Title:
RADIOPAQUE POLYMERS
Document Type and Number:
WIPO Patent Application WO/2020/003147
Kind Code:
A3
Abstract:
A hydrophilic polymer comprising pendent groups of the formula I: Wherein: W is independently selected from –OH, -COOH, -SO3H, -OPO3H, -O-(C1-4alkyl), -O-(C1-4alkyl)OH, -O-(C1-4alkyl)R2, -O-(C2H5O)qR1 –(C=O)-O-C1-4alkyl and –O-(C=O)C1-4alkyl; or a group –BZ; wherein –OH, COOH, O-PO3H and SO3H maybe in the form of a pharmaceutically acceptable salt; wherein: B is a bond, or a straight branched alkanediyl, oxyalkylene, alkylene oxaalkylene, or alkylene (oligooxalkylene) group, optionally containing one or more fluorine substituents; and Z is an ammonium, phosphonium, or sulphonium phosphate or phosphonate ester zwitterionic group; X is either a bond or a linking group having 1 to 8 carbons and optionally 1 to 4 heteroatoms selected from O, N and S; G is a coupling group through which the group of the formula I is coupled to the polymer and is selected from ether, ester, amide, carbonate, carbamate, 1,3 dioxolone, and 1,3 dioxane; R1 is H or C1-4 alkyl; R2 is –COOH, -SO3H, or –OPO3H2 q is an integer from 1 to 4; n is an integer from 1 to 4; p is an integer from 1 to 3; and n + p is from 2 to 5; and wherein -COOH, -OPO3H2 and -SO3H as well as phenolic -OH maybe in the form of a pharmaceutically acceptable salt.
Inventors:
LEWIS ANDREW (GB)
BRITTON HUGH (GB)
TANG YIQING (GB)
VINCE JONATHAN (GB)
ASHRAFI KOOROSH (GB)
GUEGEN DAMIEN (GB)
BRITTON HUGH (GB)
TANG YIQING (GB)
VINCE JONATHAN (GB)
ASHRAFI KOOROSH (GB)
GUEGEN DAMIEN (GB)
Application Number:
PCT/IB2019/055382
Publication Date:
November 26, 2020
Filing Date:
June 26, 2019
Export Citation:
Assignee:
BIOCOMPATIBLES UK LTD (GB)
International Classes:
C08F8/48; A61K9/16; A61K31/704; A61K49/04; C07C47/565; C07C47/575; C07C229/62; C07C309/11; C08F8/28; C08F8/30; C08F16/06; C08F20/06; C08L29/04; C08L101/14; A61L24/06; C07C45/63; C07C45/71; C07C227/18; C07C303/32; C08F2/14; C08F116/06; C08F216/06; C08F220/58; C08F290/12; C08L51/06
Domestic Patent References:
| WO2016115023A1 | 2016-07-21 |
Foreign References:
| US4406878A | 1983-09-27 | |||
| CN105968244A | 2016-09-28 | |||
| EP0436316A1 | 1991-07-10 | |||
| JPH06345705A | 1994-12-20 |
Other References:
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ASHRAFI KOOROSH ET AL: "Characterization of a novel intrinsically radiopaque Drug-eluting Bead for image-guided therapy: DC Bead LUMI(TM)", JOURNAL OF CONTROLLED RELEASE, ELSEVIER, AMSTERDAM, NL, vol. 250, 8 February 2017 (2017-02-08), pages 36 - 47, XP029953355, ISSN: 0168-3659, DOI: 10.1016/J.JCONREL.2017.02.001
TALEKAR, RAHUL SUBHASH ET AL: "Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines", JOURNAL OF ORGANIC CHEMISTRY , 70(21), 8590-8593 CODEN: JOCEAH; ISSN: 0022-3263, 2005, XP055732156, DOI: 10.1021/JO051191X
PAUL R. JONES ET AL: "The role of substituents and solvents in promoting "medium-size" ring-chain tautomerism", JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 12, 1 June 1990 (1990-06-01), US, pages 3891 - 3896, XP055733291, ISSN: 0022-3263, DOI: 10.1021/jo00299a036
STEPHEN HORNE ET AL: "The Regiospecific p-Deiodination of 2,4-Di-iodo Phenols; a New Synthesis of Aflatoxin B2", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 1, 1990, GB, pages 39 - 41, XP055733258, ISSN: 0022-4936, DOI: 10.1039/c39900000039
J H WILKINSON ET AL: "The Biological Action of Substances Related to Thyroxine. 3. SUBSTANCES DERIVED FROM 3,5-DIIODO-4-HYDROXYBENZALDEHYDE AND RELATED COMPOUNDS", BIOCHEMICAL JOURNAL, vol. 49, 1951, pages 714 - 718, XP055733263, ISSN: 0264-6021, DOI: 10.1042/bj0490714
PI-TAI CHOU ET AL: "Studies of the triplet state of the proton-transfer tautomer in salicylaldehydes", CHEMICAL PHYSICS LETTERS, vol. 370, no. 5-6, 21 March 2003 (2003-03-21), NL, pages 747 - 755, XP055733286, ISSN: 0009-2614, DOI: 10.1016/S0009-2614(03)00165-9
PISCOPO, EUGENIO ET AL: "Experimental observations on the iodination of phenolic compounds for the synthesis of intermediates of pharmaceutical chemical interest", BOLLETTINO - SOCIETA ITALIANA DI BIOLOGIA SPERIMENTALE , 59(1), 44-50 CODEN: BSIBAC; ISSN: 0037-8771, 1983, XP009523103
BOUGAULT, J. ET AL: "Some halogenated derivatives of salicylic aldehyde. II. Preparation of 3,5-diiodoacetylsalicylaldehyde and of the diacetyl acetals of 5-bromo and 3,5-diiodoacetylsalicylaldehyde. Pharmacodynamic data on these compounds", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE 630-2 CODEN: BSCFAS; ISSN: 0037-8968, 1949, XP009523104
COVELLO, M. ET AL: "New synthetic iodo-organic compounds: o-alkoxybenzaldehydes, o-alkyloxyacetophenones, and iodine-containing analogs", FARMACO, EDIZIONE SCIENTIFICA , 19(8), 675-87 CODEN: FRPSAX; ISSN: 0430-0920, 1964, XP009523105
PISCOPO, EUGENIO ET AL: "New synthetic iodine-containing organic compounds. 3,4,5-Triiodosalicylic acid and derivatives", RENDICONTO DELL'ACCADEMIA DELLE SCIENZE FISICHE E MATEMATICHE, NAPLES , VOLUME DATE 1980, 47, 253-62 CODEN: RASFAM; ISSN: 0370-3568, 1981, XP009523109
ASHRAFI KOOROSH ET AL: "Characterization of a novel intrinsically radiopaque Drug-eluting Bead for image-guided therapy: DC Bead LUMI(TM)", JOURNAL OF CONTROLLED RELEASE, ELSEVIER, AMSTERDAM, NL, vol. 250, 8 February 2017 (2017-02-08), pages 36 - 47, XP029953355, ISSN: 0168-3659, DOI: 10.1016/J.JCONREL.2017.02.001
TALEKAR, RAHUL SUBHASH ET AL: "Nonreductive Deiodination of ortho-Iodo-Hydroxylated Arenes Using Tertiary Amines", JOURNAL OF ORGANIC CHEMISTRY , 70(21), 8590-8593 CODEN: JOCEAH; ISSN: 0022-3263, 2005, XP055732156, DOI: 10.1021/JO051191X
PAUL R. JONES ET AL: "The role of substituents and solvents in promoting "medium-size" ring-chain tautomerism", JOURNAL OF ORGANIC CHEMISTRY, vol. 55, no. 12, 1 June 1990 (1990-06-01), US, pages 3891 - 3896, XP055733291, ISSN: 0022-3263, DOI: 10.1021/jo00299a036
STEPHEN HORNE ET AL: "The Regiospecific p-Deiodination of 2,4-Di-iodo Phenols; a New Synthesis of Aflatoxin B2", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 1, 1990, GB, pages 39 - 41, XP055733258, ISSN: 0022-4936, DOI: 10.1039/c39900000039
J H WILKINSON ET AL: "The Biological Action of Substances Related to Thyroxine. 3. SUBSTANCES DERIVED FROM 3,5-DIIODO-4-HYDROXYBENZALDEHYDE AND RELATED COMPOUNDS", BIOCHEMICAL JOURNAL, vol. 49, 1951, pages 714 - 718, XP055733263, ISSN: 0264-6021, DOI: 10.1042/bj0490714
PI-TAI CHOU ET AL: "Studies of the triplet state of the proton-transfer tautomer in salicylaldehydes", CHEMICAL PHYSICS LETTERS, vol. 370, no. 5-6, 21 March 2003 (2003-03-21), NL, pages 747 - 755, XP055733286, ISSN: 0009-2614, DOI: 10.1016/S0009-2614(03)00165-9
PISCOPO, EUGENIO ET AL: "Experimental observations on the iodination of phenolic compounds for the synthesis of intermediates of pharmaceutical chemical interest", BOLLETTINO - SOCIETA ITALIANA DI BIOLOGIA SPERIMENTALE , 59(1), 44-50 CODEN: BSIBAC; ISSN: 0037-8771, 1983, XP009523103
BOUGAULT, J. ET AL: "Some halogenated derivatives of salicylic aldehyde. II. Preparation of 3,5-diiodoacetylsalicylaldehyde and of the diacetyl acetals of 5-bromo and 3,5-diiodoacetylsalicylaldehyde. Pharmacodynamic data on these compounds", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE 630-2 CODEN: BSCFAS; ISSN: 0037-8968, 1949, XP009523104
COVELLO, M. ET AL: "New synthetic iodo-organic compounds: o-alkoxybenzaldehydes, o-alkyloxyacetophenones, and iodine-containing analogs", FARMACO, EDIZIONE SCIENTIFICA , 19(8), 675-87 CODEN: FRPSAX; ISSN: 0430-0920, 1964, XP009523105
PISCOPO, EUGENIO ET AL: "New synthetic iodine-containing organic compounds. 3,4,5-Triiodosalicylic acid and derivatives", RENDICONTO DELL'ACCADEMIA DELLE SCIENZE FISICHE E MATEMATICHE, NAPLES , VOLUME DATE 1980, 47, 253-62 CODEN: RASFAM; ISSN: 0370-3568, 1981, XP009523109
Attorney, Agent or Firm:
RODGERS, Matthew, William (GB)
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