ZA200608832B - Novel fluoroglycoside derivatives of pyrazoles, medicaments containing these compounds, and the use thereof - Google Patents

Novel fluoroglycoside derivatives of pyrazoles, medicaments containing these compounds, and the use thereof Download PDF

Info

Publication number: ZA200608832B
Authority: ZA; South Africa
Prior art keywords: alkyl; alkylene; hydrogen; replaced; phenyl
Prior art date: 2004-06-11

Application number

ZA200608832A

Other languages

English (en)

Inventor

Brummerhop Harm

Glombik Heiner

Bickel Martin

Theis Stefan

Frick Wendelin

Plettenburg Oliver

Heuer Hubert

Original Assignee

Sanofi Aventis Deutschland

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.)

2004-06-11

Filing date

2006-10-24

Publication date

2008-05-28

2006-10-24 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2008-05-28 Publication of ZA200608832B publication Critical patent/ZA200608832B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 95
239000003814 drug Substances 0.000 title claims description 14
150000003217 pyrazoles Chemical class 0.000 title description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 44
229910052731 fluorine Inorganic materials 0.000 claims description 35
229910052760 oxygen Inorganic materials 0.000 claims description 32
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
-1 COO-(C1-Cg)-alkyl Chemical group 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 20
239000011737 fluorine Substances 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 16
229910052794 bromium Inorganic materials 0.000 claims description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
239000008280 blood Substances 0.000 claims description 10
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150000003839 salts Chemical class 0.000 claims description 10
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 9
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
239000008103 glucose Substances 0.000 claims description 9
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
229910006069 SO3H Inorganic materials 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
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125000000217 alkyl group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
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YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
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HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
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FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 3
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ZA200608832A 2004-06-11 2006-10-24 Novel fluoroglycoside derivatives of pyrazoles, medicaments containing these compounds, and the use thereof ZA200608832B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE102004028241A DE102004028241B4 (de)	2004-06-11	2004-06-11	Neue Fluorglykosidderivate von Pyrazolen, diese Verbindungen enthaltende Arzneimittel und Herstellung dieser Arzneimittel

Publications (1)

Publication Number	Publication Date
ZA200608832B true ZA200608832B (en)	2008-05-28

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ZA200608832A ZA200608832B (en)	2004-06-11	2006-10-24	Novel fluoroglycoside derivatives of pyrazoles, medicaments containing these compounds, and the use thereof

Country Status (33)

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US (1)	US7820804B2 (pt)
EP (1)	EP1758914B1 (pt)
JP (1)	JP4996464B2 (pt)
CN (1)	CN100582116C (pt)
AR (1)	AR049393A1 (pt)
AU (1)	AU2005252329B2 (pt)
BR (1)	BRPI0510770A (pt)
CA (1)	CA2570042C (pt)
CR (1)	CR8773A (pt)
CY (1)	CY1107426T1 (pt)
DE (2)	DE102004028241B4 (pt)
DK (1)	DK1758914T3 (pt)
EC (1)	ECSP067054A (pt)
ES (1)	ES2296180T3 (pt)
HR (1)	HRP20080023T3 (pt)
IL (1)	IL179757A (pt)
MA (1)	MA28653B1 (pt)
MX (1)	MXPA06013513A (pt)
MY (1)	MY143565A (pt)
NO (1)	NO20070176L (pt)
NZ (1)	NZ551948A (pt)
PE (1)	PE20060297A1 (pt)
PL (1)	PL1758914T3 (pt)
PT (1)	PT1758914E (pt)
RS (1)	RS50541B (pt)
RU (1)	RU2370499C2 (pt)
SI (1)	SI1758914T1 (pt)
TN (1)	TNSN06409A1 (pt)
TW (1)	TWI382030B (pt)
UA (1)	UA89787C2 (pt)
UY (1)	UY28955A1 (pt)
WO (1)	WO2005121161A1 (pt)
ZA (1)	ZA200608832B (pt)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200637869A (en)	2005-01-28	2006-11-01	Chugai Pharmaceutical Co Ltd	The spiroketal derivatives and the use as therapeutical agent for diabetes of the same
DE102005026762A1 (de)	2005-06-09	2006-12-21	Sanofi-Aventis Deutschland Gmbh	Azolopyridin-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen
PE20110235A1 (es)	2006-05-04	2011-04-14	Boehringer Ingelheim Int	Combinaciones farmaceuticas que comprenden linagliptina y metmorfina
TW200812995A (en)	2006-05-19	2008-03-16	Taisho Pharmaceutical Co Ltd	C-phenyl glycitol compound
RU2434862C2 (ru)	2006-06-29	2011-11-27	Тайсо Фармасьютикал Ко., Лтд.	С-фенил-1-тиоглюцитолы
JP2010500300A (ja)	2006-08-08	2010-01-07	サノフィ−アベンティス	アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用
DE102006053637B4 (de)	2006-11-14	2011-06-30	Sanofi-Aventis Deutschland GmbH, 65929	Neue mit Fluor substituierte 1,4-Benzothiepin-1,1-Dioxidderivate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
AU2007332476A1 (en)	2006-12-14	2008-06-19	Taisho Pharmaceutical Co., Ltd.	1-phenyl 1-thio-D-glucitol derivative
EP2025674A1 (de)	2007-08-15	2009-02-18	sanofi-aventis	Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
JP5272395B2 (ja) *	2007-12-12	2013-08-28	セントラル硝子株式会社	４−デオキシ−４−フルオロ−ｄ−グルコース誘導体の製造方法
WO2010003624A2 (en)	2008-07-09	2010-01-14	Sanofi-Aventis	Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
MY155418A (en) *	2008-08-28	2015-10-15	Pfizer	Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives
WO2010068601A1 (en)	2008-12-08	2010-06-17	Sanofi-Aventis	A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof
SG173801A1 (en)	2009-02-23	2011-09-29	Taisho Pharmaceutical Co Ltd	4 -isopropylphenyl glucitol compounds as sglt1 inhibitors
EP2298782A1 (en)	2009-08-26	2011-03-23	Sanofi-Aventis	Method for producing pyrazole glycoside derivatives
MX2012001729A (es) *	2009-08-26	2012-06-13	Sanofi Sa	Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo.
KR20120091174A (ko)	2009-10-02	2012-08-17	사노피	골질환 치료제의 제조를 위한 ｓｇｌｔ-1/ｓｇｌｔ-2 억제제 활성을 갖는 화합물의 용도
US8163704B2 (en)	2009-10-20	2012-04-24	Novartis Ag	Glycoside derivatives and uses thereof
EA021983B1 (ru)	2009-11-02	2015-10-30	Пфайзер Инк.	Производные диоксабицикло[3.2.1]октан-2,3,4-триола
CN102711738A (zh)	2009-11-13	2012-10-03	百时美施贵宝公司	质量得以减小的二甲双胍制剂
JP5784623B2 (ja)	2009-11-13	2015-09-24	アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａＡｋｔｉｅｂｏｌａｇ	速放性錠剤製剤
EP3315124B1 (en)	2009-11-13	2021-01-06	Astrazeneca AB	Bilayer tablet formulations
WO2011107494A1 (de)	2010-03-03	2011-09-09	Sanofi	Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
WO2011157827A1 (de)	2010-06-18	2011-12-22	Sanofi	Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen
US8530413B2 (en)	2010-06-21	2013-09-10	Sanofi	Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215387A (en)	2010-07-05	2012-04-16	Sanofi Aventis	Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
TW201215388A (en)	2010-07-05	2012-04-16	Sanofi Sa	(2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201221505A (en)	2010-07-05	2012-06-01	Sanofi Sa	Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
EP2607360B1 (en)	2010-08-20	2015-08-19	Taisho Pharmaceutical Co., Ltd.	4-Isopropyl-6-methoxyphenyl glucitol compound
US8822674B2 (en)	2010-08-20	2014-09-02	Taisho Pharmaceutical Co., Ltd	Crystal form of 4-isopropylphenyl glucitol compound and process for production thereof
CN103370064A (zh)	2010-09-03	2013-10-23	百时美施贵宝公司	使用水溶性抗氧化剂的药物制剂
CA2826391C (en)	2011-02-01	2017-01-24	Bristol-Myers Squibb Company	Pharmaceutical formulations including an amine compound
EP2683701B1 (de)	2011-03-08	2014-12-24	Sanofi	Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
US8871758B2 (en)	2011-03-08	2014-10-28	Sanofi	Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
EP2683702B1 (de)	2011-03-08	2014-12-24	Sanofi	Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung
EP2683699B1 (de)	2011-03-08	2015-06-24	Sanofi	Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
EP2683705B1 (de)	2011-03-08	2015-04-22	Sanofi	Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung
US8895547B2 (en)	2011-03-08	2014-11-25	Sanofi	Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof
WO2012120052A1 (de)	2011-03-08	2012-09-13	Sanofi	Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung
US8828995B2 (en)	2011-03-08	2014-09-09	Sanofi	Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
EP2683698B1 (de)	2011-03-08	2017-10-04	Sanofi	Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
US8614195B2 (en) *	2011-04-14	2013-12-24	Novartis Ag	Glycoside derivatives and uses thereof
AR087701A1 (es) *	2011-08-31	2014-04-09	Japan Tobacco Inc	Derivados de pirazol con actividad inhibidora de sglt1
WO2013037390A1 (en)	2011-09-12	2013-03-21	Sanofi	6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
EP2760862B1 (en)	2011-09-27	2015-10-21	Sanofi	6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
UA113086C2 (xx)	2012-05-10	2016-12-12		Піразольні сполуки як інгібітори sglt1
TW201425326A (zh)	2012-10-05	2014-07-01	Lilly Co Eli	新穎脲化合物
EP2952206B1 (en)	2013-02-04	2018-10-24	Taisho Pharmaceutical Co., Ltd.	Prophylactic or therapeutic drug for constipation
EP2774619B1 (de)	2013-03-04	2016-05-18	BioActive Food GmbH	Zusammensetzung zur Behandlung von hyperglykämischen Erkrankungen
AR098670A1 (es) *	2013-11-08	2016-06-08	Lilly Co Eli	Inhibidor de sglt1
EP2944311A1 (de)	2014-05-16	2015-11-18	BioActive Food GmbH	Kombination von biologisch aktiven Substanzen zur Behandlung von hyperglykämischen Erkrankungen
MX2020010433A (es) *	2018-04-04	2020-10-28	Japan Tobacco Inc	Compuestos de pirazol sustituidos con heteroarilo y uso farmaceutico de los mismos.
KR102919209B1 (ko)	2018-08-10	2026-01-28	다이아핀 테라퓨틱스, 엘엘씨	트리-펩타이드 그리고 대사, 심장혈관 및 염증성 장애의 치료
WO2020113094A1 (en)	2018-11-30	2020-06-04	Nuvation Bio Inc.	Pyrrole and pyrazole compounds and methods of use thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU719726B2 (en) *	1996-12-26	2000-05-18	Tanabe Seiyaku Co., Ltd.	Propiophenone derivatives and process for preparing the same
ATE264337T1 (de) *	1999-08-31	2004-04-15	Kissei Pharmaceutical	Glucopyranosyloxypyrazol-derivate, diese enthaltende arzneimittel und zwischenprodukte zu deren herstellung
PH12000002657B1 (en) *	1999-10-12	2006-02-21	Bristol Myers Squibb Co	C-aryl glucoside SGLT2 inhibitors
ATE455785T1 (de) *	2000-11-02	2010-02-15	Ajinomoto Kk	Neue pyrazolderivate und diese enthaltende mittel gegen diabetes
EP1373565A2 (en) *	2001-02-14	2004-01-02	Tularik Inc.	Methods for the diagnosis and treatment of tumors employing the hepsin gene
US20030087843A1 (en) *	2001-09-05	2003-05-08	Washburn William N.	O-pyrazole glucoside SGLT2 inhibitors and method of use
PL213095B1 (pl) *	2002-08-08	2013-01-31	Kissei Pharmaceutical	Pochodna pirazolu, kompozycja farmaceutyczna, srodek do leczenia lub hamowania choroby i zastosowanie pochodnej pirazolu
JP2004137245A (ja) *	2002-08-23	2004-05-13	Kissei Pharmaceut Co Ltd	ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体
JP4606876B2 (ja) *	2002-08-27	2011-01-05	キッセイ薬品工業株式会社	ピラゾール誘導体、それを含有する医薬組成物及びその医薬用途
CA2500873C (en) *	2002-10-04	2012-01-17	Kissei Pharmaceutical Co., Ltd.	Pyrazole derivative, medicinal composition containing the same, medicinal use thereof and intermediate in producing the same
KR20050089156A (ko) *	2002-12-04	2005-09-07	깃세이 야쿠힌 고교 가부시키가이샤	고혈당증에 기인하는 질환의 예방 또는 치료제
DE10258008B4 (de) *	2002-12-12	2006-02-02	Sanofi-Aventis Deutschland Gmbh	Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel
EP1637539B1 (en) *	2003-06-20	2012-01-18	Kissei Pharmaceutical Co., Ltd.	Pyrazole derivative, drug composition containing the same and production intermediate therefor

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Publication number	Publication date
PE20060297A1 (es)	2006-05-25
MA28653B1 (fr)	2007-06-01
US20070197623A1 (en)	2007-08-23
EP1758914A1 (de)	2007-03-07
MXPA06013513A (es)	2007-03-01
ECSP067054A (es)	2007-01-26
TNSN06409A1 (en)	2008-02-22
IL179757A (en)	2010-12-30
JP2008501745A (ja)	2008-01-24
ES2296180T3 (es)	2008-04-16
NO20070176L (no)	2007-03-09
IL179757A0 (en)	2007-05-15
PT1758914E (pt)	2008-01-31
NZ551948A (en)	2010-04-30
TW200610527A (en)	2006-04-01
AU2005252329A1 (en)	2005-12-22
DE502005002056D1 (de)	2008-01-03
RU2370499C2 (ru)	2009-10-20
DE102004028241B4 (de)	2007-09-13
WO2005121161A1 (de)	2005-12-22
HK1100411A1 (zh)	2007-09-21
AU2005252329B2 (en)	2011-02-10
EP1758914B1 (de)	2007-11-21
TWI382030B (zh)	2013-01-11
HRP20080023T3 (en)	2008-06-30
CY1107426T1 (el)	2012-12-19
CN100582116C (zh)	2010-01-20
CA2570042C (en)	2013-01-15
UY28955A1 (es)	2006-01-31
US7820804B2 (en)	2010-10-26
CN1964984A (zh)	2007-05-16
CR8773A (es)	2008-02-28
AR049393A1 (es)	2006-07-26
RS50541B (sr)	2010-05-07
JP4996464B2 (ja)	2012-08-08
MY143565A (en)	2011-05-31
CA2570042A1 (en)	2005-12-22
UA89787C2 (ru)	2010-03-10
PL1758914T3 (pl)	2008-04-30
SI1758914T1 (sl)	2008-04-30
DE102004028241A1 (de)	2006-01-05
RU2007101154A (ru)	2008-07-20
DK1758914T3 (da)	2008-03-17
BRPI0510770A (pt)	2007-11-20

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