MA27660A1 - Derive heteroarylcarbamoylbenzene - Google Patents

Derive heteroarylcarbamoylbenzene

Info

Publication number
MA27660A1
MA27660A1 MA28448A MA28448A MA27660A1 MA 27660 A1 MA27660 A1 MA 27660A1 MA 28448 A MA28448 A MA 28448A MA 28448 A MA28448 A MA 28448A MA 27660 A1 MA27660 A1 MA 27660A1
Authority
MA
Morocco
Prior art keywords
mmol
acid
methyl ester
methanesulfonyl
phenoxy
Prior art date
Application number
MA28448A
Other languages
English (en)
Inventor
Eiki Jun-Ichi
Hashimoto Noriaki
Iino Tomoharu
Nakashima Hiroshi
Nishimura Teruyuki
Takahashi Keiji
Original Assignee
Banyu Pharma Co Ltd
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.)
Filing date
Publication date
Application filed by Banyu Pharma Co Ltd filed Critical Banyu Pharma Co Ltd
Publication of MA27660A1 publication Critical patent/MA27660A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
    • C07D261/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • 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
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/18—Nitrogen atoms
    • 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
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • C07D417/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Abstract

1HNMR(CDC13)(delta): 1.24(d, 3H,J=6.2Hz), 2.54(s, 3H), 3.72 (m,2H), 4.52(m,1H), 6.97(m,2H), 7.16(m/2H), 7.33(m,1H), 7.59(m,1H), 8.52(m,1H), 12.0(br,1H) ESI-MS(m/e): 402[M+H]+ Exemple de production 89 Préparation de 5-(2-hydroxy-1-méthyl-éthoxy)-3-(4-méthane-sulfonylphénoxy)-N-(3-méthyl-[1,2,4]-thiadiazol-5-yl)-benzamide Après l'addition de 33,4 g (142 mmol) de 4-méthane-sulfonyl-bromobenzène, 2,67 g (11,9 mmol) d'acétate de palladium, 5,31 g (17,8 mmol) de 2-(di-tert-butylphosphino)biphényle et 50,3 g (237 mmol) de phosphate de potassium à une solution de 25,0 g (119 mmol) d'ester méthylique de l'acide 5-hydroxy-3-méthoxyméthoxybenzoïque dans du toluène (375 ml), le réacteur a été bouché et le mélange a été agité par la suite à 130o.C pendant 6 heures. De l'ester éthylique d'acide acétique a été ajouté au mélange réactionnel, qui a alors été filtré et concentré sous pression réduite. Le résidu obtenu a été purifié par chromatographie sur colonne sur gel de silice (hexane : ester éthylique d'acide acétique = 2:1) pour obtenir 31,0 g d'ester méthylique de l'acide 3-(4-méthanesulfonyl-phénoxy) -5-méthoxyméthoxy-benzoïque (rendement : 69%) comme un solide blanc. Après l'addition de 60 ml d'acide trifluoroacétique à une solution de 30,9 g (84,3 mmol) de l'ester méthylique de l'acide 3-(4-méthanesulfonyl-phénoxy)-5-méthoxyméthoxy-benzoïque obtenu dans du chlorure de méthylène (100 ml) avec refroidissement sur glace, le mélange réactionnel a été agité à la température ambiante pendant 4 heures. Le mélange réactionnel a été concentré sous pression réduite, et le résidu obtenu a été purifié par chromatographie sur colonne sur gel de silice (hexane: ester éthylique d'acide acétique = 1:1) pour obtenir 15,2 g d'ester méthylique de l'acide 5-hydroxy- 3-(4-méthanesulfonyl-phénoxy)benzoïque (rendement: 56%) comme un solide blanc. Puis après l'addition de 11,8 g (62,1 mmol) de (2R)-1-(t-butyldiméthylsiloxy)-2-hydroxypropane et 16,3 g (62,1 mmol) de triphénylphosphine à une solution de 10,0 g (31,0 mmol) de l'ester méthylique de l'acide 5-hydroxy-3-(4-méthanesulfonyl-phénoxy)benzoïque obtenu dans du tétrahydrofurane (200 ml), 33,8 ml (77,6 mmol) d'une solution d'azodicarboxylate de diéthyle dans 40% de toluène ont été ajoutés avec refroidissement sur glace, et le mélange a été agité à la température ambiante pendant 12 heures. Le mélange réactionnel a été XX Composés ayant des effets d'activation de la glucokinase et étant utiles dans les traitements du diabète, qui sont représentés par la formule (I) suivante : [dans laquelle X1 représente l'oxygène, etc., X2 représente l'oxygène, etc., R1 représente un groupement sur le Noyau A tel que l'alkylsulfonyle, etc., R2 représente un C3-7 alkyle cyclique facultativement substitué par un halogène, etc., R3 représente un substituant sur le Noyau B tel que l'alkyle inférieur, etc., la formule (II): représente un aryle de 6 à 10 éléments, et la formule (III): représente un hétéroaryle monocyclique ou bicyclique ayant facultativement sur le Noyau B un substituant représenté par R3 ci-dessus, dans lequel l'atome de carbone du Noyau B est lié à l'atome d'azote du groupement amide dans la formule (I) forme une liaison C=N avec l'atome d'azote du noyau], ainsi que leurs sels pharmaceutiquement acceptables.
MA28448A 2003-02-26 2005-08-22 Derive heteroarylcarbamoylbenzene MA27660A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2003049466 2003-02-26
JP2003400882 2003-11-28
JP2004031298 2004-02-06

Publications (1)

Publication Number Publication Date
MA27660A1 true MA27660A1 (fr) 2005-12-01

Family

ID=32931126

Family Applications (1)

Application Number Title Priority Date Filing Date
MA28448A MA27660A1 (fr) 2003-02-26 2005-08-22 Derive heteroarylcarbamoylbenzene

Country Status (17)

Country Link
US (2) US7432287B2 (fr)
EP (1) EP1600442B1 (fr)
JP (1) JP4432901B2 (fr)
KR (1) KR20050105488A (fr)
CN (1) CN101712657A (fr)
AU (1) AU2004215514B2 (fr)
BR (1) BRPI0407810A (fr)
CA (1) CA2516407C (fr)
EC (1) ECSP055987A (fr)
HK (1) HK1091204A1 (fr)
MA (1) MA27660A1 (fr)
MX (1) MXPA05009059A (fr)
NO (1) NO20054425L (fr)
NZ (1) NZ541824A (fr)
RU (1) RU2330030C2 (fr)
UA (1) UA81468C2 (fr)
WO (1) WO2004076420A1 (fr)

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE0102299D0 (sv) 2001-06-26 2001-06-26 Astrazeneca Ab Compounds
SE0102764D0 (sv) * 2001-08-17 2001-08-17 Astrazeneca Ab Compounds
WO2004050645A1 (fr) 2002-10-03 2004-06-17 Novartis Ag Sulfamide ou amide a substitution (thiazol-2-yl) utile en tant qu'activateur de glycokinase dans le traitement du diabete de type 2
GB0226930D0 (en) 2002-11-19 2002-12-24 Astrazeneca Ab Chemical compounds
GB0226931D0 (en) 2002-11-19 2002-12-24 Astrazeneca Ab Chemical compounds
NZ540791A (en) 2003-02-13 2009-09-25 Banyu Pharma Co Ltd Novel 2-pyridinecarboxamide derivatives
GB0325402D0 (en) * 2003-10-31 2003-12-03 Astrazeneca Ab Compounds
GB0327761D0 (en) * 2003-11-29 2003-12-31 Astrazeneca Ab Compounds
KR20060105872A (ko) * 2003-12-29 2006-10-11 반유 세이야꾸 가부시끼가이샤 신규한 2-헤테로아릴 치환된 벤즈이미다졸 유도체
KR20070007103A (ko) * 2004-02-18 2007-01-12 아스트라제네카 아베 벤즈아미드 유도체 및 이의 글루코키나아제 활성화제로서의용도
AU2005214137B2 (en) * 2004-02-18 2008-05-29 Astrazeneca Ab Compounds
JP4700684B2 (ja) 2004-04-02 2011-06-15 ノバルティス アーゲー ２型糖尿病の処置に有用なグルコキナーゼアクティベーターとしてのスルホンアミド−チアゾロピリジン誘導体
EP1737870A1 (fr) 2004-04-02 2007-01-03 Novartis AG Derives thiazolopyridine, compositions pharmaceutiques les contenant et procedes de traitement de troubles a mediation par glucokinase
TW200600086A (en) * 2004-06-05 2006-01-01 Astrazeneca Ab Chemical compound
GB0423042D0 (en) * 2004-10-16 2004-11-17 Astrazeneca Ab Chemical process
GB0423044D0 (en) * 2004-10-16 2004-11-17 Astrazeneca Ab Compounds
WO2006040527A1 (fr) * 2004-10-16 2006-04-20 Astrazeneca Ab Procede de fabrication de composes de phenoxy benzamide
GB0423043D0 (en) * 2004-10-16 2004-11-17 Astrazeneca Ab Compounds
BRPI0607583A2 (pt) 2005-03-04 2009-09-15 Hoffmann La Roche derivados de piridin-2-carboxamida como antagonistas mglur5, método para sua preparação, medicamento contendo os mesmos, bem como uso relacionado aos referidos compostos
JP2008542247A (ja) * 2005-05-24 2008-11-27 アストラゼネカ アクチボラグ グルコキナーゼモジュレーターとしての２−フェニル置換イミダゾール［４，５ｂ］ピリジン／ピラジンおよびプリン誘導体
TW200714597A (en) * 2005-05-27 2007-04-16 Astrazeneca Ab Chemical compounds
NZ575514A (en) 2005-07-09 2009-11-27 Astrazeneca Ab Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes
GB0514173D0 (en) * 2005-07-09 2005-08-17 Astrazeneca Ab Chemical compounds
JP2009500442A (ja) * 2005-07-09 2009-01-08 アストラゼネカ アクチボラグ ２型糖尿病を処置するためのグルコキナーゼのモジュレーターとしての２−ヘテロシクリルオキシベンゾイルアミノヘテロシクリル化合物
JP2009504621A (ja) * 2005-08-09 2009-02-05 アストラゼネカ アクチボラグ 糖尿病の処置のためのヘテロアリールカルバモイルベンゼン誘導体
US9202182B2 (en) * 2005-08-11 2015-12-01 International Business Machines Corporation Method and system for analyzing business architecture
JP2007063225A (ja) 2005-09-01 2007-03-15 Takeda Chem Ind Ltd イミダゾピリジン化合物
JP2009508832A (ja) * 2005-09-16 2009-03-05 アストラゼネカ アクチボラグ グルコキナーゼ活性化剤としてのヘテロ二環式化合物
US7799820B2 (en) 2005-09-30 2010-09-21 Banyu Pharmaceutical Co., Ltd. 2-Heterocycle-substituted indole derivatives for treating diabetes and associated conditions
GT200600429A (es) 2005-09-30 2007-04-30 Compuestos organicos
GT200600428A (es) 2005-09-30 2007-05-21 Compuestos organicos
RU2418799C2 (ru) 2005-10-05 2011-05-20 Ф. Хоффманн-Ля Рош Аг Производные нафтиридина
TW200738621A (en) 2005-11-28 2007-10-16 Astrazeneca Ab Chemical process
WO2007104034A2 (fr) 2006-03-08 2007-09-13 Takeda San Diego, Inc. Activateurs de la glucokinase
PE20080251A1 (es) 2006-05-04 2008-04-25 Boehringer Ingelheim Int Usos de inhibidores de dpp iv
US8008332B2 (en) 2006-05-31 2011-08-30 Takeda San Diego, Inc. Substituted indazoles as glucokinase activators
US7910747B2 (en) * 2006-07-06 2011-03-22 Bristol-Myers Squibb Company Phosphonate and phosphinate pyrazolylamide glucokinase activators
EP2046755A2 (fr) 2006-07-24 2009-04-15 F. Hoffmann-Roche AG Pyrazoles comme activateurs de glucokinase
AR063028A1 (es) * 2006-10-06 2008-12-23 Banyu Pharma Co Ltd Derivados heterociclicos de piridin-2-carboxamida activadores de glucoquinasas, utiles para el tratamiento de diabetes y obesidad y composiciones farmaceuticas que los contienen.
TW200825063A (en) * 2006-10-23 2008-06-16 Astrazeneca Ab Chemical compounds
SA07280576B1 (ar) * 2006-10-26 2011-06-22 استرازينيكا ايه بي مركبات بنزويل أمينو سيكليل غير متجانسة بأعتبارها عوامل منشطة للجلوكوكيناز
UA95815C2 (en) * 2006-10-26 2011-09-12 Астразенека Аб Benzoyl amino heterocyclyl compounds as glucokinase (glk) activators
TW200827346A (en) 2006-11-03 2008-07-01 Astrazeneca Ab Chemical compounds
WO2008079787A2 (fr) 2006-12-20 2008-07-03 Takeda San Diego, Inc. Activateurs de glucokinase
BRPI0721143A2 (pt) * 2006-12-21 2014-03-11 Astrazeneca Ab Forma cristalina do composto processo para a formação da mesma, uso de um composto, método para tratar doenças mediadas por ativador de glicocinase
CA2674237C (fr) * 2006-12-28 2015-11-24 Rigel Pharmaceuticals, Inc. Composes d'heterocycloalkyloxybenzamide n-substitues, et procedes d'utilisation
WO2008084872A1 (fr) 2007-01-10 2008-07-17 Mitsubishi Tanabe Pharma Corporation Dérivé d'hydrazone
TW200836719A (en) 2007-02-12 2008-09-16 Astrazeneca Ab Chemical compounds
US8173645B2 (en) 2007-03-21 2012-05-08 Takeda San Diego, Inc. Glucokinase activators
JP2010138073A (ja) * 2007-03-30 2010-06-24 Taisho Pharmaceutical Co Ltd ピコリン酸アミド化合物
JP2010534722A (ja) * 2007-07-27 2010-11-11 ブリストル−マイヤーズ スクイブ カンパニー 新規グルコキナーゼ活性化薬およびその使用方法
CA2695517C (fr) 2007-08-03 2016-09-20 J. Edward Semple Composes thiazolide a substitution alkylsulfonyle
CN106279283A (zh) 2007-08-13 2017-01-04 症变治疗公司 新颖的葡糖激酶活化剂
AR068540A1 (es) * 2007-09-28 2009-11-18 Merck & Co Inc Metodos de produccion de un derivado de pirazol-3-il-benzamida.
US8236824B2 (en) * 2007-10-09 2012-08-07 MERCK Patent Gesellschaft mit beschränkter Haftung N-(pyrazole-3-yl)-benzamide derivatives as glucokinase activators
AU2008310097B2 (en) * 2007-10-09 2013-05-16 Merck Patent Gmbh Pyridine derivatives useful as glucokinase activators
EP2221301B1 (fr) 2007-11-12 2014-06-04 Msd K.K. Dérivé d'hétéroaryloxy quinazoline
JPWO2009081782A1 (ja) * 2007-12-25 2011-05-06 萬有製薬株式会社 Ｎ−ピラゾール−２−ピリジンカルボキサミド誘導体
MX2010008637A (es) * 2008-02-06 2010-08-30 Daiichi Sankyo Co Ltd Derivado de fenilpirrol novedoso.
WO2009106209A1 (fr) * 2008-02-27 2009-09-03 Merck Patent Gmbh Dérivés d'hétéroaryl-carboxamides utilisés pour le traitement du diabète
US8258134B2 (en) 2008-04-16 2012-09-04 Hoffmann-La Roche Inc. Pyridazinone glucokinase activators
US7741327B2 (en) 2008-04-16 2010-06-22 Hoffmann-La Roche Inc. Pyrrolidinone glucokinase activators
EP2324028A2 (fr) 2008-08-04 2011-05-25 AstraZeneca AB Agents thérapeutiques 414
US8592428B2 (en) 2008-08-15 2013-11-26 Msd K. K. Acetyl pyrrolidinyl indole derivative
CA2734981A1 (fr) * 2008-08-29 2010-03-04 Banyu Pharmaceutical Co., Ltd. Derive d'oxotetrahydrofurann-2-yl-benzimidazole
EP2344458A1 (fr) 2008-09-11 2011-07-20 Pfizer Inc. Dérivés d'amides d'hétéroaryles et leur utilisation comme activateurs de la glucokinase
CA2743489A1 (fr) 2008-11-17 2010-05-20 Merck Sharp & Dohme Corp. Amines bicycliques substituees pour le traitement du diabete
UA104742C2 (uk) * 2008-12-19 2014-03-11 Эли Лилли Энд Компани Похідні арилциклопропілацетаміду, застосовні як активатори глюкокінази
WO2010082601A1 (fr) * 2009-01-16 2010-07-22 第一三共株式会社 Nouveau dérivé de pyrrole 2,5-disubstitué
GB0902434D0 (en) 2009-02-13 2009-04-01 Astrazeneca Ab Chemical process
GB0902406D0 (en) 2009-02-13 2009-04-01 Astrazeneca Ab Crystalline polymorphic form
EA018894B1 (ru) * 2009-03-11 2013-11-29 Пфайзер Инк. N,n-диметил-5-(2-метил-6-((5-метилпиразин-2-ил)карбамоил)бензо-фуран-4-илокси)пиримидин-2-карбоксамид, используемый в качестве активатора глюкокиназы, и содержащая его фармацев-тическая композиция
WO2010107610A1 (fr) * 2009-03-17 2010-09-23 Merck Sharp & Dohme Corp. Méthode de traitement du diabète et des états pathologiques correspondants par thérapie combinatoire et compositions contenant de tels composés
AR076221A1 (es) * 2009-04-09 2011-05-26 Astrazeneca Ab Derivado de pirazol [4,5-e] pirimidina y su uso para tratar diabetes y obesidad
AR076220A1 (es) 2009-04-09 2011-05-26 Astrazeneca Ab Derivados de pirazol [4,5 - e] pirimidina
CN105853415A (zh) 2009-05-12 2016-08-17 罗马克实验室有限公司 卤代烷基杂芳基苯甲酰胺化合物
JP5932640B2 (ja) 2009-06-26 2016-06-08 ロマーク ラボラトリーズ エル．シー． インフルエンザを治療するための化合物および方法
US20110021570A1 (en) * 2009-07-23 2011-01-27 Nancy-Ellen Haynes Pyridone glucokinase activators
US20120220567A1 (en) 2009-07-23 2012-08-30 Shipps Jr Gerald W Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors
WO2011011506A1 (fr) 2009-07-23 2011-01-27 Schering Corporation Composés oxazépine spirocyclique en tant qu'inhibiteurs de la stéaroyl-coenzyme a delta-9 désaturase
DK2459554T3 (da) 2009-07-31 2014-01-06 Cadila Healthcare Ltd Substituerede benzamidderivater som glucokinase (GK)-aktivatorer
BR112012016025A2 (pt) * 2009-12-11 2018-11-06 Astellas Pharma Inc. composto de benzamida
US8222416B2 (en) * 2009-12-14 2012-07-17 Hoffmann-La Roche Inc. Azaindole glucokinase activators
WO2011095997A1 (fr) * 2010-02-08 2011-08-11 Advinus Therapeutics Private Limited Composés de benzamide à titre d'activateurs de glucokinase et leur application pharmaceutique
US8178689B2 (en) 2010-06-17 2012-05-15 Hoffman-La Roche Inc. Tricyclic compounds
WO2011158149A1 (fr) * 2010-06-18 2011-12-22 Pfizer Inc. Dérivés de 2-(3,5-disubstitutedphenyl)pyrimidin-4(3h)-one
JP5769326B2 (ja) * 2010-10-19 2015-08-26 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｒｈｏキナーゼ阻害薬
CA3094762C (fr) * 2011-06-02 2023-09-26 CHINOIN Zrt. Nouveau procede pour la preparation d'amides de prostaglandines
CN104230892B (zh) * 2011-11-09 2016-12-07 福建海西新药创制有限公司 一组提高激酶活性的化合物及其应用
CN104411710A (zh) 2012-04-16 2015-03-11 卡内克制药公司 作为ptp-1b抑制剂前体的稠合的芳族膦酸酯衍生物
JP6234443B2 (ja) 2012-05-17 2017-11-22 ブイティーブイ・セラピューティクス・エルエルシー 糖尿病治療のためのグルコキナーゼ活性化因子組成物
JP7072557B2 (ja) * 2016-07-22 2022-05-20 ブリストル－マイヤーズ スクイブ カンパニー グルコキナーゼ活性化剤およびその使用方法
WO2019023651A2 (fr) 2017-07-28 2019-01-31 Massachusetts Institute Of Technology Modulateurs du récepteur des androgènes à petite molécule
GB201714777D0 (en) 2017-09-14 2017-11-01 Univ London Queen Mary Agent
MX2020008905A (es) 2018-06-12 2020-12-03 Vtv Therapeutics Llc Usos terapeuticos de activadores de glucoquinasa en combinacion con insulina o analogos de insulinas.
CN113527146B (zh) * 2021-08-19 2023-04-18 广东药科大学 分子氧促进谐二氟烯烃羟化磺酰酯化反应制备β-羟基-谐二氟磺酰酯类化合物的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3091392A (en) * 1991-12-11 1993-07-19 Sasol Chemicals Europe Limited Method to produce single cell oil containing gamma-linolenic acid
GB9725298D0 (en) * 1997-11-28 1998-01-28 Zeneca Ltd Insecticidal thiazole derivatives
SE0102300D0 (sv) * 2001-06-26 2001-06-26 Astrazeneca Ab Compounds
SE0102764D0 (sv) * 2001-08-17 2001-08-17 Astrazeneca Ab Compounds
JP4419571B2 (ja) * 2002-03-26 2010-02-24 萬有製薬株式会社 新規アミノベンズアミド誘導体
GB0327761D0 (en) * 2003-11-29 2003-12-31 Astrazeneca Ab Compounds
AU2005214137B2 (en) * 2004-02-18 2008-05-29 Astrazeneca Ab Compounds
KR20070007103A (ko) * 2004-02-18 2007-01-12 아스트라제네카 아베 벤즈아미드 유도체 및 이의 글루코키나아제 활성화제로서의용도

Also Published As

Publication number Publication date
US20060167053A1 (en) 2006-07-27
EP1600442A1 (fr) 2005-11-30
JPWO2004076420A1 (ja) 2006-06-01
US7432287B2 (en) 2008-10-07
CN101712657A (zh) 2010-05-26
EP1600442A4 (fr) 2006-11-02
RU2005129729A (ru) 2006-03-20
US7754743B2 (en) 2010-07-13
HK1091204A1 (en) 2007-01-12
NZ541824A (en) 2010-04-30
AU2004215514A1 (en) 2004-09-10
UA81468C2 (en) 2008-01-10
NO20054425L (no) 2005-09-23
KR20050105488A (ko) 2005-11-04
CA2516407C (fr) 2013-07-09
RU2330030C2 (ru) 2008-07-27
MXPA05009059A (es) 2005-10-19
CA2516407A1 (fr) 2004-09-10
ECSP055987A (es) 2006-01-16
EP1600442B1 (fr) 2018-01-17
JP4432901B2 (ja) 2010-03-17
BRPI0407810A (pt) 2006-03-01
US20090018056A1 (en) 2009-01-15
WO2004076420A1 (fr) 2004-09-10
AU2004215514B2 (en) 2010-03-04

Similar Documents

Publication Publication Date Title
MA27660A1 (fr) Derive heteroarylcarbamoylbenzene
EP1840125B1 (fr) Intermédiaires pour la production de dioxane-2-alkylcarbamates
JP2853227B2 (ja) ７置換‐ヘプト‐６‐エン酸、ヘプタン酸及び誘導体並びにそれらの中間体の製法
WO2003084930A1 (fr) Derives de diphenylpyridine, leur preparation, les compositions pharmaceutiques en contenant
EP0610134A1 (fr) Dérivés de l'indole, de l'indazole et du benzisoxazole comme 5-Ht1-like agonistes
FR2671083A1 (fr) Nouvelles 4-(4-imidazolyl) piperidines substituees en 1, leur preparation ainsi que leurs applications therapeutiques.
JP4322685B2 (ja) イソキノリン誘導体
WO1992019604A1 (fr) Nouveau derive d'isoxazole et sel de ce derive
FR2681325A1 (fr) Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique.
EP0424244A1 (fr) Dérivés d'aryl-3 oxazolidinone, leur procédé de préparation et leur application en thérapeutique
US5239080A (en) Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents
Liang et al. N-Arylated pyrrolidin-2-ones and morpholin-3-ones as potassium channel openers
JP6429016B2 (ja) トリフルオロメタンスルホンアニリド化合物の製造方法
EP0348257A2 (fr) Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique
EP0211698A2 (fr) Dérivés de (dihydro-4,5 1H-imidazolyl-2)-2 dihydro-2,3 indole, leur préparation et leur application en thérapeutique
EP0511031B1 (fr) Dérivés d'aryl-3 oxazolidinone, leur procédé de préparation et leur application en thérapeutique
WO2002006228A1 (fr) Procede de production de 5-fluorooxyindole et procede de production d'un produit intermediaire de celui-ci
CH626341A5 (en) Process for the stereospecific synthesis of N-substituted pyrrolidines and their use
KR100578425B1 (ko) 캐테콜 히드라진 유도체, 이의 제조 방법 및 이를 함유한 약제학적 조성물
FR2670780A1 (fr) Derives de 4-(acylamino)benzopyranes, leur preparation et leur application en therapeutique.
JPH10139768A (ja) ナフタレン誘導体の製造方法
CH616659A5 (fr)
EP1019376A1 (fr) Derives de pyridone, leur preparation et leur utilisation comme intermediaires de synthese
KR100426534B1 (ko) 아젤라스틴의 개선된 합성방법
EP1140841B1 (fr) Derives de 3-phenyl-2, 6-dioxopiperidin-3-yl propionamide et leur procede de preparation