AU751213B2 (en) *	1997-07-25	2002-08-08	Phytera, Inc.	Substituted aurone derivatives
AU9001698A (en) *	1997-09-11	1999-03-29	Snow Brand Milk Products Co., Ltd.	Remedies for hormone-dependent diseases
ES2232590T3 (es)	2000-01-28	2005-06-01	Merck Patent Gmbh	Frmulacion que contiene derivados de benzofuranona para la proteccion contra el stress por oxidacion.
USD685271S1 (en)	2012-04-04	2013-07-02	Colgate-Palmolive Company	Container
USD688951S1 (en)	2012-04-04	2013-09-03	Colgate-Palmolive Company	Container
USD685269S1 (en)	2012-04-04	2013-07-02	Colgate-Palmolive Company	Container
USD685270S1 (en)	2012-04-04	2013-07-02	Colgate-Palmolive Company	Container
USD1108268S1 (en) *	2023-12-04	2026-01-06	Alpina Productos Alimenticios S.A.S.—BIC	Bottle

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT277985B (de) *	1967-11-14	1970-01-12	Schering Ag	Verfahren zur Herstellung von neuen Nitro-furan-, -thiophen- oder -pyrrol-derivaten
US4115567A (en) *	1973-12-27	1978-09-19	Carlo Erba S. P. A.	6-Carboxy-2-(2'-pyrazinyl)-chromones and esters thereof
US3975380A (en) *	1974-06-03	1976-08-17	Smithkline Corporation	Substituted aurones
US4067993A (en) *	1975-09-24	1978-01-10	Riker Laboratories, Inc.	Antimicrobial 2-nitro-3-phenylbenzofurancarboxylic acids
US4143145A (en) *	1977-01-12	1979-03-06	Carlo Erba S. P. A.	Substituted 2-vinyl-chromones and process for their preparation
FR2396756A1 (fr) *	1977-07-06	1979-02-02	Inst Nat Sante Rech Med	Nouvelles benzylidene-2-benzofurannones-3, leur obtention et leur application a titre de medicaments
IT1093805B (it) *	1978-01-31	1985-07-26	Erba Carlo Spa	Derivati del 2h-benzofuran-3-one e procedimento per la loro preparazione
US4143055A (en) *	1978-03-27	1979-03-06	Gruppo Lepetit S.P.A.	2,4,6-trisubstituted-2,3-dihydro-benzofuran derivatives

1979
- 1979-09-11 IL IL58229A patent/IL58229A/xx unknown
- 1979-09-11 GR GR60011A patent/GR71200B/el unknown
- 1979-09-11 CH CH820379A patent/CH644603A5/fr not_active IP Right Cessation
- 1979-09-11 AR AR278010A patent/AR228020A1/es active
- 1979-09-11 AT AT0598079A patent/AT376968B/de not_active IP Right Cessation
- 1979-09-11 EG EG544/79A patent/EG14105A/xx active
- 1979-09-11 SE SE7907532A patent/SE447382B/sv not_active IP Right Cessation
- 1979-09-12 SU SU792816201A patent/SU1138027A3/ru active
- 1979-09-12 CA CA000335522A patent/CA1202309A/fr not_active Expired
- 1979-09-12 ES ES484115A patent/ES484115A1/es not_active Expired
- 1979-09-12 PH PH23026A patent/PH15712A/en unknown
- 1979-09-12 IT IT50245/79A patent/IT1162395B/it active
- 1979-09-12 YU YU02220/79A patent/YU222079A/xx unknown
- 1979-09-12 BG BG044838A patent/BG43187A3/xx unknown
- 1979-09-12 NZ NZ191556A patent/NZ191556A/xx unknown
- 1979-09-12 DK DK382579A patent/DK382579A/da not_active Application Discontinuation
- 1979-09-12 AU AU50780/79A patent/AU535369B2/en not_active Ceased
- 1979-09-12 PT PT70170A patent/PT70170A/pt unknown
- 1979-09-12 IE IE1729/79A patent/IE48824B1/en unknown
- 1979-09-12 BG BG046265A patent/BG40315A3/xx unknown
- 1979-09-12 HU HU79LI349A patent/HU181450B/hu unknown
- 1979-09-12 MX MX798376U patent/MX6232E/es unknown
- 1979-09-12 DD DD79215501A patent/DD146046A5/de unknown
- 1979-09-12 ZA ZA00794836A patent/ZA794836B/xx unknown
- 1979-09-13 KR KR1019790003145A patent/KR830001919B1/ko not_active Expired
- 1979-09-13 FI FI792850A patent/FI792850A7/fi not_active Application Discontinuation
- 1979-09-13 PL PL1979218277A patent/PL124296B1/pl unknown
- 1979-09-13 JP JP11781279A patent/JPS5540692A/ja active Pending
- 1979-09-13 CS CS796201A patent/CS214806B2/cs unknown
1981
- 1981-05-06 AR AR285217A patent/AR226210A1/es active
1982
- 1982-05-19 US US06/379,793 patent/USRE32196E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IE791729L (en)	1980-03-13
GR71200B (fr)	1983-04-11
AR226210A1 (es)	1982-06-15
YU222079A (en)	1983-02-28
PT70170A (en)	1979-10-01
HU181450B (en)	1983-07-28
IL58229A (en)	1984-05-31
IL58229A0 (en)	1979-12-30
KR830001919B1 (ko)	1983-09-23
BG40315A3 (bg)	1986-11-14
IT7950245A0 (it)	1979-09-12
SU1138027A3 (ru)	1985-01-30
AU535369B2 (en)	1984-03-15
IT1162395B (it)	1987-03-25
ATA598079A (de)	1984-06-15
ES484115A1 (es)	1980-04-16
SE7907532L (sv)	1980-03-14
PL218277A1 (fr)	1980-07-14
CS214806B2 (en)	1982-06-25
CH644603A5 (en)	1984-08-15
FI792850A7 (fi)	1981-01-01
DD146046A5 (de)	1981-01-21
IE48824B1 (en)	1985-05-29
BG43187A3 (bg)	1988-04-15
NZ191556A (en)	1981-03-16
MX6232E (es)	1985-01-14
AT376968B (de)	1985-01-25
USRE32196E (en)	1986-07-01
JPS5540692A (en)	1980-03-22
PH15712A (en)	1983-03-14
ZA794836B (en)	1981-03-25
PL124296B1 (en)	1983-01-31
DK382579A (da)	1980-03-14
SE447382B (sv)	1986-11-10
EG14105A (en)	1983-03-31
AR228020A1 (es)	1983-01-14
AU5078079A (en)	1980-03-20

Legal Events

Date	Code	Title	Description
2003-03-25	MKEX	Expiry

Publication	Publication Date	Title
US4327222A (en)	1982-04-27	3,4-Diarylisoxazol-5-acetic acids and process for making same
JPS582936B2 (ja)	1983-01-19	５↓−アロイルピロ−ル酢酸およびその塩類の製法
IE871041L (en)	1987-11-09	Pyrazole and isoxazoles as 5-lipoxygenase inhibitors.
CA2016326C (fr)	1995-05-30	Acides pyrido-pyridazinone acetiques pour traiter les complications chroniques du diabete
US4111962A (en)	1978-09-05	Certain substituted 2-phenylnaphtho[1,2-b]furane and -[2,1-b]furane
SI9400003A (en)	1994-09-30	Process for the preparation of biphenyl derivatives
US4320133A (en)	1982-03-16	Penicillins and their antibacterial use
US4866076A (en)	1989-09-12	Biologically active compounds
US4259340A (en)	1981-03-31	Aurone derivatives
US4025552A (en)	1977-05-24	3-(4'-Alkoxy-benzoyl)-1,2,2-trimethylcyclopentane-carboxylic acids, methods of use and compositions containing such compounds
Chien et al.	1934	Stereochemistry of Diphenyls. XXXV. 1 The Effect of 3'Substituents on the Rate of Racemization of 2-Nitro-6-carboxy-2'-methoxydiphenyl
EP0156331B1 (fr)	1989-05-31	Dérivés de benzofuranne, procédé pour leur préparation et agents antihypertensifs les contenant
USRE32196E (en)	1986-07-01	Aurone derivatives
US4997847A (en)	1991-03-05	Biologically active compounds
PL123811B1 (en)	1982-11-30	Process for preparing novel derivatives of pyran-4-one
US3829446A (en)	1974-08-13	Oxobenzofuran intermediates
US3984534A (en)	1976-10-05	Tetrazolyl anthraquinones for inhibiting the release of spasmogen mediators
US4574128A (en)	1986-03-04	5-(4-Chloro-3-sulfamoylbenzoyl)-2,3-dihydro-2-benzofurancarboxylic acids and their compositions having diuretic, saluretic and uricosuric activity
CA1284332C (fr)	1991-05-21	N-{6-[4-(2-hhydroxyphenyl)-1,3-dioxan-5-yl]hexenoyl}sulfona m ides
CA1110249A (fr)	1981-10-06	Indolopyrones ayant des proprietes antiallergiques
US3450698A (en)	1969-06-17	Phenthiazine derivatives
US4131614A (en)	1978-12-26	Process for preparing cis-hexahydrodibenzopyranones
US3442890A (en)	1969-05-06	Substituted 3-benzazocin-16-ones
PT88245B (pt)	1995-03-01	Processo para a preparacao de derivados de tetrazole antagonistas de leucotrienos
JPH0174A (ja)	1989-01-05	ベンズイミダゾ−ル誘導体