JP5608221B2 - [4−(2−クロロ−4−メトキシ−5−メチルフェニル)−5−メチル−チアゾロ−2−イル]−[2−シクロプロピル−1−(3−フルオロ−4−メチルフェニル)−エチル]−アミンを調製するための方法 - Google Patents
[4−(2−クロロ−4−メトキシ−5−メチルフェニル)−5−メチル−チアゾロ−2−イル]−[2−シクロプロピル−1−(3−フルオロ−4−メチルフェニル)−エチル]−アミンを調製するための方法 Download PDFInfo
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- JP5608221B2 JP5608221B2 JP2012507828A JP2012507828A JP5608221B2 JP 5608221 B2 JP5608221 B2 JP 5608221B2 JP 2012507828 A JP2012507828 A JP 2012507828A JP 2012507828 A JP2012507828 A JP 2012507828A JP 5608221 B2 JP5608221 B2 JP 5608221B2
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- Prior art keywords
- formula
- methylphenyl
- methyl
- iii
- amine
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- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims description 20
- -1 2-Chloro-4-methoxy-5-methylphenyl Chemical group 0.000 title claims description 14
- 150000001412 amines Chemical class 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 35
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 34
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- SOHMWVXOAKNVTH-UHFFFAOYSA-N [1-(2-chloro-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl] thiocyanate Chemical compound COC1=CC(Cl)=C(C(=O)C(C)SC#N)C=C1C SOHMWVXOAKNVTH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- NQCCWXKFKYSSBV-UHFFFAOYSA-N 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethanamine Chemical group C1=C(F)C(C)=CC=C1C(N)CC1CC1 NQCCWXKFKYSSBV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 101000957724 Catostomus commersonii Corticoliberin-1 Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GCPRCXZISRDEDG-UHFFFAOYSA-N 2-bromo-1-(2-chloro-4-methoxy-5-methylphenyl)propan-1-one Chemical compound COC1=CC(Cl)=C(C(=O)C(C)Br)C=C1C GCPRCXZISRDEDG-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1466—Monomers containing sulfur
- C08F216/1483—Monomers containing sulfur and nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
b.)その結果得られた式(III)の2−チオシアナト−1−(2−クロロ−4−メトキシ−5−メチルフェニル)−プロパン−1−オン
291.5gの2−ブロモ−1−(2−クロロ−4−メトキシ−5−メチルフェニル)−プロパン−1−オン(II)を、291gのDCMに溶解し、そこに、5.3gのTBAB(臭化テトラブチルアンモニウム)触媒を添加する。167gのKSCNを、83.6gの水に溶解する。この水溶液をDCM溶液に添加する。得られた二成分系を40℃まで加熱(還流)して、3−4時間撹拌する。この反応は塩析沈殿を伴う。塩が溶解するまで混合物に水を添加する。下側の水相を分離し、上側の有機相は蒸発させ、一方で870mlのメタノール(MeOH)をそこに添加する。このメタノール溶液から、化合物(III)が、冷却したときに結晶化する。この結晶をろ過して、数回MeOHで洗浄する。
収率:90−95%
IRスペクトル:2158cm−1(CN)、1664cm−1(C=O)
1Hスペクトル(DMSO−d6,TMS):7.73(1H,s)、7.14(1H,s)、5.28(1H,q,J=7,2Hz)、3.89(3H,s)、2.16(3H,s)、1.60(3H,d,J=7.2Hz)
13C−NMRスペクトル:194.7、160.9、132.6、131.5、126.3、125.5、113.5、111.4、56.7、49.4、18.8、15.8
調製手順は実施例1に記載した通りであるが、DCMの代わりにMCHを溶媒として使用する。生成物は、MCHから冷却したときに結晶化する。
収率:60%
26.4gの化合物(III)(実施例1または2に記載したように調製)を、52mlのMCH中に懸濁する。化学量論量のアミン(好ましくはベンジルアミン)を該混合物に添加する。この混合物を0.5−1時間、撹拌する(アミンの構造は反応時間に影響を与える。)。濃厚な沈殿物が得られ、これをろ過して、メチル−シクロヘキサンで数回洗浄する。
収率:85%。
調製手順は実施例3に記載した通りであるが、化合物(III)を、MCH中ではなく、溶媒としてのトリエチル−アミン中に懸濁させ、他のアミンは該混合物に添加しないという点が異なる。
収率:85%。
融点:106℃(EtOH)
IRスペクトル:3253cm−1(NH)、1679cm−1(C=N)
1Hスペクトル(DMSO−d6,TMS):7.30(1H,s)、7.14(1H,s)、3.86(3H,s)、2.14(3H,s)、1.88(3H,s)
13C−NMRスペクトル:163.1(s)、158.9(s)、138.9(d)、133.0(s)、131.4(s)、125.3(s)、118.3(s)、111.8(d)、111.5(s)、56.0(t)、15.3(t)、11.6(t)
26.3gの単離生成物(III)を、52mlのMCHに溶解する。反応混合物を85−90℃まで加熱して、19.2gのアミン(IV)のMCH(20%)中溶液(85−90℃)に添加する。添加期間は2−4時間である。添加の後、反応混合物を85−90℃で1時間撹拌する。粗生成物(I)のMCH溶液を冷却し、沈殿した結晶をろ過する。結晶生成物は、少量のMCHによって覆われている。
収率:80%。
調製手順は実施例5に記載した通りであるが、生成物(I)は、溶媒の交換後、MCHではなく、MeOHから結晶化する。
収率:90%
調製手順は実施例5および6に記載した通りであるが、化合物(III)の代わりに、化合物(V)を同量で使用する。
収率:85%
Claims (12)
- 式(I)の[4−(2−クロロ−4−メトキシ−5−メチルフェニル)−5−メチル−チアゾロ−2−イル]−[2−シクロプロピル−1−(3−フルオロ−4−メチルフェニル)−エチル]−アミン
a.)一般式(II)の化合物
b.)その結果得られた式(III)の2−チオシアナト−1−(2−クロロ−4−メトキシ−5−メチルフェニル)−プロパン−1−オン
- ステップb.)において、式(III)のケトンが、式(IV)のアミンに添加されることを特徴とする、請求項1に記載の方法。
- 式(III)のケトンの式(IV)のアミンへの添加に、少なくとも1時間をかけることを特徴とする、請求項2に記載の方法。
- ステップa.)において、反応が、非プロトン性溶媒および水からなる二成分系において行われることを特徴とする、請求項1から3のいずれかに記載の方法。
- ステップb.)が、無極性非プロトン性溶媒中で実施されることを特徴とする、請求項1から4のいずれかに記載の方法。
- ステップb.)において用いられる無極性非プロトン性溶媒が、メチル−シクロヘキサンまたはトルエンであることを特徴とする、請求項5に記載の方法。
- ステップb.)が、25℃から還流温度の間の温度において実施されることを特徴とする、請求項1から6のいずれかに記載の方法。
- ステップb.)が、還流温度において実施されることを特徴とする、請求項7に記載の方法。
- 一般式(II)において、Xがブロモ基を意味することを特徴とする、請求項1から8のいずれかに記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU0900267A HUP0900267A2 (en) | 2009-04-30 | 2009-04-30 | Process for preparing of thiazole amines and intermediates thereof |
HUP0900267 | 2009-04-30 | ||
PCT/HU2010/000047 WO2010125414A1 (en) | 2009-04-30 | 2010-04-26 | Process for the preparation of [4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-thiazolo-2-yl]-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-ethyl]-amine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012525368A JP2012525368A (ja) | 2012-10-22 |
JP5608221B2 true JP5608221B2 (ja) | 2014-10-15 |
Family
ID=89988941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012507828A Expired - Fee Related JP5608221B2 (ja) | 2009-04-30 | 2010-04-26 | [4−(2−クロロ−4−メトキシ−5−メチルフェニル)−5−メチル−チアゾロ−2−イル]−[2−シクロプロピル−1−(3−フルオロ−4−メチルフェニル)−エチル]−アミンを調製するための方法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US8314249B2 (ja) |
EP (1) | EP2424848B1 (ja) |
JP (1) | JP5608221B2 (ja) |
KR (1) | KR20120014005A (ja) |
CN (1) | CN102414185B (ja) |
AR (1) | AR076478A1 (ja) |
AU (1) | AU2010243362B2 (ja) |
BR (1) | BRPI1014627A2 (ja) |
CA (1) | CA2760384A1 (ja) |
HU (1) | HUP0900267A2 (ja) |
IL (1) | IL216017A0 (ja) |
IN (1) | IN2011KN04192A (ja) |
MX (1) | MX2011011530A (ja) |
MY (1) | MY152269A (ja) |
RU (1) | RU2523793C2 (ja) |
SG (1) | SG175829A1 (ja) |
TW (1) | TWI461413B (ja) |
UY (1) | UY32594A (ja) |
WO (1) | WO2010125414A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8943551B2 (en) * | 2008-08-14 | 2015-01-27 | Microsoft Corporation | Cloud-based device information storage |
HUP0900267A2 (en) | 2009-04-30 | 2011-03-28 | Sanofi Aventis | Process for preparing of thiazole amines and intermediates thereof |
EP3096756B1 (en) | 2014-01-21 | 2024-06-12 | Neurocrine Biosciences, Inc. | Crf1 receptor antagonists for the treatment of congenital adrenal hyperplasia |
US10207974B1 (en) | 2017-12-05 | 2019-02-19 | Chevron Phillips Chemical Company Lp | Synthesis of gamma dicarbonyl and pyrrole compounds |
KR20210100669A (ko) | 2018-12-07 | 2021-08-17 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 선천성 부신 증식증의 치료를 위한 crf1 수용체 길항제, 그의 제약 제제 및 고체 형태 |
JP2022549496A (ja) * | 2019-09-27 | 2022-11-25 | ニューロクライン バイオサイエンシーズ,インコーポレイテッド | Crf受容体アンタゴニストおよび使用方法 |
TW202214235A (zh) | 2020-06-10 | 2022-04-16 | 美商紐羅克里生物科學有限公司 | 用於治療先天性腎上腺增生之crf1受體拮抗劑 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB823251A (en) | 1955-07-02 | 1959-11-11 | Thomae Gmbh Dr K | Improvements in or relating to preparations containing benzoxathiol derivatives for the care of hair and skin |
US3222248A (en) * | 1961-12-12 | 1965-12-07 | Stauffer Chemical Co | Method of controlling microorganisms by means of organic thiocyanates |
US3433803A (en) | 1966-12-01 | 1969-03-18 | Olin Mathieson | Substituted imino-1,3-oxathiols and their preparation |
IL103586A (en) | 1991-10-30 | 1997-09-30 | Astra Ab | Process for the preparation of 4-methyl-5- (2-chloroethyl)-thiazole and analogues thereof |
JPH1036360A (ja) | 1996-02-21 | 1998-02-10 | Kuraray Co Ltd | 2−クロロ−5−クロロメチル−1,3−チアゾールの製造方法 |
FR2796380B3 (fr) * | 1999-07-15 | 2001-08-17 | Sanofi Synthelabo | Nouveaux derives d'aminothiazoles, leur preparation et les compositions pharmaceutiques les contenant |
HUP0900267A2 (en) | 2009-04-30 | 2011-03-28 | Sanofi Aventis | Process for preparing of thiazole amines and intermediates thereof |
-
2009
- 2009-04-30 HU HU0900267A patent/HUP0900267A2/hu unknown
-
2010
- 2010-04-26 WO PCT/HU2010/000047 patent/WO2010125414A1/en active Application Filing
- 2010-04-26 KR KR1020117028054A patent/KR20120014005A/ko not_active Application Discontinuation
- 2010-04-26 MX MX2011011530A patent/MX2011011530A/es active IP Right Grant
- 2010-04-26 JP JP2012507828A patent/JP5608221B2/ja not_active Expired - Fee Related
- 2010-04-26 BR BRPI1014627-0A patent/BRPI1014627A2/pt not_active IP Right Cessation
- 2010-04-26 RU RU2011148584/04A patent/RU2523793C2/ru not_active IP Right Cessation
- 2010-04-26 IN IN4192KON2011 patent/IN2011KN04192A/en unknown
- 2010-04-26 CA CA2760384A patent/CA2760384A1/en active Pending
- 2010-04-26 EP EP10718684A patent/EP2424848B1/en not_active Not-in-force
- 2010-04-26 SG SG2011079696A patent/SG175829A1/en unknown
- 2010-04-26 MY MYPI2011005171 patent/MY152269A/en unknown
- 2010-04-26 AU AU2010243362A patent/AU2010243362B2/en not_active Ceased
- 2010-04-26 CN CN201080018790.6A patent/CN102414185B/zh not_active Expired - Fee Related
- 2010-04-28 AR ARP100101422A patent/AR076478A1/es unknown
- 2010-04-29 TW TW099113599A patent/TWI461413B/zh not_active IP Right Cessation
- 2010-04-30 UY UY0001032594A patent/UY32594A/es not_active Application Discontinuation
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CN102414185A (zh) | 2012-04-11 |
AU2010243362B2 (en) | 2015-07-30 |
MX2011011530A (es) | 2011-11-18 |
KR20120014005A (ko) | 2012-02-15 |
SG175829A1 (en) | 2011-12-29 |
TW201105640A (en) | 2011-02-16 |
HUP0900267A2 (en) | 2011-03-28 |
MY152269A (en) | 2014-09-15 |
BRPI1014627A2 (pt) | 2015-08-25 |
RU2523793C2 (ru) | 2014-07-27 |
EP2424848B1 (en) | 2013-03-13 |
CA2760384A1 (en) | 2010-11-04 |
IN2011KN04192A (ja) | 2015-10-02 |
AR076478A1 (es) | 2011-06-15 |
AU2010243362A1 (en) | 2011-11-17 |
RU2011148584A (ru) | 2013-06-10 |
US8314249B2 (en) | 2012-11-20 |
CN102414185B (zh) | 2014-02-26 |
EP2424848A1 (en) | 2012-03-07 |
HU0900267D0 (en) | 2009-07-28 |
TWI461413B (zh) | 2014-11-21 |
WO2010125414A8 (en) | 2011-04-07 |
WO2010125414A1 (en) | 2010-11-04 |
JP2012525368A (ja) | 2012-10-22 |
US20120083608A1 (en) | 2012-04-05 |
IL216017A0 (en) | 2012-01-31 |
UY32594A (es) | 2010-11-30 |
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