AR046638A1 - QUINOLONA ANTIBACTERIAL AGENTS - Google Patents

QUINOLONA ANTIBACTERIAL AGENTS

Info

Publication number
AR046638A1
AR046638A1 ARP040104261A ARP040104261A AR046638A1 AR 046638 A1 AR046638 A1 AR 046638A1 AR P040104261 A ARP040104261 A AR P040104261A AR P040104261 A ARP040104261 A AR P040104261A AR 046638 A1 AR046638 A1 AR 046638A1
Authority
AR
Argentina
Prior art keywords
alkyl
independently
heteroaryl
aryl
unsubstituted
Prior art date
Application number
ARP040104261A
Other languages
Spanish (es)
Original Assignee
Warner Lambert Co
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 Warner Lambert Co filed Critical Warner Lambert Co
Publication of AR046638A1 publication Critical patent/AR046638A1/en

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Classifications

    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La presente se refiere a agentes antibacterianos de quinolona, una composición farmacéutica que los comprende, y usos. Reivindicación 1: Un compuesto de fórmula (1), o una sal farmacéuticamente aceptable del mismo, donde: X es N o C, con la condición de que cuando X sea N, R5 esté ausente en esa posición; R1 es alquilo C1-6; halo-alquilo C1-6; cicloalquilo C3-6; halo-cicloalquilo C3-6; heterociclilo; arilo; heteroarilo; y CH2-cicloalquilo C3-6; R2 es OH; OBF2; O-alquilo C1-6; O- cicloalquilo C3-6; O-(CHR2a)m-O-C(=O)-QR2b, donde m es un número entero de 1 a 10, Q es O ó NH o N-alquilo C1-6 o está ausente, y R2a es H o alquilo C1-6 y R2b es alquilo C1-6, arilo o heteroarilo; O-(CHR2a)n-Y donde R2a es como se ha definido anteriormente, n es un número entero de 2 a 10, Y es OH o NR2cR2d, donde cada uno de R2c y R2d es independientemente H, alquilo C1-6 o cicloalquilo C3-6; o NR2a, donde R2a es como se ha definido anteriormente; o un grupo de fórmula (2), donde "la línea zig-zag" indica el punto de unión, R2a es como se ha definido anteriormente, cada uno de R2e y R2e' es independientemente H o alquilo C1-6 o tomados junto con el átomo de carbono al que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido, e es un número entero de 1 a 10, p es un número entero de 2 a 10 y cada uno de X1 e Y1 es independientemente NH ó O; cada uno de R3, R4, y R5 independientemente H; OH; halo; NRyRz, donde cada uno de Ry y Rz es independientemente H o alquilo C1-6; alquilo C1-6; halo-alquilo C1-6; O-alquilo C1-6; O-haloalquilo C1-6; nitrilo; R1 y R5 tomados junto con los carbonos a los que están unidos forman un anillo de 5 ó 6 miembros sustituido o no sustituido que contiene 0, 1 ó 2 heteroátomos seleccionados entre O, S, SO, SO2 o NRx, donde Rx es H o alquilo C1-6; y A es un compuesto seleccionado de las fórmulas (3) a (5), donde z es 0, 1 ó 2 y q es 0, 1, 2 ó 3; cada uno de Ra y Rb es independientemente H, alquilo C1-6, alcoxi C1-6, halo-alquilo C1-6, halo, o Ra y Rb tomados junto con el carbono al que están unidos forman C=O, C=NO-alquilo C1-6, o un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido; cada uno de R', R'', R''' y R'''' es independientemente H; alquilo C1-6; -O-alquilo C1-6; halo-alquilo C1-6; arilo; o heteroarilo; y B es un compuesto seleccionado de las fórmulas (6) a (8), con la condición de que cuando B sea un compuesto de fórmula (8) en un compuesto de fórmula (9) o fórmula (4), R' no sea -O-alquilo C1-6, y donde "la línea zig-zag" indica el punto de unión; cada uno de Rc y Rd es independientemente H; alquil C1-6-nitrilo; -P(=O)-(OH)2; -P(=O)-(Oalquilo C1-6)2; alquilo C1-6; cicloalquilo C3-6; heteroarilo; SO2- alquilo C1-6; SO2-arilo; SO2-heteroarilo; -(CR2aR2a')g-O-C(=O)-QR2b, donde g es un número donde g es un número entero de 1 a 10, Q es como se ha definido anteriormente y cada uno de R2a y R2a' es independientemente H o alquilo C1-6, o tomados junto con los carbonos a los que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido, y R2b es alquilo C1-6, arilo o heteroarilo; (CR2aRa2')g-O-P(=O)-(OH)2 o (CR2aR2a')g-O-P(=O)-(Oalquilo C1-6)2, donde R2a y R2a' son como se han definido anteriormente, o un compuesto de fórmula (10), donde "la línea zig-zag" indica el punto de unión, p es 0 ó 1 y R2c es H; alquilo C1-6; O-alquilo C1-6; cicloalquilo C3-7; arilo; heterociclo; heteroarilo; o -(CHR2a)h-O-C(=O)-QR2b o - (CHR2a)j-Y, donde R2a, R2b y Q son como se han definido anteriormente, y cada uno de h y j son independientemente números enteros de 0 a 10, e Y es OH, OPO(OH)2, OPO(OC1-6)2 o NR2dR2e, donde cada uno de R2d y R2e es independientemente H, alquilo C1- 6 o cicloalquilo C3-7, o un compuesto de fórmula (11), donde q es 0 ó 1, cada uno de R2f y R2r es independientemente H, alquilo C1-6, arilo o heteroarilo, o tomados junto con el carbono al que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido, y R2g es alquilo C1-6; cicloalquilo C3-7; arilo; o heterociclo; o heteroarilo; cada uno de Re y Rf es independientemente H, alquilo C1-6, haloalquilo, halo, o Re y Rf tomados junto con el carbono al que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituidos o no sustituido; cada uno de Rg y Rh es independientemente H, alquilo C1-6, haloalquilo, o tomados junto con el carbono al que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido; y cada uno de Rj y Rk es independientemente H, alquilo C1-6, haloalquilo, alquil C1-6-NRcRd, alquil C1-6-ORc, arilo, heteroarilo, heterociclo, alquilo C1-6-C(=O)-Z-Rd, donde Z es O ó NRc, o Rj y Rk tomados junto con el carbono al que están unidos forman un anillo de 3, 4, 5 ó 6 miembros sustituido o no sustituido.This refers to quinolone antibacterial agents, a pharmaceutical composition comprising them, and uses. Claim 1: A compound of formula (1), or a pharmaceutically acceptable salt thereof, wherein: X is N or C, with the proviso that when X is N, R5 is absent in that position; R1 is C1-6 alkyl; halo C1-6 alkyl; C3-6 cycloalkyl; C3-6 halocycloalkyl; heterocyclyl; aryl; heteroaryl; and CH2- C3-6 cycloalkyl; R2 is OH; OBF2; C 1-6 alkyl; C3-6 O-cycloalkyl; O- (CHR2a) mOC (= O) -QR2b, where m is an integer from 1 to 10, Q is O or NH or N-C1-6 alkyl or is absent, and R2a is H or C1-6 alkyl and R2b is C1-6 alkyl, aryl or heteroaryl; O- (CHR2a) nY where R2a is as defined above, n is an integer from 2 to 10, Y is OH or NR2cR2d, where each of R2c and R2d is independently H, C1-6 alkyl or C3- cycloalkyl 6; or NR2a, where R2a is as defined above; or a group of formula (2), where "the zigzag line" indicates the point of attachment, R2a is as defined above, each of R2e and R2e 'is independently H or C1-6 alkyl or taken together with the carbon atom to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring, e is an integer from 1 to 10, p is an integer from 2 to 10 and each of X1 e Y1 is independently NH or O; each of R3, R4, and R5 independently H; OH; halo; NRyRz, where each of Ry and Rz is independently H or C1-6 alkyl; C1-6 alkyl; halo C1-6 alkyl; C 1-6 alkyl; C1-6 O-haloalkyl; nitrile; R1 and R5 taken together with the carbons to which they are attached form a substituted or unsubstituted 5 or 6-membered ring containing 0, 1 or 2 heteroatoms selected from O, S, SO, SO2 or NRx, where Rx is H or C1-6 alkyl; and A is a compound selected from formulas (3) to (5), where z is 0, 1 or 2 and q is 0, 1, 2 or 3; each of Ra and Rb is independently H, C1-6 alkyl, C1-6 alkoxy, halo- C1-6 alkyl, halo, or Ra and Rb taken together with the carbon to which they are attached form C = O, C = NO -C1-6 alkyl, or a substituted or unsubstituted 3, 4, 5 or 6-membered ring; each of R ', R' ', R' '' and R '' '' is independently H; C1-6 alkyl; -O-C 1-6 alkyl; halo C1-6 alkyl; aryl; or heteroaryl; and B is a compound selected from formulas (6) to (8), with the proviso that when B is a compound of formula (8) in a compound of formula (9) or formula (4), R 'is not -O-C1-6 alkyl, and where "the zigzag line" indicates the point of attachment; each of Rc and Rd is independently H; C1-6 alkyl nitrile; -P (= O) - (OH) 2; -P (= O) - (C1-6 alkyl) 2; C1-6 alkyl; C3-6 cycloalkyl; heteroaryl; SO2- C1-6 alkyl; SO2-aryl; SO2-heteroaryl; - (CR2aR2a ') gOC (= O) -QR2b, where g is a number where g is an integer from 1 to 10, Q is as defined above and each of R2a and R2a' is independently H or C1 alkyl -6, or taken together with the carbons to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring, and R2b is C1-6 alkyl, aryl or heteroaryl; (CR2aRa2 ') gOP (= O) - (OH) 2 or (CR2aR2a') gOP (= O) - (C1-6 alkyl) 2, where R2a and R2a 'are as defined above, or a compound of formula (10), where "the zigzag line" indicates the point of attachment, p is 0 or 1 and R2c is H; C1-6 alkyl; C 1-6 alkyl; C3-7 cycloalkyl; aryl; heterocycle; heteroaryl; or - (CHR2a) hOC (= O) -QR2b or - (CHR2a) jY, where R2a, R2b and Q are as defined above, and each of h and j are independently integers from 0 to 10, and Y is OH , OPO (OH) 2, OPO (OC1-6) 2 or NR2dR2e, where each of R2d and R2e is independently H, C1-6 alkyl or C3-7 cycloalkyl, or a compound of formula (11), where q is 0 or 1, each of R2f and R2r is independently H, C1-6 alkyl, aryl or heteroaryl, or taken together with the carbon to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring, and R2g is C1-6 alkyl; C3-7 cycloalkyl; aryl; or heterocycle; or heteroaryl; each of Re and Rf is independently H, C1-6 alkyl, haloalkyl, halo, or Re and Rf taken together with the carbon to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring; each of Rg and Rh is independently H, C1-6 alkyl, haloalkyl, or taken together with the carbon to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring; and each of Rj and Rk is independently H, C1-6 alkyl, haloalkyl, C1-6-NRcRd alkyl, C1-6-ORc alkyl, aryl, heteroaryl, heterocycle, C1-6-C alkyl (= O) -Z -Rd, where Z is O or NRc, or Rj and Rk taken together with the carbon to which they are attached form a substituted or unsubstituted 3, 4, 5 or 6-membered ring.

ARP040104261A 2003-11-18 2004-11-18 QUINOLONA ANTIBACTERIAL AGENTS AR046638A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US52307103P 2003-11-18 2003-11-18
US60549604P 2004-08-31 2004-08-31

Publications (1)

Publication Number Publication Date
AR046638A1 true AR046638A1 (en) 2005-12-14

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ID=34623167

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP040104261A AR046638A1 (en) 2003-11-18 2004-11-18 QUINOLONA ANTIBACTERIAL AGENTS

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AR (1) AR046638A1 (en)
NL (1) NL1027545C2 (en)
PE (1) PE20050582A1 (en)
TW (1) TW200524930A (en)
UY (1) UY28622A1 (en)
WO (1) WO2005049602A1 (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101077755B1 (en) 2003-09-10 2011-10-27 교린 세이야꾸 가부시키 가이샤 7-(4-substituted 3-cyclopropylaminomethyl-1 pyrrolidinyl)quinolonecarboxylic acid derivative
ES2431050T3 (en) 2005-08-04 2013-11-22 Sirtris Pharmaceuticals, Inc. Benzothiazoles and thiazolopyridines as modulators of sirtuin
DE102006005861A1 (en) * 2006-02-09 2007-08-23 Aicuris Gmbh & Co. Kg Substituted quinolones III
CN101622240B (en) * 2007-01-05 2014-07-23 第一三共株式会社 Fused substituted aminopyrrolidine derivative
AU2007339692B2 (en) * 2007-01-05 2012-01-19 Daiichi Sankyo Company, Limited Fused substituted aminopyrrolidine derivative
JP5322927B2 (en) 2007-05-24 2013-10-23 杏林製薬株式会社 A mutilin derivative having a heteroaromatic carboxylic acid structure at the 14-position substituent.
DE102007036068A1 (en) * 2007-08-01 2009-02-05 Wacker Chemie Ag Process for the preparation of alkylmethoxymethyltrimethylsilanylmethylamines
CN102112440A (en) 2008-05-30 2011-06-29 武田药品工业株式会社 Heterocyclic compound
JP5263304B2 (en) 2009-02-06 2013-08-14 日本新薬株式会社 Aminopyrazine derivatives and medicines
AR091858A1 (en) 2012-07-25 2015-03-04 Sova Pharmaceuticals Inc CISTATIONIN-g-LIASA INHIBITORS (CSE)
EA035465B1 (en) 2015-06-09 2020-06-22 Байер Фарма Акциенгезельшафт 7-substituted 1-arylnaphthyridine-3-carboxamides as positive allosteric modulators of muscarinic m2 receptor, process for preparation thereof, use thereof for treatment and/or prevention of diseases and medicament comprising these compounds
CN109689654A (en) * 2016-07-11 2019-04-26 拜耳医药股份有限公司 1- pyridyl group-naphthyridines -3- benzamide type and application thereof that 7- replaces
EP3296298A1 (en) 2016-09-14 2018-03-21 Bayer Pharma Aktiengesellschaft 7-substituted 1-aryl-naphthyridin-3-carboxamides and their use
JOP20190045A1 (en) 2016-09-14 2019-03-14 Bayer Ag 7-substituted 1-aryl-naphthyridine-3-carboxylic acid amides and use thereof
EP3519392A1 (en) 2016-09-29 2019-08-07 Bayer CropScience Aktiengesellschaft Novel 5-substituted imidazole derivatives

Also Published As

Publication number Publication date
NL1027545C2 (en) 2006-01-17
PE20050582A1 (en) 2005-08-25
TW200524930A (en) 2005-08-01
UY28622A1 (en) 2005-06-30
WO2005049602A1 (en) 2005-06-02
NL1027545A1 (en) 2005-05-23

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