TW201201846A - Iodo precursor for a PET imaging agent of amyloid plaques - Google Patents

Iodo precursor for a PET imaging agent of amyloid plaques Download PDF

Info

Publication number: TW201201846A
Authority: TW; Taiwan
Prior art keywords: compound; formula; solution; acid; doc
Prior art date: 2010-02-08

Application number

TW100104039A

Other languages

English (en)

Chinese (zh)

Inventor

Heribert Schmitt-Willich

Tobias Heinrich

Damian Brockschnieder

Original Assignee

Bayer Schering Pharma Ag

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.)

2010-02-08

Filing date

2011-02-01

Publication date

2012-01-16

2011-02-01 Application filed by Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag

2012-01-16 Publication of TW201201846A publication Critical patent/TW201201846A/zh

Links

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AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
230000008499 blood brain barrier function Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
210000001218 blood-brain barrier Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
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238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
229960003009 clopidogrel Drugs 0.000 description 1
230000019771 cognition Effects 0.000 description 1
239000002872 contrast media Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
DXVWRJRZCMCNEU-UHFFFAOYSA-N dimercaptoamine Chemical compound SNS DXVWRJRZCMCNEU-UHFFFAOYSA-N 0.000 description 1
238000011979 disease modifying therapy Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
AYVAZAHAUWGLQH-UHFFFAOYSA-N heptane hexane Chemical compound CCCCCC.CCCCCCC.CCCCCCC AYVAZAHAUWGLQH-UHFFFAOYSA-N 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
WABAEEDHTRIFPM-UHFFFAOYSA-N hydroxy-sulfanyl-sulfanylidene-$l^{4}-sulfane Chemical compound SS(S)=O WABAEEDHTRIFPM-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000003446 ligand Substances 0.000 description 1
231100000863 loss of memory Toxicity 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
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238000012544 monitoring process Methods 0.000 description 1
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000017854 proteolysis Effects 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
LPCNYUJFUWWFHQ-UHFFFAOYSA-N tert-butyl n-[2-oxo-2-[4-(5-phenylmethoxypyridin-2-yl)piperazin-1-yl]ethyl]carbamate Chemical compound C1CN(C(=O)CNC(=O)OC(C)(C)C)CCN1C(N=C1)=CC=C1OCC1=CC=CC=C1 LPCNYUJFUWWFHQ-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
UVVFKNZCYIIHGM-UHFFFAOYSA-L tetrabutylazanium;carbonate Chemical compound [O-]C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC UVVFKNZCYIIHGM-UHFFFAOYSA-L 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
210000004885 white matter Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Landscapes

Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

TW100104039A 2010-02-08 2011-02-01 Iodo precursor for a PET imaging agent of amyloid plaques TW201201846A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP10075054		2010-02-08

Publications (1)

Publication Number	Publication Date
TW201201846A true TW201201846A (en)	2012-01-16

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TW100104039A TW201201846A (en)	2010-02-08	2011-02-01	Iodo precursor for a PET imaging agent of amyloid plaques

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AR (1)	AR080289A1 (fr)
TW (1)	TW201201846A (fr)
UY (1)	UY33218A (fr)
WO (1)	WO2011095593A1 (fr)

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* Cited by examiner, † Cited by third party
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CN103724207B (zh) *	2013-12-20	2016-07-06	北京智博高科生物技术有限公司	苯基苄基醚类衍生物及其制备方法和应用
US10377701B2 (en)	2016-11-08	2019-08-13	The Regents Of The University Of California	Methods for multi-dose synthesis of [F-18]FDDNP for clinical settings

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* Cited by examiner, † Cited by third party
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UY27003A1 (es) *	2000-11-06	2002-07-31	Schering Ag	Productos radiofarmacéuticos para el diagnóstico de la enfermedad de alzheimer
EP2163541A1 (fr) *	2008-09-12	2010-03-17	Bayer Schering Pharma Aktiengesellschaft	Dérivés de piprazine pour la liaison et l'imagerie de plaques amyloïdes et leur utilisation

2011
- 2011-02-01 TW TW100104039A patent/TW201201846A/zh unknown
- 2011-02-04 WO PCT/EP2011/051660 patent/WO2011095593A1/fr not_active Ceased
- 2011-02-04 AR ARP110100377A patent/AR080289A1/es unknown
- 2011-02-08 UY UY0001033218A patent/UY33218A/es not_active Application Discontinuation

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WO2011095593A1 (fr)	2011-08-11
UY33218A (es)	2011-09-30
AR080289A1 (es)	2012-03-28

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