SK507089A3 - Substituted beta-diketones, process of their preparation and pharmaceutical compositions containing thereof - Google Patents

Substituted beta-diketones, process of their preparation and pharmaceutical compositions containing thereof Download PDF

Info

Publication number: SK507089A3
Authority: SK; Slovakia
Prior art keywords: pentanedione; formula; compound; substituted; diketone
Prior art date: 1988-09-01

Application number

SK5070-89A

Other languages

English (en)

Slovak (sk)

Other versions

SK280095B6 (sk

Inventor

Pentti Pohto

Paivi A Aho

Reijo J Backstrom

Erkki J Honkanen

Inge-Britt Y Linden

Erkki A O Nissinen

Original Assignee

Orion Yhtymae Oy

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.)

1988-09-01

Filing date

1989-08-31

Publication date

1999-08-06

1988-09-01 Priority claimed from GB888820729A external-priority patent/GB8820729D0/en

1989-08-31 Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy

1999-08-06 Publication of SK280095B6 publication Critical patent/SK280095B6/sk

1999-08-06 Publication of SK507089A3 publication Critical patent/SK507089A3/sk

Links

238000000034 method Methods 0.000 title claims description 15
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 30
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
WXGVASWIUBFCHW-UHFFFAOYSA-N 3-(2-acetyl-3-oxobut-1-enyl)benzonitrile Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CC(C#N)=C1 WXGVASWIUBFCHW-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
XTOFQLSGPNRDQY-UHFFFAOYSA-N 3-[[4-(trifluoromethyl)phenyl]methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(C(F)(F)F)C=C1 XTOFQLSGPNRDQY-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 2
TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical class CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 9
230000001120 cytoprotective effect Effects 0.000 abstract description 5
150000003839 salts Chemical class 0.000 abstract description 5
150000002170 ethers Chemical class 0.000 abstract description 4
230000002178 gastroprotective effect Effects 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract 3
125000001072 heteroaryl group Chemical group 0.000 abstract 3
125000003118 aryl group Chemical group 0.000 abstract 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 19
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
230000003902 lesion Effects 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
210000001198 duodenum Anatomy 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
UTMLRLRTBBLOAN-UHFFFAOYSA-N 3-(thiophen-2-ylmethylidene)pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CS1 UTMLRLRTBBLOAN-UHFFFAOYSA-N 0.000 description 3
ANEDNAUPNRTQKL-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methylidene]pentane-2,4-dione Chemical compound COC1=CC=C(C=C(C(C)=O)C(C)=O)C=C1 ANEDNAUPNRTQKL-UHFFFAOYSA-N 0.000 description 3
NYRGMNMVISROGJ-UHFFFAOYSA-N 3-benzylidenepentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CC=C1 NYRGMNMVISROGJ-UHFFFAOYSA-N 0.000 description 3
WAJQTBOWJRUOOO-UHFFFAOYSA-N 3-benzylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)CC1=CC=CC=C1 WAJQTBOWJRUOOO-UHFFFAOYSA-N 0.000 description 3
XWPCVQXBBFGWQE-UHFFFAOYSA-N 4-(2-acetyl-3-oxobut-1-enyl)benzoic acid Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(C(O)=O)C=C1 XWPCVQXBBFGWQE-UHFFFAOYSA-N 0.000 description 3
WMUQCKSADOZOCX-UHFFFAOYSA-N 4-(2-acetyl-3-oxobut-1-enyl)benzonitrile Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(C#N)C=C1 WMUQCKSADOZOCX-UHFFFAOYSA-N 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
235000019257 ammonium acetate Nutrition 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
239000012230 colorless oil Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
210000001035 gastrointestinal tract Anatomy 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000011282 treatment Methods 0.000 description 3
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
LYUYRWISWALFBB-UHFFFAOYSA-N 3-(furan-2-ylmethylidene)pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CO1 LYUYRWISWALFBB-UHFFFAOYSA-N 0.000 description 2
FXQGVTAPVGLEIL-UHFFFAOYSA-N 3-[(3,4-dihydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(O)C(O)=C1 FXQGVTAPVGLEIL-UHFFFAOYSA-N 0.000 description 2
GJUCUNOUBFJRNR-UHFFFAOYSA-N 3-[(4-hydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(O)C=C1 GJUCUNOUBFJRNR-UHFFFAOYSA-N 0.000 description 2
RUEJWIRKEKYDAZ-UHFFFAOYSA-N 3-[[2-(trifluoromethyl)phenyl]methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=CC=C1C(F)(F)F RUEJWIRKEKYDAZ-UHFFFAOYSA-N 0.000 description 2
SVRWFDBCXSSJRD-UHFFFAOYSA-N 3-ethylidenepentane-2,4-dione Chemical compound CC=C(C(C)=O)C(C)=O SVRWFDBCXSSJRD-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
UPMRZALMHVUCIN-UHFFFAOYSA-N Nitecapone Chemical compound CC(=O)C(C(C)=O)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 UPMRZALMHVUCIN-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
230000002183 duodenal effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
MCHDHQVROPEJJT-UHFFFAOYSA-N 1-(chloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CCl)C=C1 MCHDHQVROPEJJT-UHFFFAOYSA-N 0.000 description 1
MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 description 1
FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 1
ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 1
QOQYLKURADQSEA-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]pentane-2,4-dione Chemical compound COC1=CC=C(CC(C(C)=O)C(C)=O)C=C1 QOQYLKURADQSEA-UHFFFAOYSA-N 0.000 description 1
GCFLTOLIWWOBOI-UHFFFAOYSA-N 3-[[4-(2-acetyl-3-oxobut-1-enyl)phenyl]methylidene]pentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)=CC1=CC=C(C=C(C(C)=O)C(C)=O)C=C1 GCFLTOLIWWOBOI-UHFFFAOYSA-N 0.000 description 1
HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 1
LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 description 1
BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
-1 4-trifluoromethylbenzylidene Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
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 1
DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000000026 anti-ulcerogenic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
HPLVTKYRGZZXJF-UHFFFAOYSA-N dimethyl 2-benzylidenepropanedioate Chemical group COC(=O)C(C(=O)OC)=CC1=CC=CC=C1 HPLVTKYRGZZXJF-UHFFFAOYSA-N 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000014674 injury Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
USBYXBPPZWUIKN-UHFFFAOYSA-N methyl 4-(2-acetyl-3-oxobut-1-enyl)benzoate Chemical compound COC(=O)C1=CC=C(C=C(C(C)=O)C(C)=O)C=C1 USBYXBPPZWUIKN-UHFFFAOYSA-N 0.000 description 1
SATDLKYRVXFXRE-UHFFFAOYSA-N methyl 4-(chloromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCl)C=C1 SATDLKYRVXFXRE-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000009854 mucosal lesion Effects 0.000 description 1
208000013435 necrotic lesion Diseases 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
CTYRPMDGLDAWRQ-UHFFFAOYSA-N phenyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=CC=C1 CTYRPMDGLDAWRQ-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/12—Ketones containing more than one keto group
- C07C49/15—Ketones containing more than one keto group containing rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
- A61K31/06—Phenols the aromatic ring being substituted by nitro groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
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Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Two-Way Televisions, Distribution Of Moving Picture Or The Like (AREA)
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Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Saccharide Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK5070-89A 1988-09-01 1989-08-31 Substituted beta-diketones, process of their preparation and pharmaceutical compositions containing thereof SK507089A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888820729A GB8820729D0 (en)	1987-12-24	1988-09-01	Substituted beta-diketones

Publications (2)

Publication Number	Publication Date
SK280095B6 SK280095B6 (sk)	1999-08-06
SK507089A3 true SK507089A3 (en)	1999-08-06

Family

ID=10643048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK5070-89A SK507089A3 (en)	1988-09-01	1989-08-31	Substituted beta-diketones, process of their preparation and pharmaceutical compositions containing thereof

Country Status (28)

Country	Link
US (1)	US5288750A (sv)
EP (1)	EP0357403B1 (sv)
JP (1)	JP2800052B2 (sv)
KR (1)	KR0151378B1 (sv)
CN (1)	CN1019010B (sv)
AT (1)	ATE115534T1 (sv)
AU (1)	AU631566B2 (sv)
BG (1)	BG61364B2 (sv)
CA (1)	CA1338420C (sv)
CZ (1)	CZ284238B6 (sv)
DD (1)	DD294010A5 (sv)
DE (1)	DE68919945T2 (sv)
DK (1)	DK37691D0 (sv)
ES (1)	ES2065994T3 (sv)
FI (1)	FI93103C (sv)
GR (1)	GR3015322T3 (sv)
HU (1)	HU206867B (sv)
IE (1)	IE892813L (sv)
IL (1)	IL91382A (sv)
LV (1)	LV10076B (sv)
NO (1)	NO174848C (sv)
NZ (1)	NZ230503A (sv)
PL (1)	PL163044B1 (sv)
PT (1)	PT91607B (sv)
RU (1)	RU1836320C (sv)
SK (1)	SK507089A3 (sv)
WO (1)	WO1990002724A1 (sv)
ZA (1)	ZA896685B (sv)

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US5185370A (en) *	1988-09-01	1993-02-09	Orion-Yhtyma Oy	Substituted β-diketones and their use
IL91382A (en) *	1988-09-01	1995-06-29	Orion Yhtymae Oy	Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them
IL112205A0 (en) *	1994-01-06	1995-03-15	Res Dev Foundation	Curcumin, analogues of curcumin and novel uses thereof
RU2251543C2 (ru) *	1995-05-25	2005-05-10	Джи.Ди.Сирл энд Ко.	Дикетон в качестве промежуточного продукта при получении 3-галоген-1н-пиразолов
GB9626472D0 (en)	1996-12-20	1997-02-05	Aperia Anita C	New use of comt inhibitors
US6540976B1 (en) *	1997-09-23	2003-04-01	The Board Of Trustees Of The University Of Arkansas	Method for reducing radiation toxicity
FI981521A0 (sv)	1998-07-01	1998-07-01	Orion Corp	Substituerade beta-diketoner och användning därav
GB2373249B (en) *	1999-12-30	2004-04-14	Orion Corp	A process for preparing 3-{[3-chloro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione
WO2011156181A1 (en) *	2010-06-08	2011-12-15	Montefiore Medical Center	Methods and compositions for treating conditions mediated by oxidative stress or electrophilic environmental toxins
US8414870B2 (en) *	2010-12-06	2013-04-09	Sytheon, Ltd.	Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers
US8617528B2 (en) *	2010-12-06	2013-12-31	Sytheon Ltd.	Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds
WO2014179187A1 (en) *	2013-04-29	2014-11-06	Montefiore Medical Center	Methods and compositions for preventing and treating electrophile-mediated toxicities
KR20210000113A (ko)	2019-06-24	2021-01-04	현대자동차주식회사	후석 승객 알림 장치, 및 이를 포함하는 차량 및 그 제어 방법

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US3280069A (en) *	1965-03-31	1966-10-18	Ethyl Corp	Polypropylene containing ethyl 3, 5-ditert-butyl-4-hydroxy-alpha-cyanocinnamate
US3465022A (en) *	1965-08-20	1969-09-02	Merck & Co Inc	((2,2-diacylvinyl)aryloxy(and arylthio))alkanoic acid derivatives
US3856911A (en) *	1969-07-21	1974-12-24	Takeda Chemical Industries Ltd	Cholagogic composition containing pentanedione derivatives
US3998872A (en) *	1970-10-05	1976-12-21	Universal Oil Products Company	Preparation of unsaturated carbonyl compounds
DE2155495A1 (de) *	1971-11-09	1973-05-10	Bayer Ag	Verfahren zur herstellung von benzylidenverbindungen
DE2210633C2 (de) *	1972-03-06	1983-09-22	Bayer Ag, 5090 Leverkusen	Kondensierte Pyridinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US4096280A (en) *	1977-01-24	1978-06-20	Sterling Drug Inc.	Arylenedioxy-bis-diketones
US4153719A (en) *	1977-09-06	1979-05-08	Sterling Drug Inc.	Aromatic diketones
DE2836945A1 (de) *	1978-08-24	1980-03-13	Hoechst Ag	Derivate des 1,2,4-triazols
DE3042769A1 (de) *	1980-11-13	1982-06-09	Bayer Ag, 5090 Leverkusen	C-3 verknuepfte 1,4-dihydropyridine, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung
US4456770A (en) *	1982-09-07	1984-06-26	Ethyl Corportation	Chemical process for preparing 1,3 diketones
DE3303066A1 (de) *	1983-01-29	1984-12-06	Cassella Ag, 6000 Frankfurt	Substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
FI864875A0 (fi) *	1986-11-28	1986-11-28	Orion Yhtymae Oy	Nya farmakologiskt aktiva foereningar, dessa innehaollande kompositioner samt foerfarande och mellanprodukter foer anvaendning vid framstaellning av dessa.
YU213587A (en) *	1986-11-28	1989-06-30	Orion Yhtymae Oy	Process for obtaining new pharmacologic active cateholic derivatives
DE3732380A1 (de) *	1987-09-25	1989-04-06	Bayer Ag	Dihydropyridinether, verfahren zu ihrer herstellung und ihre verwendung
MTP1031B (en) *	1987-12-24	1990-10-04	Orion Yhtymae Oy	New use of cathecol-o-methyl transferase (comt) inhibitors and their physiologically acceptable salts and esters
LU87271A1 (fr) *	1988-07-08	1990-02-07	Oreal	Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique
IL91382A (en) *	1988-09-01	1995-06-29	Orion Yhtymae Oy	Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them
US5185370A (en) *	1988-09-01	1993-02-09	Orion-Yhtyma Oy	Substituted β-diketones and their use

1989
- 1989-08-22 IL IL9138289A patent/IL91382A/en not_active IP Right Cessation
- 1989-08-30 AT AT89308779T patent/ATE115534T1/de not_active IP Right Cessation
- 1989-08-30 ES ES89308779T patent/ES2065994T3/es not_active Expired - Lifetime
- 1989-08-30 EP EP89308779A patent/EP0357403B1/en not_active Expired - Lifetime
- 1989-08-30 DE DE68919945T patent/DE68919945T2/de not_active Expired - Fee Related
- 1989-08-31 SK SK5070-89A patent/SK507089A3/sk unknown
- 1989-08-31 CN CN89106656A patent/CN1019010B/zh not_active Expired
- 1989-08-31 DD DD89332261A patent/DD294010A5/de not_active IP Right Cessation
- 1989-08-31 CZ CS895070A patent/CZ284238B6/cs not_active IP Right Cessation
- 1989-08-31 ZA ZA896685A patent/ZA896685B/xx unknown
- 1989-08-31 PT PT91607A patent/PT91607B/pt not_active IP Right Cessation
- 1989-08-31 CA CA000609963A patent/CA1338420C/en not_active Expired - Fee Related
- 1989-08-31 PL PL89281243A patent/PL163044B1/pl unknown
- 1989-08-31 NZ NZ230503A patent/NZ230503A/xx unknown
- 1989-09-01 IE IE892813A patent/IE892813L/xx not_active IP Right Cessation
- 1989-09-01 WO PCT/FI1989/000165 patent/WO1990002724A1/en not_active Ceased
- 1989-09-01 US US07/646,714 patent/US5288750A/en not_active Expired - Fee Related
- 1989-09-01 AU AU42000/89A patent/AU631566B2/en not_active Ceased
- 1989-09-01 HU HU895050A patent/HU206867B/hu not_active IP Right Cessation
- 1989-09-01 JP JP1509438A patent/JP2800052B2/ja not_active Expired - Fee Related
- 1989-09-01 KR KR1019900700883A patent/KR0151378B1/ko not_active Expired - Fee Related
1991
- 1991-02-28 NO NO910804A patent/NO174848C/no unknown
- 1991-02-28 FI FI911016A patent/FI93103C/sv active
- 1991-02-28 RU SU4894881A patent/RU1836320C/ru active
- 1991-03-01 DK DK91376A patent/DK37691D0/da not_active Application Discontinuation
1992
- 1992-12-15 LV LVP-92-297A patent/LV10076B/en unknown
1994
- 1994-02-18 BG BG098491A patent/BG61364B2/bg unknown
1995
- 1995-03-07 GR GR950400500T patent/GR3015322T3/el unknown

Also Published As

Publication number	Publication date
JP2800052B2 (ja)	1998-09-21
CN1040976A (zh)	1990-04-04
CA1338420C (en)	1996-06-25
RU1836320C (ru)	1993-08-23
EP0357403A3 (en)	1992-02-05
SK280095B6 (sk)	1999-08-06
ES2065994T3 (es)	1995-03-01
FI911016A0 (sv)	1991-02-28
FI93103B (sv)	1994-11-15
DK37691A (da)	1991-03-01
US5288750A (en)	1994-02-22
JPH04500205A (ja)	1992-01-16
CZ284238B6 (cs)	1998-10-14
CN1019010B (zh)	1992-11-11
AU631566B2 (en)	1992-12-03
LV10076A (lv)	1994-05-10
NO910804D0 (no)	1991-02-28
GR3015322T3 (en)	1995-06-30
WO1990002724A1 (en)	1990-03-22
EP0357403B1 (en)	1994-12-14
CZ507089A3 (cs)	1998-07-15
PT91607B (pt)	1995-05-31
DE68919945T2 (de)	1995-05-04
KR900701716A (ko)	1990-12-04
NO174848B (no)	1994-04-11
FI93103C (sv)	1995-02-27
IL91382A (en)	1995-06-29
DK37691D0 (da)	1991-03-01
ATE115534T1 (de)	1994-12-15
NO174848C (no)	1994-07-20
NO910804L (no)	1991-02-28
NZ230503A (en)	1991-11-26
IE892813L (en)	1990-03-01
PL163044B1 (pl)	1994-02-28
EP0357403A2 (en)	1990-03-07
HU895050D0 (en)	1991-11-28
LV10076B (en)	1995-02-20
DD294010A5 (de)	1991-09-19
AU4200089A (en)	1990-04-02
HUT57694A (en)	1991-12-30
IL91382A0 (en)	1990-04-29
BG61364B2 (bg)	1997-06-30
KR0151378B1 (ko)	1999-05-15
ZA896685B (en)	1990-06-27
PT91607A (pt)	1990-03-30
DE68919945D1 (de)	1995-01-26
HU206867B (en)	1993-01-28

Publication	Publication Date	Title
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
IE49902B1 (en)	1986-01-08	4-substituted-3-hydroxy-3-pyrroline-2,5-dione compounds,process for their preparation and pharmaceutical compositions containing the same
SK507089A3 (en)	1999-08-06	Substituted beta-diketones, process of their preparation and pharmaceutical compositions containing thereof
JPH059424B2 (sv)	1993-02-04
US4116972A (en)	1978-09-26	Anti-inflammatory 1-oxo-isoindoline derivatives and processes for their preparation
EP0440324B1 (en)	2000-04-12	Substituted beta-diketones and their use in the treatment of inflammatory bowel disease
EP1507523A1 (en)	2005-02-23	Cinnamic acid dimers, their preparation and the use thereof for treating neurodegenerative disease
DE2039426B2 (sv)	1974-06-27
JPH0710863B2 (ja)	1995-02-08	エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用
JPH02172920A (ja)	1990-07-04	抗潰瘍剤
RU2068415C1 (ru)	1996-10-27	5,7-диокси-2-метил-8-/4-(3-окси-1-(1-пропил)пиперидинил/-4н-1-бензопиран-4-он или его стереоизомеры или фармакологически приемлемые кислотно-аддитивные соли и способ их получения
DE2234715C3 (de)	1976-04-15	2-(Trifluormethylthio-3'-anilino) -benzoesäure und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusa mmensetzungen
JPH03106870A (ja)	1991-05-07	共役γ―オキシブテノライド化合物およびこれを有効成分とする抗潰瘍剤
JPH072776A (ja)	1995-01-06	アンジオテンシンｉｉ拮抗性ピリジン誘導体
WO1991017973A1 (en)	1991-11-28	5H-DIBENZO(a,d)CYCLOHEPTENES AS MUSCARINIC RECEPTOR ANTAGONISTS
DE3212591A1 (de)	1983-10-13	2-pyrrolin-3-carbonitril-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
EP0251858A1 (fr)	1988-01-07	N-imidazolylméthyl-diphénylazo-méthines, leur préparation et leur application en thérapeutique
CN1048034A (zh)	1990-12-26	新颖的环状邻氨基苯甲酸乙酸衍生物及其制备方法
GB2063263A (en)	1981-06-03	A 1-isopropyl-4-phenyl-2(1H)- quinazolinone Derivative
CH635335A5 (en)	1983-03-31	2,3-Diphenylchromone derivatives, process for their preparation and their therapeutic application
DE2234715B2 (de)	1975-09-04	2-(Trifluormethylthio-3'-anilino) -benzoesäure und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
EP0168658A1 (en)	1986-01-22	Pyrrolecarboxylic acid derivative having analgesic activity, preparation thereof and compositions therefrom