AR049583A2 - COMPOUND DERIVED FROM PIRAZOLO-PYRIMIDINE, PHARMACEUTICAL COMPOSITION AND THE USE OF SUCH COMPOUND IN THE MANUFACTURE OF MEDICINES - Google Patents

COMPOUND DERIVED FROM PIRAZOLO-PYRIMIDINE, PHARMACEUTICAL COMPOSITION AND THE USE OF SUCH COMPOUND IN THE MANUFACTURE OF MEDICINES

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Publication number
AR049583A2
AR049583A2 ARP050102868A ARP050102868A AR049583A2 AR 049583 A2 AR049583 A2 AR 049583A2 AR P050102868 A ARP050102868 A AR P050102868A AR P050102868 A ARP050102868 A AR P050102868A AR 049583 A2 AR049583 A2 AR 049583A2
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AR
Argentina
Prior art keywords
alkyl
cycloalkyl
haloalkyl
optionally substituted
case
Prior art date
Application number
ARP050102868A
Other languages
Spanish (es)
Inventor
Liqi He
Paul Joseph Gilligan
Argyrios Georgios Arvanitis
Original Assignee
Bristol Myers Squibb Pharma Co
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Publication date
Priority claimed from US08/899,242 external-priority patent/US6124289A/en
Application filed by Bristol Myers Squibb Pharma Co filed Critical Bristol Myers Squibb Pharma Co
Publication of AR049583A2 publication Critical patent/AR049583A2/en

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Abstract

Un compuesto derivado de pirazolo-pirimidina, que responde a las formulas (1) o (2), e isomeros del mismo, forma estereoisoméricas del mismo, o mezclas de formas estereoisoméricas del mismo, y sus sales aceptables para uso farmacéutico o sus formas de prodroga en donde: A es CR; Z es N o CR2; Ar se selecciona entre fenilo, naftilo, piridilo, pirimidinilo, triazinilo, furanilo, tienilo, benzotienilo, benzofuranilo, 2,3-dihidrobenzofuranilo, 2,3-dihidrobenzotienilo, indanilo, 1,2-benzopiranilo, 3,4-dihidro-1,2-benzopiranilo, tetralinilo, cada Ar está opcionalmente sustituido con entre 1 y 5 grupos R4 y cada Ar está unido a un átomo de C insaturado; R se selecciona en forma independiente en cada caso entre H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, cicloalquilo C3-6, cicloalquilalquilo C4-7, halo, CN, haloalquilo C1-4; R1 se selecciona en forma independiente en cada caso entre H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, halo, CN, haloalquilo C1-4, hidroxialquilo C1-12, alcoxialquilo C2-12, cianoalquilo C2-10, cicloalquilo C3-6, cicloalquilalquilo C4-10, NR9R10, alquil C1-4-NR9R10, NR9COR10, OR11, SH o S(O)nR12; R2 se selecciona entre H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4, cicloalquilo C3-6, cicloalquilalquilo C4-10, hidroxialquilo C1-4, halo, CN, -NR6R7, NR9COR10, haloalquilo C1-4, -OR7, SH o -S(O)nR12; R3 se selecciona entre -H, OR7, SH, S(O)nR13, COR7, CO2R7, OC(O)R13, NR8COR7, N(COR7)2, NR8CONR6R7, NR8CO2R13, NR6R7, NR6aR7a, N(OR7)R6, CONR6R7, arilo, heteroarilo y heterociclilo, o alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-8, cicloalquenilo C5-8, cicloalquilalquilo C4-12 o cicloalquenilalquilo C6-10, cada uno opcionalmente sustituido con entre 1 y 3 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR13, COR15, CO2R15, OC(O)R13, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R13, NR16R15, CONR16R15, arilo, heteroarilo y heterociclilo; R4 se selecciona en forma independiente en cada caso entre: alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-6, cicloalquilalquilo C4-12, NO2, halo, CN, haloalquilo C1-4, NR6R7, NR8COR7, NR8CO2R7, COR7, OR7, CONR6R7, CO(NOR9)R7, CO2R7, o S(O)nR7, donde cada uno de tales alquilo C1-10, alquenilo C2-10, alquinilo C2-10, cicloalquilo C3-6 y cicloalquilalquilo C4-12 son opcionalmente sustituidos con entre 1 y 3 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-4, NO2, halo, CN, NR6R7, NR8COR7, NR8CO2R7, COR7, OR7, CONR6R7, CO2R7, CO(NOR9)R7, o S(O)nR7; R6 y R7, R6a y R7a se seleccionan en forma independiente en cada caso entre -H, alquilo C1-10, alquenilo C3-10, alquinilo C3-10, haloalquilo C1-10 con 1-10 halogenos, alcoxialquilo C2-8, cicloalquilo C3-6, cicloalquilalquilo C4-12, cicloalquenilo C5-10, o cicloalquenilalquilo C6-14, cada uno opcionalmente sustituido con entre 1 y 3 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR13, COR15, CO2R15, OC(O)R13, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R13, NR16R15, CONR16R15, arilo, heteroarilo o heterociclilo, -arilo, aril(alquilo C1-4), heteroarilo, heteroaril(alquilo C1-4), heterociclilo o heterociclil(alquilo C1-4), como alternativa, NR6R7 y NR6aR7a en forma independiente piperidina, pirrolidina, piperazina, N-metilpiperazina, morfolina o tiomorfolina, cada uno opcionalmente sustituido con 1-3 grupos alquilo C1-4; R8 se selecciona en forma independiente en cada caso entre H o alquilo C1-4; R9 y R10 se seleccionan en forma independiente en cada caso entre H, alquilo C1-4, o cicloalquilo C3-6; R11 se selecciona entre alquilo C1-4, haloalquilo C1-4, o cicloalquilo C3-6; R12 es alquilo C1-4 o haloalquilo C1-4; R13 se selecciona entre alquilo C1-4, haloalquilo C1-4, alcoxialquilo C2-8, cicloalquilo C3-6, cicloalquilalquilo C4-12, arilo, aril(alquil C1-4)-, heteroarilo o heteroaril(alquil C1-4)-; R14 se selecciona entre alquilo C1-10, alquenilo C3-10, alquinilo C3-10, cicloalquilo C3-8 o cicloalquilalquilo C4-12, cada uno opcionalmente sustituido con entre 1 y 3 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR15, COR15, CO2R15, OC(O)R15, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R15, NR16R15, CONR16R15, y alquiltio C1-6, alquilsulfinilo C1-6 y alquilsulfonilo C1-6; R15 y R16 se seleccionan en forma independiente en cada caso entre H, alquilo C1-6, cicloalquilo C3-10, cicloalquilalquilo C4-16, excepto que para S(O)nR15, R15 no puede ser H; arilo es fenilo o naftilo, cada uno opcionalmente sustituido con entre 1 y 5 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR15, COR15, CO2R15, OC(O)R15, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R15, NR16R15, y CONR16R15; heteroarilo es piridilo, pirimidinilo, triazinilo, furanilo, piranilo, quinolinilo, isoquinolinilo, tienilo, imidazolilo, tiazolilo, indolilo, pirrolilo, oxazolilo, benzofuranilo, benzotienilo, benzotiazolilo, isoxazolilo, pirazolilo, 2,3-dihidrobenzotienilo o 2,3-dihidrobenzofuranilo, cada uno opcionalmente sustituido con entre 1 y 5 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR15, -COR15, CO2R15, OC(O)R15, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R15, NR16R15, y CONR16R15; heterociclilo es heteroarilo saturado o parcialmente saturado, opcionalmente sustituido con entre 1 y 5 sustituyentes seleccionados en forma independiente en cada caso entre alquilo C1-6, cicloalquilo C3-6, halo, haloalquilo C1-4, ciano, OR15, SH, S(O)nR15, COR15, CO2R15, OC(O)R15, NR8COR15, N(COR15)2, NR8CONR16R15, NR8CO2R15, NR15R16, y CONR16R15; n es en forma independiente en cada caso 0, 1 o 2, a condicion de que: (A) cuando R es H, y Z es CR2, Ar no sea fenilo o fenilo sustituido; (B) cuando Z es CR2, entonces R2 no sea -NR6SO2R7 o -SO2NR6R7; (C) cuando R es H, Z es CR2, R1 es OR11, R2 es H, R3 es OR7, y R7 y R11 son ambos H, entonces Ar no sea piridilo o naftilo; (D) cuando R1 es -(alquilen C1-2)-O-(alquil C1-2) o -(alquilen C1-2)-OH, entonces que se cumpla al menos una de las siguientes condiciones (i), (ii) y (iii): (i) que el compuesto sea un compuesto de formula (2); (ii) que Ar se selecciona entre naftilo, triazinilo, furanilo, tienilo, benzotienilo, benzofuranilo, 2,3-dihidrobenzofuranilo, 2,3-dihidrobenzotienilo, indanilo, 1,2- benzopiranilo, 3,4-dihidro-1,2-benzopiranilo, y tetralinilo opcionalmente sustituido; (iii) que R3 se seleccione entre H, SH, S(O)nR13 en donde n = 1, CO2R7, OC(O)R13, NR8COR7, N(COR7)2, NR8CONR6R7, NR8CO2R13, N(OR7)R6, CONR6R7, arilo distinto de fenilo opcionalmente sustituido, heteroarilo distinto de (a) pirazinilo opcionalmente sustituido, (b) pirimidilo opcionalmente sustituido o (c) piradizinilo o heterociclilo opcionalmente sustituido; y (E) cuando R3 es cicloalquenilo C5-8 o cicloalquenilalquilo C6-10, entonces que se cumpla al menos una de las siguientes condiciones (i), (ii) y (iii): (i) que el compuesto sea un compuesto de formula (2); (ii) que Ar se seleccione entre naftilo, triazinilo, furanilo, tienilo, benzotienilo, benzofuranilo, 2,3-dihidrobenzofuranilo, 2,3-dihidrobenzotienilo, indanilo, 1,2-benzopiranilo, 3,4-dihidro-1,2-benzopiranilo, y tetralinilo opcionalmente sustituido; (iii) que R1 se selecciona entre alquenilo C2-4, alquinilo C2-4, CN, haloalquilo C1-4, hidroxialquilo C3-12, alcoxialquilo C4-12 distinto de -(alquilen C1-2)-O-(alquilo C1-2), cianoalquilo C2-10, cicloalquilo C3-6, cicloalquilalquilo C4-10, NR9R16, alquil C1-4-NR9R10, NR9COR16, OR11, SH o S(O)nR12. También se describen las composiciones farmacéuticas que comprenden dichos compuestos y el uso de los mismos en la fabricacion de medicamentos para el tratamiento de un trastorno afectivo, ansiedad, depresion, dolor de cabeza, síndrome de intestino irritable, trastorno de estrés post-traumático, parálisis supranuclear progresiva, supresion inmune, enfermedad de Alzheimer, enfermedades gastrointestinales, anorexia nervosa u otros trastornos de la alimentacion, drogadiccion, síndrome de abstinencia a las drogas o al alcohol, enfermedades inflamatorias, problemas de fertilidad, infecciones por el virus de inmunodeficiencia humana, estrés hemorrágico, obesidad, infertilidad, traumatismos cerebrales y de la espina dorsal, epilepsia, accidente cerebrovascular, ulceras, esclerosis lateral amiotrofica, hipoglucemia o un trastorno cuyo tratamiento pueda ser efectuado o facilitado antagonizando el CRF, incluyendo sin carácter limitativo los trastornos inducidos o facilitados por el CRF, en mamíferos.A compound derived from pyrazolo-pyrimidine, which responds to formulas (1) or (2), and isomers thereof, stereoisomeric form thereof, or mixtures of stereoisomeric forms thereof, and their salts acceptable for pharmaceutical use or their forms of prodroga where: A is CR; Z is N or CR2; Ar is selected from phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, furanyl, thienyl, benzothienyl, benzofuranyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, indanyl, 1,2-benzopyranyl, 3,4-dihydro-1, 2-benzopyranyl, tetralinyl, each Ar is optionally substituted with between 1 and 5 R4 groups and each Ar is attached to an unsaturated C atom; R is independently selected in each case from H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 3-6 cycloalkyl, C 4-7 cycloalkylalkyl, halo, CN, C 1-4 haloalkyl; R1 is independently selected in each case from H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, halo, CN, C1-4 haloalkyl, C1-12 hydroxyalkyl, C2-12 alkoxyalkyl, C2-10 cyanoalkyl , C3-6 cycloalkyl, C4-10 cycloalkylalkyl, C1-4-NR9R10 alkyl, NR9COR10, OR11, SH or S (O) nR12; R2 is selected from H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C3-6 cycloalkyl, C4-10 cycloalkylalkyl, C1-4 hydroxyalkyl, halo, CN, -NR6R7, NR9COR10, C1-4 haloalkyl, -OR7, SH or -S (O) nR12; R3 is selected from -H, OR7, SH, S (O) nR13, COR7, CO2R7, OC (O) R13, NR8COR7, N (COR7) 2, NR8CONR6R7, NR8CO2R13, NR6R7, NR6aR7a, N (OR7) R6, CONR6R7 , aryl, heteroaryl and heterocyclyl, or C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-8 cycloalkyl, C5-8 cycloalkenyl, C4-12 cycloalkylalkyl or C6-10 cycloalkenyl alkyl, each optionally substituted with between 1 and 3 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O) nR13, COR15, CO2R15, OC (O) R13, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R13, NR16R15, CONR16R15, aryl, heteroaryl and heterocyclyl; R4 is independently selected in each case from: C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-6 cycloalkyl, C4-12 cycloalkylalkyl, NO2, halo, CN, C1-4 haloalkyl, NR6R7, NR8COR7 , NR8CO2R7, COR7, OR7, CONR6R7, CO (NOR9) R7, CO2R7, or S (O) nR7, where each of such C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-6 cycloalkyl and cycloalkylalkyl alkyl C4-12 are optionally substituted with between 1 and 3 substituents independently selected in each case from C1-4 alkyl, NO2, halo, CN, NR6R7, NR8COR7, NR8CO2R7, COR7, OR7, CONR6R7, CO2R7, CO (NOR9) R7 , or S (O) nR7; R6 and R7, R6a and R7a are independently selected in each case from -H, C1-10 alkyl, C3-10 alkenyl, C3-10 alkynyl, C1-10 haloalkyl with 1-10 halogens, C2-8 alkoxyalkyl, cycloalkyl C3-6, C4-12 cycloalkylalkyl, C5-10 cycloalkenyl, or C6-14 cycloalkenyl alkyl, each optionally substituted with between 1 and 3 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O) nR13, COR15, CO2R15, OC (O) R13, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R13, NR16R15, CONR16R15, aryl, heteroaryl or heterocyclyl, - aryl, aryl (C1-4 alkyl), heteroaryl, heteroaryl (C1-4 alkyl), heterocyclyl or heterocyclyl (C1-4 alkyl), alternatively, NR6R7 and NR6aR7a independently piperidine, pyrrolidine, piperazine, N-methylpiperazine, morpholine or thiomorpholine, each optionally substituted with 1-3 C1-4 alkyl groups; R8 is independently selected in each case from H or C1-4 alkyl; R9 and R10 are independently selected in each case from H, C1-4 alkyl, or C3-6 cycloalkyl; R11 is selected from C1-4 alkyl, C1-4 haloalkyl, or C3-6 cycloalkyl; R12 is C1-4 alkyl or C1-4 haloalkyl; R13 is selected from C1-4 alkyl, C1-4 haloalkyl, C2-8 alkoxyalkyl, C3-6 cycloalkyl, C4-12 cycloalkylalkyl, aryl, aryl (C1-4 alkyl) -, heteroaryl or heteroaryl (C1-4 alkyl) - ; R14 is selected from C1-10 alkyl, C3-10 alkenyl, C3-10 alkynyl, C3-8 cycloalkyl or C4-12 cycloalkylalkyl, each optionally substituted with between 1 and 3 substituents independently selected in each case from C1- alkyl 6, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O) nR15, COR15, CO2R15, OC (O) R15, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R15, NR16R15, CONR16R15, and C1-6 alkylthio, C1-6 alkylsulfinyl and C1-6 alkylsulfonyl; R15 and R16 are independently selected in each case from H, C1-6 alkyl, C3-10 cycloalkyl, C4-16 cycloalkylalkyl, except that for S (O) nR15, R15 cannot be H; aryl is phenyl or naphthyl, each optionally substituted with between 1 and 5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O ) nR15, COR15, CO2R15, OC (O) R15, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R15, NR16R15, and CONR16R15; heteroaryl is pyridyl, pyrimidinyl, triazinyl, furanyl, pyranyl, quinolinyl, isoquinolinyl, thienyl, imidazolyl, thiazolyl, indolyl, pyrrolyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, isoxazolyl, pyrazolyl, 2,3-dihydrobenzothienyl or 2,3-dihydrobenzofuranyl, each optionally substituted with between 1 and 5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O) nR15, -COR15, CO2R15, OC (O) R15, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R15, NR16R15, and CONR16R15; heterocyclyl is saturated or partially saturated heteroaryl, optionally substituted with between 1 and 5 substituents independently selected in each case from C1-6 alkyl, C3-6 cycloalkyl, halo, C1-4 haloalkyl, cyano, OR15, SH, S (O ) nR15, COR15, CO2R15, OC (O) R15, NR8COR15, N (COR15) 2, NR8CONR16R15, NR8CO2R15, NR15R16, and CONR16R15; n is independently in each case 0, 1 or 2, provided that: (A) when R is H, and Z is CR2, Ar is not phenyl or substituted phenyl; (B) when Z is CR2, then R2 is not -NR6SO2R7 or -SO2NR6R7; (C) when R is H, Z is CR2, R1 is OR11, R2 is H, R3 is OR7, and R7 and R11 are both H, then Ar is not pyridyl or naphthyl; (D) when R1 is - (C1-2 alkyl) -O- (C1-2 alkyl) or - (C1-2 alkyl) -OH, then at least one of the following conditions is met (i), (ii ) and (iii): (i) that the compound is a compound of formula (2); (ii) that Ar is selected from naphthyl, triazinyl, furanyl, thienyl, benzothienyl, benzofuranyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, indanyl, 1,2-benzopyranyl, 3,4-dihydro-1,2- benzopyranyl, and optionally substituted tetralinyl; (iii) that R3 is selected from H, SH, S (O) nR13 where n = 1, CO2R7, OC (O) R13, NR8COR7, N (COR7) 2, NR8CONR6R7, NR8CO2R13, N (OR7) R6, CONR6R7 , aryl other than optionally substituted phenyl, heteroaryl other than (a) optionally substituted pyrazinyl, (b) optionally substituted pyrimidyl or (c) optionally substituted pyrazizyl or heterocyclyl; and (E) when R3 is C5-8 cycloalkenyl or C6-10 cycloalkenyl alkyl, then at least one of the following conditions (i), (ii) and (iii) is met: (i) that the compound is a compound of formula (2); (ii) that Ar is selected from naphthyl, triazinyl, furanyl, thienyl, benzothienyl, benzofuranyl, 2,3-dihydrobenzofuranyl, 2,3-dihydrobenzothienyl, indanyl, 1,2-benzopyranyl, 3,4-dihydro-1,2- benzopyranyl, and optionally substituted tetralinyl; (iii) that R1 is selected from C2-4 alkenyl, C2-4 alkynyl, CN, C1-4 haloalkyl, C3-12 hydroxyalkyl, C4-12 alkoxyalkyl other than - (C1-2 alkylene) -O- (C1- alkyl 2), C2-10 cyanoalkyl, C3-6 cycloalkyl, C4-10 cycloalkylalkyl, C1-4-NR9R10 alkyl, NR9COR16, OR11, SH or S (O) nR12. The pharmaceutical compositions comprising said compounds and their use in the manufacture of medicaments for the treatment of an affective disorder, anxiety, depression, headache, irritable bowel syndrome, post-traumatic stress disorder, paralysis are also described. progressive supranuclear, immune suppression, Alzheimer's disease, gastrointestinal diseases, anorexia nervosa or other eating disorders, drug addiction, drug or alcohol withdrawal syndrome, inflammatory diseases, fertility problems, human immunodeficiency virus infections, stress hemorrhagic, obesity, infertility, brain and spinal trauma, epilepsy, stroke, ulcers, amyotrophic lateral sclerosis, hypoglycemia or a disorder whose treatment can be effected or facilitated by antagonizing the CRF, including but not limited to disorders induced or facilitated by the CRF , in mammals.

ARP050102868A 1996-07-24 2005-07-11 COMPOUND DERIVED FROM PIRAZOLO-PYRIMIDINE, PHARMACEUTICAL COMPOSITION AND THE USE OF SUCH COMPOUND IN THE MANUFACTURE OF MEDICINES AR049583A2 (en)

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US68604796A 1996-07-24 1996-07-24
US2329096P 1996-07-24 1996-07-24
US08/899,242 US6124289A (en) 1996-07-24 1997-07-23 Azolo triazines and pyrimidines

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