AR036876A1 - HETEROCICLIC DERIVATIVES, ITS PREPARATION PROCEDURE AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM - Google Patents

HETEROCICLIC DERIVATIVES, ITS PREPARATION PROCEDURE AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

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Publication number
AR036876A1
AR036876A1 ARP020103521A ARP020103521A AR036876A1 AR 036876 A1 AR036876 A1 AR 036876A1 AR P020103521 A ARP020103521 A AR P020103521A AR P020103521 A ARP020103521 A AR P020103521A AR 036876 A1 AR036876 A1 AR 036876A1
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Argentina
Prior art keywords
branched
linear
group
groups
alkyl
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ARP020103521A
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Spanish (es)
Inventor
Daniel Lesieur
Elodie Blanc-Delmas
Caroline Bennejean
Phillippe Chavatte
Gerald Guillaumet
Catherine Dacquet
Nigel Levens
Jean-Albert Boutin
Pierre Renard
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Servier Lab
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Publication of AR036876A1 publication Critical patent/AR036876A1/en

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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Rheumatology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicación 1: Compuestos de la fórmula (1) en la cual: X representa un átomo de oxígeno o de azufre, un grupo CH2 ó CHR'2 (en el cual R'2 forma con R2 una enlace suplementario); Y representa un átomo de oxígeno ó de azufre, R1 y R2, idénticos o diferentes representan un átomo de hidrógeno, un grupo alquilo (C1-6) lineal o ramificado, arilo, arilalquilo (C1-6) lineal o ramificado, ariloxi, arilalquiloxi (C1-6) lineal o ramificado, alcoxi (C1-6) lineal o ramificado, hidroxi, amino, alquilamino (C1-6) lineal o ramificado ó dialquilamino (C1-6) lineal o ramificado, ó R1 y R2 forman juntos un grupo oxo, tioxo ó imino, R2 puede además formar con R'2 un enlace suplementario; A representa una cadena alquileno (C1-6) en la cual uno de sus grupos CH2 puede estar reemplazado por un heteroátomo elegido entre oxígeno o azufre, o por un grupo NRn (donde Rn representa un átomo de hidrógeno ó un grupo alquilo (C1-6) lineal o ramificado), ó por un grupo fenileno ó naftileno, B representa un grupo alquilo (C1-6) lineal o ramificado, ó alquenilo (C2-6) lineal o ramificado, ó alquinileno (C2-6) lineal o ramificado; D y D', idénticos o diferentes, representan un núcleo bencénico ó un núcleo piridínico, esos núcleos son no sustituidos o sustituidos por 1 a 3 grupos, idénticos o diferentes elegidos entre un átomo de halógeno y un grupo ciano, nitro, R, OR, S(O)nR, C(Z)R, -CH(OR)-R', C(Z)OR, NRR', C(Z)NRR', -C(=N-OR')R, -NR-C(Z)R', -NR-C(Z)OR' ó OC(Me)2COOR, (donde R y R' idénticos o diferentes representan un átomo de hidrógeno ó un grupo alquilo (C1-6) lineal o ramificado, alquenilo (C2-6) lineal o ramificado, alquinilo (C2-6) lineal o ramificado, arilo, arilalquilo (C1-6) lineal o ramificado, heteroarilo, heteroarilalquilo (C1-6) lineal o ramificado, cicloalquilo (C3-8) ó cicloalquil (C3-8)-alquilo (C1-6) lineal o ramificado; Z representa un átomo de oxígeno ó de azufre y n representa un número entero comprendido entre 0 y 2 inclusive); R3 y R4, idénticos o diferentes, representan un átomo de hidrógeno, de halógeno, un grupo R, OR ó NRR' (donde R y R' son tal como se los ha definido precedentemente), ó R3 y R4 forman junto con los átomos de carbono que los llevan, cuando son llevados por dos átomos de carbono adyacentes, un ciclo que presenta 5 ó 6 eslabones y que pueden contener un heteroátomo elegido entre oxígeno, azufre y nitrógeno; R5 representa un átomo de hidrógeno, un grupo alquilo (C1-6) lineal o ramificado, alquenilo (C2-6) lineal o ramificado, alquinilo (C2-6) lineal o ramificado, arilo, heteroarilo, alquilcarbonilo (C1-6), arilcarbonilo, ó heteroarilcarbonilo, siendo eventualmente sustituido cada uno de esos grupos: -por uno ó varios grupos R6 tal como R6 representa un grupo -(CH2)t-C(=Z)Z' (donde Z es tal como se ha definido precedentemente, Z' representa un grupo OR ó NRR' con R y R' tal como se los ha definido precedentemente y t es un entero comprendido entre 0 y 6 inclusive); -por un grupo de fórmula (2), en la cual la línea punteada significa que el enlace es simple ó doble y R7 y R8, idénticos o diferentes, representan un grupo -C(=Z)Z' (donde Z y Z' son tal como se los ha definido precedentemente), ó -por un átomo de halógeno, un grupo hidroxi, nitro, ciano, amino ó alcoxi (C1-6) lineal o ramificado, y se entiende que, salvo indicación en contrario: se entiende por arilo, un grupo fenilo, naftilo ó bifenilo, esos grupos pueden estar parcialmente hidrogenados; se entiende por heteroarilo, cualquier grupo aromático mono ó bicíclico que contiene de 5 a 10 eslabones, que puede ser parcialmente hidrogenado en uno de los ciclos en el caso de los heteroarilos bicíclicos, y que contienen 1 a 3 heteroátomos elegidos entre oxígeno, nitrógeno y azufre, los grupos arilo y heteroarilo pueden ser eventualmente sustituidos por 1 a 3 átomos de halógeno ó grupos alquilo (C1-6) lineal o ramificado, alcoxi (C1-6) lineal o ramificado, carboxi, formilo, amino, alquilamino (C1-6) lineal o ramificado, dialquilamino (C1-6) lineal o ramificado, éster, amido, nitro, ciano, y O-C(Me)2COOR (donde R es tal como se ha definido precedentemente), sus enantiómeros y diastereoisómeros así como sus sales de adición con un ácido o con una base farmacéuticamente aceptables. Reivindicación 9: Compuestos de fórmula (1) de acuerdo con una cualquiera de las reivindicaciones 1 a 8, caracterizados porque es la 3-(2-{4-[(5-benzoil-2-oxo-2,3-dihidro-1H-indol-3-il)metil]fenoxi}etil)-1,3-benzotiazol-2(3H)-ona, así como sus sales de adición con un ácido farmacéuticamente aceptable. Reivindicación 10: Compuestos de fórmula (1) de acuerdo con una cualquiera de las reivindicaciones 1 a 8, caracterizados porque es la 6-benzoil-3-(2-{4-[(2-oxo-2,3-dihidro-1H-indol-3-il)metil]fenoxi}etil)-1,3-benzotiazol-2(3H)-ona, así como sus sales de adición con un ácido farmacéuticamente aceptable. Reivindicación 13: Composiciones farmacéuticas de acuerdo con la reivindicación 12, caracterizadas porque son útiles para la fabricación de un medicamento para el tratamiento y/o profilaxis de las hiperglucemias, de las dislipidemias y más particularmente en el tratamiento de las diabetes no insulinodependientes de tipo II, de la resistencia a la insulina, de la intolerancia a la glucosa, de los desórdenes relacionados con el síndrome X, de las enfermedades arteriales coronarias y otras enfermedades cardiovasculares, de las enfermedades renales, de las retionopatías, de los desórdenes relacionados con la activación de las células endoteliales, de la psoriasis, del síndrome poliquístico de ovario, de la demencia, de la osteoporosis, de las enfermedades inflamatorias intestinales, de las distrofias miotónicas, de las pancreatitis, de la arterioesclerosis, del xantoma , pero también en el tratamiento o la prevención de la diabetes de tipo I, de la obesidad, de la regulación del apetito, de la anorexia, de la bulimia, de la anorexia nerviosa, así como de las patologías cancerosas y en especial de los cánceres hormonodependientes tales como el cáncer de pecho y el cáncer de colon y como inhibidores de angiogénesis.Claim 1: Compounds of the formula (1) in which: X represents an oxygen or sulfur atom, a CH2 or CHR'2 group (in which R'2 forms a supplementary bond with R2); Y represents an oxygen or sulfur atom, R1 and R2, identical or different, represent a hydrogen atom, a linear or branched (C1-6) alkyl group, aryl, linear or branched (C1-6) alkyl, aryloxy, arylaxyloxy (C1-6) linear or branched, linear or branched (C1-6) alkoxy, hydroxy, amino, linear or branched (C1-6) alkylamino or linear or branched (C1-6) dialkylamino, or R1 and R2 together form a oxo, thioxo or imino group, R2 can also form a supplementary bond with R'2; A represents an (C1-6) alkylene chain in which one of its CH2 groups can be replaced by a heteroatom chosen from oxygen or sulfur, or by an NRn group (where Rn represents a hydrogen atom or a (C1-) alkyl group 6) linear or branched), or by a phenylene or naphthylene group, B represents a linear or branched (C1-6) alkyl or linear or branched (C2-6) alkenyl group, or linear or branched (C2-6) alkynylene ; D and D ', identical or different, represent a benzene nucleus or a pyridine nucleus, these nuclei are unsubstituted or substituted by 1 to 3 groups, identical or different, chosen between a halogen atom and a cyano, nitro, R, OR group , S (O) nR, C (Z) R, -CH (OR) -R ', C (Z) OR, NRR', C (Z) NRR ', -C (= N-OR') R, - NR-C (Z) R ', -NR-C (Z) OR' or OC (Me) 2COOR, (where identical and different R and R 'represent a hydrogen atom or a linear (C1-6) alkyl group or branched, linear or branched (C2-6) alkenyl, linear or branched (C2-6) alkynyl, aryl, linear or branched (C1-6) arylalkyl, heteroaryl, straight or branched (C1-6) heteroarylalkyl, (C3-) cycloalkyl 8) or linear or branched (C1-6) cycloalkyl (C1-6) alkyl; Z represents an oxygen or sulfur atom and n represents an integer between 0 and 2 inclusive); R3 and R4, identical or different, represent a hydrogen atom, a halogen, a group R, OR or NRR '(where R and R' are as defined above), or R3 and R4 form together with the atoms of carbon that carry them, when they are carried by two adjacent carbon atoms, a cycle that has 5 or 6 links and can contain a heteroatom chosen from oxygen, sulfur and nitrogen; R5 represents a hydrogen atom, a linear or branched (C1-6) alkyl, linear or branched (C2-6) alkenyl, linear or branched (C2-6) alkynyl, aryl, heteroaryl, (C1-6) alkylcarbonyl group, arylcarbonyl, or heteroarylcarbonyl, each of these groups being eventually substituted: - by one or several groups R6 such as R6 represents a group - (CH2) tC (= Z) Z '(where Z is as defined above, Z 'represents an OR or NRR group' with R and R 'as defined above and t is an integer between 0 and 6 inclusive); -by a group of formula (2), in which the dotted line means that the bond is single or double and R7 and R8, identical or different, represent a group -C (= Z) Z '(where Z and Z' they are as defined above), or - by a halogen atom, a linear or branched hydroxy, nitro, cyano, amino or (C1-6) alkoxy group, and it is understood that, unless otherwise indicated: it is understood by aryl, a phenyl, naphthyl or biphenyl group, these groups may be partially hydrogenated; heteroaryl is understood as any mono or bicyclic aromatic group containing 5 to 10 links, which can be partially hydrogenated in one of the cycles in the case of bicyclic heteroaryls, and containing 1 to 3 heteroatoms chosen from oxygen, nitrogen and sulfur, the aryl and heteroaryl groups may be substituted by 1 to 3 halogen atoms or linear or branched (C1-6) alkyl groups, linear or branched (C1-6) alkoxy, carboxy, formyl, amino, (C1-) alkylamino groups 6) linear or branched, dialkylamino (C1-6) linear or branched, ester, amido, nitro, cyano, and OC (Me) 2COOR (where R is as defined above), its enantiomers and diastereoisomers as well as its salts of addition with a pharmaceutically acceptable acid or base. Claim 9: Compounds of formula (1) according to any one of claims 1 to 8, characterized in that it is 3- (2- {4 - [(5-benzoyl-2-oxo-2,3-dihydro-1H -indole-3-yl) methyl] phenoxy} ethyl) -1,3-benzothiazol-2 (3H) -one, as well as its addition salts with a pharmaceutically acceptable acid. Claim 10: Compounds of formula (1) according to any one of claims 1 to 8, characterized in that it is 6-benzoyl-3- (2- {4 - [(2-oxo-2,3-dihydro-1H -indole-3-yl) methyl] phenoxy} ethyl) -1,3-benzothiazol-2 (3H) -one, as well as its addition salts with a pharmaceutically acceptable acid. Claim 13: Pharmaceutical compositions according to claim 12, characterized in that they are useful for the manufacture of a medicament for the treatment and / or prophylaxis of hyperglycemia, of dyslipidemias and more particularly in the treatment of non-insulin-dependent type II diabetes. , insulin resistance, glucose intolerance, disorders related to syndrome X, coronary artery disease and other cardiovascular diseases, kidney diseases, rethiopathies, disorders related to activation of endothelial cells, psoriasis, polycystic ovary syndrome, dementia, osteoporosis, inflammatory bowel diseases, myotonic dystrophies, pancreatitis, arteriosclerosis, xanthoma, but also in treatment or the prevention of type I diabetes, obesity, regulation Onion of appetite, anorexia, bulimia, anorexia nervosa, as well as cancerous pathologies and especially hormone-dependent cancers such as breast cancer and colon cancer and as angiogenesis inhibitors.

ARP020103521A 2001-09-21 2002-09-19 HETEROCICLIC DERIVATIVES, ITS PREPARATION PROCEDURE AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AR036876A1 (en)

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FR0112205A FR2830012B1 (en) 2001-09-21 2001-09-21 NOVEL HETEROCYCLIC DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARAMACEUTICAL COMPOSITIONS CONTAINING THEM

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AR (1) AR036876A1 (en)
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WO (1) WO2003027108A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2858321B1 (en) * 2003-07-28 2006-01-20 Servier Lab NOVEL HETEROCYCLIC OXIMIC DERIVATIVES, PROCESS FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
KR20050040746A (en) * 2003-10-27 2005-05-03 주식회사 엘지생명과학 Novel Compounds As Agonist For PPARγ And PPARα, Method For Preparation Of The Same, And Pharmaceutical Composition Containing The Same
US20090099176A1 (en) * 2004-12-02 2009-04-16 Thomas Martin Krulle Pyrrolopyridine-2-carboxylic acid amides
FR2881137B1 (en) * 2005-01-27 2007-03-02 Servier Lab NOVEL HETEROCYCLIC OXIMIC DERIVATIVES, PROCESS FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME

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US5089514A (en) * 1990-06-14 1992-02-18 Pfizer Inc. 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents
WO1998052946A1 (en) * 1997-12-02 1998-11-26 Dr. Reddy's Research Foundation Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension

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FR2830012A1 (en) 2003-03-28
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