FI85585C - Foerfarande foer framstaellning av 4-acetyl-isokinolinon. - Google Patents
Foerfarande foer framstaellning av 4-acetyl-isokinolinon. Download PDFInfo
- Publication number
- FI85585C FI85585C FI870453A FI870453A FI85585C FI 85585 C FI85585 C FI 85585C FI 870453 A FI870453 A FI 870453A FI 870453 A FI870453 A FI 870453A FI 85585 C FI85585 C FI 85585C
- Authority
- FI
- Finland
- Prior art keywords
- acetyl
- pyridyl
- added
- isoquinolinone
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 4
- ALQFTBSPRXKAAU-UHFFFAOYSA-N 4-acetyl-2h-isoquinolin-1-one Chemical compound C1=CC=C2C(C(=O)C)=CNC(=O)C2=C1 ALQFTBSPRXKAAU-UHFFFAOYSA-N 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 11
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HWHKJOULOUZDEU-UHFFFAOYSA-N 2-acetyl-4-pyridin-4-ylcyclohexan-1-one Chemical compound C1CC(=O)C(C(=O)C)CC1C1=CC=NC=C1 HWHKJOULOUZDEU-UHFFFAOYSA-N 0.000 description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- YMMHAIJRFWRDMG-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-1h-quinolin-2-one Chemical compound C1C=CC=C2NC(=O)CCC21 YMMHAIJRFWRDMG-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- -1 isoquinolinone compound Chemical class 0.000 description 5
- NVTWQACIVZHUPA-UHFFFAOYSA-N 4-acetyl-1-methyl-7-pyridin-4-yl-5,6,7,8-tetrahydro-2h-isoquinolin-3-one Chemical compound C1C2=C(C)NC(=O)C(C(=O)C)=C2CCC1C1=CC=NC=C1 NVTWQACIVZHUPA-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000010446 mirabilite Substances 0.000 description 4
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HZFHHFAPODBZDO-UHFFFAOYSA-N 2-(2-acetylpyridin-4-yl)cyclohexan-1-one Chemical compound C1=NC(C(=O)C)=CC(C2C(CCCC2)=O)=C1 HZFHHFAPODBZDO-UHFFFAOYSA-N 0.000 description 2
- IIBDUHHNKOFCHQ-UHFFFAOYSA-N 4-acetyl-1-methyl-7-pyridin-2-yl-5,6,7,8-tetrahydro-2h-isoquinolin-3-one Chemical compound C1C2=C(C)NC(=O)C(C(=O)C)=C2CCC1C1=CC=CC=N1 IIBDUHHNKOFCHQ-UHFFFAOYSA-N 0.000 description 2
- RSDGRRJTGIGGBP-UHFFFAOYSA-N 4-pyridin-4-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=NC=C1 RSDGRRJTGIGGBP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000003293 cardioprotective effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RGEJCUIWCMDOOK-UHFFFAOYSA-N 2-pyridin-4-ylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=NC=C1 RGEJCUIWCMDOOK-UHFFFAOYSA-N 0.000 description 1
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 1
- NAVNEMDRBCCOTJ-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2h-isoquinolin-3-one Chemical compound C1CCCC2=CNC(=O)C=C21 NAVNEMDRBCCOTJ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000648351 Cophes Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002371 cardiac agent Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2697086 | 1986-02-12 | ||
| JP61026970A JPS62187467A (ja) | 1986-02-12 | 1986-02-12 | ４−アセチルイソキノリノン化合物の新規製造法 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI870453A0 FI870453A0 (fi) | 1987-02-02 |
| FI870453L FI870453L (fi) | 1987-08-13 |
| FI85585B FI85585B (fi) | 1992-01-31 |
| FI85585C true FI85585C (fi) | 1992-05-11 |
Family
ID=12208012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI870453A FI85585C (fi) | 1986-02-12 | 1987-02-02 | Foerfarande foer framstaellning av 4-acetyl-isokinolinon. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4814458A (en, 2012) |
| EP (1) | EP0236754B1 (en, 2012) |
| JP (1) | JPS62187467A (en, 2012) |
| KR (1) | KR890001241B1 (en, 2012) |
| CN (1) | CN1007622B (en, 2012) |
| AU (1) | AU578858B2 (en, 2012) |
| CA (1) | CA1286674C (en, 2012) |
| DE (1) | DE3764494D1 (en, 2012) |
| DK (1) | DK60287A (en, 2012) |
| FI (1) | FI85585C (en, 2012) |
| HU (1) | HU197894B (en, 2012) |
| NO (1) | NO167457C (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2515119A1 (en) | 2003-02-07 | 2004-08-19 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivative |
| US8280673B2 (en) | 2007-12-04 | 2012-10-02 | Honeywell International Inc. | System for determining ambient temperature |
| US9335769B2 (en) | 2007-12-04 | 2016-05-10 | Honeywell International Inc. | System for determining ambient temperature |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480634A (en) * | 1966-02-28 | 1969-11-25 | Hoffmann La Roche | 1,4-dihydro-3(2h)-isoquinolones and process for their preparation |
| JPS61291570A (ja) * | 1985-06-19 | 1986-12-22 | Mitsui Toatsu Chem Inc | イソキノリン誘導体 |
| JPS624266A (ja) * | 1985-07-01 | 1987-01-10 | Mitsui Toatsu Chem Inc | 新規４−ピリジル−４−シアノピメリン酸エステルおよびその製造法 |
| JPS624265A (ja) * | 1985-07-01 | 1987-01-10 | Mitsui Toatsu Chem Inc | 新規４−ピリジルピメリン酸エステルおよびその製造法 |
| JPS625963A (ja) * | 1985-07-02 | 1987-01-12 | Mitsui Toatsu Chem Inc | イソキノリン誘導体 |
| JPH06210063A (ja) * | 1993-01-14 | 1994-08-02 | Kousaku Ishikawa | パチンコゲーム機における持ち玉返却機構 |
-
1986
- 1986-02-12 JP JP61026970A patent/JPS62187467A/ja active Granted
-
1987
- 1987-02-02 FI FI870453A patent/FI85585C/fi not_active IP Right Cessation
- 1987-02-02 US US07/010,304 patent/US4814458A/en not_active Expired - Fee Related
- 1987-02-02 CA CA000528786A patent/CA1286674C/en not_active Expired - Lifetime
- 1987-02-05 DK DK060287A patent/DK60287A/da not_active Application Discontinuation
- 1987-02-06 DE DE8787101637T patent/DE3764494D1/de not_active Expired - Lifetime
- 1987-02-06 EP EP87101637A patent/EP0236754B1/en not_active Expired - Lifetime
- 1987-02-11 KR KR1019870001118A patent/KR890001241B1/ko not_active Expired
- 1987-02-11 HU HU87535A patent/HU197894B/hu not_active IP Right Cessation
- 1987-02-11 CN CN87100838A patent/CN1007622B/zh not_active Expired
- 1987-02-11 NO NO870543A patent/NO167457C/no unknown
- 1987-02-11 AU AU68686/87A patent/AU578858B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU6868687A (en) | 1987-08-13 |
| FI870453L (fi) | 1987-08-13 |
| DE3764494D1 (de) | 1990-10-04 |
| NO167457B (no) | 1991-07-29 |
| HUT44532A (en) | 1988-03-28 |
| KR890001241B1 (ko) | 1989-04-28 |
| HU197894B (en) | 1989-06-28 |
| AU578858B2 (en) | 1988-11-03 |
| DK60287D0 (da) | 1987-02-05 |
| EP0236754B1 (en) | 1990-08-29 |
| NO870543L (no) | 1987-08-13 |
| FI870453A0 (fi) | 1987-02-02 |
| CA1286674C (en) | 1991-07-23 |
| DK60287A (da) | 1987-08-13 |
| CN1007622B (zh) | 1990-04-18 |
| JPS62187467A (ja) | 1987-08-15 |
| US4814458A (en) | 1989-03-21 |
| EP0236754A1 (en) | 1987-09-16 |
| KR870007917A (ko) | 1987-09-22 |
| NO167457C (no) | 1991-11-06 |
| FI85585B (fi) | 1992-01-31 |
| JPH041746B2 (en, 2012) | 1992-01-14 |
| CN87100838A (zh) | 1987-09-09 |
| NO870543D0 (no) | 1987-02-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110627736B (zh) | 一种1-苯基-5-羟基四氮唑的回收利用方法 | |
| JPS61251650A (ja) | （ｚ）−１−フエニル−１−ジエチルアミノカルボニル−２−アミノメチルシクロプロパン塩酸塩の製造方法 | |
| FI76809C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara nya 5-(3-pyridyl)pyrrolo/1,2-c/tiazol-7- karboxamid-derivat. | |
| KR920002295B1 (ko) | 프롤리디논 유도체의 제조방법 | |
| FI85585C (fi) | Foerfarande foer framstaellning av 4-acetyl-isokinolinon. | |
| HU182636B (en) | Process for producing pyrazolo-imidazol derivatives | |
| US4719303A (en) | Preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids | |
| US4847386A (en) | Process for preparing thiophene derivatives | |
| US4022766A (en) | Pharmacologically active pyrrolodiazepines | |
| CA1025865A (fr) | Procedes de preparation de nouvelles amides heterocycliques | |
| US4180578A (en) | 2,4-Diamino-5-(4'-methylthio)benzylpyrimidenes, compounds, compositions and method of use | |
| KR880001105B1 (ko) | 1-벤질-4-[4-(2-피리미디닐아미노)벤질]-2,3-디옥소피페라진 유도체의 제조방법 | |
| US3245998A (en) | Processes for the production of picolinic acid dericatives | |
| US4421756A (en) | Quinolinoneimine carboxylic acid anti-inflammatory and analgesic composition containing the compound | |
| JP3527255B2 (ja) | ６−ｎ−置換アミノピコリン酸誘導体及びその製造法 | |
| RU2032681C1 (ru) | Способ получения 1-(2-[(5-диметиламинометил-2-фурил) -метилтио]-этил)-амино-1- метиламино-2-нитроэтилена | |
| KR800001048B1 (ko) | 4-할로 메틸-2-피롤리디논의 제조방법 | |
| FI80459C (fi) | Nya 3- eller 5-(3-pyridyl)substituerade 1h,3h-pyrrolo/1,2-c/tiazol-7-karboxylsyror, vilka aer mellanprodukter vid framstaellning av motsvarande terapeutiskt anvaendbara pyrrolotiazol-7-karboxylsyraamider och foerfarande foer framstaellning daerav. | |
| JPH0692988A (ja) | ２，２′−アンヒドロアラビノシルチミン誘導体の合成法 | |
| KR0139260B1 (ko) | 고리화된 이미다졸을 가지는 벤즈이미다졸 유도체 | |
| JP2840855B2 (ja) | ジヒドロピリジン誘導体の製造方法 | |
| JPS61158962A (ja) | １，４−ジヒドロピリジン誘導体の製造法 | |
| CN110078674A (zh) | 一种2-烃基胺基嘧啶酮的制备方法 | |
| PL111897B1 (en) | Method of preparation of novel beta-cyanoethylbarbituric acids | |
| NO772673L (no) | Fremgangsm}te ved fremstilling av d-2-(6-methoxy-2-nafthyl)-propionsyre |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: MITSUI TOATSU CHEMICALS, INCORPORATED |