UA73125C2 - Похідні амінотіазолу, спосіб їх одержання, фармацевтична композиція та їх використання як лігандів рецептора crf - Google Patents

Похідні амінотіазолу, спосіб їх одержання, фармацевтична композиція та їх використання як лігандів рецептора crf Download PDF

Info

Publication number: UA73125C2
Authority: UA; Ukraine
Prior art keywords: methylphenyl; alkyl; methylthiazol; methoxy; hydrochloride
Prior art date: 1999-07-15

Application number

UA2001129084A

Other languages

English (en)

Russian (ru)

Ukrainian (uk)

Inventor

Евеллін Фонтен

Мішель Жеслен

Даніель Гюллі

Антуан Прадін

П'єр Роже

Original Assignee

Санофі-Авантіс

Priority date (The priority date 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 date listed.)

1999-07-15

Filing date

2000-11-07

Publication date

2005-06-15

2000-11-07 Application filed by Санофі-Авантіс filed Critical Санофі-Авантіс

2005-06-15 Publication of UA73125C2 publication Critical patent/UA73125C2/uk

Links

238000000034 method Methods 0.000 title claims description 36
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title description 14
239000003446 ligand Substances 0.000 title description 2
108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 154
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 66
125000000217 alkyl group Chemical group 0.000 claims description 57
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000000654 additive Substances 0.000 claims description 9
230000004054 inflammatory process Effects 0.000 claims description 9
230000000996 additive effect Effects 0.000 claims description 8
150000004677 hydrates Chemical class 0.000 claims description 8
230000007170 pathology Effects 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
208000024827 Alzheimer disease Diseases 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
208000019901 Anxiety disease Diseases 0.000 claims description 5
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230000036506 anxiety Effects 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
230000001850 reproductive effect Effects 0.000 claims description 5
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
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MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
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208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 2
206010046851 Uveitis Diseases 0.000 claims description 2
125000005332 alkyl sulfoxy group Chemical group 0.000 claims description 2
230000000747 cardiac effect Effects 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims description 2
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239000003814 drug Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000002560 nitrile group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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229910052760 oxygen Inorganic materials 0.000 claims description 2
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125000003226 pyrazolyl group Chemical group 0.000 claims description 2
206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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IKXNIQJDNKPPCH-UHFFFAOYSA-N hydron;prop-2-yn-1-amine;chloride Chemical compound [Cl-].[NH3+]CC#C IKXNIQJDNKPPCH-UHFFFAOYSA-N 0.000 claims 3
206010001488 Aggression Diseases 0.000 claims 1
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208000005107 Premature Birth Diseases 0.000 claims 1
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231100000001 growth retardation Toxicity 0.000 claims 1
230000000968 intestinal effect Effects 0.000 claims 1
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238000012876 topography Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
-1 1 -pyridyl Chemical group 0.000 description 85
239000000243 solution Substances 0.000 description 76
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 38
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 36
239000000203 mixture Substances 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
239000012074 organic phase Substances 0.000 description 28
150000003585 thioureas Chemical class 0.000 description 28
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 17
150000001412 amines Chemical class 0.000 description 16
239000000047 product Substances 0.000 description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
235000011121 sodium hydroxide Nutrition 0.000 description 14
239000000741 silica gel Substances 0.000 description 13
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
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HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
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238000006243 chemical reaction Methods 0.000 description 9
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239000011780 sodium chloride Substances 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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102000005962 receptors Human genes 0.000 description 8
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
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239000012312 sodium hydride Substances 0.000 description 7
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VHKLGKYMXNRCFN-UHFFFAOYSA-N 1-(4-chloro-3-fluorophenyl)-2-methoxy-n-phenylmethoxyethanimine Chemical compound C=1C=C(Cl)C(F)=CC=1C(COC)=NOCC1=CC=CC=C1 VHKLGKYMXNRCFN-UHFFFAOYSA-N 0.000 description 6
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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UA2001129084A 1999-07-15 2000-11-07 Похідні амінотіазолу, спосіб їх одержання, фармацевтична композиція та їх використання як лігандів рецептора crf UA73125C2 (uk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9909144A FR2796380B3 (fr)	1999-07-15	1999-07-15	Nouveaux derives d'aminothiazoles, leur preparation et les compositions pharmaceutiques les contenant
PCT/FR2000/001995 WO2001005776A1 (fr)	1999-07-15	2000-07-11	Derives d'aminothiazole et leur utilisation comme ligands des recepteurs crf

Publications (1)

Publication Number	Publication Date
UA73125C2 true UA73125C2 (uk)	2005-06-15

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UA2001129084A UA73125C2 (uk)	1999-07-15	2000-11-07	Похідні амінотіазолу, спосіб їх одержання, фармацевтична композиція та їх використання як лігандів рецептора crf

Country Status (36)

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US (2)	US6586456B1 (sr)
EP (1)	EP1200419B1 (sr)
JP (1)	JP4949582B2 (sr)
KR (1)	KR100707320B1 (sr)
CN (1)	CN1167692C (sr)
AR (1)	AR024747A1 (sr)
AT (1)	ATE264315T1 (sr)
AU (1)	AU772683B2 (sr)
BR (1)	BR0012478B1 (sr)
CA (1)	CA2378792C (sr)
CO (1)	CO5200792A1 (sr)
CZ (1)	CZ300937B6 (sr)
DE (1)	DE60009911T2 (sr)
DK (1)	DK1200419T3 (sr)
EA (1)	EA005159B1 (sr)
EE (1)	EE05004B1 (sr)
ES (1)	ES2220504T3 (sr)
FR (1)	FR2796380B3 (sr)
HK (1)	HK1045692B (sr)
HU (1)	HU229069B1 (sr)
IL (2)	IL147282A0 (sr)
IS (1)	IS2314B (sr)
ME (1)	MEP26608A (sr)
MX (1)	MXPA02000545A (sr)
NO (1)	NO324352B1 (sr)
NZ (1)	NZ516397A (sr)
PL (1)	PL206515B1 (sr)
PT (1)	PT1200419E (sr)
RS (1)	RS50443B (sr)
SI (1)	SI1200419T1 (sr)
SK (1)	SK287069B6 (sr)
TR (1)	TR200200125T2 (sr)
TW (1)	TWI278453B (sr)
UA (1)	UA73125C2 (sr)
WO (1)	WO2001005776A1 (sr)
ZA (1)	ZA200200221B (sr)

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WO2002024200A1 (en) *	2000-09-21	2002-03-28	Bristol-Myers Squibb Company	Substituted azole derivatives as inhibitors of corticotropin releasing factor
WO2003015777A1 (en) *	2001-08-13	2003-02-27	Lion Bioscience Ag	Nr1h4 nuclear receptor binding compounds
US6993173B2 (en)	2001-10-12	2006-01-31	Duke University	Methods for estimating probe cell locations in high-density synthetic DNA microarrays
EP1766014A4 (en)	2004-06-03	2008-12-10	Athlomics Pty Ltd	AGENTS AND METHODS FOR THE DIAGNOSIS OF STRESS
BRPI0515012A (pt) *	2004-08-13	2008-07-01	Genentech Inc	substáncia quìmica, composição e formulação farmacêutica, método de tratamento, método de inibição de pelo menos uma enzima que utiliza atp e uso
EP1834641A1 (en)	2006-03-16	2007-09-19	Sanofi-Aventis	Use of CRF1 receptor antagonists for preparing a drug for treating metabolic syndrome and/or obesity and/or dyslipoproteinemia
HUP0900267A2 (en)	2009-04-30	2011-03-28	Sanofi Aventis	Process for preparing of thiazole amines and intermediates thereof
JP2015516979A (ja) *	2012-04-23	2015-06-18	ホルスボールマッシュマイヤーニューロケミーゲーエムベーハーＨｏｌｓｂｏｅｒｍａｓｃｈｍｅｙｅｒＮｅｕｒｏｃｈｅｍｉｅＧｍｂｈ	Ｃｒｈ過剰活性を有する患者の治療に用いるためのｃｒｈｒ１アンタゴニスト
GB201210686D0 (en)	2012-06-15	2012-08-01	Holsboermaschmeyer Neurochemie Gmbh	V1B receptor antagonist for use in the treatment of patients having an elevated AVP level and/or an elevated copeptin level
GB201310782D0 (en)	2013-06-17	2013-07-31	Max Planck Innovation Gmbh	Method for predicting a treatment response to a CRHR1 antagonist and/or V1B antagonist in a patient with depressive and/or anxiety symptoms
KR20210064407A (ko)	2014-01-21	2021-06-02	뉴로크린 바이오사이언시즈 인코퍼레이티드	선천성 부신 과형성 치료를 위한 ｃｒｆ1 수용체 길항제
MX2020011344A (es)	2018-04-27	2021-02-09	Spruce Biosciences Inc	Métodos para tratar tumores en reposo suprarrenales testiculares y de ovarios.
PL3984523T3 (pl) *	2018-12-07	2026-02-02	Neurocrine Biosciences, Inc.	Antagonista receptora crf1, jego formulacje farmaceutyczne i postacie stałe do leczenia wrodzonego przerostu nadnerczy
JP7532328B2 (ja) *	2018-12-07	2024-08-13	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	先天性副腎過形成を処置するためのｃｒｆ１受容体アンタゴニスト、その医薬製剤および固体形態
US12383536B2 (en)	2019-09-27	2025-08-12	Neurocrine Biosciences, Inc.	CRF receptor antagonists and methods of use
ES3039926T3 (en)	2019-12-04	2025-10-27	Neurocrine Biosciences Inc	Crf receptor antagonists and methods of use
CA3181084A1 (en)	2020-06-10	2021-12-16	Robert H. FARBER	Crf1 receptor antagonist for the treatment of congenital adrenal hyperplasia
WO2026128582A1 (en)	2024-12-11	2026-06-18	Neurocrine Biosciences, Inc.	Methods for the administration of crf antagonist
WO2026128584A1 (en)	2024-12-11	2026-06-18	Neurocrine Biosciences, Inc.	Methods for the administration of the orf antagonist crinecerfont and a strong cytochrome p4503a4 (cyp3a4) inducer

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Publication number	Priority date	Publication date	Assignee	Title
FR2692893B1 (fr) *	1992-06-24	1994-09-02	Sanofi Elf	Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent.
FR2714059B1 (fr)	1993-12-21	1996-03-08	Sanofi Elf	Dérivés amino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent.
FR2735777B1 (fr)	1995-06-21	1997-09-12	Sanofi Sa	Derives de 4-phenylaminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
FR2754258B1 (fr) *	1996-10-08	1998-12-31	Sanofi Sa	Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant

1999
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2000
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2001
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2002
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2007
- 2007-04-25 US US11/740,001 patent/US8420679B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
NO324352B1 (no)	2007-09-24
EE200200022A (et)	2003-04-15
BR0012478A (pt)	2002-04-02
EA200101234A1 (ru)	2002-08-29
EE05004B1 (et)	2008-04-15
KR100707320B1 (ko)	2007-04-13
TR200200125T2 (tr)	2002-09-23
AR024747A1 (es)	2002-10-23
MEP26608A (en)	2010-06-10
US20070281919A1 (en)	2007-12-06
DK1200419T3 (da)	2004-07-19
KR20020015373A (ko)	2002-02-27
IS6219A (is)	2002-01-03
NZ516397A (en)	2004-01-30
SK287069B6 (sk)	2009-11-05
HK1045692B (zh)	2004-11-26
IL147282A (en)	2008-04-13
JP2003505380A (ja)	2003-02-12
FR2796380B3 (fr)	2001-08-17
DE60009911T2 (de)	2005-03-10
HK1045692A1 (en)	2002-12-06
ES2220504T3 (es)	2004-12-16
CN1370154A (zh)	2002-09-18
ATE264315T1 (de)	2004-04-15
CZ300937B6 (cs)	2009-09-16
PL206515B1 (pl)	2010-08-31
ZA200200221B (en)	2003-04-30
US6586456B1 (en)	2003-07-01
SI1200419T1 (en)	2004-08-31
PL352901A1 (en)	2003-09-22
WO2001005776A1 (fr)	2001-01-25
CO5200792A1 (es)	2002-09-27
HUP0202387A2 (hu)	2002-11-28
EA005159B1 (ru)	2004-12-30
PT1200419E (pt)	2004-07-30
JP4949582B2 (ja)	2012-06-13
SK382002A3 (en)	2002-07-02
NO20020155D0 (no)	2002-01-11
MXPA02000545A (es)	2002-07-30
DE60009911D1 (de)	2004-05-19
TWI278453B (en)	2007-04-11
YU1302A (sh)	2005-03-15
FR2796380A1 (fr)	2001-01-19
BR0012478B1 (pt)	2013-10-15
CZ2002137A3 (cs)	2002-04-17
CA2378792C (en)	2009-11-10
NO20020155L (no)	2002-03-15
RS50443B (sr)	2010-03-02
AU6452100A (en)	2001-02-05
CA2378792A1 (en)	2001-01-25
US8420679B2 (en)	2013-04-16
AU772683B2 (en)	2004-05-06
EP1200419B1 (fr)	2004-04-14
IS2314B (is)	2007-11-15
HUP0202387A3 (en)	2004-12-28
HU229069B1 (en)	2013-07-29
IL147282A0 (en)	2002-08-14
EP1200419A1 (fr)	2002-05-02
CN1167692C (zh)	2004-09-22

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