AR059592A1 - Procesos para preparar compuestos derivados de caliqueamicina - Google Patents
Procesos para preparar compuestos derivados de caliqueamicinaInfo
- 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
Links
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- -1 N-methylpyrrolyl Chemical group 0.000 abstract 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 230000003115 biocidal effect Effects 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 239000011230 binding agent Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000005309 thioalkoxy group Chemical group 0.000 abstract 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 abstract 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 abstract 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 abstract 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 abstract 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 229910052722 tritium Inorganic materials 0.000 abstract 1
Classifications
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- 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
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- 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
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (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).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77537006P | 2006-02-21 | 2006-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| 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 (31)
| 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) |
| 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)
| 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 |
| US20120316106A1 (en) | 2009-12-29 | 2012-12-13 | Yeda Research And Development Co. Ltd. | Synergistic antibiotic combinations and derivatives |
| PL2885007T3 (pl) | 2012-08-16 | 2019-02-28 | Pfizer Inc. | Sposoby glikokoniugacji i kompozycje |
| CA2929283C (en) * | 2013-11-04 | 2022-07-19 | Pfizer Inc. | Intermediates and methods for synthesizing calicheamicin derivatives |
| PE20161413A1 (es) | 2013-11-04 | 2017-01-10 | Stemcentrx Inc | Conjugados de anticuerpo anti-efna4-farmaco |
| SG11201608953WA (en) | 2014-04-30 | 2016-11-29 | Pfizer | Anti-ptk7 antibody-drug conjugates |
| 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 |
| US20190048073A1 (en) | 2017-07-20 | 2019-02-14 | Pfizer Inc. | Anti-gd3 antibodies and antibody-drug conjugates |
| CA3084092A1 (en) * | 2017-12-06 | 2019-06-13 | Ontario Institute For Cancer Research (Oicr) | Acyl hydrazone linkers, methods and uses thereof |
| EP3728273A4 (en) | 2017-12-22 | 2021-12-29 | 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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4970198A (en) | 1985-10-17 | 1990-11-13 | American Cyanamid Company | Antitumor antibiotics (LL-E33288 complex) |
| US5108912A (en) * | 1987-01-30 | 1992-04-28 | 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 |
| 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 |
| JP2002539071A (ja) * | 1998-07-16 | 2002-11-19 | リサーチ ディベロップメント ファンデーション | 新規ｄｎａ開裂抗腫瘍剤 |
| TW200806685A (en) * | 2006-02-21 | 2008-02-01 | Wyeth Corp | Processes for the convergent synthesis of calicheamicin derivatives |
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2007
- 2007-02-08 TW TW096104537A patent/TW200806685A/zh unknown
- 2007-02-13 PE PE2007000151A patent/PE20071229A1/es not_active Application Discontinuation
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