SK284016B6 - Spôsob výroby derivátov chinolínu - Google Patents
Spôsob výroby derivátov chinolínu Download PDFInfo
- Publication number
- SK284016B6 SK284016B6 SK124-2002A SK1242002A SK284016B6 SK 284016 B6 SK284016 B6 SK 284016B6 SK 1242002 A SK1242002 A SK 1242002A SK 284016 B6 SK284016 B6 SK 284016B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- ethyl
- substances
- synthesising
- acid derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 230000003115 biocidal effect Effects 0.000 title abstract description 4
- 239000000126 substance Substances 0.000 title abstract description 4
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- -1 cyclic acetal Chemical class 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 101150058891 alc1 gene Proteins 0.000 abstract 1
- 101150117093 alc2 gene Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- FLXFRSZKOVKKPQ-UHFFFAOYSA-N 1,2-dihydroquinoline-2-carboxylic acid Chemical class C1=CC=C2C=CC(C(=O)O)NC2=C1 FLXFRSZKOVKKPQ-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
- QVBFLDFDHPPYDW-UHFFFAOYSA-N ethyl 2-diethoxyphosphoryl-4-[2-(1,3-dioxolan-2-yl)ethyl]-2h-quinoline-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OCC)C(P(=O)(OCC)OCC)C=C1CCC1OCCO1 QVBFLDFDHPPYDW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- FEQNYQNBZBIQOI-UHFFFAOYSA-N 2-diethoxyphosphoryl-2H-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(O)=O)C(P(=O)(OCC)OCC)C=CC2=C1 FEQNYQNBZBIQOI-UHFFFAOYSA-N 0.000 description 2
- ZYXNAQRXUFIBIF-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethyl]quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCC1OCCO1 ZYXNAQRXUFIBIF-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- BPOHTPXUFXFFDG-UHFFFAOYSA-N ethyl 2-diethoxyphosphoryl-4-[2-(1,3-dioxan-2-yl)ethyl]-2h-quinoline-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OCC)C(P(=O)(OCC)OCC)C=C1CCC1OCCCO1 BPOHTPXUFXFFDG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OUENQTLZIRDXRS-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)quinoline Chemical compound O1CCOC1C1=CC=C(C=CC=C2)C2=N1 OUENQTLZIRDXRS-UHFFFAOYSA-N 0.000 description 1
- ODGUJNOUOLYPOD-UHFFFAOYSA-N 2-(2-iodoethyl)-1,3-dioxane Chemical compound ICCC1OCCCO1 ODGUJNOUOLYPOD-UHFFFAOYSA-N 0.000 description 1
- SHNMAZJVVFUXAQ-UHFFFAOYSA-N 2h-quinoline-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CC=CC2=C1 SHNMAZJVVFUXAQ-UHFFFAOYSA-N 0.000 description 1
- GXWYIVBMNGINSM-UHFFFAOYSA-N 4-[2-(1,3-dioxan-2-yl)ethyl]quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCC1OCCCO1 GXWYIVBMNGINSM-UHFFFAOYSA-N 0.000 description 1
- LMYZMMYPJKIWEW-UHFFFAOYSA-N Cl.C=1C=C2C=CC=CC2=NC=1CCC1OCCCO1 Chemical compound Cl.C=1C=C2C=CC=CC2=NC=1CCC1OCCCO1 LMYZMMYPJKIWEW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- GMNGYMOAWNIQSO-UHFFFAOYSA-N O1C(OCCC1)CCC1=NC2=CC=CC=C2C=C1 Chemical compound O1C(OCCC1)CCC1=NC2=CC=CC=C2C=C1 GMNGYMOAWNIQSO-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9602473A FR2745289B1 (fr) | 1996-02-28 | 1996-02-28 | Nouveaux derives de l'acide 1(2h) quinoleine carboxylique, leur procede de preparation et leur application a la synthese de produits doues de proprietes antibiotiques |
| PCT/FR1997/000352 WO1997031926A1 (fr) | 1996-02-28 | 1997-02-27 | Nouveaux derives de l'acide 1(2h) quinoleine carboxylique, leur procede de preparation et leur application a la synthese de produits doues de proprietes antibiotiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK284016B6 true SK284016B6 (sk) | 2004-08-03 |
Family
ID=9489660
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1122-98A SK283620B6 (sk) | 1996-02-28 | 1997-02-27 | Deriváty kyseliny 1(2H)-chinolínkarboxylovej a spôsob ich prípravy |
| SK124-2002A SK284016B6 (sk) | 1996-02-28 | 1997-02-27 | Spôsob výroby derivátov chinolínu |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1122-98A SK283620B6 (sk) | 1996-02-28 | 1997-02-27 | Deriváty kyseliny 1(2H)-chinolínkarboxylovej a spôsob ich prípravy |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6002006A (uk) |
| EP (1) | EP0885232B1 (uk) |
| JP (1) | JP3856241B2 (uk) |
| KR (1) | KR19990087323A (uk) |
| CN (1) | CN1072226C (uk) |
| AT (1) | ATE231153T1 (uk) |
| AU (1) | AU708022B2 (uk) |
| BR (1) | BR9707777A (uk) |
| CA (1) | CA2247172C (uk) |
| CZ (2) | CZ254598A3 (uk) |
| DE (1) | DE69718444T2 (uk) |
| DK (1) | DK0885232T3 (uk) |
| EA (1) | EA001157B1 (uk) |
| ES (1) | ES2186871T3 (uk) |
| FR (1) | FR2745289B1 (uk) |
| HU (1) | HUP9900937A3 (uk) |
| IL (1) | IL125873A (uk) |
| NO (1) | NO983956D0 (uk) |
| NZ (1) | NZ331599A (uk) |
| OA (1) | OA10846A (uk) |
| PL (1) | PL185497B1 (uk) |
| PT (1) | PT885232E (uk) |
| SK (2) | SK283620B6 (uk) |
| TR (1) | TR199801708T2 (uk) |
| UA (1) | UA61069C2 (uk) |
| WO (1) | WO1997031926A1 (uk) |
| YU (1) | YU37198A (uk) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018195098A1 (en) * | 2017-04-17 | 2018-10-25 | Ohio State Innovation Foundation | Type ii topoisomerase inhibitors and methods of making and using thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61221192A (ja) * | 1985-03-27 | 1986-10-01 | Toyo Soda Mfg Co Ltd | ホスホナ−ト誘導体 |
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
1996
- 1996-02-28 FR FR9602473A patent/FR2745289B1/fr not_active Expired - Fee Related
-
1997
- 1997-02-27 CA CA002247172A patent/CA2247172C/fr not_active Expired - Lifetime
- 1997-02-27 SK SK1122-98A patent/SK283620B6/sk unknown
- 1997-02-27 HU HU9900937A patent/HUP9900937A3/hu unknown
- 1997-02-27 DE DE69718444T patent/DE69718444T2/de not_active Expired - Lifetime
- 1997-02-27 WO PCT/FR1997/000352 patent/WO1997031926A1/fr active IP Right Grant
- 1997-02-27 CZ CZ982545A patent/CZ254598A3/cs unknown
- 1997-02-27 ES ES97907142T patent/ES2186871T3/es not_active Expired - Lifetime
- 1997-02-27 CN CN97192624A patent/CN1072226C/zh not_active Expired - Fee Related
- 1997-02-27 EP EP97907142A patent/EP0885232B1/fr not_active Expired - Lifetime
- 1997-02-27 TR TR1998/01708T patent/TR199801708T2/xx unknown
- 1997-02-27 UA UA98095030A patent/UA61069C2/uk unknown
- 1997-02-27 EA EA199800767A patent/EA001157B1/ru not_active IP Right Cessation
- 1997-02-27 SK SK124-2002A patent/SK284016B6/sk unknown
- 1997-02-27 BR BR9707777A patent/BR9707777A/pt not_active Application Discontinuation
- 1997-02-27 AU AU19299/97A patent/AU708022B2/en not_active Ceased
- 1997-02-27 KR KR1019980706732A patent/KR19990087323A/ko not_active Application Discontinuation
- 1997-02-27 AT AT97907142T patent/ATE231153T1/de not_active IP Right Cessation
- 1997-02-27 NZ NZ331599A patent/NZ331599A/xx unknown
- 1997-02-27 IL IL12587397A patent/IL125873A/xx not_active IP Right Cessation
- 1997-02-27 DK DK97907142T patent/DK0885232T3/da active
- 1997-02-27 PT PT97907142T patent/PT885232E/pt unknown
- 1997-02-27 US US09/125,537 patent/US6002006A/en not_active Expired - Lifetime
- 1997-02-27 CZ CZ2004510A patent/CZ294483B6/cs not_active IP Right Cessation
- 1997-02-27 JP JP53067297A patent/JP3856241B2/ja not_active Expired - Lifetime
- 1997-02-27 PL PL97328601A patent/PL185497B1/pl not_active IP Right Cessation
-
1998
- 1998-08-27 NO NO983956A patent/NO983956D0/no not_active Application Discontinuation
- 1998-08-28 OA OA9800151A patent/OA10846A/fr unknown
- 1998-08-28 YU YU37198A patent/YU37198A/sh unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR940001774B1 (ko) | 치환 및 이치환 피리딘-2,3-디카르복실레이트의 제조방법과 치환된 니코티네이트의 제조방법 | |
| Bagley et al. | Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann–Rahtz reaction | |
| GB2137992A (en) | New 3,4-dihydro isoquinoline, 3,4-dihydronaphthalene derivatives and the process for preparing the same | |
| FR2670491A1 (fr) | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant. | |
| KR100632188B1 (ko) | 신규한피페라진및피페리딘화합물 | |
| JPS6094961A (ja) | ピセナドール前駆体の製造法およびその新規な中間体 | |
| JPS6112910B2 (uk) | ||
| FR2618437A1 (fr) | Nouveaux derives du benzopyranne, leur preparation et les medicaments qui les contiennent | |
| CS183391A3 (en) | Process for preparing dialkylpyridine-2,3-dicarboxylates and derivatives thereof | |
| KR20090037445A (ko) | 몬테루카스트 정제 방법 | |
| WO2018185711A1 (en) | Solvates of eluxadoline | |
| SK284016B6 (sk) | Spôsob výroby derivátov chinolínu | |
| JPH11246547A (ja) | 置換ヘテロ環ベンゾシクロアルケン及びその鎮痛作用を有する物質としての使用 | |
| JP2007099640A (ja) | 含窒素複素環化合物、その製造方法およびそれを用いた医薬組成物 | |
| WO2018185664A1 (en) | Solvates of eluxadoline | |
| FI89354B (fi) | Foerfarande foer framstaellning av farmakologiskt anvaendbara tetrahydrofuraner | |
| JPH0665269A (ja) | ホスホン酸ジエステル誘導体 | |
| MXPA98006851A (en) | New derivatives of the 1 (24) quinolin carboxylic acid, its procedure for preparation, and its application to the synthesis of products with antibioti provided properties | |
| RU2060252C1 (ru) | ПРОИЗВОДНЫЕ N-(2,4- ИЛИ 2,5-ДИЗАМЕЩЕННОГО ТЕТРАГИДРОФУРИЛАЛКИЛ)-N-(ФЕНИЛЭТИЛ- β -ОЛ)АМИНА В РАЦЕМИЧЕСКОЙ ИЛИ ЭНАНТИОМЕРНОЙ ФОРМЕ, ИЛИ ИХ ФАРМАЦЕВТИЧЕСКИ ПРИЕМЛЕМАЯ СОЛЬ, СПОСОБ ИХ ПОЛУЧЕНИЯ И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ | |
| HU194176B (en) | Process for production of derivatives of new 7-phormildekahydridinoline | |
| JP2704231B2 (ja) | ２―（４―フェニル―１―ピペラジニルアルキル）アミノ―５―エチニルピリミジン誘導体並びにその中間体及びその製造法 | |
| KR100376280B1 (ko) | 신남알데하이드 유도체의 제조방법 | |
| HU194859B (en) | Process for production of derivatives of 2-/2-tienil/ and 2-/3-tienil/-ethil-amin | |
| JP3919251B2 (ja) | ジシアノピラジン誘導体及びその製造方法 | |
| JPS6243977B2 (uk) |