DK200201957A - 10-substituted erythromycin ketolides and methods of making - Google Patents

10-substituted erythromycin ketolides and methods of making Download PDF

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DK200201957A
DK200201957A DK200201957A DKPA200201957A DK200201957A DK 200201957 A DK200201957 A DK 200201957A DK 200201957 A DK200201957 A DK 200201957A DK PA200201957 A DKPA200201957 A DK PA200201957A DK 200201957 A DK200201957 A DK 200201957A
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previously defined
optionally substituted
heteroaryl
substituted
aryl
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DK200201957A
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Gunnes Soelvi
Undheim Kjell
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Alpharma Aps
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Priority to DK200201957A priority Critical patent/DK200201957A/da
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Priority to CA2509419A priority patent/CA2509419C/en
Priority to EP03782698A priority patent/EP1575970A2/en
Priority to PCT/GB2003/005659 priority patent/WO2004056843A2/en
Priority to US10/539,759 priority patent/US7608596B2/en
Priority to EP10010725.9A priority patent/EP2371833A3/en
Priority to EP10010724.2A priority patent/EP2354147A3/en
Priority to AU2003290339A priority patent/AU2003290339B8/en
Priority to CNA2003801069659A priority patent/CN1729200A/zh
Priority to CA2789415A priority patent/CA2789415C/en
Priority to US12/569,926 priority patent/US8076301B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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

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  • Animal Behavior & Ethology (AREA)
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  • Genetics & Genomics (AREA)
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Description

Claims 1. A compound having a formula chosen among the group consisting of L II, III, and IV,
Figure DK200201957AD00031
or being a salt, ester or prodrug thereof, wherein R is selected from the group consisting of (1) methyl substituted with one or more substituents selected from the group consisting of (i) CN, (ϋ) F, (iii) CO2R3 wherein R3 is selected from hydrogen, Ci-C3-alkyl or aryl substituted C\-C3-alkyl, or heteraryl substituted CrC3-alkyl, (iv) OR4 wherein R4 is selected from hydrogen, C|-C4-alkyl or aryl substituted Ci-Chalky!, or heteraryl substituted C|-C4-alkyl, heterocycloalkyl and optionally substituted cycloalky], C|-C3-alkoxy-Ci-C3-alkoxy, CrC-i-alkenyl or aryl substituted Ci-C^alkenyl, or heteraryl substituted Ci-Ci-alkenyi, heterocycloalkyl and optionally substituted cycloalkyl, aryl or optionally substituted aryl, heteroaryl or optionally substituted heteroaryl, (v) S(0)nR3 where n = 0, 1 or 2 and RJ is as previously defined (vi) NR4C(0)R3 wherein RJ and R4 are as previously defined (vii) NR4C(0)NR:iR6 wherein R4 is defined as defined previously, and R5 and R6 are independently selected from hydrogen, Ci-C3-alkyl, C4-C3 alkyl substituted with aryl, substituted aryl, heteroaryl, substituted heteroaryl (viii) NR7Rx wherein R7 and R8 are independently selected from the group consisting of (a) hydrogen (b) C]-Ci2-alkyl, and optionally substituted Ci-C 12-alkyl (c) Ci-Ci2-alkenyl, and optionally substituted Ci-Cn alkenyl (d) Ci-Ci2-alkynyl, and optionally substituted Ci-Ci2-alkynvl (e) aryl, and optionally substituted aryl (f) heteroaryl, and optionally substituted heteroaryl (g) heterocycloalkyl, and optionally substituted heterocvcloalkyl (h) C1-C12 alkyl substituted with aryl, and optionally substituted with substituted aryl (i) C1 -Cj2 alkyl substituted with heteroaryl, and optionally substituted with substituted heteroaryl (j) Ci-Cu-alkvl substituted with heterocycloalkyl, and with optionally substituted heterocycloalkyl, and (k) R7 and Rs taken together with the atom to which they are attached form a 3-10-membered heterocycloalkyl ring which may cointain one or more additional heteroatoms and may be substituted with one or more substituents independently selected from the group consisting of (aa) halogen, hydroxy, Ci-C;,-alkoxy, alkoxy-Ci-C3-alkoxy, oxo, C[-Cy alkyl, aryl and optionally substituted aryl, heteroaryl and optional substituted heteroaryl (bb) CO2R3 wherein R3 is as previously defined, and (cc) C(0)NR5R6 wherein R5 asnd R6 are as previously defined, (ix) aryl, and optionally substituted aryl, and (x) heteroaryl, and optionally substituted heteroaryl, (2) Cj-Cio-alkyl, (3) C2-Cio-alkyl substituted with one or more substituents selected from the group consisting of (i) halogen. (ii) OR4 wherein R4 is as defined previously (iii) -CHO. (iv) oxo. (v) NR7R8 wherein R7 and R8 are defined as previously (vi) =N-0-R4 is wherein RJ is as previously defined
(vii) -CN (viii) -S(0)nR3 wherein n = 0. 1 or 2 and RJ is as previously defined (ix) aryl, and optionally substituted aryl (x) heteroaryl, and optionally substituted heteroaryl (xi) C3-Cs-cycloalkyl, and optionally substituted Cs-Cs-cycloalkyl (xii) heterocycloalkvl, and optionally substituted cycloalkyl (xiii) NR4C(0)RJ where R3 and R4 are as previously defined (xiv) NR4C(0)NR3R6 wherein R4. R5 and R6 are as previously defined (xv) =N-NR7R8 wherein R7 and Rs are as previously defined (xvi) =N-R4 wherein R4 is as previously defined (xvii) =N-N4C(0)Rj wherein RJ and R4 are as previously defined, and (xviii) =N-NR4C(0)NRiR6 wherein R4. R^ and R6 are as previously defined, (4) C[-C|o-alkenyl, (5) Cj-Cio-alkenyl substituted with one or more substituents selected from the group consisting of (i) halogen, (ii) OR4 wherein R4 is as previously defined (iii) 0-S(0)"R3 where R3 is as previously defined (iv) -CHO, (v) oxo, (vi) -COjR3 where R3 is as previously defined (vii) -C(0)-R4 where R4 is as previously defined
(viii) -CN (ix) aryl, and optionally substituted aryl (x) heteroaryl, and optionally substituted heteroaryl (xi) C3-C7-cycloalkyl (xii) C i -Ci 2-alkyl substituted with heteroaryl (xiii) NR7R8 wherein R7 and R8 are as previously defined (xiv) NR4C(0)Rj where R3 and R4 are as previously defined (xv) NR4C(0)NR:iR6 where R4, R5 and R6 are as previously defined (xvi) =N-0-R4 where R4 is as previously defined (xvii) =N-NR7Rs wherein R7 and R8 are as previously defined (xviii) =N-NR4 wherein R4 is as previously defined (xix) =N-NR4C(0)R3 wherein R3 and R4 are as previously defined, and (xx) =N-NR4C(0)NR5R6 wherein R4, R3 and R6 are as previously defined, (6) Cz-Cio-alkynyl (7) C2-Cio-alkynyl substituted with one or more substituents selected from the group consisting of (i) trialkylsilyl (ii) halogen
(iii) -CN (iv) OR4 where R4 is defined as previously
(v) -CHO (vi) oxo (vii) CO2R3 where RJ is as previously defined (viii) -C(0)NR3R6 wherein R3 and R6 are as previously defined (ix) NR7R8 wherein R7 and R 8 are as previously defined (x) 0-S(0)nR3 where R3 is as previously defined (xi) C3-C7-cycloalkyl (xii) C1-Ci2-alkyl substituted with heteroaryl (xiii) aryl, and optionally substituted aryl (xiv) heteroaryl, and optionally substituted heteroaryl (xv) NR4C(0)R3 where R3 nd R4 are as previously defined (xvi) NR4C(0)NR5R6 where R4, R5 and R6 are as previously defined (xvii) =N-0-R4 where R4 is as previously defined (xviii) =N-NR7R8 wherein R7 and R8 are as previously defined (xix) =N-NR4C(0)R3 where RJ and R4 are as previously defined, and (xxi) =N-NR4C(0)NR5R6 wherein R4, R3 and R6 are as previously defined, (8) cyclic substituents (i) aryl, and optionally substituted aryl (ii) heteroaryl, and optionally substituted heteroaryl (iii) heterocycloalkvl, and optionally substituted heterocycloalkyl, and (iv) C3-C7-cvcloalkyl, and optionally substituted C3-C7-cycloalkyl, and (9) C| substituents with the exception of 10-methyl derivatives which are part of the above definitions under (1)
(i) -CHO
(ii) -CN (iii) COiR3 wherein RJ is as previously defined (iv) C(0)NR:'R6 wherein R5 and R6 are as previously defined (v) C^NR^R6 wherein R5 and R6 are as previously defined (vi) C(NR4)NRSNR6 where R4, N3 and R6 are as previously defined (vii) CH=N-0-R4 is wherein R4 is as previously defined (viii) CH=N-R4 wherein R4 is as previously defined (ix) CH=N-NR7R8 wherein R7 and R8 are as previously defined (x) CH=N-NR4C(0)R3 where RJ and R4 are as previously defined, and (xi) CH=N-NR4C(0)NR5R6 wherein R4, R5 and R6 are as previously defined; R1 is selected from the group consisting of
(1) H (2) methyl (3) methyl substituted with one or more substituents selected from the group consisting of
(i) F
(ii) -CN (iii) -CCFR11 where R11 is Ci-Ci-alkyl or aryl substituted Ci-Cj-alkyl, or heteroalkyl substituted Ci-Qs-alkyl (iv) -C(0)NRDR6 where R5 and R6 are defined as previously (v) aryl, and optionally substituted aryl, and (vi) heteroaryl, and optionally substituted heteroaryl, (4) C2-Cio-alkyl (5) substituted Ci-Cio-alkyl with one or more substituents selected from the group consisting of (i) halogen (ii) OR11 where R4 is defined as previously (iii) Ci-C3-aIkoxy-Ci-C3-alkoxy
(iv) -CHO (v) 0X0 (vi) NR7R8 wherein R7 and R8 are as defined previously (vii) =N-0-R4 is wherein R4 is as previously defined
(viii) -CN (ix) -S(0)nR wherein n = 0, 1 or 2 and RJ is as previously defined (x) aryl, and optionally substituted aryl (xi) heteroaryl, and optionally substituted heteroaryl (xii) C3-Cg-cycIoalkyl, and optionally substituted C3-Cg-cycloalkyl (xiii) Ci-Ci2-alkyl substituted with heteroaryl, and optionally substituted heteroarvl (xiv) heterocycloalkyl (xv) NHC(0)RJ where R3 is as previously defined (xvi) NHC(0)NR3R6 wherein R3 and R6 are as previously defined (xvii) =N-NR7R8 wherein R7 and R8 are as previously defined (xviii) =N-R4 wherein R4 as previously defined, and (xix) =N-NHC(0)RJ wherein R3 is 5and R6 are as previously defined. (4) C i-Cio-alkenvl substituted with one or more substituents selected from the group consisting of (i) halogen (ii) OR4 where R4 is as previously defined
(iii) -CHO (iv) oxo (v) 0-S(0)"R3 where R3 is as previously defined
(vi) -CN (vii) -COiR3 where R3 is as previously defined (viii) NR7R8 wherein R7 and Rs are as previously defined (ix) =N-0-R4 where R4 is as previously defined (x) -C(0)-R4 where R4 is as previously defined (xi) -C(0)NR5R6 wherein RD and R6 are as previously defined (xii) aryl, and optionally substituted aryl (xiii) heteroaryl, and optionally substituted heteroaryl (xiv) C3-C7-cycloalkyl (xv) C|-C|2-alk:yl substituted with heteroaryl (xvi) NHC(0)R3 where R3 is as previously defined (xvii) NHC(0)NR:>R6 where Rs and R5 are as previously defined (xviii) =N-NR R wherein R and R are as previously defined (xix) =N-NR4 wherein R4 is as previously defined (xx) =N-NHC(0)RJ where R3 is as previously defined, and (xxi) =N-NHC(0)NR3R6 wherein R5 and R6 are as previously defined, (5) CrCio-alkynyl, and (6) C[-Cio-alkynyl substituted with one or more substituents selected from the group consisting of (i) halogen (ii) OR4 where R4 is as previously defined
(iii) -CHO (iv) oxo (v) -COiR3 where R3 is as previously defined (vi) -C(0)NR5R6 wherein R5 and R6 are as previously defined
(vii) -CN (vifi) NR7Rs wherein R7 and R8 are as previously defined (ix) =N-0-R4 where R4 is as previously defined (x) 0-S(0)nRJ where R3 is as previously defined (xi) aryl, and optionally substituted aryl (xii) heteroaryl, and optionally substituted heteroaryl (xiii) C3-C7-cycloalkyl (xiv) Ci-Ci2-alkyl substituted with heteroaryl (xv) NHC(0)R3 where R3 is as previously defined (xvi) NHC(0)NR5R6 where R' and R6 are as previously defined (xvii) =N-NR7R8 wherein R7 and Rs are as previously defined (xviii) =N-NR9 wherein R9 is as previously defined (xix) =N-NHC(0)R3 where RJ is as previously defined, and (xx) =N-NHC(0)NR:,R6 wherein R5 and R6 are as previously defined; R2 is selected from the group consisting of (1) hydrogen
(2) OH (3) ORJ where R3 is as previously defined (4) 0C(O)R3 where R3 is as previously defined, and (5) 0(C0)0R3 where R3 is as previously defined: and X and Y taken together are selected from the group consisting of (1)0 (2) NOR4 wherein R4 is as defined previously (3) N-0 C(R9)(CRi0)-O-R4 where R4 is as previously defined and (i) R9 and R'° are each independently defined as R4, or (ii) R9 and R10 taken together with the atom to which they are attached form a C3-C12 cycloalkyl ring, (4) NR4 wherein R4 is as previously defined, and (5) N-NR7Rs wherein R7 and R8 are as previously defined. or one of X and Y is hydrogen and the other is selected from the group consisting of (1) -OR4 wherein R4 is as previously defined, and (2) -NR7R3 wherein R7 and Rs are as previously defined.
Rp is selected from the group consisting of (1) hydrogen (2) RJ as previously defined Λ (3) COR where R" is as previously defined; subject to the proviso that when the structure is III, Z and M are part of a five- or six-membered ring, said rings optionally being fully or partially unsaturated; for the six-membered ring, the bonding between Z and M is through a carbonyl group; for the five-membered ring, the bonding is directly between Z and M excluding CO; Z and M are independently selected from the group consisting of carbon, oxygen or N; and when M = Na second bridge may exist between this nitrogen and the oxygen of the 12-OH group whereby either an additional annulated oxazole or oxazine ring constitutes part of the molecule; and subject to the proviso that when the structure is IV, Z and M are part of a five- or six-membered ring, said rings optionally being fully saturated or fully or partially unsaturated; for the six-membered ring, the bonding between Z and M is through a carbonyl group; for the five-membered ring, the bonding is directly between Z and M excluding CO; Z and M are independently selected from the group consisting of carbon, oxygen or nitrogen; and when M - N a second bridge may exist between this nitrogen and the urethane nitrogen. 2. Intermediate for the manufacture of a compound according to claim 1, said intermediate being a derivative of erythrolosamine and in particular an erythromycin ketolide characterized in having an R substituent comprising a halogeno derivative, preferably a halogenoalkyl, more preferred chloromethyl, bromomethvl, iodomethyl, most preferred bromomethvl. 3. Intermediate for the manufacture of a compound according to claim 1, said intermediate having a formula chosen among the group consisting of 3. 4, 5, 5a, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20,21,22,23,24, 25,26, 27,28,29,30,31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41,42, 43, 44, 45, 46, 47, 48,49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62. 63, 64, 65. and 66; preferably chosen among the group consisting of 3, 4, 5, 5a, 6,7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,29, 30,31,32,33, and 37. 4. Process for manufacturing a compound according to claim 1-3, comprising the steps of (a) protection of the nitrogen in the amino group in structure 2, preferably by oxidation, (b) halogenation, preferably bromination, (c) deprotection of said amino group, and optionally further comprising (d) protection of OH-groups, preferably as a silyl ether. 5. Process for manufacturing a compound according to claim 1-3, comprising the steps of (e) selective protection of the 2'-OH group, preferably using acetic anhydride with triethylamine, (f) oxidation, preferably Corey-Kim oxidation, (g) deprotection of the 2'-OH group, (h) oxidation and bromination. 6. Process for manufacturing a compound according to claim 1-3, comprising the step of (i) cross-coupling of a compound of formula 4 or 5. 7. Process for manufacturing a compound according to claim 1 -3, comprising the step of (j) reacting trimethylaluminum with a compound of formula 5a under palladium-mediated catalysis. 8. Process for manufacturing a compound according to claim 1-3, comprising the step of (k) introducing a functionalized alkene in a compound of formula 4, preferably under Stille conditions. 9. Process for manufacturing a compound according to claim 1-3. comprising the step of (l) performing acid catalysed cleavage of the vinyl ether of a compound of formula 16 for obtaining a methyl ketone. 10. Process for manufacturing a compound according to claim 1-3, comprising the step of (m) providing a hydroxymethyl derivative by subjecting a compound of formula 4 or 5 to hydrolytic conditions. 11. Use of a compound or intermediate according to claim 1-3, for the manufacture of a medicament, preferably for the treatment or prevention of infection in mammals. 12. Pharmaceutical composition comprising a compound or intermediate, according to claim 1-3, in a pharmaceutically acceptable form, said composition optionally further comprising at least one pharmaceutical excipient.
DK200201957A 2002-12-20 2002-12-20 10-substituted erythromycin ketolides and methods of making DK200201957A (da)

Priority Applications (11)

Application Number Priority Date Filing Date Title
DK200201957A DK200201957A (da) 2002-12-20 2002-12-20 10-substituted erythromycin ketolides and methods of making
CA2789415A CA2789415C (en) 2002-12-20 2003-12-22 Macrolides
US10/539,759 US7608596B2 (en) 2002-12-20 2003-12-22 10-substituted macrolide antibiotics
EP03782698A EP1575970A2 (en) 2002-12-20 2003-12-22 10-substituted macrolide antibiotics
PCT/GB2003/005659 WO2004056843A2 (en) 2002-12-20 2003-12-22 10-substituted macrolide antibiotics
CA2509419A CA2509419C (en) 2002-12-20 2003-12-22 Macrolides
EP10010725.9A EP2371833A3 (en) 2002-12-20 2003-12-22 10-substituted macrolide antibiotics
EP10010724.2A EP2354147A3 (en) 2002-12-20 2003-12-22 10-substituted macrolide antibiotics
AU2003290339A AU2003290339B8 (en) 2002-12-20 2003-12-22 10-Substituted macrolide antibiotics
CNA2003801069659A CN1729200A (zh) 2002-12-20 2003-12-22 大环内酯类
US12/569,926 US8076301B2 (en) 2002-12-20 2009-09-30 10-substituted macrolide antibiotics

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EP (3) EP1575970A2 (da)
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AU (1) AU2003290339B8 (da)
CA (2) CA2789415C (da)
DK (1) DK200201957A (da)
WO (1) WO2004056843A2 (da)

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SG11202001163UA (en) 2017-08-30 2020-03-30 Ecolab Usa Inc Molecules having one hydrophobic group and two identical hydrophilic ionic groups and compositions thereof
JP7150975B2 (ja) * 2018-08-29 2022-10-11 エコラボ ユーエスエー インコーポレイティド 水系における微生物汚損制御のための一級アミンまたはポリアミンから誘導される多重荷電カチオン性化合物の使用
US11084974B2 (en) 2018-08-29 2021-08-10 Championx Usa Inc. Use of multiple charged cationic compounds derived from polyamines for clay stabilization in oil and gas operations
US11292734B2 (en) 2018-08-29 2022-04-05 Ecolab Usa Inc. Use of multiple charged ionic compounds derived from poly amines for waste water clarification
CN116396183A (zh) 2018-08-29 2023-07-07 埃科莱布美国股份有限公司 衍生自多胺的离子化合物、其组合物和其制备方法
CN112584910B (zh) 2018-08-29 2023-03-14 埃科莱布美国股份有限公司 衍生自多胺的带多个电荷的离子化合物及其组合物和其作为反相破乳剂用于油气操作的用途
CN113365498B (zh) 2019-01-29 2022-10-25 埃科莱布美国股份有限公司 阳离子糖基化合物用于在水系统中进行微生物结垢控制的用途
AU2019441168B2 (en) 2019-04-16 2023-02-02 Ecolab Usa Inc. Use of multiple charged cationic compounds derived from polyamines and compositions thereof for corrosion inhibition in a water system
CN117624172B (zh) * 2023-11-29 2024-07-16 山东第一医科大学附属眼科研究所(山东省眼科研究所、山东第一医科大学附属青岛眼科医院) 一种有机分子笼、有机分子笼纳米酶滴眼液及其制备方法

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US8076301B2 (en) 2011-12-13
CA2789415A1 (en) 2004-07-08
WO2004056843A2 (en) 2004-07-08
US20100137234A1 (en) 2010-06-03
WO2004056843A3 (en) 2004-10-21
CA2509419C (en) 2013-07-02
AU2003290339A1 (en) 2004-07-14
CN1729200A (zh) 2006-02-01
EP2371833A2 (en) 2011-10-05
EP2354147A2 (en) 2011-08-10
AU2003290339B8 (en) 2011-02-24
CA2789415C (en) 2014-09-09
US20060241060A1 (en) 2006-10-26
EP1575970A2 (en) 2005-09-21
EP2371833A3 (en) 2013-07-03
EP2354147A3 (en) 2013-07-03
AU2003290339B2 (en) 2010-10-28
CA2509419A1 (en) 2004-07-08

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