MA27660A1 - Derive heteroarylcarbamoylbenzene - Google Patents

Derive heteroarylcarbamoylbenzene

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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

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    • 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
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    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • 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
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    • 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
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    • 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
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    • 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
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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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)

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JP2003049466 2003-02-26
JP2003400882 2003-11-28
JP2004031298 2004-02-06

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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)
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)

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