IL96434A - Cascade polymers, processes for the preparation thereof and pharmaceutical compositions containing the same - Google Patents

Cascade polymers, processes for the preparation thereof and pharmaceutical compositions containing the same

Info

Publication number: IL96434A
Authority: IL; Israel
Prior art keywords: mmol; mixture; analysis; cascade; solution
Prior art date: 1989-11-21

Application number

IL9643490A

Other languages

English (en)

Other versions

IL96434A0 (en

Original Assignee

Schering 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.)

1989-11-21

Filing date

1990-11-21

Publication date

1995-01-24

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6394147&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL96434(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-11-21 Application filed by Schering Ag filed Critical Schering Ag

1991-08-16 Publication of IL96434A0 publication Critical patent/IL96434A0/xx

1995-01-24 Publication of IL96434A publication Critical patent/IL96434A/en

Links

229920000642 polymer Polymers 0.000 title claims abstract description 85
238000000034 method Methods 0.000 title description 38
230000008569 process Effects 0.000 title description 10
238000002360 preparation method Methods 0.000 title description 3
239000008194 pharmaceutical composition Substances 0.000 title description 2
150000002500 ions Chemical class 0.000 claims abstract description 37
150000001413 amino acids Chemical class 0.000 claims abstract description 18
150000001768 cations Chemical class 0.000 claims abstract description 11
150000007530 organic bases Chemical class 0.000 claims abstract description 9
150000007529 inorganic bases Chemical class 0.000 claims abstract description 8
-1 imino, phenylene, phenylenoxy, phenylenimino, amide Chemical class 0.000 claims description 77
229920002521 macromolecule Polymers 0.000 claims description 25
150000002148 esters Chemical class 0.000 claims description 21
125000000524 functional group Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
102000004169 proteins and genes Human genes 0.000 claims description 8
108090000623 proteins and genes Proteins 0.000 claims description 8
229910052720 vanadium Inorganic materials 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000013522 chelant Substances 0.000 claims description 6
239000002738 chelating agent Substances 0.000 claims description 6
239000012634 fragment Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 5
108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
229920002307 Dextran Polymers 0.000 claims description 4
150000004676 glycans Chemical class 0.000 claims description 4
229920001282 polysaccharide Polymers 0.000 claims description 4
239000005017 polysaccharide Substances 0.000 claims description 4
239000004593 Epoxy Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
108010088751 Albumins Proteins 0.000 claims description 2
102000009027 Albumins Human genes 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
102000004856 Lectins Human genes 0.000 claims description 2
108090001090 Lectins Proteins 0.000 claims description 2
229920002472 Starch Polymers 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
239000002523 lectin Substances 0.000 claims description 2
235000019698 starch Nutrition 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000464 thioxo group Chemical group S=* 0.000 claims description 2
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230000000536 complexating effect Effects 0.000 abstract description 25
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239000008139 complexing agent Substances 0.000 abstract description 4
238000002560 therapeutic procedure Methods 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 162
150000001875 compounds Chemical class 0.000 description 100
238000004458 analytical method Methods 0.000 description 99
239000000203 mixture Substances 0.000 description 92
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
229910001868 water Inorganic materials 0.000 description 87
239000000243 solution Substances 0.000 description 83
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
239000003921 oil Substances 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 35
239000002872 contrast media Substances 0.000 description 28
229910052688 Gadolinium Inorganic materials 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
239000000843 powder Substances 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
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239000012071 phase Substances 0.000 description 19
239000000047 product Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
206010028980 Neoplasm Diseases 0.000 description 17
239000002253 acid Substances 0.000 description 17
238000007792 addition Methods 0.000 description 17
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238000000108 ultra-filtration Methods 0.000 description 17
239000007983 Tris buffer Substances 0.000 description 16
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
229910052740 iodine Inorganic materials 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 13
239000008367 deionised water Substances 0.000 description 13
229910021641 deionized water Inorganic materials 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 13
LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
210000001519 tissue Anatomy 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
239000000538 analytical sample Substances 0.000 description 11
238000010168 coupling process Methods 0.000 description 11
229940012017 ethylenediamine Drugs 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
239000012528 membrane Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 10
230000002378 acidificating effect Effects 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
239000000427 antigen Substances 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
239000008280 blood Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
229960001701 chloroform Drugs 0.000 description 10
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238000005859 coupling reaction Methods 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
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CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
102000036639 antigens Human genes 0.000 description 9
108091007433 antigens Proteins 0.000 description 9
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
238000003384 imaging method Methods 0.000 description 9
150000002540 isothiocyanates Chemical class 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
229910052751 metal Chemical class 0.000 description 9
239000002184 metal Chemical class 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
UOTMYNBWXDUBNX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinolin-2-ium;chloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 UOTMYNBWXDUBNX-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
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YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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230000029936 alkylation Effects 0.000 description 4
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150000001720 carbohydrates Chemical class 0.000 description 4
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
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238000004128 high performance liquid chromatography Methods 0.000 description 4
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SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
108090001008 Avidin Chemical group 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
150000004032 porphyrins Chemical class 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
WCWKKSOQLQEJTE-UHFFFAOYSA-N praseodymium(3+) Chemical compound [Pr+3] WCWKKSOQLQEJTE-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
238000000163 radioactive labelling Methods 0.000 description 1
230000003439 radiotherapeutic effect Effects 0.000 description 1
108700034465 rat GOPC Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229940069575 rompun Drugs 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
DOSGOCSVHPUUIA-UHFFFAOYSA-N samarium(3+) Chemical compound [Sm+3] DOSGOCSVHPUUIA-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
238000004904 shortening Methods 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 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
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
HKCRVXUAKWXBLE-UHFFFAOYSA-N terbium(3+) Chemical compound [Tb+3] HKCRVXUAKWXBLE-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
150000003553 thiiranes Chemical class 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000006276 transfer reaction Methods 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000012800 visualization Methods 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/12—Macromolecular compounds
- A61K49/124—Macromolecular compounds dendrimers, dendrons, hyperbranched compounds
- 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
- 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
- A61K51/06—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules
- A61K51/065—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules conjugates with carriers being macromolecules
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Radiology & Medical Imaging (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Optics & Photonics (AREA)
Pharmacology & Pharmacy (AREA)
Physics & Mathematics (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Compounds Of Unknown Constitution (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Magnetic Resonance Imaging Apparatus (AREA)
Steroid Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

IL9643490A 1989-11-21 1990-11-21 Cascade polymers, processes for the preparation thereof and pharmaceutical compositions containing the same IL96434A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3938992A DE3938992A1 (de)	1989-11-21	1989-11-21	Kaskadenpolymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel

Publications (2)

Publication Number	Publication Date
IL96434A0 IL96434A0 (en)	1991-08-16
IL96434A true IL96434A (en)	1995-01-24

Family

ID=6394147

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9643490A IL96434A (en)	1989-11-21	1990-11-21	Cascade polymers, processes for the preparation thereof and pharmaceutical compositions containing the same

Country Status (19)

Country	Link
US (10)	US5364614A (fr)
EP (1)	EP0430863B2 (fr)
JP (2)	JP3179092B2 (fr)
KR (1)	KR100202796B1 (fr)
AT (1)	ATE122698T1 (fr)
AU (1)	AU684453C (fr)
CA (1)	CA2030472C (fr)
DE (2)	DE3938992A1 (fr)
DK (1)	DK0430863T4 (fr)
ES (1)	ES2073006T5 (fr)
FI (1)	FI107931B (fr)
GR (1)	GR3031629T3 (fr)
HU (1)	HUT56121A (fr)
IE (1)	IE69317B1 (fr)
IL (1)	IL96434A (fr)
NO (1)	NO178032C (fr)
NZ (1)	NZ236162A (fr)
PT (1)	PT95944B (fr)
ZA (1)	ZA909352B (fr)

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1989
- 1989-11-21 DE DE3938992A patent/DE3938992A1/de not_active Withdrawn
1990
- 1990-11-19 DK DK90730017T patent/DK0430863T4/da active
- 1990-11-19 EP EP90730017A patent/EP0430863B2/fr not_active Expired - Lifetime
- 1990-11-19 ES ES90730017T patent/ES2073006T5/es not_active Expired - Lifetime
- 1990-11-19 AT AT90730017T patent/ATE122698T1/de not_active IP Right Cessation
- 1990-11-19 DE DE59009093T patent/DE59009093D1/de not_active Expired - Fee Related
- 1990-11-20 NZ NZ236162A patent/NZ236162A/xx unknown
- 1990-11-20 HU HU907217A patent/HUT56121A/hu unknown
- 1990-11-21 PT PT95944A patent/PT95944B/pt not_active IP Right Cessation
- 1990-11-21 NO NO905037A patent/NO178032C/no unknown
- 1990-11-21 IL IL9643490A patent/IL96434A/en not_active IP Right Cessation
- 1990-11-21 AU AU66859/90A patent/AU684453C/en not_active Ceased
- 1990-11-21 FI FI905744A patent/FI107931B/fi not_active IP Right Cessation
- 1990-11-21 JP JP31444090A patent/JP3179092B2/ja not_active Expired - Fee Related
- 1990-11-21 ZA ZA909352A patent/ZA909352B/xx unknown
- 1990-11-21 KR KR1019900018949A patent/KR100202796B1/ko not_active Expired - Fee Related
- 1990-11-21 US US07/617,077 patent/US5364614A/en not_active Expired - Lifetime
- 1990-11-21 CA CA002030472A patent/CA2030472C/fr not_active Expired - Fee Related
- 1990-11-21 IE IE419990A patent/IE69317B1/en not_active IP Right Cessation
1994
- 1994-12-02 US US08/353,390 patent/US5650136A/en not_active Expired - Fee Related
1996
- 1996-11-04 US US08/743,535 patent/US5911971A/en not_active Expired - Fee Related
1998
- 1998-09-17 US US09/156,047 patent/US6054117A/en not_active Expired - Fee Related
- 1998-09-17 US US09/156,048 patent/US6183724B1/en not_active Expired - Fee Related
1999
- 1999-10-15 GR GR990402638T patent/GR3031629T3/el unknown
2000
- 2000-02-22 US US09/510,363 patent/US6193950B1/en not_active Expired - Fee Related
- 2000-04-28 JP JP2000130116A patent/JP2000355593A/ja active Pending
- 2000-07-28 US US09/628,179 patent/US6299859B1/en not_active Expired - Fee Related
2001
- 2001-10-11 US US09/973,836 patent/US6576222B2/en not_active Expired - Fee Related
2002
- 2002-12-11 US US10/316,094 patent/US6855309B2/en not_active Expired - Fee Related
2004
- 2004-09-30 US US10/953,582 patent/US7208139B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DK0430863T4 (da)	2000-01-31
PT95944A (pt)	1991-09-13
PT95944B (pt)	1999-12-31
FI905744A0 (fi)	1990-11-21
DK0430863T3 (da)	1995-07-10
US6855309B2 (en)	2005-02-15
GR3031629T3 (en)	2000-01-31
HUT56121A (en)	1991-07-29
HU907217D0 (en)	1991-05-28
KR100202796B1 (ko)	1999-06-15
US5650136A (en)	1997-07-22
NO905037D0 (no)	1990-11-21
NZ236162A (en)	1993-03-26
US6576222B2 (en)	2003-06-10
US6183724B1 (en)	2001-02-06
US6299859B1 (en)	2001-10-09
DE59009093D1 (de)	1995-06-22
FI107931B (fi)	2001-10-31
US6054117A (en)	2000-04-25
NO178032C (no)	1996-01-10
US20030232017A1 (en)	2003-12-18
IL96434A0 (en)	1991-08-16
US5911971A (en)	1999-06-15
AU684453C (en)	2001-08-02
JP2000355593A (ja)	2000-12-26
US6193950B1 (en)	2001-02-27
EP0430863A2 (fr)	1991-06-05
US7208139B2 (en)	2007-04-24
ES2073006T5 (es)	2000-01-16
EP0430863B2 (fr)	1999-08-25
IE69317B1 (en)	1996-09-04
JPH03246234A (ja)	1991-11-01
FI905744L (fi)	1991-05-22
ZA909352B (en)	1991-12-24
AU684453B2 (en)	1997-12-18
JP3179092B2 (ja)	2001-06-25
AU6685990A (en)	1991-05-30
KR910009786A (ko)	1991-06-28
ES2073006T3 (es)	1995-08-01
US20020068037A1 (en)	2002-06-06
EP0430863A3 (en)	1992-03-04
CA2030472A1 (fr)	1991-05-22
NO905037L (no)	1991-05-22
IE904199A1 (en)	1991-05-22
ATE122698T1 (de)	1995-06-15
US20050118105A1 (en)	2005-06-02
US5364614A (en)	1994-11-15
NO178032B (no)	1995-10-02
CA2030472C (fr)	2003-06-10
EP0430863B1 (fr)	1995-05-17
DE3938992A1 (de)	1991-05-23

Legal Events

Date	Code	Title
1997-01-10	KB	Patent renewed
2001-04-30	KB	Patent renewed
2005-02-20	KB	Patent renewed
2010-02-14	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US6193950B1 (en)	2001-02-27	Cascade polymer bound complexing compounds, their complexes and conjugates, processes for their production, and pharmaceutical agents containing them
US5403572A (en)	1995-04-04	Macrocyclic polyaza compounds containing 5 or 6 membered rings, process for producing them and pharmaceutical media containing them
EP0607222B1 (fr)	1998-12-23	Polychelateurs dendrimeres
AU661305B2 (en)	1995-07-20	Macrocyclic polymer complexing agents, their complexes, process for their production and pharmaceutical agents containing these compounds
FI94758B (fi)	1995-07-14	Makrosyklisiä yhdisteitä, joissa on 3,6,9,15-tetra-atsabisyklo/9.3.1/pentadekaanirakenne, niiden käyttö NMR-, röntgen- tai radiodiagnostiikkaan käytettävissä koostumuksissa ja tällaiset koostumukset
DE3713842A1 (de)	1988-11-17	Substituierte cyclische komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel
JPH04504436A (ja)	1992-08-06	キーラント
DE3806795A1 (de)	1989-09-07	Polymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel
DE3701665A1 (de)	1988-07-28	Polymer-komplexe, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel
HK1002101B (en)	2000-03-17	Dendrimeric polychelants