AR030022A1 - NEW COMPOUNDS, PHARMACEUTICAL COMPOSITIONS OF THE SAME, TREATMENT METHOD, USE AND PREPARATION OF THEM - Google Patents

NEW COMPOUNDS, PHARMACEUTICAL COMPOSITIONS OF THE SAME, TREATMENT METHOD, USE AND PREPARATION OF THEM

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Publication number
AR030022A1
AR030022A1 ARP000102461A ARP000102461A AR030022A1 AR 030022 A1 AR030022 A1 AR 030022A1 AR P000102461 A ARP000102461 A AR P000102461A AR P000102461 A ARP000102461 A AR P000102461A AR 030022 A1 AR030022 A1 AR 030022A1
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AR
Argentina
Prior art keywords
alkyl
aryl
heteroaryl
acyl
ring
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ARP000102461A
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Spanish (es)
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Biovitrum Ab
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Publication of AR030022A1 publication Critical patent/AR030022A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-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
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-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
    • C07D241/20—Nitrogen atoms
    • 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
    • C07D405/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Abstract

La invencion se relaciona con compuestos de la formula general (1) donde Ar es arilo o heteroarilo, que puede estar independientemente sustituido en una o más posiciones por C1-6 alquilo, C1-6 alcoxilo, C1-6 alquiltio, C1-6 acilo, C1-6 alquilsulfonilo, ciano, nitro, hidroxilo, C2-6 alquenilo, C2-6 alquinilo, fluorometilo, difluorometilo, trifluorometilo, difluorometoxilo, trifluorometoxilo, difluorometiltiol, trifluorometiltiol, halogeno, -N(R2)(R3), arilo, ariloxilo, ariltio, aril-C1-4 alquilo, arilûC2-4 alquenilo, arilûC2-4 alquinilo, heterociclilo, heterocicloxilo, heterocicliltio, heterociclil-C1-4 alquilo, donde los residuos arilo y heterociclilo están opcionalmente sustituidos en una o más posiciones independientemente de cada una por halogeno, C1-6 alquilo, C1-6 alcoxilo, C1-6alquiltio, C1-6 acilo, C1-6 alquilsulfonilo, nitro, trifluorometilo, trifluorometiltio, ciano, hidroxi, amino, C1-6 alquilamino o di(C1-6 alquil)amino; A es (i) ûCl, -O-, -S-, -SO2-, -NH -, (ii) un átomo de nitrogeno sustituido con C1-4 alquilo o C1-6 arilo, o (iii) una cadena de C1-8 alquileno o una cadena de heteroalquileno con 2 a 8 átomos en la cadena, que opcionalmente contiene por lo menos una insaturacion, donde C1-8 alquileno y heteroalquileno puede ser independientemente sustituido en una o más posiciones por C1-4 alquilo, trifluorometil u oxo, y donde dos átomos de la cadena yuxtapuestos o espaciados en el C1-8 alquileno o heteroalquileno están unidos opcionalmente a través de un puente alquileno con cadena de 1 a 5 átomos de carbono o un puente heteroalquileno con una cadena de 2 a 5 átomos, a dos átomos de la cadena separados en el C1-8 alquileno o el heteroalquileno opcionalmente están unidos a través de una union puente para formar un anillo carbocíclico saturado o parcialmente a completamente insaturado con 3 a 8 miembros en el anillo. B es ûC(R4)(R5) -, -OC(R4)(R5) -, -N(R6)C(R4)(R5)-, -N(R6)-, -O-, -S- o ûSO2, R es un C3-8 cicloalquilo, arilo o heteroarilo, cada uno de los cuales puede ser sustituido en una o más posiciones independientemente de cada una de las otras por C1-6 alquilo, C1-6 alcoxi, C1-6 alquiltio, fluorometilo, difluorometilo, trifluorometilo, difluorometoxi, difluorometiltio, trifluorometoxi, trifluorometiltio, halogeno, hidroxi, nitro, ciano, trifluorometilsulfoniloxi, metansulfonamida, C2-6 alquenilo, C2-6 alquinilo, C1-6 acilo, C1-6 alquilcarbonilo, C1-6alquilo, C1-6 alquiltio, C1-6 alquilsulfonilo, C1-6 alquilsulfoniloxi, C1-6 alquiloxi-C1-6 alquilo, C1-6 alquiloxicarbonilo, C1-6 alquiloxicarbonil-C1-6, alquilo, C1-6aciloxi-C1-6 alquilo, hidroxi-C1-6alquilo, C3-8-cicloalquilo, arilo ariloxi, ariltio, arilsulfonilo, aril-C1-6 acilo, aril-C1-6 alquilo, aril-C2-6, alquenilo, aril-C2-6 alquinilo, heteroarilC1-6 alquilo, heteroaril-C2-6 alquenilo, heteroaril-C2-6 alquinilo, heterociclilo, heterocicliloxi, heterocicliltio, heteociclilsulfonilo, heterociclilamino, heterociclil-C1-6 acilo, N(R2)(R3), -CON(R7)(R8) o (cuando R es C3-8cicloalquilo)oxo, donde cualquier residuo cicloalquilo, arilo, heteroarilo y heterociclilo a su vez puede ser sustituido en una o más posiciones independientemente cada una de la otra por C1-6alquilo, alcoxi, metansulfonamida, C1-6 alquiltio, C1-6alquilsulfonilo, C1-6 acilo, aril C1-6 acilo, heterocicliloxi, heterocicliltio, ariloxi, ariltio, fluorometilo, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, difluorometiltio, trifluorometiltio, halogeno, hidroxi, nitro, ciano, N(R2)(R3) o (para cicloalquilo) oxo; R1 es (i) un anillo azacíclico o aminoazacíclico saturado o insaturado, o un anillo saturado diazacíclico o aminodiazacíclico, que tiene cuyo anillo tiene de 4 a 7 miembros, o un anillo aminoazabicíclico saturado, azabicíclico o diazabicíclico que tiene de 7 a 10 miembros en el anillo, cuyos anillos mono o bicíclicos pueden ser mono o disustituidos en una o más posiciones independientemente cada una de la otra por C1-6 alquilo, C3-6alquenilo, C1-6 alcoxi, fluorometilo, trifluorometilo, difluorometilo, oxo, halogeno, hidroximetilo, C1-6-2-hidroxietilo (preferiblemente unido a un átomo de nitrogeno del anillo), 2-cianoetilo (preferiblemente unido a un grupo de nitrogeno del anillo), o unido a un átomo de nitrogeno del anillo, C1-6 acilo, aril-C1-6 acilo, heteroaril-C1-6 acilo, arilcarbonilo, heteroarilcarbamoilo, C1-4 ûalcoxicarbonilo, tetrahidropiránû2-ilo, y donde un anillo azacíclico saturado puede contener un heteroátomo adicional o (ii) un grupo û[C(R4)(R5)]xN(R2)(R3); R2 y R3 independientemente cada uno del otro son hidrogeno, C1-6 alquilo, C1-6 acilo, -CON(R7)(R8), arilo, heteroarilo, aril-C1-6 alquilo, heteroaril C1-6 alquilo, aril-C1-6 acilo o heteroaril-C1-6 acilo, donde cualquier residuo arilo y heteroarilo puede a su vez ser sustituido en una o más posiciones independientemente cada una de la otra por halogeno, C1-6 alquilo, C1-6 alcoxi, C1-6 alquiltio C1-6 alquilsulfonilo, C1-6 acilo, metansulfonamida, nitro, ciano, hidroxi, trifluorometilo, difluorometoxi, difluorometiltio, trifluorometoxi, trifluorometiltio, C2-4 alquenilo, C2-4 alquinilo o ûN(R2)(R3); o R2 y R3 junto con el átomo de nitrogeno a al cual ellos están unidos forman un anillo heterocíclico saturado con 4 û 7 miembros en el anillo y que opcionalmente contiene un heteroátomo adicional, cuyo anillo puede ser sustituido por C1-6 alquilo u oxo; R4 y R5 independientemente cada una de la otra, e independientemente de cada átomo de carbono sustituido, son hidrogeno o C1-6 alquilo; R6 es hidrogeno o C1-6 alquilo; R7 y R8 independientemente cada una de la otra son hidrogeno, C1-6 alquilo, arilo, heteroarilo, aril-C1-4 alquilo o heteroaril C1-4 alquilo, donde los residuos arilo y heteroarilo, aril-C1-4 alquilo heteroaril-C1-2 alquilo, donde los residuos arilo y heteroarilo pueden a la vez ser sustituidos en una o más posiciones independientemente cada una de la otra por halogeno, C1-6 alquilo, C1-6 alcoxi, C1-6 alquiltio, C1-6 alquilsulfonilo, C1-6 acilo, metansulfonamida, nitro, ciano, hidroxi, trifluorometilo, difluorometoxi, difluorometiltio, trifluorometoxi, trifluorometiltio, C2-4 alquenilo, C2-4 alquinilo o ûN(R2)(R3) o R7 y R8 junto con el átomo de nitrogeno al cual ellos están unidos forman un anillo heterocíclico saturado que tiene 4 û7 miembros en el anillo y opcionalmente contiene un heteroátomo adicional: n es 0 o 1, y x es 2, 3 o 4; con la condicion de que (i) cuando ûA-R es fenoxi o feniltio, entonces Ar es distinto de quinoxalinilo o piridilo, y (ii) cuando A es etenileno, entonces Ar es distinto de quinoxalinilo y sales aceptables para uso farmacéutico, hidratos y formas prodroga de las mismas. Los compuestos se pueden preparar por métodos convencionales y se pueden utilizar para el tratamiento de un sujeto humano o animal afectado por un trastorno relacionado con la serotonina, por ejemplo trastornos de la alimentacion, especialmente la obesidad, dolor, disfunciones sexuales y trastornos urinarios. También se relaciona con dicho uso y con composiciones farmacéuticas que comprende un compuesto de formula (1).The invention relates to compounds of the general formula (1) wherein Ar is aryl or heteroaryl, which may be independently substituted in one or more positions by C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, C1-6 acyl , C1-6 alkylsulfonyl, cyano, nitro, hydroxyl, C2-6 alkenyl, C2-6 alkynyl, fluoromethyl, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthiol, trifluoromethylthiol, halogen, -N) , arylthio, aryl-C1-4 alkyl, aryl arC2-4 alkenyl, arylûC2-4 alkynyl, heterocyclyl, heterocycloxyl, heterocyclyl, heterocyclyl-C1-4 alkyl, where aryl and heterocyclyl residues are optionally substituted at one or more positions independently of each one per halogen, C1-6 alkyl, C1-6 alkoxy, C1-6alkylthio, C1-6 acyl, C1-6 alkylsulfonyl, nitro, trifluoromethyl, trifluoromethylthio, cyano, hydroxy, amino, C1-6 alkylamino or di (C1-6 alkyl) amino; A is (i) ûCl, -O-, -S-, -SO2-, -NH -, (ii) a nitrogen atom substituted with C1-4 alkyl or C1-6 aryl, or (iii) a C1 chain -8 alkylene or a heteroalkylene chain with 2 to 8 atoms in the chain, which optionally contains at least one unsaturation, where C1-8 alkylene and heteroalkylene can be independently substituted in one or more positions by C1-4 alkyl, trifluoromethyl or oxo, and where two chain atoms juxtaposed or spaced on the C1-8 alkylene or heteroalkylene are optionally linked through an alkylene bridge with a chain of 1 to 5 carbon atoms or a heteroalkylene bridge with a chain of 2 to 5 atoms , to two chain atoms separated in the C1-8 alkylene or the heteroalkylene are optionally linked through a bridge bond to form a saturated or partially to completely unsaturated carbocyclic ring with 3 to 8 ring members. B is ûC (R4) (R5) -, -OC (R4) (R5) -, -N (R6) C (R4) (R5) -, -N (R6) -, -O-, -S- or ûSO2, R is a C3-8 cycloalkyl, aryl or heteroaryl, each of which can be substituted in one or more positions independently of each other by C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, fluoromethyl, difluoromethyl, trifluoromethyl, difluoromethoxy, difluoromethylthio, trifluoromethoxy, trifluoromethylthio, halogen, hydroxy, nitro, cyano, trifluoromethylsulfonyloxy, methanesulfonamide, C2-6 alkenyl, C2-6 alkynyl, C1-6alkylalkyl, C1-6alkylalkyl C1-6 alkylthio, C1-6 alkylsulfonyl, C1-6 alkylsulfonyloxy, C1-6 alkyloxy-C1-6 alkyl, C1-6 alkyloxycarbonyl, C1-6 alkyloxycarbonyl-C1-6, alkyl, C1-6 acyloxy-C1-6 alkyl, hydroxy-C1-6alkyl, C3-8-cycloalkyl, aryl aryloxy, arylthio, arylsulfonyl, aryl-C1-6 acyl, aryl-C1-6 alkyl, aryl-C2-6, alkenyl, aryl-C2-6 alkynyl, heteroarylC1- 6 alkyl, heteroaryl-C2-6 alkenyl, heteroaryl-C2-6 alkynyl, heterocyclyl, heteroc icyloxy, heterocyclylthio, heterocyclylsulfonyl, heterocyclylamino, heterocyclyl-C1-6 acyl, N (R2) (R3), -CON (R7) (R8) or (when R is C3-8cycloalkyl) oxo, where any cycloalkyl, aryl, heteroaryl residue and heterocyclyl in turn can be substituted in one or more positions independently of each other by C1-6alkyl, alkoxy, methanesulfonamide, C1-6 alkylthio, C1-6alkylsulfonyl, C1-6 acyl, aryl C1-6 acyl, heterocyclyloxy, heterocyclylthio, aryloxy, arylthio, fluoromethyl, difluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, halogen, hydroxy, nitro, cyano, N (R2) (R3) or (for cycloalkyl) oxo; R1 is (i) a saturated or unsaturated azacyclic or aminoazacyclic ring, or a saturated diazacyclic or aminodiazacyclic ring, which has a ring having 4 to 7 members, or a saturated, azabicyclic or diazabicyclic aminoazabicyclic ring having 7 to 10 members in the ring, whose mono or bicyclic rings can be mono or disubstituted in one or more positions independently of each other by C1-6 alkyl, C3-6alkenyl, C1-6 alkoxy, fluoromethyl, trifluoromethyl, difluoromethyl, oxo, halogen, hydroxymethyl , C1-6-2-hydroxyethyl (preferably attached to a ring nitrogen atom), 2-cyanoethyl (preferably attached to a ring nitrogen group), or attached to a ring nitrogen atom, C1-6 acyl, aryl-C1-6 acyl, heteroaryl-C1-6 acyl, arylcarbonyl, heteroarylcarbamoyl, C1-4 coalkoxycarbonyl, tetrahydropyranû2-yl, and where a saturated azacyclic ring may contain an additional heteroatom or (ii) a group û [C (R4) (R5)] xN (R2) (R 3); R2 and R3 independently of each other are hydrogen, C1-6 alkyl, C1-6 acyl, -CON (R7) (R8), aryl, heteroaryl, aryl-C1-6 alkyl, heteroaryl C1-6 alkyl, aryl-C1 -6 acyl or heteroaryl-C1-6 acyl, where any aryl and heteroaryl residue can in turn be substituted in one or more positions independently of each other by halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 C1-6 alkylthio sulfonyl, C1-6 acyl, methanesulfonamide, nitro, cyano, hydroxy, trifluoromethyl, difluoromethoxy, difluoromethylthio, trifluoromethoxy, trifluoromethylthio, C2-4 alkenyl, C2-4 alkynyl or ûN (R2) (R3) (R3) (R3) (R3) (R3); or R2 and R3 together with the nitrogen atom to which they are attached form a saturated heterocyclic ring with 4 û 7 members in the ring and optionally contains an additional heteroatom, the ring of which may be substituted by C1-6 alkyl or oxo; R4 and R5 independently of each other, and independently of each substituted carbon atom, are hydrogen or C1-6 alkyl; R6 is hydrogen or C1-6 alkyl; R7 and R8 independently of each other are hydrogen, C1-6 alkyl, aryl, heteroaryl, aryl-C1-4 alkyl or heteroaryl C1-4 alkyl, where aryl and heteroaryl residues, aryl-C1-4 alkyl heteroaryl-C1 -2 alkyl, where the aryl and heteroaryl residues can be substituted at one or more positions independently from each other by halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, C1-6 alkylsulfonyl, C1-6 acyl, methanesulfonamide, nitro, cyano, hydroxy, trifluoromethyl, difluoromethoxy, difluoromethylthio, trifluoromethoxy, trifluoromethylthio, C2-4 alkenyl, C2-4 alkynyl or ûN (R2) (R3) or R7 and R8 nitrogen with the atom to which they are attached form a saturated heterocyclic ring that has 4 û7 members in the ring and optionally contains an additional heteroatom: n is 0 or 1, and x is 2, 3 or 4; with the proviso that (i) when ûA-R is phenoxy or phenylthio, then Ar is different from quinoxalinyl or pyridyl, and (ii) when A is ethenylene, then Ar is different from quinoxalinyl and salts acceptable for pharmaceutical use, hydrates and prodrug forms of them. The compounds can be prepared by conventional methods and can be used for the treatment of a human or animal subject affected by a serotonin-related disorder, for example eating disorders, especially obesity, pain, sexual dysfunctions and urinary disorders. It also relates to said use and pharmaceutical compositions comprising a compound of formula (1).

ARP000102461A 1999-05-21 2000-05-19 NEW COMPOUNDS, PHARMACEUTICAL COMPOSITIONS OF THE SAME, TREATMENT METHOD, USE AND PREPARATION OF THEM AR030022A1 (en)

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JP4960085B2 (en) * 2003-03-19 2012-06-27 エクセリクシス， インク． TIE-2 modulator and usage
CL2004000826A1 (en) * 2003-04-25 2005-03-04 Pfizer USE OF AN AGONIST FOR THE 5-HT2C RECEPTOR TO PREPARE A USEFUL MEDICINAL PRODUCT IN THE TREATMENT OF URINARY INCONTINENCE CAUSED BY STRESS, WITH THE CONDITION THAT THE AGONIST IS NOT 1- [6-CHLORINE-5- (TRIFLUOROMETIL) -2- PIRIDINIL] PIPERAZINA (ORG-129
KR101270841B1 (en) * 2005-02-28 2013-06-05 가부시키가이샤 메이지 Hydroquinone long-chain derivatives and/or phenoxy long-chain derivatives, and pharmaceuticals comprising the same
EP1939189A4 (en) * 2005-08-26 2013-03-13 Shionogi & Co Derivative having ppar agonistic activity
JP6635999B2 (en) * 2017-10-13 2020-01-29 株式会社ダイセル Method for producing potassium salt, and potassium salt

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