AR059592A1 - Procesos para preparar compuestos derivados de caliqueamicina - Google Patents

Procesos para preparar compuestos derivados de caliqueamicina

Info

Publication number
AR059592A1
AR059592A1 ARP070100723A ARP070100723A AR059592A1 AR 059592 A1 AR059592 A1 AR 059592A1 AR P070100723 A ARP070100723 A AR P070100723A AR P070100723 A ARP070100723 A AR P070100723A AR 059592 A1 AR059592 A1 AR 059592A1
Authority
AR
Argentina
Prior art keywords
formula
alkyl
heteroaryl
trivalent
divalent
Prior art date
Application number
ARP070100723A
Other languages
English (en)
Inventor
Jianxin Gu
Justin Keith Morando
Original Assignee
Wyeth Corp
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38437933&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR059592(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Wyeth Corp filed Critical Wyeth Corp
Publication of AR059592A1 publication Critical patent/AR059592A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Procesos para la síntesis convergente de derivados de caliqueamicina y análogos similares que utilizan intermedios de ligador bifuncional y trifuncional. Reivindicacion 1:Un proceso para preparar compuestos derivados de caliqueamicina de la formula (1), en donde Z se selecciona del grupo que consiste de formulas (2); Alq1 es una cadena de alquileno ramificada o no ramificada de 2 a 6 átomos de C; Sp1 se selecciona de -S-, -O-, -CONH-, NHCO- y NR'-; Z1 es H, o alquilo C1-5; Ar es 1,2-1,3-O 1,4- fenileno opcionalmente sustituido con 1, 2, o 3 grupos independientemente seleccionados de alquilo C1-6, alcoxi C1-5, tioalcoxi C1-4, halogeno, nitro, -COOR', -COONHR', -O(CH2)nCOOR', -S(CH2)nCOOR', -O(CH2)nCONHR', y -S(CH2)nCONHR' o 1,2-, 1,3-, 1,4- , 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- o 2,7-Naftilideno opcionalmente sustituido con uno, dos, tres, o cuatro grupos independientemente seleccionados de alquilo C1-6, alcoxi C1-5, tioalcoxi C1-4, halogeno, nitro, -COOR', -COONHR', -O(CH2)nCOOR', - S(CH2)nCOOR', -O(CH2)nCONHR',y -S(CH2)nCONHR';n es un entero de 0 a 5: R' es un alquilo recto o ramificado C1-5 opcionalmente sustituido por 1 o 2 grupos de OH, alcoxi C1-4, tioalcoxi C1-4, Sp es un radical alquilo divalente o trivalente de cadena recta o ramificada de 1 a 18 átomos de carbono, un radical arilo o heteroarilo divalente o trivalente, cicloaIquilo divalente o trivalente de 3 a 18 átomos de carbono o un radica heterocicloalquilo, un radical arilo o heteroarilo-alquilo C1-18 divalente o trivalente, un radical cicloalquilo o heterociclo-alquilo C1-18 divalente o trivalente o un radical alquilo no saturado divalente o trivalente de 2 a 18 átomos de C, en donde el heteroarilo es furilo, tienilo, N-metilpirrolilo, piridinilo, N-metilimidazolilo, oxazolilo, pirimidinilo, quinolilo, isoquinolilo, N-metil-carbazoilo, aminocoumarinilo o fenazinilo y en donde si Sp es un radical trivalente, este puede ser adicionalmente sustituido por los grupos dialquilamino C1- 5, alcoxi C1-5, hidroxi, o alquiltio C1-5; W' es como formula (3); R1 es formula (49 o CH3; R2 es formula (59 o H; R3 es formula (6) o H; R4 formula (7) o H; R6 o R7 es H o formula (8); R5 es CH3, -C2H5, o H(CH3)2; X es un átomo de i o Br; R5' es un H o el grupo RCO, en donde R es H, alquilo ramificado o no ramificado C1-10, alquileno C2-10, arilo C6-11, un grupo arilo C6-11-alquil C1-5, o un grupo heteroarilo o heteroaril-alquilo C1-5 en donde el heteroarilo se define como 2- o 3-furilo, 2- o 3-tienilo, 2- o 3- (N-metilpirolilo), 2-, 3-, o 4-piridinilo, 2-, 4- o 5- (N-metilimidazolilo), 2-, 4-, o 5- oxazolilo, 2-, 3-, 5- o 6- pirimidinilo, 2-, 3-, 4-, 5-, 6- 7-, u 8- quinolilo, o 1-, 3-, 4-, 5-, 6-, 7- u 8-, isoquinolilo, todos grupos arilo o heteroarilo opcionalmente sustituidos con 1 o más hidroxi, amino, carboxi, halo, nitro, alcoxi C1-3 o tioalquilo C1-5; y Q se selecciona del grupo que consiste de -NNHCO-, NNHCS-, NNHCONH-, NNHCSNH-, y NO-; caracterizado por comprender las etapas de: a) hacer reaccionar el ácido carboxílico de la formula HO-(=O)-Alk1-Sp1-Ar-(=O)-Z1 con el compuesto mercapto de la formula H2Q-Sp-SH en un disolvente de alcohol en la presencia de un ácido alquilcarboxílico, alq2CO2H donde alq2 es 1-4 átomos de C 20° a 70°C durante 1 a 24 horas, en donde Alq1, Sp1, Ar, Z1, Q son como se definio anteriormente, para producir un ácido carboxílico biligador de la formula, en donde el compuesto mercapto y el ácido carboxílico están presentes en una proporcion de 1.2:1;HO-(=O)-Alk1-Sp1-Ar-Z1=Q-Sp-SH; (b) aislar el ácido carboxílico biligador de la etapa (a); (c) hacer reaccionar el ácido carboxílico biligador aislado de la etapa (b) con al menos un exceso molar de 3 veces de N- hidroxisulfosuccinimida 2, 3, 5, 6-tetrafluorofenol, pentafluorofenol, 4-Nitrofenol, 2,4-dinitrofenol o N-hidroxisulfosuccinimida en la presencia de 1, 3-diciclohexicalbordiimida (DCC), 1-(3-dimetilaminopropil)-3-etilcarbodiimida (EDCI), o N,N'- disuccinimidil carbonato en un disolvente inerte que contiene 0-50% de N,N-dimetilformamida (DMF) para generar un éster activado triligador de formula HO-(=O)-Alk1-Sp1-Ar-Z1=Q-Sp-SH, donde Z es como se definio anteriormente; (d) Hacer reaccionar un éster activado triligador formado en la etapa C con un antibiotico antitumor metil tritio CH3-S-S-S-W' en la presencia de una base o una base orgánica con un antibiotico antitumor metiltrio CH3-S-S-S-W' en un disolvente orgánico inerte para generar un éster activado de la formula de adelante, en donde el éster activado triligador en la etapa C y el CH3-S-S-S-W' están en una proporcion 3:3:1 y la temperatura de reaccion es <=5°C. Z-(=O)-Alk1-Sp1-Ar-Z1=Q-Sp-S-S-W'; ( e) Aislar el éster activado en la etapa (d) y purificar para producir antibioticos antitumorales de la formula (1).
ARP070100723A 2006-02-21 2007-02-20 Procesos para preparar compuestos derivados de caliqueamicina AR059592A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US77537006P 2006-02-21 2006-02-21

Publications (1)

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AR059592A1 true AR059592A1 (es) 2008-04-16

Family

ID=38437933

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070100723A AR059592A1 (es) 2006-02-21 2007-02-20 Procesos para preparar compuestos derivados de caliqueamicina

Country Status (32)

Country Link
US (6) US20070197455A1 (es)
EP (2) EP1987048B1 (es)
JP (4) JP5179383B2 (es)
KR (1) KR101454489B1 (es)
CN (1) CN101389639B (es)
AR (1) AR059592A1 (es)
AU (1) AU2007217795B2 (es)
BR (1) BRPI0708149B1 (es)
CA (1) CA2642194C (es)
CL (1) CL2009001487A1 (es)
CR (1) CR10230A (es)
CY (1) CY1120206T1 (es)
DK (2) DK2799441T3 (es)
EC (1) ECSP088691A (es)
ES (2) ES2670709T3 (es)
GT (1) GT200800161A (es)
HK (1) HK1203515A1 (es)
HU (1) HUE037880T2 (es)
IL (1) IL193343A (es)
MX (1) MX2008010768A (es)
NO (1) NO20083698L (es)
PE (1) PE20071229A1 (es)
PL (2) PL1987048T3 (es)
PT (2) PT1987048E (es)
RU (1) RU2436790C2 (es)
SG (1) SG170013A1 (es)
SI (2) SI2799441T1 (es)
SV (1) SV2009003002A (es)
TR (1) TR201808220T4 (es)
TW (1) TW200806685A (es)
WO (1) WO2007098124A2 (es)
ZA (1) ZA200807196B (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200806685A (en) * 2006-02-21 2008-02-01 Wyeth Corp Processes for the convergent synthesis of calicheamicin derivatives
WO2011080739A2 (en) 2009-12-29 2011-07-07 Yeda Research And Development Co. Ltd. Synergistic antibiotic combinations and derivatives
RU2724840C2 (ru) * 2012-08-16 2020-06-25 Пфайзер Инк. Способы гликоконъюгирования и композиции
RU2640197C1 (ru) * 2013-11-04 2017-12-27 Пфайзер Инк. Промежуточные соединения и способы синтеза производных калихеамицина
US9381205B2 (en) 2013-11-04 2016-07-05 Pfizer, Inc. Anti-EFNA4 antibody-drug conjugates
PL3137114T3 (pl) 2014-04-30 2021-06-28 Pfizer Inc. Koniugaty przeciwciało anty-ptk7-lek
US10464442B2 (en) * 2016-10-11 2019-11-05 Honda Motor Co., Ltd. Non-contact power supply system and power transmission apparatus, and designing method and installing method of power transmission apparatus
WO2019018647A1 (en) 2017-07-20 2019-01-24 Pfizer Inc. ANTI-GD3 ANTIBODIES AND CONJUGATES ANTIBODY-MEDICATION
EP3720842A4 (en) 2017-12-06 2021-11-03 Ontario Institute For Cancer Research ACYLHYDRAZONE LINKERS, METHODS, AND USES THEREOF
CA3086366A1 (en) 2017-12-22 2019-06-27 Ontario Institute For Cancer Research (Oicr) Heterocyclic acyl hydrazone linkers, methods and uses thereof
CN111647865B (zh) * 2020-08-06 2020-11-24 北京卓立汉光仪器有限公司 溅射镀膜方法、装置及系统

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4970198A (en) 1985-10-17 1990-11-13 American Cyanamid Company Antitumor antibiotics (LL-E33288 complex)
US5079233A (en) * 1987-01-30 1992-01-07 American Cyanamid Company N-acyl derivatives of the LL-E33288 antitumor antibiotics, composition and methods for using the same
US5108912A (en) * 1987-01-30 1992-04-28 American Cyanamid Company Antitumor antibiotics (LL-E33288 complex)
US5053394A (en) 1988-09-21 1991-10-01 American Cyanamid Company Targeted forms of methyltrithio antitumor agents
US5770701A (en) * 1987-10-30 1998-06-23 American Cyanamid Company Process for preparing targeted forms of methyltrithio antitumor agents
US5773001A (en) * 1994-06-03 1998-06-30 American Cyanamid Company Conjugates of methyltrithio antitumor agents and intermediates for their synthesis
US5712374A (en) 1995-06-07 1998-01-27 American Cyanamid Company Method for the preparation of substantiallly monomeric calicheamicin derivative/carrier conjugates
TW200806685A (en) * 2006-02-21 2008-02-01 Wyeth Corp Processes for the convergent synthesis of calicheamicin derivatives

Also Published As

Publication number Publication date
NO20083698L (no) 2008-11-12
CN101389639B (zh) 2012-07-18
US20180016228A1 (en) 2018-01-18
ECSP088691A (es) 2008-09-29
JP2009527557A (ja) 2009-07-30
CA2642194A1 (en) 2007-08-30
EP2799441B1 (en) 2018-04-18
SI1987048T1 (sl) 2015-01-30
US9802890B2 (en) 2017-10-31
JP2013040213A (ja) 2013-02-28
SV2009003002A (es) 2009-01-28
BRPI0708149A2 (pt) 2011-05-17
EP2799441A1 (en) 2014-11-05
JP5179383B2 (ja) 2013-04-10
DK2799441T3 (en) 2018-05-28
EP1987048B1 (en) 2014-11-19
PT2799441T (pt) 2018-05-29
JP2014196352A (ja) 2014-10-16
CA2642194C (en) 2015-12-08
ES2527107T3 (es) 2015-01-20
PT1987048E (pt) 2015-01-14
CN101389639A (zh) 2009-03-18
US8546549B2 (en) 2013-10-01
IL193343A (en) 2017-03-30
KR20080094925A (ko) 2008-10-27
DK1987048T3 (en) 2014-12-15
US20130018179A1 (en) 2013-01-17
WO2007098124A2 (en) 2007-08-30
ES2670709T3 (es) 2018-05-31
RU2436790C2 (ru) 2011-12-20
ZA200807196B (en) 2009-05-27
US10343989B2 (en) 2019-07-09
HUE037880T2 (hu) 2018-09-28
PL2799441T3 (pl) 2018-08-31
CL2009001487A1 (es) 2009-10-16
WO2007098124A3 (en) 2007-12-27
CR10230A (es) 2008-10-03
HK1203515A1 (en) 2015-10-30
MX2008010768A (es) 2008-11-28
PE20071229A1 (es) 2007-11-30
AU2007217795A1 (en) 2007-08-30
IL193343A0 (en) 2009-08-03
SI2799441T1 (en) 2018-07-31
EP1987048A2 (en) 2008-11-05
JP2016011316A (ja) 2016-01-21
GT200800161A (es) 2009-01-15
SG170013A1 (en) 2011-04-29
BRPI0708149B1 (pt) 2022-01-25
AU2007217795B2 (en) 2012-09-13
TW200806685A (en) 2008-02-01
US8273862B2 (en) 2012-09-25
US20070197455A1 (en) 2007-08-23
PL1987048T3 (pl) 2015-03-31
US20150315138A1 (en) 2015-11-05
RU2008132777A (ru) 2010-03-27
CY1120206T1 (el) 2018-12-12
TR201808220T4 (tr) 2018-07-23
US20140081010A1 (en) 2014-03-20
KR101454489B1 (ko) 2014-10-27
US20090312530A1 (en) 2009-12-17

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