WO2008028688A2 - Compounds and methods for 18f labeled agents - Google Patents

Compounds and methods for 18f labeled agents Download PDF

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Publication number
WO2008028688A2
WO2008028688A2 PCT/EP2007/008042 EP2007008042W WO2008028688A2 WO 2008028688 A2 WO2008028688 A2 WO 2008028688A2 EP 2007008042 W EP2007008042 W EP 2007008042W WO 2008028688 A2 WO2008028688 A2 WO 2008028688A2
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WO
WIPO (PCT)
Prior art keywords
trp
ala
val
gln
leu
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Ceased
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PCT/EP2007/008042
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English (en)
French (fr)
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WO2008028688A3 (en
Inventor
Lutz Lehmann
Ananth Srinivasan
Thomas Brumby
Detlev Sülzle
Timo Stellfeld
Keith Graham
Mylène KARRAMKAM
Simon Ametamey
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Bayer Pharma AG
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Bayer Schering Pharma AG
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Filing date
Publication date
Priority claimed from EP06090166A external-priority patent/EP1897885A1/en
Priority claimed from EP07090079A external-priority patent/EP1985624A3/en
Priority to EP07802326.4A priority Critical patent/EP2063918B1/en
Priority to JP2009527069A priority patent/JP5603074B2/ja
Priority to CA002662449A priority patent/CA2662449A1/en
Priority to BRPI0716554-4A2A priority patent/BRPI0716554A2/pt
Priority to MX2009002492A priority patent/MX2009002492A/es
Priority to AU2007294124A priority patent/AU2007294124A1/en
Application filed by Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG
Publication of WO2008028688A2 publication Critical patent/WO2008028688A2/en
Publication of WO2008028688A3 publication Critical patent/WO2008028688A3/en
Priority to TN2009000063A priority patent/TN2009000063A1/fr
Priority to IL197363A priority patent/IL197363A0/en
Anticipated expiration legal-status Critical
Priority to NO20091428A priority patent/NO20091428L/no
Priority to IL211033A priority patent/IL211033A0/en
Priority to IL211526A priority patent/IL211526A0/en
Priority to IL211527A priority patent/IL211527A0/en
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/655—Somatostatins
    • C07K14/6555—Somatostatins at least 1 amino acid in D-form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
    • 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
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/57545—Neuropeptide Y

Definitions

  • E.Garcia Garayoa et al. (“Chemical and biological characterization of new Re(CO) 3 /r m Tc](CO)3 bombesin Analogues.” Nucl. Med. Biol., 17-28; 2007) disclose a spacer between the radionuclide [ 99m Tc] and the bombesin wherein the spacer is - ⁇ -Ala- ⁇ - AIa- and 3,6-dioxa- ⁇ -aminooctanoic acid. E.Garcia Garayoa et al. conclude that the different spacer does not have a significant effect on stability or on receptor affinity.
  • nucleotide refers to molecules comprising a nitrogen-containing base, a 5-carbon sugar, and one or more phosphate groups.
  • bases comprise, but are not limited to, adenine, guanine, cytosine, uracil, and thymine.
  • non-natural, substituted or non-substituted bases are included.
  • 5-carbon sugar comprise, but are not limited to, D-ribose, and D-2- desoxyribose. Also other natural and non-natural, substituted or non-substituted 5-carbon sugars are included.
  • Nucleotides as used in this invention may comprise from one to three phosphates.
  • the compounds having general chemical Formula I 1 -G is selected from a group comprising - F, -NO 2 , -OCF 2 CF 3 -OCF 3 , -C ⁇ N, -COCF 3 , -CF 3 , -CF 2 CF 3 , -CF 2 -CF 2 -CF 3 , -COCF 2 CF 2 CF 3 , -SO 2 CF 3 , -SO 2 CN, -SO 2 CF 2 CF 3 , -SO 2 N(R 5 J 2 and SC(CF 3 J 3 wherein the respective subtituent can be in ortho, para or meta position in respect of the K group.
  • Bombesin is a fourteen amino acid peptide that is an analog of human Gastrin releasing peptide (GRP) that binds with high specificity to human GRP receptors present in prostate tumor, breast tumor and metastasis. Accordingly, as to a ninth aspect of the present invention, bombesin analogs are provided.
  • GRP Gastrin releasing peptide
  • U is NR 7 -peptide, or -(CH 2 ) n -peptide, -O-(CH 2 ) n - peptide or -S- (CH 2 J n - peptide , NR 7 - small-molecule, or -(CH 2 J n - small-molecule, -O-(CH 2 ) n - small- molecule or -S-(CH 2 J n - small-molecule, NR 7 - oligonucleotide, or -(CH 2 J n - oligonucleotide, - O-(CH 2 ) n - oligonucleotide or -S-(CH 2 ) n - oligonucleotide - wherein n is an integer of from 1 to 6.
  • U is -NR 7 -oligonucleotide or -(CH 2 ),,- oligonucleoptide, wherein n is an integer of from 1 to 6.
  • IIA-a-1 4-[1 ⁇ JFIuoro-S-cyano-benzoyl-Arg-Ava-Gln-Trp-Ala-Val-NMeGly-His-Sta-Leu-
  • the radiopharmaceutical labelled with 18 F or 19 F is selected from the following list, wherein U is a small molecule:
  • the use is for imaging of tumors, imaging of inflammatory and/or neurodegenerative diseases, such as multiple sclerosis or Alzheimer's disease, or imaging of angiogenesis-associated diseases, such as growth of solid tumors, and rheumatoid arthritis.
  • inflammatory and/or neurodegenerative diseases such as multiple sclerosis or Alzheimer's disease
  • angiogenesis-associated diseases such as growth of solid tumors, and rheumatoid arthritis.
  • the present invention relates to compound having general chemical Formula II for use in biological assays and chromatographic identification. More preferably, the invention relates to compounds having general chemical Formula HB for use in biological assays and chromatographic identification, wherein the fluorine isotope is 19 F. More preferably, the invention relates to the use of compounds having general chemical Formula I for the manufacture of compounds having general chemical Formula IIB as a measurement agent.
  • Alzheimer's disease or imaging of angiogenesis-associated diseases, such as growth of solid tumors, and rheumatoid arthritis.
  • the compound having general chemical Formula I and its pharmaceutically acceptable salts of inorganic or organic acids thereof, hydrates, complexes, esters, amides, solvates and prodrugs thereof is any preferred compound described above for obtaining any preferred compound having general chemical Formula II, more specifically any preferred compound having general chemical Formulae IIA and HB, or pharmaceutically acceptable salt, hydrate, ester, amide, solvate or prodrug thereof as described above.
  • Typical condensating agents for those kinds of couplings are diisopropylcarbodiimid or dicyclohexylcarbodiimid, but also other condensating agents are possible and described. Examples are given in, but are not limited to, the methods described and cited in the book: Chan and White - "Fmoc Solid Phase Peptide Synthesis - A Practical Approach”.
  • the resin-bound trimethylammonium peptide 17 is then cleaved from the resin by acidification to obtain liberated peptide (18).
  • the cleavage is also possible by other appropriate methods which are very much dependent on the kind of linker.
  • the methods of peptide cleavage from resin are very well known to experts.
  • Trifluoroacetic acid system was used as a mobile phase to measure the stability of the entire molecule.
  • the crude reaction mixture was analyzed using an analytical HPLC (Column Zorbax SB C18, 50 ⁇ 4.6mm, 1.8 ⁇ , 2ml/min, solvent A: H 2 O, solvent B: MeCN, gradient: 5%-95% B in 7 mins or Column Econosphere C18 , 53 ⁇ 7mm, 3 ⁇ , 3ml/min (Alltech), solvent A: H2O + 0.1%TFA, solvent B: MeCN/Water 9/1 + 0.1% TFA, gradient: 5-95% B in 7 mins.
  • the F-18 labeled product (2g) was confirmed by co-injection with the cold F-19 fluoro standard on the Econsphere analytical HPLC.
  • the crude reaction mixture was analyzed using an analytical HPLC (Column Zorbax SB C18, 50 ⁇ 4.6mm, 1.8 ⁇ , 2ml/min, solvent A: H2O, solvent B: MeCN, gradient: 5%-95% B in 7 mins or Column Econosphere C18 , 53 ⁇ 7mm, 3 ⁇ , 3ml/min (Alltech), solvent A: H2O + 0.1%TFA, solvent B: MeCN/Water 9/1 + 0.1% TFA, gradient: 5-95% B in 7 mins.
  • the F- 18 labeled product 9e was confirmed by co-injection with the non-radioactive F-19 fluoro standard on the Econsphere analytical HPLC.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Physics & Mathematics (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Optics & Photonics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2007/008042 2006-09-08 2007-09-07 Compounds and methods for 18f labeled agents Ceased WO2008028688A2 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
EP07802326.4A EP2063918B1 (en) 2006-09-08 2007-09-07 Compounds and methods for 18f labeled agents
JP2009527069A JP5603074B2 (ja) 2006-09-08 2007-09-07 １８ｆ標識物質のための化合物と方法
CA002662449A CA2662449A1 (en) 2006-09-08 2007-09-07 Compounds and methods for 18f labeled agents
BRPI0716554-4A2A BRPI0716554A2 (pt) 2006-09-08 2007-09-07 compostos de mÉtodos para agentes rotulados de 18f
MX2009002492A MX2009002492A (es) 2006-09-08 2007-09-07 Agentes que comprenden compuestos marcados con 18f y metodos relacionados.
AU2007294124A AU2007294124A1 (en) 2006-09-08 2007-09-07 Compounds and methods for 18F labeled agents
TN2009000063A TN2009000063A1 (en) 2006-09-08 2009-02-27 Compounds and methods for 18f labeled agents
IL197363A IL197363A0 (en) 2006-09-08 2009-03-03 Compounds and methods for 18f labeled agents
NO20091428A NO20091428L (no) 2006-09-08 2009-04-07 Forbindelser og metoder for 18F-merkede midler
IL211033A IL211033A0 (en) 2006-09-08 2011-02-03 Peptides as derivatives for compounds for labeled with 18f
IL211527A IL211527A0 (en) 2006-09-08 2011-03-03 Compounds and methods for 18f labeled agents, compositions comprising such compounds and their use for diagnostic imaging
IL211526A IL211526A0 (en) 2006-09-08 2011-03-03 Compounds and methods for 18f labeled agents, compositions comprising such compounds and their use for diagnostic imaging

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06090166.7 2006-09-08
EP06090166A EP1897885A1 (en) 2006-09-08 2006-09-08 Compounds and methods for F labelled agents
EP07090079A EP1985624A3 (en) 2007-04-23 2007-04-23 Single step method of radiofluorination of biologically active compounds or biomolecules
EP07090079.0 2007-04-23

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP11193716.5A Previously-Filed-Application EP2455105B1 (en) 2006-09-08 2007-09-07 Bombesin analogues

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WO2008028688A2 true WO2008028688A2 (en) 2008-03-13
WO2008028688A3 WO2008028688A3 (en) 2008-11-13

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PCT/EP2007/008042 Ceased WO2008028688A2 (en) 2006-09-08 2007-09-07 Compounds and methods for 18f labeled agents

Country Status (20)

Country Link
US (1) US8557776B2 (enExample)
EP (5) EP2063918B1 (enExample)
JP (2) JP5603074B2 (enExample)
KR (1) KR20090058553A (enExample)
AR (1) AR062726A1 (enExample)
AU (1) AU2007294124A1 (enExample)
BR (1) BRPI0716554A2 (enExample)
CA (2) CA2858907A1 (enExample)
CL (1) CL2007002620A1 (enExample)
CO (1) CO6150196A2 (enExample)
CR (1) CR10654A (enExample)
IL (4) IL197363A0 (enExample)
MA (1) MA30780B1 (enExample)
MX (1) MX2009002492A (enExample)
NO (1) NO20091428L (enExample)
PE (1) PE20080850A1 (enExample)
RU (1) RU2009112716A (enExample)
TN (1) TN2009000063A1 (enExample)
TW (1) TW200829277A (enExample)
WO (1) WO2008028688A2 (enExample)

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US8557776B2 (en) 2006-09-08 2013-10-15 Bayer Pharma AG Compounds and methods for 18F labeled agents
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EP3781149A4 (en) * 2018-04-20 2022-03-16 The General Hospital Corporation ACETYLATED PRODRUGS FOR ADMINISTRATION ACROSS THE BLOOD-BRAIN BARRIER
WO2024204842A1 (ja) 2023-03-31 2024-10-03 日産化学株式会社 ピラゾール化合物及び有害生物防除剤
EP4306533A4 (en) * 2021-03-11 2025-03-12 Wuhan Innerse Pharmaceutical Inc. SYNTHETIC PEPTIDE AND ITS APPLICATION

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GB201013808D0 (en) 2010-08-18 2010-09-29 Ge Healthcare Ltd Peptide radiotracer compositions
CA2838198A1 (en) * 2011-06-09 2012-12-13 Ge Healthcare Limited Distillation device and method
GB201314936D0 (en) 2013-08-21 2013-10-02 Ge Healthcare Ltd Radiolabelling method
GB201322456D0 (en) 2013-12-18 2014-02-05 Ge Healthcare Ltd Radiotracer compositions and methods
WO2018152339A1 (en) * 2017-02-17 2018-08-23 Yale University Radiolabeled pharmaceuticals and methods of making and using same
CN111051512A (zh) 2017-07-11 2020-04-21 辛索克斯公司 非天然核苷酸的掺入及其方法
SG11202000939PA (en) 2017-08-03 2020-02-27 Synthorx Inc Cytokine conjugates for the treatment of proliferative and infectious diseases
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