JP6615212B2 - 1−(2−ハロゲン−エチル)−4−ピぺリジンカルボン酸エチルエステルの製法 - Google Patents
1−(2−ハロゲン−エチル)−4−ピぺリジンカルボン酸エチルエステルの製法 Download PDFInfo
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- JP6615212B2 JP6615212B2 JP2017542369A JP2017542369A JP6615212B2 JP 6615212 B2 JP6615212 B2 JP 6615212B2 JP 2017542369 A JP2017542369 A JP 2017542369A JP 2017542369 A JP2017542369 A JP 2017542369A JP 6615212 B2 JP6615212 B2 JP 6615212B2
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- acetaldehyde
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- ethyl
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 239000003638 chemical reducing agent Substances 0.000 claims description 15
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 claims description 14
- -1 Sodium triacetoxyborohydride Chemical compound 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000006268 reductive amination reaction Methods 0.000 claims description 7
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910001617 alkaline earth metal chloride Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002373 hemiacetals Chemical class 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical group ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- OTUFGRVWNPWRJD-UHFFFAOYSA-N ethyl 1-(2-chloroethyl)piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(CCCl)CC1 OTUFGRVWNPWRJD-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- FVTWTVQXNAJTQP-UHFFFAOYSA-N diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol Chemical compound C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 FVTWTVQXNAJTQP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- IYFCAAUQJJZDHW-UHFFFAOYSA-N ethyl 1-ethylpiperidine-4-carboxylate Chemical class CCOC(=O)C1CCN(CC)CC1 IYFCAAUQJJZDHW-UHFFFAOYSA-N 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960004258 umeclidinium Drugs 0.000 description 1
- PEJHHXHHNGORMP-AVADPIKZSA-M umeclidinium bromide Chemical compound [Br-].C=1C=CC=CC=1C([C@@]12CC[N@@+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 PEJHHXHHNGORMP-AVADPIKZSA-M 0.000 description 1
- 229960004541 umeclidinium bromide Drugs 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
実施例1で得られた生成物を、DMSO中での1H−NMRによって分析した。スペクトル(図1に示す)は、所望の化合物の構造に係るシグナルのみを示し、化合物が純粋であることを示した(1H−NMR、400MHz)。
Claims (15)
- Xが、塩素原子である請求項1に記載の方法。
- 溶媒が、低級アルコール及びアセトニトリルから選ばれるものである請求項2に記載の方法。
- 溶媒が、メタノール又はアセトニトリルであることを特徴とする請求項3に記載の方法。
- 溶媒系が、弱酸も含んでなることを特徴とする請求項1〜4のいずれかに記載の方法。
- 酸が、酢酸であることを特徴とする請求項5に記載の方法。
- 溶媒系が、8〜10/1(v/v)又はそれ以上の溶媒/酢酸混合物であることを特徴とする請求項1〜6のいずれかに記載の方法。
- 水の存在下で行うことを特徴とする請求項1〜7のいずれかに記載の方法。
- イソニペコチン酸エチル/X−アセトアルデヒドの比が、1/1〜1.5であることを特徴とする請求項1〜8のいずれかに記載の方法。
- 還元剤が、シアノ水素化ホウ素ナトリウム(NaCNBH 3 )、トリアセトキシ水素化ホウ素ナトリウム(NaBH(OAc) 3 )、3−ピリジンボラン(pyr−BH3)、Ti(Oi−Pr) 4 /NaBH 4 、樹脂に担持された水素化ホウ素、Zn(BH 4 ) 2 /SiO 2 、Bu 3 SnH/SiO 2 、又はフェニル−SiH 4 /Bu 2 SnCl 2 から選ばれるものであることを特徴とする請求項1〜9のいずれかに記載の方法。
- 還元剤が、シアノ水素化ホウ素ナトリウム(NaCNBH 3 )及びトリアセトキシ水素化ホウ素ナトリウム(NaBH(OAc) 3 )から選ばれるものであることを特徴とする請求項10に記載の方法。
- イソニペコチン酸エチル/X−アセトアルデヒド/シアノ水素化ホウ素ナトリウムのモル比が、1/1〜1.5/0.3〜1.5であることを特徴とする請求項1〜11のいずれかに記載の方法。
- イソニペコチン酸エチル/X−アセトアルデヒド/トリアセトキシ水素化ホウ素ナトリウムのモル比が、1/1〜1.5/4〜6であることを特徴とする請求項1〜12のいずれかに記載の方法。
- 反応が、ハロゲン塩の存在下で生ずることを特徴とする請求項1〜13のいずれかに記載の方法。
- 反応が、アルカリ金属及びアルカリ土類金属の塩化物の存在下で生ずることを特徴とする請求項14に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI20141875 | 2014-11-03 | ||
ITMI2014A001875 | 2014-11-03 | ||
PCT/IB2015/058145 WO2016071792A1 (en) | 2014-11-03 | 2015-10-22 | Method for the preparation of 1-(2-halogen-ethyl)-4 piperidine-carboxylic acid ethyl esters |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017534686A JP2017534686A (ja) | 2017-11-24 |
JP6615212B2 true JP6615212B2 (ja) | 2019-12-04 |
Family
ID=52130631
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2017542369A Active JP6615212B2 (ja) | 2014-11-03 | 2015-10-22 | 1−(2−ハロゲン−エチル)−4−ピぺリジンカルボン酸エチルエステルの製法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10023535B2 (ja) |
EP (1) | EP3215489B1 (ja) |
JP (1) | JP6615212B2 (ja) |
CA (1) | CA2965590A1 (ja) |
ES (1) | ES2751698T3 (ja) |
WO (1) | WO2016071792A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PT109740B (pt) | 2016-11-14 | 2020-07-30 | Hovione Farmaciencia Sa | Processo para a preparação de brometo de umeclidínio |
PT117440B (pt) | 2021-09-03 | 2024-04-26 | Hovione Farm S A | Processo para a preparação de aminas cíclicas cloroaquilo substituídas |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5696267A (en) * | 1995-05-02 | 1997-12-09 | Schering Corporation | Substituted oximes, hydrazones and olefins as neurokinin antagonists |
US6531475B1 (en) * | 1998-11-12 | 2003-03-11 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods relating thereto |
US20080139532A1 (en) | 2004-03-08 | 2008-06-12 | Glaxo Group Limited | Tetrahydrobenzazepine Derivatives as Modulators of Dopamine D3 Receptors (Antipsychotic Agents) |
UY28871A1 (es) | 2004-04-27 | 2005-11-30 | Glaxo Group Ltd | Antagonistas del receptor de acetilcolina muscarinico |
US20060223792A1 (en) | 2005-03-31 | 2006-10-05 | Butler Christopher R | Phenyl and pyridyl LTA4H modulators |
JP2010515744A (ja) * | 2007-01-10 | 2010-05-13 | アルバニー モレキュラー リサーチ, インコーポレイテッド | 5−ピリジノン置換インダゾール |
US20100113391A1 (en) * | 2007-04-19 | 2010-05-06 | Astellas Pharma Inc. | Bicyclic heterocyclic compound |
EP2305660A1 (en) * | 2009-09-25 | 2011-04-06 | Almirall, S.A. | New thiadiazole derivatives |
CN102617502A (zh) * | 2012-03-19 | 2012-08-01 | 江苏先声药物研究有限公司 | 一类苯并噁唑衍生物及其医药应用 |
US9273001B2 (en) | 2012-08-15 | 2016-03-01 | Glaxo Group Limited | Chemical process |
-
2015
- 2015-10-22 ES ES15804951T patent/ES2751698T3/es active Active
- 2015-10-22 CA CA2965590A patent/CA2965590A1/en not_active Abandoned
- 2015-10-22 WO PCT/IB2015/058145 patent/WO2016071792A1/en active Application Filing
- 2015-10-22 JP JP2017542369A patent/JP6615212B2/ja active Active
- 2015-10-22 US US15/520,256 patent/US10023535B2/en active Active
- 2015-10-22 EP EP15804951.0A patent/EP3215489B1/en active Active
Also Published As
Publication number | Publication date |
---|---|
EP3215489B1 (en) | 2019-07-24 |
US10023535B2 (en) | 2018-07-17 |
JP2017534686A (ja) | 2017-11-24 |
ES2751698T3 (es) | 2020-04-01 |
EP3215489A1 (en) | 2017-09-13 |
WO2016071792A1 (en) | 2016-05-12 |
CA2965590A1 (en) | 2016-05-12 |
US20170313657A1 (en) | 2017-11-02 |
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