CA2539469C - Pyridylacetylenes for use as radiotracers and imaging agents - Google Patents
Pyridylacetylenes for use as radiotracers and imaging agents Download PDFInfo
- Publication number
- CA2539469C CA2539469C CA2539469A CA2539469A CA2539469C CA 2539469 C CA2539469 C CA 2539469C CA 2539469 A CA2539469 A CA 2539469A CA 2539469 A CA2539469 A CA 2539469A CA 2539469 C CA2539469 C CA 2539469C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- methyl
- enone
- free base
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 239000012216 imaging agent Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 101001032845 Homo sapiens Metabotropic glutamate receptor 5 Proteins 0.000 claims description 8
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 claims description 8
- 238000002372 labelling Methods 0.000 claims description 7
- 238000000338 in vitro Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 5
- 210000000133 brain stem Anatomy 0.000 claims description 4
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 239000003550 marker Substances 0.000 claims description 2
- 238000002610 neuroimaging Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ACZNCLRHSFNGTB-UHFFFAOYSA-N 3-[2-(6-methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-one Chemical compound CC1=CC=CC(C#CC=2CCCC(=O)C=2)=N1 ACZNCLRHSFNGTB-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UWOHEEOCHCCCNH-UHFFFAOYSA-N n-[3-[2-(6-methylpyridin-2-yl)ethynyl]cyclohex-2-en-1-ylidene]hydroxylamine Chemical compound CC1=CC=CC(C#CC=2CCCC(C=2)=NO)=N1 UWOHEEOCHCCCNH-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- STDHINPODVHROK-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)ethynyl]-6-methylpyridine Chemical compound COC1=CC=CC(C#CC=2N=C(C)C=CC=2)=C1 STDHINPODVHROK-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 210000001638 cerebellum Anatomy 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000001320 hippocampus Anatomy 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 210000001577 neostriatum Anatomy 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LZIPBJBQQPZLOR-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOS(=O)(=O)C1=CC=C(C)C=C1 LZIPBJBQQPZLOR-UHFFFAOYSA-N 0.000 description 1
- RUFOVPQUNXLVFW-UHFFFAOYSA-N 2-ethynyl-6-methylpyridine Chemical compound CC1=CC=CC(C#C)=N1 RUFOVPQUNXLVFW-UHFFFAOYSA-N 0.000 description 1
- BVSMYYHGYVHWCD-UHFFFAOYSA-N 3-bromocyclohex-2-en-1-one Chemical compound BrC1=CC(=O)CCC1 BVSMYYHGYVHWCD-UHFFFAOYSA-N 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 description 1
- NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0322612.3 | 2003-09-26 | ||
| GBGB0322612.3A GB0322612D0 (en) | 2003-09-26 | 2003-09-26 | Organic compounds |
| PCT/EP2004/010743 WO2005030723A1 (en) | 2003-09-26 | 2004-09-24 | Pyridylacetylenes for use as radiotracers and imaging agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2539469A1 CA2539469A1 (en) | 2005-04-07 |
| CA2539469C true CA2539469C (en) | 2012-06-19 |
Family
ID=29286926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2539469A Expired - Fee Related CA2539469C (en) | 2003-09-26 | 2004-09-24 | Pyridylacetylenes for use as radiotracers and imaging agents |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8674110B2 (enExample) |
| EP (1) | EP1670762B1 (enExample) |
| JP (1) | JP4965255B2 (enExample) |
| CN (1) | CN100430380C (enExample) |
| AU (2) | AU2004275971B2 (enExample) |
| BR (1) | BRPI0414732A (enExample) |
| CA (1) | CA2539469C (enExample) |
| ES (1) | ES2400713T3 (enExample) |
| GB (1) | GB0322612D0 (enExample) |
| MX (1) | MXPA06003424A (enExample) |
| PL (1) | PL1670762T3 (enExample) |
| PT (1) | PT1670762E (enExample) |
| WO (1) | WO2005030723A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| WO2011092293A2 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Cyclohexyl amide derivatives as crf receptor antagonists |
| AR080055A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de pirazolo-[5,1-b]-oxazol como antagonistas de los receptores de crf -1 |
| CN102753527B (zh) | 2010-02-02 | 2014-12-24 | 诺华股份有限公司 | 用作crf受体拮抗剂的环己基酰胺衍生物 |
| CN103097391B (zh) | 2010-07-09 | 2015-04-08 | 雷科尔达蒂爱尔兰有限公司 | 作为mGlu5拮抗剂的新型螺环杂环化合物 |
| US8546416B2 (en) | 2011-05-27 | 2013-10-01 | Novartis Ag | 3-spirocyclic piperidine derivatives as ghrelin receptor agonists |
| AU2013255458A1 (en) | 2012-05-03 | 2014-10-09 | Novartis Ag | L-malate salt of 2, 7 - diaza - spiro [4.5 ] dec- 7 - yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6843979B2 (en) | 1999-04-26 | 2005-01-18 | Emory University | 4-haloethenylphenyl tropane:serotonin transporter imaging agents |
| EP1048302A3 (en) | 1999-04-30 | 2002-07-17 | Pfizer Products Inc. | Radiotracers for in vivo study of acetylcholinesterase and Alzheimer's disease |
| AU5613900A (en) * | 1999-06-30 | 2001-01-31 | Sun Microsystems, Inc. | Customizing web content based on network conditions |
| JP4815083B2 (ja) | 1999-08-31 | 2011-11-16 | メルク・シャープ・エンド・ドーム・コーポレイション | 複素環化合物およびそれの使用方法 |
| GB0103045D0 (en) * | 2001-02-07 | 2001-03-21 | Novartis Ag | Organic Compounds |
| JP4070431B2 (ja) | 2001-07-10 | 2008-04-02 | ジーイー・ヘルスケア・リミテッド | モノアミン再取込み部位のマッピング用ヨウ素付加神経プローブ |
| EP1556142A4 (en) | 2002-10-24 | 2006-11-08 | Merck & Co Inc | ALKYN DERIVATIVES AS TRACERS FOR THE METABOTROPE GLUTAMATE RECEPTOR BINDING |
-
2003
- 2003-09-26 GB GBGB0322612.3A patent/GB0322612D0/en not_active Ceased
-
2004
- 2004-09-24 MX MXPA06003424A patent/MXPA06003424A/es active IP Right Grant
- 2004-09-24 US US10/573,162 patent/US8674110B2/en not_active Expired - Fee Related
- 2004-09-24 AU AU2004275971A patent/AU2004275971B2/en not_active Ceased
- 2004-09-24 BR BRPI0414732-4A patent/BRPI0414732A/pt not_active IP Right Cessation
- 2004-09-24 CN CNB2004800273094A patent/CN100430380C/zh not_active Expired - Fee Related
- 2004-09-24 ES ES04765586T patent/ES2400713T3/es not_active Expired - Lifetime
- 2004-09-24 CA CA2539469A patent/CA2539469C/en not_active Expired - Fee Related
- 2004-09-24 EP EP04765586A patent/EP1670762B1/en not_active Expired - Lifetime
- 2004-09-24 PL PL04765586T patent/PL1670762T3/pl unknown
- 2004-09-24 WO PCT/EP2004/010743 patent/WO2005030723A1/en not_active Ceased
- 2004-09-24 PT PT47655865T patent/PT1670762E/pt unknown
- 2004-09-24 JP JP2006527359A patent/JP4965255B2/ja not_active Expired - Fee Related
-
2008
- 2008-12-23 AU AU2008261192A patent/AU2008261192B2/en not_active Ceased
-
2014
- 2014-01-24 US US14/162,885 patent/US20140142318A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06003424A (es) | 2006-06-20 |
| AU2004275971B2 (en) | 2008-10-02 |
| US20140142318A1 (en) | 2014-05-22 |
| EP1670762A1 (en) | 2006-06-21 |
| AU2008261192A1 (en) | 2009-01-22 |
| PL1670762T3 (pl) | 2013-05-31 |
| CA2539469A1 (en) | 2005-04-07 |
| WO2005030723A1 (en) | 2005-04-07 |
| AU2004275971A1 (en) | 2005-04-07 |
| US8674110B2 (en) | 2014-03-18 |
| US20090010838A1 (en) | 2009-01-08 |
| JP4965255B2 (ja) | 2012-07-04 |
| GB0322612D0 (en) | 2003-10-29 |
| AU2008261192B2 (en) | 2011-08-04 |
| ES2400713T3 (es) | 2013-04-11 |
| PT1670762E (pt) | 2013-02-07 |
| BRPI0414732A (pt) | 2006-11-21 |
| CN1856468A (zh) | 2006-11-01 |
| JP2007506698A (ja) | 2007-03-22 |
| EP1670762B1 (en) | 2012-12-05 |
| CN100430380C (zh) | 2008-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150924 |