JP2014514268A - Pet前駆体の製造 - Google Patents
Pet前駆体の製造 Download PDFInfo
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- JP2014514268A JP2014514268A JP2013557076A JP2013557076A JP2014514268A JP 2014514268 A JP2014514268 A JP 2014514268A JP 2013557076 A JP2013557076 A JP 2013557076A JP 2013557076 A JP2013557076 A JP 2013557076A JP 2014514268 A JP2014514268 A JP 2014514268A
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- Prior art keywords
- compound
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- palladium
- catalyst
- acid
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000002243 precursor Substances 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 35
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 25
- 229910052763 palladium Inorganic materials 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- -1 platinum group metals Chemical class 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000011068 loading method Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- NTEDWGYJNHZKQW-DGMDOPGDSA-N fluciclovine ((18)F) Chemical compound OC(=O)[C@]1(N)C[C@H]([18F])C1 NTEDWGYJNHZKQW-DGMDOPGDSA-N 0.000 abstract description 9
- 229940027541 fluciclovine f-18 Drugs 0.000 abstract description 9
- 239000012217 radiopharmaceutical Substances 0.000 abstract description 8
- 229940121896 radiopharmaceutical Drugs 0.000 abstract description 8
- 230000002799 radiopharmaceutical effect Effects 0.000 abstract description 8
- 238000002600 positron emission tomography Methods 0.000 abstract description 6
- 229940079593 drug Drugs 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 150000003862 amino acid derivatives Chemical class 0.000 abstract description 2
- 150000001413 amino acids Chemical class 0.000 abstract description 2
- 238000011503 in vivo imaging Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006264 debenzylation reaction Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000000032 diagnostic agent Substances 0.000 description 3
- 229940039227 diagnostic agent Drugs 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- YCSWTNOOIHXDLP-UHFFFAOYSA-N ethyl 3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutane-1-carboxylate Chemical compound CC(C)(C)OC(=O)NC1(C(=O)OCC)CC(O)C1 YCSWTNOOIHXDLP-UHFFFAOYSA-N 0.000 description 3
- 238000009206 nuclear medicine Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- NMKOOYIJFNHFEK-UHFFFAOYSA-N ethyl 1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxycyclobutane-1-carboxylate Chemical compound C1C(C(=O)OCC)(NC(=O)OC(C)(C)C)CC1OCC1=CC=CC=C1 NMKOOYIJFNHFEK-UHFFFAOYSA-N 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- AOYNUTHNTBLRMT-MXWOLSILSA-N 2-Deoxy-2(F-18)fluoro-2-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H]([18F])C=O AOYNUTHNTBLRMT-MXWOLSILSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 108050005273 Amino acid transporters Proteins 0.000 description 1
- 102000034263 Amino acid transporters Human genes 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 201000010235 heart cancer Diseases 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 208000024348 heart neoplasm Diseases 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical group COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical group N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- 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
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【選択図】なし
Description
Rは1〜5の炭素原子を有するアルキル基を表し、
Yはアミンに対する保護基を表し、
Xはアルコールに対する保護基を表す。
様々な量の1−(N−(t−ブトキシカルボニル)アミノ)−3−ベンジルオキシ−シクロブタン−1−カルボン酸エチルエステル(式IIIの化合物)をエタノール(18.4〜20.0ml/g)に添加した。1−(N−(t−ブトキシカルボニル)アミノ)−3−ヒドロキシ−シクロブタン−1−カルボン酸エチルエステル(式IVの化合物)を製造するための脱ベンジル化反応を最適化するために複数回の試験を行った。式IIIの化合物及びエタノールを含む反応媒質に様々な量の酢酸を添加して、pHを約3に調整した。脱水素化分解のために様々な量の炭素上パラジウム(10%装填量)を使用して、湿潤触媒及び乾燥触媒の両方を試験した。反応はTLCによって追跡した。結果を表1中に示す。
Claims (10)
- 以下の式IIIaの化合物から以下の式IVaの化合物を製造する方法であって、式IIIaの化合物を含む反応媒質のpHを2.0〜5.0に調整する段階、及び白金族金属から選択される湿潤触媒を用いてXの水素化分解を行う段階を含んでなる方法。
Rは1〜5の炭素原子を有するアルキル基を表し、
Yはアミンに対する保護基を表し、
Xはアルコールに対する保護基を表す。 - Rがエチル基であり、YがBOCであり、Xがベンジルである、請求項1記載の方法。
- 触媒がルテニウム、ロジウム、パラジウム、オスミウム、イリジウム及び白金からなる群から選択される、請求項1又は請求項2記載の方法。
- 触媒がパラジウムである、請求項1乃至請求項3のいずれか1項記載の方法。
- 触媒が1〜10%のパラジウム装填量を有する炭素上パラジウムである、請求項1乃至請求項4のいずれか1項記載の方法。
- 反応媒質がさらに溶媒を含む、請求項1乃至請求項5のいずれか1項記載の方法。
- 溶媒がエタノールである、請求項1乃至請求項6のいずれか1項記載の方法。
- pHの調整が、反応媒質に酸を添加することで行われる、請求項1乃至請求項7のいずれか1項記載の方法。
- 酸が酢酸である、請求項8記載の方法。
- pHが2.5〜3.5に調整される、請求項1乃至請求項9のいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161450177P | 2011-03-08 | 2011-03-08 | |
US61/450,177 | 2011-03-08 | ||
PCT/EP2012/053867 WO2012120025A1 (en) | 2011-03-08 | 2012-03-07 | Preparation of a 1-amino-3-hydroxy-cyclobutane-1-carboxylic acid derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014514268A true JP2014514268A (ja) | 2014-06-19 |
JP5938422B2 JP5938422B2 (ja) | 2016-06-22 |
Family
ID=45808953
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013557076A Active JP5938422B2 (ja) | 2011-03-08 | 2012-03-07 | Pet前駆体の製造 |
Country Status (14)
Country | Link |
---|---|
US (1) | US9242924B2 (ja) |
EP (1) | EP2683684B1 (ja) |
JP (1) | JP5938422B2 (ja) |
KR (1) | KR101904565B1 (ja) |
CN (1) | CN103415503B (ja) |
AU (1) | AU2012224634B2 (ja) |
BR (1) | BR112013020627B1 (ja) |
CA (1) | CA2828975C (ja) |
DK (1) | DK2683684T3 (ja) |
ES (1) | ES2657894T3 (ja) |
MX (1) | MX341089B (ja) |
NO (1) | NO2683684T3 (ja) |
RU (1) | RU2596829C2 (ja) |
WO (1) | WO2012120025A1 (ja) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000066579A1 (fr) * | 1999-04-28 | 2000-11-09 | Banyu Pharmaceutical Co., Ltd. | Methodes de preparation de derives de piperidylmethylpyridine |
JP2006240997A (ja) * | 2005-02-28 | 2006-09-14 | Koei Chem Co Ltd | ビピリジン類の製造方法 |
WO2007063824A1 (ja) * | 2005-11-29 | 2007-06-07 | Nihon Medi-Physics Co., Ltd. | 放射性ハロゲン標識有機化合物の前駆体化合物 |
WO2009114512A1 (en) * | 2008-03-11 | 2009-09-17 | Incyte Corporation | Azetidine and cyclobutane derivatives as jak inhibitors |
WO2010047674A1 (en) * | 2008-10-20 | 2010-04-29 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Low molecular weight thyroid stimulating hormone receptor (tshr) agonists |
WO2011006621A1 (en) * | 2009-07-11 | 2011-01-20 | Bayer Schering Pharma Aktiengesellschaft | Radiolabelling method using cycloalkyl groups |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200736203A (en) * | 2005-11-18 | 2007-10-01 | Glaxo Group Ltd | New pleuromutilin derivative and its use |
JP5518337B2 (ja) * | 2006-12-27 | 2014-06-11 | 日本メジフィジックス株式会社 | 放射性ハロゲン標識有機化合物の前駆体化合物の製造方法 |
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2012
- 2012-03-07 BR BR112013020627A patent/BR112013020627B1/pt active IP Right Grant
- 2012-03-07 RU RU2013139061/04A patent/RU2596829C2/ru active
- 2012-03-07 MX MX2013010254A patent/MX341089B/es active IP Right Grant
- 2012-03-07 WO PCT/EP2012/053867 patent/WO2012120025A1/en active Application Filing
- 2012-03-07 US US14/002,184 patent/US9242924B2/en active Active
- 2012-03-07 AU AU2012224634A patent/AU2012224634B2/en active Active
- 2012-03-07 DK DK12707320.3T patent/DK2683684T3/en active
- 2012-03-07 ES ES12707320.3T patent/ES2657894T3/es active Active
- 2012-03-07 CN CN201280012007.4A patent/CN103415503B/zh active Active
- 2012-03-07 KR KR1020137023602A patent/KR101904565B1/ko active IP Right Grant
- 2012-03-07 JP JP2013557076A patent/JP5938422B2/ja active Active
- 2012-03-07 NO NO12707320A patent/NO2683684T3/no unknown
- 2012-03-07 EP EP12707320.3A patent/EP2683684B1/en active Active
- 2012-03-07 CA CA2828975A patent/CA2828975C/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20140049975A (ko) | 2014-04-28 |
NO2683684T3 (ja) | 2018-06-02 |
CN103415503B (zh) | 2015-09-16 |
CN103415503A (zh) | 2013-11-27 |
MX341089B (es) | 2016-08-08 |
RU2596829C2 (ru) | 2016-09-10 |
AU2012224634B2 (en) | 2016-09-08 |
KR101904565B1 (ko) | 2018-10-04 |
BR112013020627B1 (pt) | 2019-12-03 |
MX2013010254A (es) | 2013-11-18 |
US20130345468A1 (en) | 2013-12-26 |
WO2012120025A1 (en) | 2012-09-13 |
US9242924B2 (en) | 2016-01-26 |
JP5938422B2 (ja) | 2016-06-22 |
ES2657894T3 (es) | 2018-03-07 |
CA2828975A1 (en) | 2012-09-13 |
EP2683684B1 (en) | 2018-01-03 |
RU2013139061A (ru) | 2015-04-20 |
DK2683684T3 (en) | 2018-02-05 |
BR112013020627A2 (pt) | 2016-10-04 |
CA2828975C (en) | 2019-07-09 |
EP2683684A1 (en) | 2014-01-15 |
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