# US 2014/0193338 A1 · Compounds for use in imaging, diagnosing and/or treatment of diseases of the central nervous system > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0193338 A1 - Document ID: US20140193338A1 - Status: Published application - Kind: A1 - Application number: 14/006,325 - Filed: 2012-03-20 - Published: 2014-07-10 - Earliest claimed: 2011-03-23 - Assignees: Piramal Imaging SA - Inventors: Andrea Thiele; Georg Kettschau; Tobias Heinrich; Lutz Lehmann; Christer Halldin; Sangram Nag; Andrea Varrone; Balazs Gulyas - Web page: https://patentgrep.com/patent/US20140193338A1 ## CPC - A61K 49/0004: {Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions} - A61K 51/04: Organic compounds - A61K 51/0406: {Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines} - C07C 211/41: containing condensed ring systems - C07C 211/42: with six-membered aromatic rings being part of the condensed ring systems - C07C 307/02: Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids - C07D 291/08: condensed with carbocyclic rings or ring systems - C07B 2200/05: Isotopically modified compounds, e.g. labelled - C07C 2602/08: the other ring being five-membered, e.g. indane - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F) ## Abstract This invention relates to novel compounds suitable for labelling by 18F and the corresponding 18F labelled compounds themselves, 19F-fluorinated analogues thereof and their use as reference standards, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by Positron Emission Tomography (PET). ## Claims ### Claim at position 1 1-18. (canceled) ### Claim 19 A compound of formula I wherein (R1)(Q)(R2) is selected from the group consisting of (O)(bond)(S(O)2), ([18F]fluoro)(blank)(S(O)2(O−)(X+)), (F)(blank)(S(O)2(O−)(X+)), ([18F]fluoro)(blank)(H), and (F)(blank)(H); X+ is selected from the group consisting of Li+, Na+, K+, Cs+, and/or Rb+; bond means that the atoms or atom groups adjacent to the bond share at least one pair of electrons and thus are chemically bonded to each other; blank means that there is neither a chemical bond nor an atom or an atom group connecting R1 and R2. including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 20 (depends on 19) A compound of claim 19, characterized in that the compound is selected from a compound of formula Ia including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 21 (depends on 20) A compound of claim 20, characterized in that the compound is (1S,2S)-2-[18F]fluoro-N-[(1,1-2H2)prop-2-yn-1-yl]indan-1-amine including any pharmaceutically acceptable salt thereof. ### Claim 22 (depends on 19) A compound of claim 19, characterized in that the compound is selected from a compound of formula Ib including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 23 (depends on 22) A compound of claim 22, characterized in that the compound is (1S,2S)-2-fluoro-N-[(1,1-2H2)prop-2-yn-1-yl]indan-1-amine including any pharmaceutically acceptable salt thereof. ### Claim 24 (depends on 19) A compound of claim 19, characterized in that the compound is selected from a compound of formula Ic including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 25 (depends on 24) A compound of claim 24, characterized in that the compound is (3aS,8aR)-3-[(1,1-2H2)prop-2-yn-1-yl]-3,3a,8,8a-tetrahydroindeno[1,2d][1,2,3]oxathiazole 2,2-dioxide including any pharmaceutically acceptable salt thereof. ### Claim 26 (depends on 19) A compound of claim 19, characterized in that the compound is selected from a compound of formula Id wherein X+ is selected from the group Li+, Na+, K+, Cs+, and/or Rb+; including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 27 (depends on 26) A compound of claim 26, characterized in that the compound is potassium N-[(1S,2S)-2-[18F]fluoroindan-1-yl]-N-[(1,1-2H2)prop-2-yn-1-yl]sulfamate including any pharmaceutically acceptable salt thereof. ### Claim 28 (depends on 19) A compound of claim 19, characterized in that the compound is selected from a compound of formula Ie wherein X+ is selected from the group Li+, Na+, K+, Cs+, and/or Rb+; including all isomeric forms of said compound, including but not limited to enantiomers and diastereoisomers as well as mixtures of isomers, and any pharmaceutically acceptable salt thereof. ### Claim 29 (depends on 28) A compound of claim 28, characterized in that the compound is caesium N-[(1S,2S)-2-fluoroindan-1-yl]-N-[(1,1-2H2)prop-2-yn-1-yl]sulfamate including any pharmaceutically acceptable salt thereof. ### Claim 30 (depends on 20) A method for PET imaging, comprising performing said imaging in the presence of a compound of claim 20 as a diagnostic compound. ### Claim 31 (depends on 20) A diagnostic composition comprising a compound of claim 20 and a carrier suitable for a diagnostic composition. ### Claim 32 (depends on 30) A method according to claim 30, which is for PET imaging of a CNS disease. ### Claim 33 (depends on 30) A method according to claim 30, which is for imaging of Alzheimer's disease. ### Claim 34 (depends on 20) A method for imaging of Alzheimer's disease, comprising performing said imaging in the presence of a compound of claim 20 as a diagnostic compound. ### Claim 35 Method for the synthesis of a compound of according to formula I wherein (R1)(Q)(R2) is selected from the group consisting of (O)(bond)(S(O)2), ([18F]fluoro)(blank)(S(O)2(O−)(X+)), (F)(blank)(S(O)2(O−)(X+)), ([18F]fluoro)(blank)(H), and (F)(blank)(H); X+ is selected from the group consisting of Li+, Na+, K+, Cs+, and/or Rb+; bond means that the atoms or atom groups adjacent to the bond share at least one pair of electrons and thus are chemically bonded to each other; blank means that there is neither a chemical bond nor an atom or an atom group connecting R1 and R2; the method comprising the steps converting a compound of formula III into a compound of formula IV optionally reacting obtained compound of formula IV with a 18F— or 19F-fluorination agent, thereby obtaining a compound of formula Id or Ie, wherein X+ is selected from the group consisting of Li+, Na+, K+, Cs+, and/or Rb+, optionally reacting obtained compound of formula Ie or Id with acid, thereby obtaining a compound of formula Ia or Ib optionally converting obtained compound Ia, Ib, Ic, Id or Ie into a suitable salt of inorganic or organic bases, hydrates, and/or solvates thereof. ### Claim 36 (depends on 19) A kit comprising at least one sealed container comprising a compound or a composition according to claim 19.