DK148082B - Analogifremgangsmaade til fremstilling af 1-ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxo-nicotinsyrederivater - Google Patents
Analogifremgangsmaade til fremstilling af 1-ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxo-nicotinsyrederivater Download PDFInfo
- Publication number
- DK148082B DK148082B DK287080AA DK287080A DK148082B DK 148082 B DK148082 B DK 148082B DK 287080A A DK287080A A DK 287080AA DK 287080 A DK287080 A DK 287080A DK 148082 B DK148082 B DK 148082B
- Authority
- DK
- Denmark
- Prior art keywords
- naphthyl
- oxo
- methyl
- ethyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 title description 6
- -1 2-NAPHTHYL Chemical class 0.000 title description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FHDQRDHNKMTDLF-UHFFFAOYSA-N 1-ethyl-6-naphthalen-2-yl-4-oxopyridine-3-carboxylic acid Chemical compound CCN1C=C(C(O)=O)C(=O)C=C1C1=CC=C(C=CC=C2)C2=C1 FHDQRDHNKMTDLF-UHFFFAOYSA-N 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
- 235000011152 sodium sulphate Nutrition 0.000 claims description 3
- MIBDLWXWTGGZCY-UHFFFAOYSA-N methyl 3-methoxy-5-naphthalen-2-ylpenta-2,4-dienoate Chemical compound C1=CC=CC2=CC(C=CC(OC)=CC(=O)OC)=CC=C21 MIBDLWXWTGGZCY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- WGASDMQEZHXQJP-UHFFFAOYSA-N methyl 5-naphthalen-2-yl-3-oxopent-4-enoate Chemical compound C1=CC=CC2=CC(C=CC(=O)CC(=O)OC)=CC=C21 WGASDMQEZHXQJP-UHFFFAOYSA-N 0.000 claims 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- XXPANQJNYNUNES-UHFFFAOYSA-N nomifensine Chemical compound C12=CC=CC(N)=C2CN(C)CC1C1=CC=CC=C1 XXPANQJNYNUNES-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 3
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229960000632 dexamfetamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 229950007554 levmetamfetamine Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- IBRPASKYXURDBT-UHFFFAOYSA-N methyl 1-ethyl-6-naphthalen-2-yl-4-oxopyridine-3-carboxylate Chemical compound CCN1C=C(C(=O)OC)C(=O)C=C1C1=CC=C(C=CC=C2)C2=C1 IBRPASKYXURDBT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960001073 nomifensine Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- SSHRVPMSFQLCAG-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-5-carboxylic acid Chemical compound OC(=O)C1=CNCCC1 SSHRVPMSFQLCAG-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- HXIPLHBIHBQWGY-UHFFFAOYSA-N 2,3-dihydropyridine-3-carboxylic acid Chemical class OC(=O)C1CN=CC=C1 HXIPLHBIHBQWGY-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- WFKLXLZKZUHFGY-UHFFFAOYSA-N 6-naphthalen-2-yl-4-oxo-1H-pyridine-3-carboxylic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C=1NC=C(C(=O)O)C(C=1)=O WFKLXLZKZUHFGY-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 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
- 241000699670 Mus sp. Species 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- BHVIPQUBOSCUMR-UHFFFAOYSA-N methyl 2-(ethylaminomethylidene)-5-naphthalen-2-yl-3-oxopent-4-enoate Chemical compound C1=CC=CC2=CC(C=CC(=O)C(C(=O)OC)=CNCC)=CC=C21 BHVIPQUBOSCUMR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 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
- 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 description 1
- FWYKRJUVEOBFGH-UHFFFAOYSA-M triphenyl(prop-2-enyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 FWYKRJUVEOBFGH-UHFFFAOYSA-M 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH655579 | 1979-07-13 | ||
| CH655579 | 1979-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK287080A DK287080A (da) | 1981-01-14 |
| DK148082B true DK148082B (da) | 1985-02-25 |
Family
ID=4311435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK287080AA DK148082B (da) | 1979-07-13 | 1980-07-02 | Analogifremgangsmaade til fremstilling af 1-ethyl-1,4-dihydro-6-(2-naphthyl)-4-oxo-nicotinsyrederivater |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4278798A (cs) |
| EP (1) | EP0023593B1 (cs) |
| JP (1) | JPS5615269A (cs) |
| KR (1) | KR840001034B1 (cs) |
| AR (1) | AR225447A1 (cs) |
| AT (1) | ATE2520T1 (cs) |
| AU (1) | AU537900B2 (cs) |
| CA (1) | CA1125762A (cs) |
| DE (1) | DE3062022D1 (cs) |
| DK (1) | DK148082B (cs) |
| ES (1) | ES8105712A1 (cs) |
| FI (1) | FI802097A7 (cs) |
| GR (1) | GR69304B (cs) |
| HU (1) | HU180589B (cs) |
| IL (1) | IL60513A (cs) |
| MC (1) | MC1335A1 (cs) |
| NO (1) | NO802099L (cs) |
| NZ (1) | NZ194258A (cs) |
| PH (1) | PH16046A (cs) |
| PT (1) | PT71542B (cs) |
| ZA (1) | ZA804079B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1110234A (en) * | 1978-01-18 | 1981-10-06 | Hoffmann-La Roche Limited | 4-pyridone-3-carboxylic acids and process for the preparation thereof |
| US4649157A (en) * | 1986-03-28 | 1987-03-10 | G. D. Searle & Co. | Pharmaceutical compositions containing 5-phenyl-1,3-dioxoalkenyl compounds |
| US9988373B2 (en) | 2013-12-26 | 2018-06-05 | Shionogi & Co., Ltd. | Nitrogen-containing six-membered cyclic derivatives and pharmaceutical composition comprising the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4051142A (en) * | 1976-05-24 | 1977-09-27 | Rohm And Haas Company | 1-Aryl-4-pyridones |
| EP0001041A3 (en) * | 1977-07-27 | 1979-06-27 | Sandoz Ag | Alpha(pyridonecarboxylamino)-alpha substituted acetamido penicillins and -cephalosporins, process for their preparation, their use in pharmaceuticals; pyridones used in the process |
| CA1110234A (en) * | 1978-01-18 | 1981-10-06 | Hoffmann-La Roche Limited | 4-pyridone-3-carboxylic acids and process for the preparation thereof |
-
1980
- 1980-06-09 CA CA353,626A patent/CA1125762A/en not_active Expired
- 1980-06-11 MC MC801452A patent/MC1335A1/fr unknown
- 1980-07-01 FI FI802097A patent/FI802097A7/fi not_active Application Discontinuation
- 1980-07-02 DK DK287080AA patent/DK148082B/da unknown
- 1980-07-07 HU HU80801689A patent/HU180589B/hu unknown
- 1980-07-07 ZA ZA00804079A patent/ZA804079B/xx unknown
- 1980-07-07 US US06/166,506 patent/US4278798A/en not_active Expired - Lifetime
- 1980-07-07 AR AR281682A patent/AR225447A1/es active
- 1980-07-07 NZ NZ194258A patent/NZ194258A/en unknown
- 1980-07-07 AU AU60153/80A patent/AU537900B2/en not_active Ceased
- 1980-07-07 IL IL60513A patent/IL60513A/xx unknown
- 1980-07-08 EP EP80103895A patent/EP0023593B1/de not_active Expired
- 1980-07-08 DE DE8080103895T patent/DE3062022D1/de not_active Expired
- 1980-07-08 AT AT80103895T patent/ATE2520T1/de not_active IP Right Cessation
- 1980-07-09 PH PH24260A patent/PH16046A/en unknown
- 1980-07-11 NO NO802099A patent/NO802099L/no unknown
- 1980-07-11 PT PT71542A patent/PT71542B/pt unknown
- 1980-07-11 GR GR62435A patent/GR69304B/el unknown
- 1980-07-11 JP JP9410780A patent/JPS5615269A/ja active Pending
- 1980-07-12 ES ES493355A patent/ES8105712A1/es not_active Expired
- 1980-07-12 KR KR1019800002785A patent/KR840001034B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PT71542B (en) | 1981-12-14 |
| DK287080A (da) | 1981-01-14 |
| ES493355A0 (es) | 1981-06-16 |
| AU6015380A (en) | 1981-01-15 |
| NZ194258A (en) | 1984-07-06 |
| US4278798A (en) | 1981-07-14 |
| FI802097A7 (fi) | 1981-01-01 |
| KR830003423A (ko) | 1983-06-20 |
| CA1125762A (en) | 1982-06-15 |
| JPS5615269A (en) | 1981-02-14 |
| EP0023593A1 (de) | 1981-02-11 |
| IL60513A (en) | 1983-10-31 |
| GR69304B (cs) | 1982-05-14 |
| AR225447A1 (es) | 1982-03-31 |
| DE3062022D1 (en) | 1983-03-24 |
| HU180589B (en) | 1983-03-28 |
| AU537900B2 (en) | 1984-07-19 |
| MC1335A1 (fr) | 1981-04-21 |
| NO802099L (no) | 1981-01-14 |
| PT71542A (en) | 1980-08-01 |
| EP0023593B1 (de) | 1983-02-16 |
| IL60513A0 (en) | 1980-09-16 |
| PH16046A (en) | 1983-06-02 |
| ZA804079B (en) | 1981-07-29 |
| KR840001034B1 (ko) | 1984-07-26 |
| ES8105712A1 (es) | 1981-06-16 |
| ATE2520T1 (de) | 1983-03-15 |
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