DD294010A5 - Substituierte beta-diketone - Google Patents

Substituierte beta-diketone Download PDF

Info

Publication number: DD294010A5
Authority: DD; German Democratic Republic
Prior art keywords: dione; pentane; prophylaxis; formula; ulcers
Prior art date: 1988-09-01

Application number

DD89332261A

Other languages

German (de)

English (en)

Inventor

Pentti Pohto

Paeivi A Aho

Reijo J Baeckstroem

Erkki J Konkanen

Inge-Britt Y Linden

Erkki A O Nissinen

Original Assignee

��`��@��k��

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

1991-09-19

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

1989-08-31 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1991-09-19 Publication of DD294010A5 publication Critical patent/DD294010A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 12
239000003795 chemical substances by application Substances 0.000 claims abstract description 12
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
230000001120 cytoprotective effect Effects 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 23
230000006378 damage Effects 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical group 0.000 claims description 18
208000027418 Wounds and injury Diseases 0.000 claims description 15
208000014674 injury Diseases 0.000 claims description 15
238000011321 prophylaxis Methods 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
208000025865 Ulcer Diseases 0.000 claims description 13
210000001035 gastrointestinal tract Anatomy 0.000 claims description 13
231100000397 ulcer Toxicity 0.000 claims description 13
-1 nitro, amino Chemical group 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
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 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
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 claims description 5
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 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
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 claims description 4
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 claims description 4
SVRWFDBCXSSJRD-UHFFFAOYSA-N 3-ethylidenepentane-2,4-dione Chemical compound CC=C(C(C)=O)C(C)=O SVRWFDBCXSSJRD-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000005493 quinolyl group Chemical group 0.000 claims description 4
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 claims 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 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
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 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
150000007529 inorganic bases Chemical group 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
150000002430 hydrocarbons Chemical group 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 claims 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical group O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000005001 aminoaryl group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229940125890 compound Ia Drugs 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229960004279 formaldehyde Drugs 0.000 claims 1
235000019256 formaldehyde Nutrition 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
229930195735 unsaturated hydrocarbon Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 abstract description 5
150000002170 ethers Chemical class 0.000 abstract description 4
230000002178 gastroprotective effect Effects 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
125000003277 amino group Chemical group 0.000 abstract description 3
125000003107 substituted aryl group Chemical group 0.000 abstract description 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 24
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 11
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 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
210000001198 duodenum Anatomy 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
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 description 2
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 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
HPLVTKYRGZZXJF-UHFFFAOYSA-N dimethyl 2-benzylidenepropanedioate Chemical compound COC(=O)C(C(=O)OC)=CC1=CC=CC=C1 HPLVTKYRGZZXJF-UHFFFAOYSA-N 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
230000003902 lesion 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
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
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
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
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 description 1
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 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
OOKUSDZYOMYKEJ-UHFFFAOYSA-N 6-phenylhex-5-ene-2,4-dione Chemical compound CC(=O)CC(=O)C=CC1=CC=CC=C1 OOKUSDZYOMYKEJ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
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 1
241000700157 Rattus norvegicus Species 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 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
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
FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000000468 ketone group Chemical group 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
230000001338 necrotic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000004962 physiological condition Effects 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
238000010992 reflux Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (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)
Furan Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Two-Way Televisions, Distribution Of Moving Picture Or The Like (AREA)
Seasonings (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Hydrogenated Pyridines (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD89332261A 1988-09-01 1989-08-31 Substituierte beta-diketone DD294010A5 (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
DD294010A5 true DD294010A5 (de)	1991-09-19

Family

ID=10643048

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89332261A DD294010A5 (de)	1988-09-01	1989-08-31	Substituierte beta-diketone

Country Status (28)

Country	Link
US (1)	US5288750A (da)
EP (1)	EP0357403B1 (da)
JP (1)	JP2800052B2 (da)
KR (1)	KR0151378B1 (da)
CN (1)	CN1019010B (da)
AT (1)	ATE115534T1 (da)
AU (1)	AU631566B2 (da)
BG (1)	BG61364B2 (da)
CA (1)	CA1338420C (da)
CZ (1)	CZ284238B6 (da)
DD (1)	DD294010A5 (da)
DE (1)	DE68919945T2 (da)
DK (1)	DK37691A (da)
ES (1)	ES2065994T3 (da)
FI (1)	FI93103C (da)
GR (1)	GR3015322T3 (da)
HU (1)	HU206867B (da)
IE (1)	IE892813L (da)
IL (1)	IL91382A (da)
LV (1)	LV10076B (da)
NO (1)	NO174848C (da)
NZ (1)	NZ230503A (da)
PL (1)	PL163044B1 (da)
PT (1)	PT91607B (da)
RU (1)	RU1836320C (da)
SK (1)	SK507089A3 (da)
WO (1)	WO1990002724A1 (da)
ZA (1)	ZA896685B (da)

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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
CZ292320B6 (cs) *	1995-05-25	2003-09-17	G. D. Searle & Co.	Způsob přípravy pyrazolů
GB9626472D0 (en)	1996-12-20	1997-02-05	Aperia Anita C	New use of comt inhibitors
WO1999015168A1 (en) *	1997-09-23	1999-04-01	Board Of Trustees Of The University Of Arkansas	Method for reducing radiation toxicity
FI981521A0 (fi)	1998-07-01	1998-07-01	Orion Corp	Substituoidut beta-diketonit ja niiden käyttö
AU2519601A (en) *	1999-12-30	2001-07-16	Orion Corporation	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
US8617528B2 (en)	2010-12-06	2013-12-31	Sytheon Ltd.	Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds
US8414870B2 (en) *	2010-12-06	2013-04-09	Sytheon, Ltd.	Benzylidene substituted 2,4-pentanedione compounds and use thereof as stabilizers
US10104882B2 (en)	2013-04-29	2018-10-23	Montefiore Medical Center	Methods and compositions for preventing and treating electrophile-mediated toxicities

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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
YU213587A (en) *	1986-11-28	1989-06-30	Orion Yhtymae Oy	Process for obtaining new pharmacologic active cateholic derivatives
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.
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 EP EP89308779A patent/EP0357403B1/en not_active Expired - Lifetime
- 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 DE DE68919945T patent/DE68919945T2/de not_active Expired - Fee Related
- 1989-08-31 CA CA000609963A patent/CA1338420C/en not_active Expired - Fee Related
- 1989-08-31 SK SK5070-89A patent/SK507089A3/sk unknown
- 1989-08-31 PT PT91607A patent/PT91607B/pt not_active IP Right Cessation
- 1989-08-31 CZ CS895070A patent/CZ284238B6/cs not_active IP Right Cessation
- 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 PL PL89281243A patent/PL163044B1/pl unknown
- 1989-08-31 ZA ZA896685A patent/ZA896685B/xx unknown
- 1989-08-31 NZ NZ230503A patent/NZ230503A/xx unknown
- 1989-09-01 KR KR1019900700883A patent/KR0151378B1/ko not_active Expired - Fee Related
- 1989-09-01 JP JP1509438A patent/JP2800052B2/ja not_active Expired - Fee Related
- 1989-09-01 HU HU895050A patent/HU206867B/hu not_active IP Right Cessation
- 1989-09-01 IE IE892813A patent/IE892813L/xx not_active IP Right Cessation
- 1989-09-01 US US07/646,714 patent/US5288750A/en not_active Expired - Fee Related
- 1989-09-01 WO PCT/FI1989/000165 patent/WO1990002724A1/en not_active Ceased
- 1989-09-01 AU AU42000/89A patent/AU631566B2/en not_active Ceased
1991
- 1991-02-28 FI FI911016A patent/FI93103C/fi active
- 1991-02-28 NO NO910804A patent/NO174848C/no unknown
- 1991-02-28 RU SU4894881A patent/RU1836320C/ru active
- 1991-03-01 DK DK037691A patent/DK37691A/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
AU631566B2 (en)	1992-12-03
WO1990002724A1 (en)	1990-03-22
EP0357403A2 (en)	1990-03-07
IL91382A (en)	1995-06-29
BG61364B2 (bg)	1997-06-30
DK37691D0 (da)	1991-03-01
NO910804L (no)	1991-02-28
PT91607A (pt)	1990-03-30
CA1338420C (en)	1996-06-25
ATE115534T1 (de)	1994-12-15
GR3015322T3 (en)	1995-06-30
RU1836320C (ru)	1993-08-23
NO174848B (no)	1994-04-11
US5288750A (en)	1994-02-22
DE68919945T2 (de)	1995-05-04
ZA896685B (en)	1990-06-27
HUT57694A (en)	1991-12-30
AU4200089A (en)	1990-04-02
HU895050D0 (en)	1991-11-28
IL91382A0 (en)	1990-04-29
KR900701716A (ko)	1990-12-04
CZ507089A3 (cs)	1998-07-15
NO174848C (no)	1994-07-20
PL163044B1 (pl)	1994-02-28
LV10076B (en)	1995-02-20
KR0151378B1 (ko)	1999-05-15
PT91607B (pt)	1995-05-31
EP0357403A3 (en)	1992-02-05
CN1019010B (zh)	1992-11-11
SK280095B6 (sk)	1999-08-06
LV10076A (lv)	1994-05-10
NO910804D0 (no)	1991-02-28
FI911016A0 (fi)	1991-02-28
FI93103C (fi)	1995-02-27
CZ284238B6 (cs)	1998-10-14
FI93103B (fi)	1994-11-15
NZ230503A (en)	1991-11-26
CN1040976A (zh)	1990-04-04
EP0357403B1 (en)	1994-12-14
HU206867B (en)	1993-01-28
DK37691A (da)	1991-03-01
DE68919945D1 (de)	1995-01-26
SK507089A3 (en)	1999-08-06
IE892813L (en)	1990-03-01
JPH04500205A (ja)	1992-01-16
ES2065994T3 (es)	1995-03-01
JP2800052B2 (ja)	1998-09-21

Legal Events

Date	Code	Title	Description
2001-03-29	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69725978T2 (de)	2004-09-02	Chalcon-derivate und medikamente die diese enthalten
DD209622A5 (de)	1984-05-16	Verfahren zur herstellung von 1,4-dihydropyridinen
DE2065636C3 (de)	1979-07-19	Tricyclische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2027645A1 (de)	1971-12-09	Piperazinylalkyl chinazolon (4) den vate, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
DE2122144A1 (de)	1971-11-25	Aminoketonderivate von Phloroglucin
DE2431178A1 (de)	1975-01-16	Piperazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE68919945T2 (de)	1995-05-04	Substituierte beta-Diketone.
DE2202727A1 (de)	1972-07-27	Substituierte Indenylessigsaeuren
DE2607305A1 (de)	1976-09-02	6-oxo-7-substituiert- und -7,7-disubstituiert-6h-indeno eckige klammer auf 5,4-b eckige klammer zu furan(und thiophen) carbonsaeuren
DE1944759C3 (de)	1975-02-06	3-lndolylacetamide, ihre Salze und Verfahren zu ihrer Herstellung
CH645368A5 (de)	1984-09-28	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung.
DE2923817C2 (de)	1981-07-09	(3-Alkylamino-2-hydroxyproposy)-furan-2-carbonsäureanilide und deren physiologisch verträgliche Säureadditionssalze und Verfahren zu deren Herstellung sowie Arzneimittel mit einem Gehalt dieser Verbindungen
DE2748466A1 (de)	1978-05-03	4a-aryloctahydro-1h-2-pyrindine
DE2800015A1 (de)	1978-07-13	Neue chromderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE2412520A1 (de)	1974-10-10	Tricyclische verbindungen
DE2039426B2 (da)	1974-06-27
DE2640884A1 (de)	1977-03-24	Neue entzuendungshemmende l-oxo-isoindolin-derivate und verfahren zu ihrer herstellung
DE2642840A1 (de)	1977-04-07	Substituierte 2-nitro-3-phenylbenzofuranverbindungen
CH634545A5 (en)	1983-02-15	1-Phenyl-1-methoxy-2-aminoethane derivatives, and a process for their preparation
DE2942065A1 (de)	1980-05-08	Neue 1,6-naphthyridinderivate, verfahren zu ihrer herstellung sowie mittel gegen schwindel und zur verbesserung der zerebralen zirkulation, die diese derivate enthalten
DE3034005C2 (de)	1982-12-09	Indolessigsäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE2658938A1 (de)	1978-07-06	Neue basisch substituierte 0-propyloxime, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3212591A1 (de)	1983-10-13	2-pyrrolin-3-carbonitril-derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE2234715C3 (de)	1976-04-15	2-(Trifluormethylthio-3'-anilino) -benzoesäure und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusa mmensetzungen
DE2118929A1 (de)	1971-11-04	Acy lvinylary lalkan-(und-alken)säuren