AR035345A1 - COMPOUNDS DERIVED FROM PIRAZOL, PHARMACEUTICAL COMPOSITION, INTERMEDIARY COMPOUNDS - Google Patents

COMPOUNDS DERIVED FROM PIRAZOL, PHARMACEUTICAL COMPOSITION, INTERMEDIARY COMPOUNDS

Info

Publication number
AR035345A1
AR035345A1 ARP010104115A ARP010104115A AR035345A1 AR 035345 A1 AR035345 A1 AR 035345A1 AR P010104115 A ARP010104115 A AR P010104115A AR P010104115 A ARP010104115 A AR P010104115A AR 035345 A1 AR035345 A1 AR 035345A1
Authority
AR
Argentina
Prior art keywords
straight
members
branched chain
independently selected
nr7r8
Prior art date
Application number
ARP010104115A
Other languages
Spanish (es)
Original Assignee
Pfizer Prod Inc
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 Pfizer Prod Inc filed Critical Pfizer Prod Inc
Publication of AR035345A1 publication Critical patent/AR035345A1/en

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P3/08—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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/08—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 carbon chain containing alicyclic rings
    • 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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms

Abstract

Compuestos de la fórmula (1) donde R1 es un alquilo C1-8 de cadena lineal o ramificada, un alquenilo C2-8 de cadena lineal o ramificada, un alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, o heterobicicloalquilo (5-11 miembros); y donde R1 está opcionalmente sustituido con 1 a 6 sustituyentes R5 independientemente seleccionados de F, Cl, Br, I, nitro, ciano, -CF3, -NR7R8, -NR7C(=O)R8, -NR7C(=O)OR8, -NR7C(=O)NR8R9, -NR7S(=O)2R8, -NR7S(=O)2NR8R9, -OR7, OC(=O)R7, -OC(=O)OR7, -C(=O)OR7, -C(=O)R7, -C(=O)NR7R8, -OC(=O)NR7R8, -OC(=O)SR7, -SR7, -S(=O)R7, -S(=O)2R7, -S(=O)2NR7R8, y R7; R2 es H, -CH3, -CN o -C(=O)OR7; R3 es -C(=O)NR9-, -C(=O)O-, -C(=O)(CR10R11)n-, o -(CR10R11)n-; R4 es un alquilo C1-8 de cadena lineal o ramificada, un alquenilo C2-8 de cadena lineal o ramificada, un alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, heterobicicloalquilo (5-11 miembros), arilo C6-14, o heteroarilo (5-14 miembros); y donde R4 está opcionalmente sustituido con 1 a 3 sustituyentes R6 independientemente seleccionados de F, Cl, Br, I, nitro, ciano, -CF3, -NR7R8, -NR7C(=O)R8, NR7C(=O)OR8, -NR7C(=O)NR8R9, -NR7S(=O)2R8, -NR7S(=O)2NR8R9, -OR7, OC(=O)R7, -OC(=O)OR7, -C(=O)OR7, -C(=O)R7, -C(=O)NR7R8, -OC(=O)NR7R8, -OC(=O)SR7, -SR7, -S(=O)R7, -S(=O)2R7, -S(=O)2NR7R8, y R7; cada uno de R7, R8 y R9 se selecciona independientemente de H, alquilo C1-8 de cadena lineal o ramificada, alquenilo C2-8 de cadena lineal o ramificada, alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, heterobicicloalquilo (5-11 miembros), arilo C6-14, y heteroarilo (5-14 miembros), donde R7, R8 y R9 están cada uno independientemente opcionalmente sustituidos con 1 a 6 sustituyentes independientemente seleccionados de F, Cl, Br, I, -NO2, -CN, -CF3, -NR10R11, -NR10C(=O)R11, -NR10C(=O)OR11, -NR10C(=O)NR11R12, -NR10S(=O)2R11, NR10S(=O)2NR11R12, -OR10, OC(=O)R10, -OC(=O)OR10, -OC(=O)NR10R11, -OC(=O)SR10, -SR10, -S(=O)R10, -S(=O)2R10, -S(=O)2NR10R11, -C(=O)R10, -C(=O)OR10, -C(=O)NR10R11 y R10; o, cuando R7 y R8 están como en NR7R8, ellos pueden, por el contrario, estar opcionalmente conectados para formar con el nitrógeno de NR7R8 al que está unido un resto heterocicloalquilo de 3 a 7 miembros en el anillo, comprendiendo dicho resto heterocicloalquilo opcionalmente 1 o 2 heteroátomos adicionales independientemente seleccionados de N, O y S; cada uno de R10, R11 y R12 se selecciona independientemente de H, alquilo C1-8 de cadena lineal o ramificada, alquenilo C2-8 de cadena lineal o ramificada, alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, heterobicicloalquilo (5-11 miembros), arilo C6-14, y heteroarilo (5-14 miembros), donde R10, R11 y R12 están cada uno independientemente opcionalmente sustituidos con 1 a 6 sustituyentes independientemente seleccionados de F, Cl, Br, I, NO2, -CN, -CF3, -NR13R14, -NR13C(=O)R14, -NR13C(=O)OR14, -NR13C(=O)NR14R15, -NR13S(=O)2R14, -NR13S(=O)2NR14R15, -OR13, -OC(=O)R13, -OC(=O)OR13, -OC(=O)NR13R14, -OC(=O)SR13, -SR13, -S(=O)R13, -S(=O)2R13, -S(=O)2NR13R14, -C(=O)R13, -C(=O)OR13, -C(=O)NR13R14, y R13; cada uno de R13, R14 y R15 se selecciona independientemente de H, alquilo C1-8 de cadena lineal o ramificada, alquenilo C2-8 de cadena lineal o ramificada, alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, heterobiciciloalquilo (5-11 miembros), arilo C6-14, y heteroarilo (5-14 miembros), donde R13, R14 y R15 están cada uno independientemente opcionalmente sustituidos con 1 a 6 sustituyentes independientemente seleccionados de F, Cl, Br, I, NO2, -CN, -CF3, -NR16R17, -NR16C(=O)R17, -NR16C(=O)OR17, -NR16C(=O)NR17R18, -NR16S(=O)2R17, -NR16S(=O)2NR17R18, -OR16, -OC(=O)R16, -OC(=O)OR16, -OC(=O)NR16R17, -OC(=O)SR16, -SR16, -S(=O)R16, -(=O)2R16, -S(=O)2NR16R17, -C(=O)R16, - C(=O)OR16, -C(=O)NR16R17, y R16; cada uno de R16, R17 y R18 se selecciona independientemente de H, alquilo C1-8 de cadena lineal o ramificada, alquenilo C2-8 de cadena lineal o ramificada, alquinilo C2-8 de cadena lineal o ramificada, cicloalquilo C3-8, cicloalquenilo C4-8, heterocicloalquilo (3-8 miembros), bicicloalquilo C5-11, bicicloalquenilo C7-11, heterobicicloalquilo (5-11 miembros), arilo C6-14, y heteroarilo (5-14 miembros), n es 0, 1, 2 o 3; donde R10 y R11 en -C(=O)(CR10R11)n- y -(CR10R11)n- se definen independientemente para cada valor de n como se ha detallado antes; y sus sales farmacéuticamente aceptables. Se indica que los compuestos de la fórmula (1) tienen actividad para inhibir las cdk5, cdk2, GSK-3. Proporciona composiciones farmacéuticas y métodos que comprenden compuestos de la fórmula (1) para tratar y prevenir enfermedades y condiciones que implican crecimiento celular anormal, tales como el cáncer, y enfermedades y condiciones neurodegenerativas y las afectadas por la neurotransmisión de la dopamina. También se describen composiciones farmacéuticas y métodos que comprenden compuestos de la fórmula (1) para tratar la fertilidad masculina y la motilidad espermática; diabetes mellitus; deterioro de la tolerancia a la glucosa; síndrome metabólico o síndrome X; síndrome de poliquistosis ovárica, adipogénesis y obesidad; miogénesis y fragilidad, por ejemplo el deterioro de las características físicas relacionado con la edad; sarcopenia aguda, por ejemplo atrofia muscular y/o caquexia asociada con la quemaduras, reposo en cama, inmovilización de miembros, o importante cirugía torácica, abdominal y/o ortopédica; sepsis; caída del cabello, cabello ralo y calvicie; e inmunodeficiencia.Compounds of the formula (1) wherein R 1 is a straight or branched C 1-8 alkyl, a straight or branched C 2-8 alkenyl, a straight or branched C 2-8 alkynyl, C 3-8 cycloalkyl, C 4 cycloalkenyl -8, heterocycloalkyl (3-8 members), C5-11 bicycloalkyl, C7-11 bicycloalkenyl, or heterobicycloalkyl (5-11 members); and where R1 is optionally substituted with 1 to 6 R5 substituents independently selected from F, Cl, Br, I, nitro, cyano, -CF3, -NR7R8, -NR7C (= O) R8, -NR7C (= O) OR8, - NR7C (= O) NR8R9, -NR7S (= O) 2R8, -NR7S (= O) 2NR8R9, -OR7, OC (= O) R7, -OC (= O) OR7, -C (= O) OR7, - C (= O) R7, -C (= O) NR7R8, -OC (= O) NR7R8, -OC (= O) SR7, -SR7, -S (= O) R7, -S (= O) 2R7, -S (= O) 2NR7R8, and R7; R2 is H, -CH3, -CN or -C (= O) OR7; R3 is -C (= O) NR9-, -C (= O) O-, -C (= O) (CR10R11) n-, or - (CR10R11) n-; R4 is a C1-8 straight or branched chain alkyl, a C2-8 straight or branched chain alkenyl, a C2-8 straight or branched chain alkynyl, C3-8 cycloalkyl, C4-8 cycloalkenyl, heterocycloalkyl (3-8 members), C5-11 bicycloalkyl, C7-11 bicycloalkenyl, heterobicycloalkyl (5-11 members), C6-14 aryl, or heteroaryl (5-14 members); and where R4 is optionally substituted with 1 to 3 R6 substituents independently selected from F, Cl, Br, I, nitro, cyano, -CF3, -NR7R8, -NR7C (= O) R8, NR7C (= O) OR8, -NR7C (= O) NR8R9, -NR7S (= O) 2R8, -NR7S (= O) 2NR8R9, -OR7, OC (= O) R7, -OC (= O) OR7, -C (= O) OR7, -C (= O) R7, -C (= O) NR7R8, -OC (= O) NR7R8, -OC (= O) SR7, -SR7, -S (= O) R7, -S (= O) 2R7, - S (= O) 2NR7R8, and R7; each of R7, R8 and R9 is independently selected from H, C1-8 straight or branched chain alkyl, C2-8 straight or branched chain alkenyl, C2-8 straight or branched chain alkynyl, C3-8 cycloalkyl, cycloalkenyl C4-8, heterocycloalkyl (3-8 members), bicycloalkyl C5-11, bicycloalkenyl C7-11, heterobicycloalkyl (5-11 members), aryl C6-14, and heteroaryl (5-14 members), where R7, R8 and R9 are each independently optionally substituted with 1 to 6 substituents independently selected from F, Cl, Br, I, -NO2, -CN, -CF3, -NR10R11, -NR10C (= O) R11, -NR10C (= O) OR11, -NR10C (= O) NR11R12, -NR10S (= O) 2R11, NR10S (= O) 2NR11R12, -OR10, OC (= O) R10, -OC (= O) OR10, -OC (= O) NR10R11, - OC (= O) SR10, -SR10, -S (= O) R10, -S (= O) 2R10, -S (= O) 2NR10R11, -C (= O) R10, -C (= O) OR10, -C (= O) NR10R11 and R10; or, when R7 and R8 are as in NR7R8, they may, on the other hand, be optionally connected to form with the nitrogen of NR7R8 to which a 3- to 7-membered heterocycloalkyl moiety is attached to the ring, said heterocycloalkyl moiety optionally comprising 1 or 2 additional heteroatoms independently selected from N, O and S; each of R10, R11 and R12 is independently selected from H, C1-8 straight or branched chain alkyl, C2-8 straight or branched chain alkenyl, C2-8 straight or branched chain alkynyl, C3-8 cycloalkyl, cycloalkenyl C4-8, heterocycloalkyl (3-8 members), bicycloalkyl C5-11, bicycloalkenyl C7-11, heterobicycloalkyl (5-11 members), aryl C6-14, and heteroaryl (5-14 members), where R10, R11 and R12 are each independently optionally substituted with 1 to 6 substituents independently selected from F, Cl, Br, I, NO2, -CN, -CF3, -NR13R14, -NR13C (= O) R14, -NR13C (= O) OR14, - NR13C (= O) NR14R15, -NR13S (= O) 2R14, -NR13S (= O) 2NR14R15, -OR13, -OC (= O) R13, -OC (= O) OR13, -OC (= O) NR13R14, -OC (= O) SR13, -SR13, -S (= O) R13, -S (= O) 2R13, -S (= O) 2NR13R14, -C (= O) R13, -C (= O) OR13 , -C (= O) NR13R14, and R13; each of R13, R14 and R15 is independently selected from H, C1-8 straight or branched chain alkyl, C2-8 straight or branched chain alkenyl, C2-8 straight or branched chain alkynyl, C3-8 cycloalkyl, cycloalkenyl C4-8, heterocycloalkyl (3-8 members), C5-11 bicycloalkyl, C7-11 bicycloalkenyl, 5-11 heterobicycloalkyl, C6-14 aryl, and heteroaryl (5-14 members), where R13, R14 and R15 are each independently optionally substituted with 1 to 6 substituents independently selected from F, Cl, Br, I, NO2, -CN, -CF3, -NR16R17, -NR16C (= O) R17, -NR16C (= O) OR17, - NR16C (= O) NR17R18, -NR16S (= O) 2R17, -NR16S (= O) 2NR17R18, -OR16, -OC (= O) R16, -OC (= O) OR16, -OC (= O) NR16R17, -OC (= O) SR16, -SR16, -S (= O) R16, - (= O) 2R16, -S (= O) 2NR16R17, -C (= O) R16, - C (= O) OR16, -C (= O) NR16R17, and R16; each of R16, R17 and R18 is independently selected from H, C1-8 straight or branched chain alkyl, C2-8 straight or branched chain alkenyl, C2-8 straight or branched chain alkynyl, C3-8 cycloalkyl, cycloalkenyl C4-8, heterocycloalkyl (3-8 members), bicycloalkyl C5-11, bicycloalkenyl C7-11, heterobicycloalkyl (5-11 members), aryl C6-14, and heteroaryl (5-14 members), n is 0, 1, 2 or 3; where R10 and R11 in -C (= O) (CR10R11) n- and - (CR10R11) n- are independently defined for each value of n as detailed above; and its pharmaceutically acceptable salts. It is indicated that the compounds of the formula (1) have activity to inhibit cdk5, cdk2, GSK-3. It provides pharmaceutical compositions and methods comprising compounds of the formula (1) for treating and preventing diseases and conditions that involve abnormal cell growth, such as cancer, and neurodegenerative diseases and conditions and those affected by the neurotransmission of dopamine. Pharmaceutical compositions and methods comprising compounds of the formula (1) for treating male fertility and sperm motility are also described; Mellitus diabetes; impaired glucose tolerance; metabolic syndrome or syndrome X; polycystic ovarian syndrome, adipogenesis and obesity; myogenesis and fragility, for example the deterioration of physical characteristics related to age; acute sarcopenia, for example muscular atrophy and / or cachexia associated with burns, bed rest, limb immobilization, or major thoracic, abdominal and / or orthopedic surgery; sepsis; hair loss, thin hair and baldness; and immunodeficiency.

ARP010104115A 2000-08-31 2001-08-29 COMPOUNDS DERIVED FROM PIRAZOL, PHARMACEUTICAL COMPOSITION, INTERMEDIARY COMPOUNDS AR035345A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US22941500P 2000-08-31 2000-08-31

Publications (1)

Publication Number Publication Date
AR035345A1 true AR035345A1 (en) 2004-05-12

Family

ID=22861151

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP010104115A AR035345A1 (en) 2000-08-31 2001-08-29 COMPOUNDS DERIVED FROM PIRAZOL, PHARMACEUTICAL COMPOSITION, INTERMEDIARY COMPOUNDS

Country Status (38)

Country Link
EP (1) EP1313710A1 (en)
JP (1) JP2004507526A (en)
KR (1) KR20030027093A (en)
CN (1) CN1518543A (en)
AP (1) AP2001002266A0 (en)
AR (1) AR035345A1 (en)
AU (1) AU2001280009A1 (en)
BG (1) BG107455A (en)
BR (1) BR0113574A (en)
CA (1) CA2420363A1 (en)
CR (1) CR6881A (en)
CZ (1) CZ2003468A3 (en)
DO (1) DOP2001000243A (en)
DZ (1) DZ3398A1 (en)
EA (1) EA200300205A1 (en)
EC (1) ECSP034480A (en)
EE (1) EE200300085A (en)
GT (1) GT200100179A (en)
HN (1) HN2001000192A (en)
HR (1) HRP20030140A2 (en)
HU (1) HUP0302669A3 (en)
IL (1) IL154016A0 (en)
IS (1) IS6687A (en)
MA (1) MA26946A1 (en)
MX (1) MXPA03001785A (en)
NO (1) NO20030958D0 (en)
NZ (1) NZ523656A (en)
OA (1) OA12368A (en)
PA (1) PA8528101A1 (en)
PE (1) PE20020470A1 (en)
PL (1) PL360742A1 (en)
SK (1) SK2002003A3 (en)
SV (1) SV2002000618A (en)
TN (1) TNSN01132A1 (en)
UY (1) UY26909A1 (en)
WO (1) WO2002018346A1 (en)
YU (1) YU14703A (en)
ZA (1) ZA200301064B (en)

Families Citing this family (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8124630B2 (en) 1999-01-13 2012-02-28 Bayer Healthcare Llc ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
JP2002534468A (en) 1999-01-13 2002-10-15 バイエル コーポレイション ω-Carboxyaryl-substituted diphenylureas as p38 kinase inhibitors
US6660731B2 (en) 2000-09-15 2003-12-09 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US6610677B2 (en) 2000-09-15 2003-08-26 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US6613776B2 (en) 2000-09-15 2003-09-02 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
CA2422371C (en) 2000-09-15 2010-05-18 Vertex Pharmaceuticals Incorporated Pyrazole compounds useful as protein kinase inhibitors
US20030105090A1 (en) 2000-12-21 2003-06-05 David Bebbington Pyrazole compounds useful as protein kinase inhibitors
CA2458661A1 (en) * 2001-09-27 2003-04-03 Applied Research Systems Ars Holding N.V. Methods of increasing endogenous testosterone levels
EP2324825A1 (en) 2002-02-11 2011-05-25 Bayer Healthcare LLC Aryl ureas with angiogenesis inhibiting activity
WO2003068229A1 (en) 2002-02-11 2003-08-21 Bayer Pharmaceuticals Corporation Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors
CA2492673A1 (en) * 2002-07-17 2004-01-22 Pharmacia Italia S.P.A. Heterobicyclic pyrazole derivatives as kinase inhibitors
CA2501799C (en) 2002-10-09 2008-06-17 Pfizer Products Inc. Pyrazole compounds for treatment of neurodegenerative disorders
WO2004035588A1 (en) * 2002-10-15 2004-04-29 Smithkline Beecham Corporation Pyradazine compounds as gsk-3 inhibitors
JP2006519234A (en) * 2003-02-27 2006-08-24 スミスクライン ビーチャム コーポレーション New compounds
ATE366108T1 (en) 2003-05-20 2007-07-15 Bayer Pharmaceuticals Corp DIARYL UREAS FOR PDGFR-MEDIATED DISEASES
WO2005009344A2 (en) * 2003-06-05 2005-02-03 Elan Pharmaceuticals, Inc. Acylated amino acid amidyl pyrazoles and related compounds
PL2256106T3 (en) * 2003-07-22 2015-08-31 Astex Therapeutics Ltd 3,4-disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinases (CDK) and glycogen synthase kinase-3 (GSK-3) modulators
NZ580384A (en) 2003-07-23 2011-03-31 Bayer Pharmaceuticals Corp 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide and metabolites for the treatment and prevention of diseases and conditions
JP2006528661A (en) * 2003-07-25 2006-12-21 ファイザー・インク Aminopyrazole compounds and use as CHK1 inhibitors
ATE473967T1 (en) * 2003-11-26 2010-07-15 Pfizer Prod Inc AMINOPYRAZOLE DERIVATIVES AS GSK-3 INHIBITORS
US7244757B2 (en) * 2004-04-01 2007-07-17 Pfizer Inc Pyrazole-amine compounds for the treatment of neurodegenerative disorders
WO2005103010A2 (en) * 2004-04-21 2005-11-03 Astrazeneca Ab Pyrazole derivatives useful for the treatment of cancer
JP2007535565A (en) 2004-04-30 2007-12-06 バイエル ファーマシューティカルス コーポレーション Substituted pyrazolyl urea derivatives useful for the treatment of cancer
US7498342B2 (en) 2004-06-17 2009-03-03 Plexxikon, Inc. Compounds modulating c-kit activity
WO2006004865A1 (en) * 2004-06-29 2006-01-12 Rigel Pharmaceuticals, Inc. 2-substituted quinoline compounds and their uses as inhibitors of the ige receptor signaling cascade
US7491720B2 (en) 2004-10-29 2009-02-17 Banyu Pharmaceutical Co., Ltd. Aminopyridine derivatives having Aurora A selective inhibitory action
WO2006055831A2 (en) 2004-11-17 2006-05-26 Miikana Therapeutics, Inc. Kinase inhibitors
US8404718B2 (en) 2005-01-21 2013-03-26 Astex Therapeutics Limited Combinations of pyrazole kinase inhibitors
AR054425A1 (en) 2005-01-21 2007-06-27 Astex Therapeutics Ltd PIPERIDIN ADDITION SALTS 4-IL-ACID AMID 4- (2,6-DICLORO-BENZOILAMINO) 1H-PIRAZOL-3-CARBOXILICO.
PL1846394T3 (en) 2005-02-04 2012-04-30 Astrazeneca Ab Pyrazolylaminopyridine derivatives useful as kinase inhibitors
EP1847531A4 (en) * 2005-02-09 2009-04-22 Takeda Pharmaceutical Pyrazole compound
KR101362621B1 (en) 2005-02-16 2014-02-13 아스트라제네카 아베 Chemical compouns
AU2006248780B2 (en) 2005-05-16 2010-06-03 Astrazeneca Ab Pyrazolylaminopyrimidine derivatives useful as tyrosine kinase inhibitors
EP1741708A1 (en) 2005-06-28 2007-01-10 Sanofi-Aventis Deutschland GmbH Heteroaryl-substituted amides comprising an unsaturated or cyclic linker group, and their use as pharmaceuticals
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009506069A (en) 2005-08-26 2009-02-12 ブレインセルス，インコーポレイティド Neurogenesis through modulation of muscarinic receptors
ES2535854T3 (en) 2005-09-30 2015-05-18 Miikana Therapeutics, Inc. Substituted Pyrazole Compounds
AU2006304787A1 (en) 2005-10-21 2007-04-26 Braincells, Inc. Modulation of neurogenesis by PDE inhibition
PT1945631E (en) 2005-10-28 2012-10-15 Astrazeneca Ab 4- (3-aminopyrazole) pyrimidine derivatives for use as tyrosine kinase inhibitors in the treatment of cancer
CA2625210A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
BRPI0619708A2 (en) 2005-11-03 2011-10-11 Vertex Pharma compound, composition, method for inhibiting aurora kinase activity in a biological sample, method for treating proliferative disorder and method for treating cancer
US7572809B2 (en) * 2005-12-19 2009-08-11 Hoffmann-La Roche Inc. Isoquinoline aminopyrazole derivatives
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
EP2377531A2 (en) 2006-05-09 2011-10-19 Braincells, Inc. Neurogenesis by modulating angiotensin
BRPI0717439A2 (en) * 2006-10-18 2013-11-19 Periness Ltd PHARMACEUTICAL COMPOSITION, AND METHODS FOR TREATING MALE SUBFERTILITY, FOR DETERMINING A FERTLITY STATUS IN A MALE SEX, FOR ASSISTED REPRODUCTION TECHNIQUE FOR A SPECULAR SPULLET REPRODUCTION FOR CULLED SPLIT USE IN AN AUXILIARY REPRODUCTION TECHNIQUE.
US8642598B2 (en) * 2006-10-21 2014-02-04 Abbvie Inc. Heterocyclic compounds and their use as glycogen synthase kinase 3 inhibitors
WO2008063888A2 (en) 2006-11-22 2008-05-29 Plexxikon, Inc. Compounds modulating c-fms and/or c-kit activity and uses therefor
US7737149B2 (en) * 2006-12-21 2010-06-15 Astrazeneca Ab N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof
EP2129381A1 (en) 2007-01-24 2009-12-09 Glaxo Group Limited Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1
EP2170830B1 (en) 2007-07-17 2014-10-15 Plexxikon, Inc. 2-FLUORO-BENZENESULFONAMIDE COMPOUNDS AS Raf KINASE MODULATORS
WO2009017453A1 (en) * 2007-07-30 2009-02-05 Astrazeneca Ab New therapeutic combination of an antipsychotic and a gsk3 inhibitor 958
EP3078662A1 (en) 2007-09-21 2016-10-12 Array Biopharma, Inc. Pyridin-2-yl-amino-1,2,4-thiadiazole derivatives as glucokinase activators for the treatment of diabetes mellitus
JPWO2009130900A1 (en) * 2008-04-24 2011-08-11 日本曹達株式会社 Oxime derivatives, intermediate compounds and plant disease control agents
US20100216805A1 (en) 2009-02-25 2010-08-26 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
MY172424A (en) 2009-04-03 2019-11-25 Hoffmann La Roche Propane- i-sulfonic acid {3- (4-chloro-phenyl)-1h-pyrrolo [2, 3-b] pyridine-3-carconyl] -2, 4-difluoro-phenyl} -amide compositions and uses thereof
EP2488511A1 (en) * 2009-10-02 2012-08-22 Vertex Pharmaceuticals Incorporated Pyrazole inhibitors of phosphatidylinositol 3-kinase
BR112012012156A2 (en) 2009-11-06 2015-09-08 Plexxikon Inc compounds and methods for kinase modulation, and indications for this
CA2810954A1 (en) 2010-09-27 2012-04-05 Abbott Gmbh & Co. Kg Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors
US9090592B2 (en) 2010-12-30 2015-07-28 AbbVie Deutschland GmbH & Co. KG Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors
TR201816421T4 (en) 2011-02-07 2018-11-21 Plexxikon Inc Compounds and methods for kinase modulation and their indications.
AR085279A1 (en) 2011-02-21 2013-09-18 Plexxikon Inc SOLID FORMS OF {3- [5- (4-CHLORINE-PHENYL) -1H-PIRROLO [2,3-B] PIRIDINA-3-CARBONIL] -2,4-DIFLUOR-PHENIL} -AMIDE OF PROPANE ACID-1- SULFONIC
US9150570B2 (en) 2012-05-31 2015-10-06 Plexxikon Inc. Synthesis of heterocyclic compounds
MX2016001934A (en) * 2013-08-16 2016-06-10 Merck Patent Gmbh 3-substituted cyclopentylamine derivatives.
CN106580986B (en) * 2016-11-28 2017-09-15 王保亮 A kind of pharmaceutical composition for treating teen bra
MX2021007925A (en) 2018-12-31 2021-10-26 Biomea Fusion Llc Irreversible inhibitors of menin-mll interaction.
US11174263B2 (en) 2018-12-31 2021-11-16 Biomea Fusion, Inc. Inhibitors of menin-MLL interaction
AU2020213761C1 (en) * 2019-01-31 2023-08-10 Pfizer Inc. 3-carbonylamino-5-cyclopentyl-1 Fi-pyrazole compounds having inhibitory activity on CDK2
WO2022135442A1 (en) * 2020-12-22 2022-06-30 上海拓界生物医药科技有限公司 Cdk2 inhibitor and preparation method therefor
TW202317574A (en) 2021-06-28 2023-05-01 美商纜圖藥品公司 Cdk2 inhibitors
TW202317564A (en) * 2021-07-01 2023-05-01 大陸商上海拓界生物醫藥科技有限公司 Cdk2 inhibitor, a preparation method and a use thereof
TW202325280A (en) * 2021-11-09 2023-07-01 大陸商上海拓界生物醫藥科技有限公司 An aminopyrazole derivative, preparation method and use thereof
WO2023092088A1 (en) * 2021-11-19 2023-05-25 Blueprint Medicines Corporation Cdk2 inhibitors and methods of making and using same
WO2023239629A1 (en) * 2022-06-06 2023-12-14 Plexium, Inc. Compounds and pharmaceutical compositions that degrade cdk2

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ299156B6 (en) * 1997-12-22 2008-05-07 Bayer Corporation Substituted heterocyclic ureas, pharmaceutical compositions in which they are comprised and their use
KR100579792B1 (en) * 1998-05-13 2006-05-12 동화약품공업주식회사 Novel 2,5-pyridinedicarboxylic acid derivatives
GB9811427D0 (en) * 1998-05-29 1998-07-22 Zeneca Ltd Chemical compounds
ES2251395T3 (en) * 1999-07-26 2006-05-01 Banyu Pharmaceutical Co., Ltd. BIARILURE DERIVATIVES.
YU9602A (en) * 1999-08-12 2004-11-25 Pharmacia Italia S.P.A. 3(5)-amino-pyrazole derivatives, process for their preparation and their use as antitumor agents
US6387900B1 (en) * 1999-08-12 2002-05-14 Pharmacia & Upjohn S.P.A. 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents
JP3955468B2 (en) * 1999-11-30 2007-08-08 ファイザー・プロダクツ・インク 2,4-Diaminopyrimidine compounds useful as immunosuppressants
WO2001079198A1 (en) * 2000-04-18 2001-10-25 Agouron Pharmaceuticals, Inc. Pyrazoles for inhibiting protein kinase

Also Published As

Publication number Publication date
HRP20030140A2 (en) 2003-04-30
NZ523656A (en) 2004-11-26
CR6881A (en) 2004-03-11
EP1313710A1 (en) 2003-05-28
MA26946A1 (en) 2004-12-20
AP2001002266A0 (en) 2001-09-30
OA12368A (en) 2004-04-13
BR0113574A (en) 2003-07-22
JP2004507526A (en) 2004-03-11
PL360742A1 (en) 2004-09-20
KR20030027093A (en) 2003-04-03
MXPA03001785A (en) 2003-06-04
CA2420363A1 (en) 2002-03-07
WO2002018346A1 (en) 2002-03-07
BG107455A (en) 2003-09-30
IL154016A0 (en) 2003-07-31
DZ3398A1 (en) 2002-03-07
AU2001280009A1 (en) 2002-03-13
EA200300205A1 (en) 2003-06-26
YU14703A (en) 2006-05-25
TNSN01132A1 (en) 2005-11-10
HN2001000192A (en) 2001-08-28
IS6687A (en) 2003-01-16
ZA200301064B (en) 2004-04-19
UY26909A1 (en) 2002-03-22
SV2002000618A (en) 2002-10-24
PA8528101A1 (en) 2002-07-30
CZ2003468A3 (en) 2004-05-12
HUP0302669A3 (en) 2004-03-29
GT200100179A (en) 2002-04-22
NO20030958L (en) 2003-02-28
DOP2001000243A (en) 2002-10-15
SK2002003A3 (en) 2004-04-06
CN1518543A (en) 2004-08-04
NO20030958D0 (en) 2003-02-28
PE20020470A1 (en) 2002-06-18
EE200300085A (en) 2004-12-15
HUP0302669A2 (en) 2003-12-29
ECSP034480A (en) 2003-03-31

Similar Documents

Publication Publication Date Title
AR035345A1 (en) COMPOUNDS DERIVED FROM PIRAZOL, PHARMACEUTICAL COMPOSITION, INTERMEDIARY COMPOUNDS
AR032629A1 (en) COMPOUNDS DERIVED FROM IMIDAZOL AND PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM
ECSP099437A (en) HERBICIDE COMPOSITION
AR040031A1 (en) PIRAZOL-PYRIMIDINE ANILINE COMPOUNDS USED AS KINASE INHIBITORS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
AR057979A1 (en) PIRAZOLPIRIMIDINAS AS INHIBITORS OF PROTEIN QUINASA. PHARMACEUTICAL COMPOSITIONS.
AR041250A1 (en) SULFONAMIDE DERIVATIVES AS INHIBITORS OF TNF-ALFA CONVERTER ENZYMES
AR067397A1 (en) TRIAZOL DERIVATIVES WITH ANTI-BANERIGAN ACTIVITY
PE20070243A1 (en) HETEROCYCLIC COMPOUNDS AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
HUP0400266A2 (en) Pharmaceutical compositions containing imidazo[1,2-a]pyridine derivatives, and their use for the prophylaxis and treatment of herpes viral infections
AR054625A1 (en) OXAZOLIDINONE COMPOUNDS, PROCEDURE TO PREPARE THEM, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND USE AS ANTIMICROBIAL AGENTS.
AR037754A1 (en) HERBICIDES
AR035436A1 (en) A BENZOPHENONE OR PHARMACEUTICALLY ACCEPTABLE DERIVATIVE, SALTS, SALINE FORMS, PHARMACEUTICAL COMPOSITIONS, USES FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, AND PROCESS FOR THE PREPARATION OF A BENZOPHENONE
AR057872A1 (en) INHIBITORS OF THE 5-LIPOXYGENASE ACTIVATING PROTEIN (FLAP)
DE60208630D1 (en) Thiazole derivatives and their use as cdk inhibitors
DE60239884D1 (en) PYRIMIDINE COMPOUND AND MEDICAL COMPOSITION CONTAINING THEREOF
AR035087A1 (en) PIRIDIL-ALQUINOS AND PIRIDIL-N-OXIDO-ACTIVE HERBICIDE ALKINES, PROCEDURE FOR PREPARATION, HERBICIDE COMPOSITION AND TO INHIBIT THE GROWTH OF PLANTS, METHOD FOR CONTROLLING GROWTH OF INDESEABLE PLANTS, AND METHOD OF CREAM INHIBITION
AR062469A1 (en) AZABENZOTIOFEN AND AZABENZOFURAN COMPOUNDS AS INHIBITORS OF THE MEK QUINASE, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND THE USE OF THESE IN THE TREATMENT OF INFLAMMATORY AND HYPERPROLIFERATIVE DISORDERS.
AR063800A1 (en) DERIVATIVES OF NICOTINIC ACID, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND METHODS OF USE OF THE SAME
PE20090151A1 (en) PYRIMIDINONE DERIVATIVES AND METHODS FOR THEIR USE
AR051469A1 (en) TETRACICLIC INDOL DERIVATIVES AS ANTIVIRICAL AGENTS
AR019788A2 (en) COMPOUNDS DERIVED FROM ERYTHROMYCIN, COMPOSITIONS THAT CONTAIN THEM, USE AND PROCEDURES TO PREPARE THEM
CA2437524A1 (en) Composition and antiviral activity of substituted azaindoleoxoacetic piperazine derivatives
AR064345A1 (en) 8-OXOADENINE DERIVATIVES
PT1437349E (en) Substituted isoxazoles and the use thereof as antibiotics
AR040413A1 (en) HETEROCICLILALQUINOS ACTIVE AS HERBICIDES

Legal Events

Date Code Title Description
FB Suspension of granting procedure