HRP20010688B1 - Aktivatori glukokinaze - Google Patents

Aktivatori glukokinaze

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Publication number
HRP20010688B1
HRP20010688B1 HR20010688A HRP20010688A HRP20010688B1 HR P20010688 B1 HRP20010688 B1 HR P20010688B1 HR 20010688 A HR20010688 A HR 20010688A HR P20010688 A HRP20010688 A HR P20010688A HR P20010688 B1 HRP20010688 B1 HR P20010688B1
Authority
HR
Croatia
Prior art keywords
lower alkyl
carbon atom
perfluoro
hydrogen
ring
Prior art date
Application number
HR20010688A
Other languages
English (en)
Inventor
Thomas Bizzaro Fred
Lea Corbett Wendy
Focella Antonino
Francis Grippo Joseph
Haynes Nancy-Ellen
William Holland George
Francis Kester Robert
Sarabu Ramakath
Original Assignee
F. Hoffmann - La Roche Ag
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 F. Hoffmann - La Roche Ag filed Critical F. Hoffmann - La Roche Ag
Publication of HRP20010688A2 publication Critical patent/HRP20010688A2/hr
Publication of HRP20010688B1 publication Critical patent/HRP20010688B1/hr

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48Y being a hydrogen or a carbon atom
    • C07C275/50Y being a hydrogen or an acyclic carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/80Acids; Esters in position 3
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/88Nitrogen atoms, e.g. allantoin
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D237/00Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06Heterocyclic 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
    • C07D237/10Heterocyclic 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
    • C07D237/22Nitrogen and oxygen atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • CCHEMISTRY; METALLURGY
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D253/00Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/061,2,4-Triazines
    • C07D253/0651,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/071,2,4-Triazines 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D261/00Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06Heterocyclic 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
    • C07D261/10Heterocyclic 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
    • C07D261/14Nitrogen atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • C07D263/48Nitrogen atoms not forming part of a nitro radical
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/38Nitrogen atoms
    • C07D277/44Acylated amino or imino radicals
    • C07D277/46Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/56Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D277/20Heterocyclic 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
    • C07D277/32Heterocyclic 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
    • C07D277/58Nitro radicals
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    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01Five-membered rings
    • C07D285/02Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/121,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/1251,3,4-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
    • C07D285/135Nitrogen atoms
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
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    • C07C2601/14The ring being saturated

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Spoj naznačen time, da obuhvaća amid formule I: pri čemu* označava asimetrični atom ugljika; R1 i R2 su međusobno neovisno vodik, halo, amino, hidroksiamino, nitro, cijano, sulfonamido, niži alkil, -OR5, -C(O)OR5, perfluoro-niži alkil, niži alkil tio, perfluoro-niži alkil tio, niži alkil sulfonil, perfluoro-niži alkil sulfonil ili niži alkil sulfinil; R3 je cikloalkil s 3 do 7 ugljikova atoma; R4je -C(O)NHR40; ili nesupstituirani ili mono-supstituirani petero- ili šesteročlani heteroaromatski prsten koji je povezan preko ugljikova atoma iz prstena s prikazanom aminskom skupinom, a koji petero- ili šesteročlani heteroaromatski prsten sadrži od 1 do 3 heteroatoma koji se biraju između sumpora, kisika ili dušika, pri čemu je jedan heteroatomdušik koji ima susjedni položaj u odnosu na povezni ugljikov atom iz prstena; pritom je spomenuti monosupstituirani heteroaromatski prsten monosupstituiran na mjestu ugljikova atoma u prstenu različitom od susjednog s obzirom na spomenuti povezni ugljikov atom, a supstituent se bira iz skupine kojučine niži alkil, halo, nitro, cijano, -(CH2)n-OR6, - (CH2)n-C(O)OR7, - (CH2)n-C(O)NHR6, -C(O)-C(O)OR8, -(CH2)n-NHR6;R40 je vodik, niži alkil, niži alkenil, hidroksi niži alkil, halo niži alkil, -(CH2)n-C(O)OR5 ili -C(O)-(CH2)n-C(O)OR6;R5 je vodik, niži alkil ili perfluoro-niži alkil; R6, R7 i R8 sumeđusobno neovisno vodik ili niži alkil; in je 0,1, 2, 3 ili 4; "niži alkil" i "niži alkoksi" označavaju grupe s 1 do 7 ugljikovih atoma; i "niži alkenil" označava grupe od 2 do 6 ugljikova atoma; ili njihovu farmaceutski prihvatljivu sol. Patent sadrži još 21 patentni zahtjev.
HR20010688A 1999-03-29 2001-09-19 Aktivatori glukokinaze HRP20010688B1 (hr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12670799P 1999-03-29 1999-03-29
US16594899P 1999-11-17 1999-11-17
US16594499P 1999-11-17 1999-11-17
PCT/EP2000/002450 WO2000058293A2 (en) 1999-03-29 2000-03-20 Glucokinase activators

Publications (2)

Publication Number Publication Date
HRP20010688A2 HRP20010688A2 (en) 2003-06-30
HRP20010688B1 true HRP20010688B1 (hr) 2008-10-31

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HR20010688A HRP20010688B1 (hr) 1999-03-29 2001-09-19 Aktivatori glukokinaze

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JP (1) JP3884232B2 (hr)
KR (1) KR100455635B1 (hr)
CN (1) CN1151140C (hr)
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CO (1) CO5170534A1 (hr)
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DE (1) DE60014610T2 (hr)
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GC (1) GC0000333A (hr)
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HR (1) HRP20010688B1 (hr)
HU (1) HUP0200396A3 (hr)
IL (1) IL145322A (hr)
JO (1) JO2475B1 (hr)
MA (1) MA26780A1 (hr)
MX (1) MXPA01009814A (hr)
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NO (1) NO320697B1 (hr)
NZ (1) NZ514038A (hr)
PE (1) PE20001584A1 (hr)
PL (1) PL350669A1 (hr)
PT (1) PT1169312E (hr)
RS (1) RS50045B (hr)
SI (1) SI1169312T1 (hr)
TR (1) TR200102805T2 (hr)
TW (1) TWI229078B (hr)
WO (1) WO2000058293A2 (hr)

Families Citing this family (106)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6353111B1 (en) * 1999-12-15 2002-03-05 Hoffmann-La Roche Inc. Trans olefinic glucokinase activators
DK1282611T3 (da) * 2000-05-08 2005-02-14 Hoffmann La Roche Substituerede phenylacetatamider og anvendelse deraf som glucokinaseaktivatorer
AU8760001A (en) 2000-07-20 2002-02-05 Hoffmann La Roche Alpha-acyl and alpha-heteroatom-substituted benzene acetamide glucokinase activators
US6369232B1 (en) * 2000-08-15 2002-04-09 Hoffmann-La Roche Inc. Tetrazolyl-phenyl acetamide glucokinase activators
KR100545431B1 (ko) 2000-12-06 2006-01-24 에프. 호프만-라 로슈 아게 축합된 이종방향족 글루코키나제 활성화제
US6433188B1 (en) 2000-12-06 2002-08-13 Wendy Lea Corbett Fused heteroaromatic glucokinase activators
US6482951B2 (en) 2000-12-13 2002-11-19 Hoffmann-La Roche Inc. Isoindolin-1-one glucokinase activators
SE0102300D0 (sv) * 2001-06-26 2001-06-26 Astrazeneca Ab Compounds
SE0102299D0 (sv) * 2001-06-26 2001-06-26 Astrazeneca Ab Compounds
SE0102764D0 (sv) * 2001-08-17 2001-08-17 Astrazeneca Ab Compounds
EP1336607A1 (en) * 2002-02-19 2003-08-20 Novo Nordisk A/S Amide derivatives as glucokinase activators
JP2005526702A (ja) * 2001-12-03 2005-09-08 ノボ ノルディスク アクティーゼルスカブ グルカゴンアンタゴニストとの組み合わせにおける2型糖尿病治療のためのグルコキナーゼ活性化剤の使用
US6911545B2 (en) 2001-12-19 2005-06-28 Hoffman-La Roche Inc. Crystals of glucokinase and methods of growing them
HUP0402309A3 (en) 2001-12-21 2008-09-29 Novo Nordisk As Amide derivatives as glucokinase activators and pharmaceutical compositions containing them
AU2003221140B9 (en) 2002-03-26 2009-07-30 Banyu Pharmaceutical Co., Ltd. Novel aminobenzamide derivative
PL373701A1 (en) * 2002-04-26 2005-09-05 F.Hoffmann-La Roche Ag Substituted phenylacetamides and their use as glucokinase activators
EP2471533A1 (en) 2002-06-27 2012-07-04 Novo Nordisk A/S Aryl carbonyl derivatives as therapeutic agents
KR101124245B1 (ko) 2002-06-27 2012-07-02 노보 노르디스크 에이/에스 치료제로서 아릴 카르보닐 유도체
CN1703408A (zh) * 2002-10-03 2005-11-30 诺瓦提斯公司 作为葡糖激酶激活剂、可用于治疗ⅱ型糖尿病的取代的(噻唑-2-基)酰胺或磺酰胺
GB0226930D0 (en) * 2002-11-19 2002-12-24 Astrazeneca Ab Chemical compounds
GB0226931D0 (en) 2002-11-19 2002-12-24 Astrazeneca Ab Chemical compounds
PE20040801A1 (es) * 2002-12-12 2004-11-25 Hoffmann La Roche Derivados de pirazina y piridina 5-sustituidos como activadores de glucoquinasa
PL378117A1 (pl) * 2003-02-11 2006-03-06 Prosidion Limited Tricyklopodstawione związki amidowe
CA2551324C (en) 2004-01-06 2012-11-27 Novo Nordisk A/S Heteroaryl-ureas and their use as glucokinase activators
JP2007523142A (ja) 2004-02-18 2007-08-16 アストラゼネカ アクチボラグ ベンズアミド誘導体、およびグルコキナーゼ活性化物質としてのそれらの使用
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 (en) 2004-04-02 2007-01-03 Novartis AG Thiazolopyridine derivates, pharmaceutical conditions containing them and methods of treating glucokinase mediated conditions
EP1740560A1 (en) * 2004-04-21 2007-01-10 Prosidion Limited Tri(cyclo) substituted amide compounds
BRPI0510679A (pt) 2004-05-10 2007-12-26 Hoffmann La Roche compostos, processo para a sua manufatura, composições farmacêuticas que os contêm, método para o tratamento e/ou profilaxia de enfermidades que estão associadas com a modulação dos receptores de cb1 e utilização desses compostos
TW200600086A (en) 2004-06-05 2006-01-01 Astrazeneca Ab Chemical compound
CN101137631A (zh) * 2004-12-03 2008-03-05 转化技术制药公司 杂芳族葡糖激酶激活剂
DK1868999T3 (da) 2005-04-06 2009-08-17 Hoffmann La Roche Pyridin-3-carboxamidderivater som omvendte CB1-agonister
ATE547396T1 (de) 2005-07-08 2012-03-15 Novo Nordisk As Dicycloalkylcarbamoyl-harnstoffe als glucokinase- aktivatoren
JP2009500377A (ja) 2005-07-08 2009-01-08 ノボ・ノルデイスク・エー/エス ジシクロアルキルウレア型グルコキナーゼ活性化剤
NZ575513A (en) 2005-07-09 2009-11-27 Astrazeneca Ab Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes
US7884210B2 (en) 2005-07-14 2011-02-08 Novo Nordisk A/S Ureido-thiazole glucokinase activators
EP1910317B1 (en) 2005-07-20 2013-07-03 Eli Lilly And Company 1-amino linked compounds
ATE430744T1 (de) 2005-08-18 2009-05-15 Hoffmann La Roche Thiazolylpiperidin-derivate nützlich als h3 rezeptor modulatoren
WO2007026761A1 (ja) 2005-08-31 2007-03-08 Astellas Pharma Inc. チアゾール誘導体
JP2007063225A (ja) 2005-09-01 2007-03-15 Takeda Chem Ind Ltd イミダゾピリジン化合物
CA2624102A1 (en) 2005-09-29 2007-04-12 Sanofi-Aventis Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals
GT200600428A (es) * 2005-09-30 2007-05-21 Compuestos organicos
GT200600429A (es) * 2005-09-30 2007-04-30 Compuestos organicos
ES2393757T3 (es) 2005-11-17 2012-12-27 Eli Lilly & Company Antagonistas de receptor de glucagón, preparación y usos terapéuticos
DE602006021626D1 (de) 2005-11-30 2011-06-09 Hoffmann La Roche 1,1-dioxo-thiomorpholinyl-indolyl-methanon-derivate zur verwendung als h3-modulatoren
EP1960383B1 (en) 2005-11-30 2010-04-28 F. Hoffmann-la Roche AG 5-substituted indole-2-carboxamide derivatives
CN101316840B (zh) 2005-11-30 2012-08-08 霍夫曼-拉罗奇有限公司 1,5-取代的吲哚-2-基酰胺衍生物
US7579351B2 (en) 2005-12-09 2009-08-25 Hoffmann-La Roche Inc. Tricyclic amide derivatives
JP2009519290A (ja) 2005-12-15 2009-05-14 エフ.ホフマン−ラ ロシュ アーゲー ピロロ[2,3−c]ピリジン誘導体
US8034822B2 (en) 2006-03-08 2011-10-11 Takeda San Diego, Inc. Glucokinase activators
US8211925B2 (en) 2006-04-28 2012-07-03 Transtech Pharma, Inc. Benzamide glucokinase activators
PE20110235A1 (es) 2006-05-04 2011-04-14 Boehringer Ingelheim Int Combinaciones farmaceuticas que comprenden linagliptina y metmorfina
US7432255B2 (en) 2006-05-16 2008-10-07 Hoffmann-La Roche Inc. 1H-indol-5-yl-piperazin-1-yl-methanone derivatives
WO2007137955A1 (en) 2006-05-30 2007-12-06 F. Hoffmann-La Roche Ag Piperidinyl pyrimidine derivatives
JP5386350B2 (ja) 2006-05-31 2014-01-15 タケダ カリフォルニア インコーポレイテッド グルコキナーゼ活性剤としての、インダゾールおよびイソインドール誘導体
US7888504B2 (en) 2006-07-06 2011-02-15 Bristol-Myers Squibb Company Glucokinase activators and methods of using same
US7910747B2 (en) 2006-07-06 2011-03-22 Bristol-Myers Squibb Company Phosphonate and phosphinate pyrazolylamide glucokinase activators
AU2007278261A1 (en) 2006-07-24 2008-01-31 F. Hoffmann-La Roche Ag Pyrazoles as glucokinase activators
CN107007581A (zh) 2006-08-24 2017-08-04 田纳西大学研究基金会 取代的n‑酰基苯胺及其使用方法
CL2007003061A1 (es) 2006-10-26 2008-08-01 Astrazeneca Ab Compuestos derivados de 3,5-dioxi-benzamida; proceso de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar una enfermedad mediada a traves de glk, tal como la diabetes tipo 2.
JP5419706B2 (ja) 2006-12-20 2014-02-19 タケダ カリフォルニア インコーポレイテッド グルコキナーゼアクチベーター
TW200831081A (en) 2006-12-25 2008-08-01 Kyorin Seiyaku Kk Glucokinase activator
EP2118083A1 (en) 2007-01-09 2009-11-18 Novo Nordisk A/S Urea glucokinase activators
AU2008204530B2 (en) 2007-01-11 2013-08-01 Vtv Therapeutics Llc Urea glucokinase activators
JP5491871B2 (ja) 2007-02-28 2014-05-14 アドビナス セラピュティックス プライベート リミテッド グルコキナーゼ活性化因子としての2,2,2−三置換アセトアミド誘導体、その方法及び薬学的応用
US8173645B2 (en) 2007-03-21 2012-05-08 Takeda San Diego, Inc. Glucokinase activators
WO2008136428A1 (ja) 2007-04-27 2008-11-13 Takeda Pharmaceutical Company Limited 含窒素5員複素環化合物
BRPI0814532A2 (pt) 2007-07-25 2015-01-27 Hoffmann La Roche Compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento e/ou prevenção de enfermidades que estão associadas com a modulação dos receptores de h3, e uso desses compostos para a preparação de medicamentos.
US8143280B2 (en) 2007-09-27 2012-03-27 Hoffmann-La Roche Inc. Glucocorticoid receptor antagonists
KR20100113518A (ko) 2008-01-18 2010-10-21 아스텔라스세이야쿠 가부시키가이샤 페닐아세트아미드 유도체
WO2009099080A1 (ja) 2008-02-06 2009-08-13 Daiichi Sankyo Company, Limited 新規フェニルピロール誘導体
US7741327B2 (en) 2008-04-16 2010-06-22 Hoffmann-La Roche Inc. Pyrrolidinone glucokinase activators
US8258134B2 (en) 2008-04-16 2012-09-04 Hoffmann-La Roche Inc. Pyridazinone glucokinase activators
WO2009128481A1 (ja) 2008-04-16 2009-10-22 武田薬品工業株式会社 含窒素5員複素環化合物
AU2009241137B2 (en) 2008-04-28 2013-10-03 Kyorin Pharmaceutical Co., Ltd. Cyclopentylacrylic acid amide derivative
CA2724116A1 (en) 2008-05-16 2009-11-19 Takeda San Diego, Inc. Glucokinase activators
US8268820B2 (en) 2009-03-26 2012-09-18 Hoffmann-La Roche Inc. 2,3-diaryl- or heteroaryl-substituted 1,1,1-trifluoro-2-hydroxypropyl compounds
US8138189B2 (en) 2009-03-26 2012-03-20 Hoffman-La Roche Inc. Substituted benzene compounds as modulators of the glucocorticoid receptor
US20110040091A1 (en) * 2009-08-13 2011-02-17 Stephan Bachmann Process for the preparation of (r)-2-phenyl propionic acid derivatives
JP2013510834A (ja) 2009-11-16 2013-03-28 メリテク [1,5]‐ジアゾシン誘導体
MX2012005994A (es) 2009-12-04 2012-08-08 Taisho Pharmaceutical Co Ltd Compuestos de 2-piridona.
US8222416B2 (en) 2009-12-14 2012-07-17 Hoffmann-La Roche Inc. Azaindole glucokinase activators
US8420647B2 (en) 2010-01-21 2013-04-16 Hoffmann-La Roche Inc. 4-phenoxy-nicotinamide or 4-phenoxy-pyrimidine-5-carboxamide compounds
US8252826B2 (en) 2010-03-24 2012-08-28 Hoffmann-La Roche Inc. Cyclopentyl- and cycloheptylpyrazoles
EP3199623B1 (en) 2010-03-31 2021-07-28 The Scripps Research Institute Reprogramming cells
RU2579114C9 (ru) 2010-07-12 2016-05-27 Ф. Хоффманн-Ля Рош Аг 1-гидроксиимино-3-фенил-пропаны
US8987307B2 (en) 2011-03-03 2015-03-24 Hoffmann-La Roche Inc. 3-amino-pyridines as GPBAR1 agonists
EP2771313A1 (en) 2011-10-26 2014-09-03 F.Hoffmann-La Roche Ag 1-cycloalkyl- or 1-heterocyclyl-hydroxyimino-3-phenyl-propanes
RU2014142971A (ru) 2012-04-04 2016-05-27 Ф.Хоффманн-Ля Рош Аг Производные 1,2-пиридазина, 1,6-пиридазина или пиримидин-бензамида в качестве модуляторов сопряженного с белком g рецептора желчных кислот 1 (gpbar1)
US9744149B2 (en) 2012-07-13 2017-08-29 Gtx, Inc. Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs)
US10258596B2 (en) 2012-07-13 2019-04-16 Gtx, Inc. Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS)
US10314807B2 (en) 2012-07-13 2019-06-11 Gtx, Inc. Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS)
US9969683B2 (en) 2012-07-13 2018-05-15 Gtx, Inc. Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS)
US9622992B2 (en) 2012-07-13 2017-04-18 Gtx, Inc. Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs)
US10987334B2 (en) 2012-07-13 2021-04-27 University Of Tennessee Research Foundation Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs)
AU2013203600C1 (en) 2012-07-13 2016-11-24 University Of Tennessee Research Foundation A method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMS)
IN2015DN03869A (hr) 2012-11-13 2015-10-02 Taisho Pharmaceutical Co Ltd
CN104672218A (zh) * 2015-02-13 2015-06-03 佛山市赛维斯医药科技有限公司 含葡萄糖酰胺结构的葡萄糖激酶活化剂、制备方法及其在治疗2型糖尿病上的用途
CN104672219A (zh) * 2015-02-13 2015-06-03 佛山市赛维斯医药科技有限公司 一类含葡萄糖酰胺结构的葡萄糖激酶活化剂及其用途
BR112017021311A2 (pt) * 2015-04-07 2018-06-26 Intercept Pharmaceuticals Inc composições farmacêuticas para terapia de combinação
EP3101005A1 (en) * 2015-06-05 2016-12-07 Lead Pharma Cel Models IP B.V. Ror gamma (rory) modulators
GB201714777D0 (en) 2017-09-14 2017-11-01 Univ London Queen Mary Agent
CN112040945A (zh) 2018-06-12 2020-12-04 Vtv治疗有限责任公司 葡萄糖激酶激活剂与胰岛素或胰岛素类似物组合的治疗用途
TW202315608A (zh) 2021-07-06 2023-04-16 中國大陸商甘萊製藥有限公司 用於治療肝臟疾病的聯合治療
CN117915914A (zh) 2021-07-06 2024-04-19 甘莱制药有限公司 治疗肝病的组合疗法
CN116687850A (zh) 2022-02-24 2023-09-05 甘莱制药有限公司 包含环状膦酸酯化合物的药物组合物及其制备方法与用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE249241C (hr) * 1910-05-01 1912-07-13
US3776917A (en) * 1972-06-05 1973-12-04 Schering Corp 2-amino-6-phenalkyl-aminopyridines and derivatives thereof

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