JP6603242B2 - ピペリジン−4−カルボチオアミドの製造 - Google Patents
ピペリジン−4−カルボチオアミドの製造 Download PDFInfo
- Publication number
- JP6603242B2 JP6603242B2 JP2016572238A JP2016572238A JP6603242B2 JP 6603242 B2 JP6603242 B2 JP 6603242B2 JP 2016572238 A JP2016572238 A JP 2016572238A JP 2016572238 A JP2016572238 A JP 2016572238A JP 6603242 B2 JP6603242 B2 JP 6603242B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- butanol
- piperidine
- carbothioamide
- reaction
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4465—Non condensed piperidines, e.g. piperocaine only substituted in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dentistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
[項目1]
下記式(I)のピペリジン−4−カルボチオアミド
の製造方法において、
下記式(II)の4−シアノピペリジン:
を、溶媒の存在下に硫化水素(III)と反応させて、式(I)の化合物を得ることを特徴とする方法。
[項目2]
前記反応を密閉反応容器中で行う、項目1に記載の方法。
[項目3]
前記反応を、≧0℃の反応温度で、好ましくは20℃から100℃で、より好ましくは40℃から80℃で行う項目1および2のいずれかに記載の方法。
[項目4]
前記溶媒が1級、2級もしくは3級アルコールまたはそれらの混合物であり、またはこれらアルコールのいずれかをさらに別の溶媒と混合する項目1から3のいずれか1項に記載の方法。
[項目5]
前記溶媒が1から10個の炭素原子を含むアルコールである項目1から3のいずれか1項に記載の方法。
[項目6]
前記溶媒がメタノール、エタノール、イソプロパノール、tert−ブタノール、i−ブタノール、n−ブタノール、シクロペンタノールまたはシクロヘキサノールである項目1から3のいずれか1項に記載の方法。
[項目7]
活性医薬成分および農薬成分を製造するための、項目1から6のいずれか1項に記載の式(I)の化合物の使用。
[項目8]
活性農薬成分を製造するための、項目1から6のいずれか1項に記載の式(I)の化合物の使用。
[項目9]
活性殺菌剤成分を製造するための、項目1から6のいずれか1項に記載の式(I)の化合物の使用。
250mL圧力リアクター中、n−ブタノール100mLおよびシアノピペリジン25g(220mmol)を加熱してて60℃とし、硫化水素をリアクターに導入して、4バールの一定の過圧を維持する(合計17.5g(513mmol)の硫化水素を、その反応時間中にリアクターに導入する。)。6時間後、それ以上の硫化水素は導入せず、反応混合物を60℃でさらに6時間撹拌し、2時間かけて冷却して10℃とする。過剰の硫化水素を塩素系漂白剤スクラバーを通して放出し、リアクターの気体空間を窒素で15分間パージし、沈澱固体を、ガラス吸引フィルターによって吸引濾過する。得られた固体をn−ブタノールで1回洗浄し、吸引によって乾燥させてから、40℃で真空乾燥する。
13C NMR(DMSO−d6、125MHz)δ=212.1、50.2、45.5、32.2ppm。
Claims (6)
- 前記反応を密閉反応容器中で行う、請求項1に記載の方法。
- 前記反応を、≧0℃の反応温度で行う請求項1および2のいずれかに記載の方法。
- 前記溶媒が1級、2級もしくは3級アルコールまたはそれらの混合物であり、またはこれらアルコールのいずれかをさらに別の溶媒と混合する請求項1から3のいずれか1項に記載の方法。
- 前記溶媒が1から10個の炭素原子を含むアルコールである請求項1から3のいずれか1項に記載の方法。
- 前記溶媒がメタノール、エタノール、イソプロパノール、tert−ブタノール、i−ブタノール、n−ブタノール、シクロペンタノールまたはシクロヘキサノールである請求項1から3のいずれか1項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14172038.3 | 2014-06-11 | ||
EP14172038 | 2014-06-11 | ||
PCT/EP2015/062650 WO2015189115A1 (en) | 2014-06-11 | 2015-06-08 | Preparation of piperidine-4-carbothioamide |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017517531A JP2017517531A (ja) | 2017-06-29 |
JP6603242B2 true JP6603242B2 (ja) | 2019-11-06 |
Family
ID=50896206
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016572238A Active JP6603242B2 (ja) | 2014-06-11 | 2015-06-08 | ピペリジン−4−カルボチオアミドの製造 |
Country Status (12)
Country | Link |
---|---|
US (1) | US9790182B2 (ja) |
EP (1) | EP3154942B1 (ja) |
JP (1) | JP6603242B2 (ja) |
KR (1) | KR102430612B1 (ja) |
CN (1) | CN106458898B (ja) |
BR (1) | BR112016028698B1 (ja) |
DK (1) | DK3154942T3 (ja) |
ES (1) | ES2753582T3 (ja) |
IL (1) | IL249130B (ja) |
MX (1) | MX2016016398A (ja) |
TW (1) | TWI666199B (ja) |
WO (1) | WO2015189115A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6700292B2 (ja) * | 2015-03-05 | 2020-05-27 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | ピペリジン−4−カルボチオアミド塩酸塩を調製する方法 |
DE102018212696B3 (de) | 2018-07-30 | 2019-11-07 | Thyssenkrupp Ag | Verstellantrieb für eine Lenksäule und Lenksäule für ein Kraftfahrzeug |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1143364A (zh) * | 1994-03-11 | 1997-02-19 | 山之内制药株式会社 | 5-ht3受体激动剂、新颖的噻唑衍生物及其中间体 |
DE10252102A1 (de) | 2002-11-08 | 2004-05-27 | Merck Patent Gmbh | Indolderivate |
KR20060017929A (ko) * | 2004-08-04 | 2006-02-28 | 동화약품공업주식회사 | 티아졸 유도체가 치환된 신규한 벤즈아미딘 유도체, 그의제조방법 및 이를 유효성분으로 하는 약학 조성물 |
CN1807409A (zh) * | 2006-02-09 | 2006-07-26 | 朱凯琴 | 硫代酰胺类化合物的合成方法 |
WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
WO2009019295A2 (en) | 2007-08-06 | 2009-02-12 | Nv Remynd | Phenyl- and benzylthiazolylpiperazine derivatives for the treatment of neurodegenerative diseases |
US20090054392A1 (en) * | 2007-08-20 | 2009-02-26 | Wyeth | Naphthylpyrimidine, naphthylpyrazine and naphthylpyridazine analogs and their use as agonists of the wnt-beta-catenin cellular messaging system |
TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
MX2010007974A (es) | 2008-01-25 | 2010-08-04 | Du Pont | Amidas fungicidas. |
CA2780905A1 (en) | 2009-12-11 | 2011-06-16 | E.I. Du Pont De Nemours And Company | Azocyclic inhibitors of fatty acid amide hydrolase |
ES2553620T3 (es) | 2009-12-21 | 2015-12-10 | Bayer Cropscience Ag | Bis(difluorometil)pirazoles como fungicidas |
AU2011256730B2 (en) | 2010-05-20 | 2015-07-09 | E. I. Du Pont De Nemours And Company | Fungicidal oximes and hydrazones |
CN109674753A (zh) * | 2010-06-23 | 2019-04-26 | 希玛贝治疗股份有限公司 | 固态分散体 |
US20150031541A1 (en) | 2012-03-02 | 2015-01-29 | Syngenta Participations Ag | Microbiocidal pyrazole derivatives |
-
2015
- 2015-06-08 ES ES15729776T patent/ES2753582T3/es active Active
- 2015-06-08 MX MX2016016398A patent/MX2016016398A/es unknown
- 2015-06-08 BR BR112016028698-7A patent/BR112016028698B1/pt active IP Right Grant
- 2015-06-08 US US15/317,923 patent/US9790182B2/en active Active
- 2015-06-08 KR KR1020167036798A patent/KR102430612B1/ko active IP Right Grant
- 2015-06-08 JP JP2016572238A patent/JP6603242B2/ja active Active
- 2015-06-08 DK DK15729776T patent/DK3154942T3/da active
- 2015-06-08 WO PCT/EP2015/062650 patent/WO2015189115A1/en active Application Filing
- 2015-06-08 EP EP15729776.3A patent/EP3154942B1/en active Active
- 2015-06-08 CN CN201580030993.XA patent/CN106458898B/zh active Active
- 2015-06-09 TW TW104118564A patent/TWI666199B/zh active
-
2016
- 2016-11-22 IL IL249130A patent/IL249130B/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
MX2016016398A (es) | 2017-04-06 |
WO2015189115A1 (en) | 2015-12-17 |
EP3154942A1 (en) | 2017-04-19 |
BR112016028698B1 (pt) | 2021-05-04 |
TWI666199B (zh) | 2019-07-21 |
DK3154942T3 (da) | 2019-11-18 |
IL249130A0 (en) | 2017-01-31 |
TW201625530A (zh) | 2016-07-16 |
JP2017517531A (ja) | 2017-06-29 |
US20170137381A1 (en) | 2017-05-18 |
US9790182B2 (en) | 2017-10-17 |
CN106458898B (zh) | 2019-11-12 |
CN106458898A (zh) | 2017-02-22 |
ES2753582T3 (es) | 2020-04-13 |
EP3154942B1 (en) | 2019-08-28 |
KR102430612B1 (ko) | 2022-08-08 |
BR112016028698A2 (pt) | 2017-08-22 |
KR20170016387A (ko) | 2017-02-13 |
IL249130B (en) | 2018-12-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3129356B1 (en) | A process for producing enzalutamide | |
JP2016500106A5 (ja) | ||
JP2014097981A (ja) | 2−アミノ−n−(2,2,2−トリフルオロエチル)アセトアミド化合物又はその塩の製造方法 | |
JP6603242B2 (ja) | ピペリジン−4−カルボチオアミドの製造 | |
KR20080102422A (ko) | 이소우레아 니트로화 방법 | |
JPWO2016121777A1 (ja) | ピラジンカルボキサミド化合物の製造方法及びその合成中間体 | |
JPWO2011001976A1 (ja) | スレオ−3−(3,4−ジヒドロキシフェニル)−l−セリンの製造法 | |
KR101276667B1 (ko) | 3,4-디클로로이소티아졸카복실산의 제조방법 | |
CN115279746A (zh) | 制备杀节肢动物的邻氨基苯甲酰胺化合物的方法 | |
JP6700292B2 (ja) | ピペリジン−4−カルボチオアミド塩酸塩を調製する方法 | |
JP7279134B2 (ja) | プロリンアミド化合物の製造方法 | |
JP2013531640A (ja) | エステルアミド化合物を調製する方法 | |
JP2007277232A (ja) | ニトロ化方法 | |
JP2016199489A (ja) | 2−アミノ−6−メチルニコチン酸エステルの製造方法 | |
CA3229553A1 (en) | A process for making osimertinib | |
JP6169721B2 (ja) | パピローマウイルスの治療で用いることができるヒドラジンの合成方法 | |
JP5243729B2 (ja) | 2,6−ジクロロプリンの製造方法 | |
KR100543345B1 (ko) | 6-클로로벤족사졸-2-온의 새로운 제조방법 | |
JP2007210930A (ja) | ピリジンスルフェンアミド化合物の製造方法 | |
JP2021504337A (ja) | フルオピコリドの調製方法 | |
JP2006321749A (ja) | 2−シアノマロンアルデヒドのアルカリ金属塩の製法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20180605 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190131 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190205 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190424 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190924 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20191010 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6603242 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |