CA2297413A1 - Novel polyamine analogues as therapeutic and diagnostic agents - Google Patents
Novel polyamine analogues as therapeutic and diagnostic agents Download PDFInfo
- Publication number
- CA2297413A1 CA2297413A1 CA002297413A CA2297413A CA2297413A1 CA 2297413 A1 CA2297413 A1 CA 2297413A1 CA 002297413 A CA002297413 A CA 002297413A CA 2297413 A CA2297413 A CA 2297413A CA 2297413 A1 CA2297413 A1 CA 2297413A1
- Authority
- CA
- Canada
- Prior art keywords
- polyamine
- composition according
- group
- alkyl
- cells
- 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.)
- Abandoned
Links
- 229920000768 polyamine Polymers 0.000 title claims abstract description 427
- 239000003814 drug Substances 0.000 title abstract description 26
- 230000001225 therapeutic effect Effects 0.000 title description 8
- 229940124597 therapeutic agent Drugs 0.000 title description 3
- 229940039227 diagnostic agent Drugs 0.000 title description 2
- 239000000032 diagnostic agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 239000003112 inhibitor Substances 0.000 claims abstract description 93
- 238000003556 assay Methods 0.000 claims abstract description 75
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 38
- 230000005764 inhibitory process Effects 0.000 claims abstract description 35
- 201000011510 cancer Diseases 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 28
- 230000006378 damage Effects 0.000 claims abstract description 7
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 6
- 208000014674 injury Diseases 0.000 claims abstract description 6
- 238000002399 angioplasty Methods 0.000 claims abstract description 4
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical group NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 claims description 161
- 210000004027 cell Anatomy 0.000 claims description 105
- 230000015572 biosynthetic process Effects 0.000 claims description 92
- 238000003786 synthesis reaction Methods 0.000 claims description 88
- 230000027455 binding Effects 0.000 claims description 85
- -1 SO2NH Chemical group 0.000 claims description 81
- 229940063675 spermine Drugs 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 67
- 125000005647 linker group Chemical group 0.000 claims description 62
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- 239000007787 solid Substances 0.000 claims description 39
- 102000004190 Enzymes Human genes 0.000 claims description 35
- 108090000790 Enzymes Proteins 0.000 claims description 35
- 229940063673 spermidine Drugs 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 108090000623 proteins and genes Proteins 0.000 claims description 26
- 102000004169 proteins and genes Human genes 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 24
- 238000001514 detection method Methods 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 claims description 14
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000006853 reporter group Chemical group 0.000 claims description 14
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical group C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims description 13
- 239000005700 Putrescine Substances 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 10
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 claims description 10
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 9
- 230000004663 cell proliferation Effects 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- GUNURVWAJRRUAV-UHFFFAOYSA-N N(1)-acetylspermine Chemical compound CC(=O)NCCCNCCCCNCCCN GUNURVWAJRRUAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 230000001413 cellular effect Effects 0.000 claims description 8
- 108020004707 nucleic acids Proteins 0.000 claims description 8
- 102000039446 nucleic acids Human genes 0.000 claims description 8
- 150000007523 nucleic acids Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- RZOHQCYUTFAJLA-UHFFFAOYSA-N Canavalmine Chemical compound NCCCCNCCCNCCCCN RZOHQCYUTFAJLA-UHFFFAOYSA-N 0.000 claims description 6
- NSUSGNAFCIMCDH-UHFFFAOYSA-N n-[3-[4-(3-aminopropylamino)butylamino]propyl]-5-(dimethylamino)naphthalene-1-sulfonamide Chemical group C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCCCNCCCCNCCCN NSUSGNAFCIMCDH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000012216 screening Methods 0.000 claims description 6
- 210000004881 tumor cell Anatomy 0.000 claims description 6
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 5
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 5
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 5
- JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 claims description 5
- 241000723346 Cinnamomum camphora Species 0.000 claims description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 5
- 229960000846 camphor Drugs 0.000 claims description 5
- 229930008380 camphor Natural products 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000269 nucleophilic effect Effects 0.000 claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 4
- NMSWNFUNBWTSMA-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-1,2-oxazole Chemical compound O1C(C)=CC(C=2C(=CC=CC=2)Cl)=N1 NMSWNFUNBWTSMA-UHFFFAOYSA-N 0.000 claims description 4
- 229960005141 piperazine Drugs 0.000 claims description 4
- 230000035755 proliferation Effects 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- UODZHRGDSPLRMD-UHFFFAOYSA-N sym-homospermidine Chemical compound NCCCCNCCCCN UODZHRGDSPLRMD-UHFFFAOYSA-N 0.000 claims description 4
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 claims description 4
- XNCRUNXWPDJHGV-BQYQJAHWSA-N (e)-2-methyl-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(/C)=C/C1=CC=CC=C1 XNCRUNXWPDJHGV-BQYQJAHWSA-N 0.000 claims description 3
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- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 3
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- FONIWJIDLJEJTL-UHFFFAOYSA-N N(8)-acetylspermidine Chemical compound CC(=O)NCCCCNCCCN FONIWJIDLJEJTL-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
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- GKQPCPXONLDCMU-UHFFFAOYSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1C=CC(=O)OC(C)(C)C GKQPCPXONLDCMU-UHFFFAOYSA-N 0.000 claims description 3
- QMXSDTGNCZVWTB-UHFFFAOYSA-N n',n'-bis(3-aminopropyl)propane-1,3-diamine Chemical compound NCCCN(CCCN)CCCN QMXSDTGNCZVWTB-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C233/40—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/5308—Immunoassay; Biospecific binding assay; Materials therefor for analytes not provided for elsewhere, e.g. nucleic acids, uric acid, worms, mites
Landscapes
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Tropical Medicine & Parasitology (AREA)
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- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Cell Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5258697P | 1997-07-15 | 1997-07-15 | |
| US6572897P | 1997-11-14 | 1997-11-14 | |
| US8553898P | 1998-05-15 | 1998-05-15 | |
| US60/065,728 | 1998-05-15 | ||
| US60/085,538 | 1998-05-15 | ||
| US60/052,586 | 1998-05-15 | ||
| PCT/US1998/014896 WO1999003823A2 (en) | 1997-07-15 | 1998-07-15 | Novel polyamine analogues as therapeutic and diagnostic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2297413A1 true CA2297413A1 (en) | 1999-01-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002297413A Abandoned CA2297413A1 (en) | 1997-07-15 | 1998-07-15 | Novel polyamine analogues as therapeutic and diagnostic agents |
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| Country | Link |
|---|---|
| US (2) | US6172261B1 (https=) |
| EP (1) | EP1001927A2 (https=) |
| JP (1) | JP4044728B2 (https=) |
| AU (1) | AU758570B2 (https=) |
| CA (1) | CA2297413A1 (https=) |
| WO (1) | WO1999003823A2 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7208528B1 (en) | 1997-07-15 | 2007-04-24 | Mediquest Therapeutics, Inc. | Polyamine analogues as therapeutic and diagnostic agents |
| US6646149B1 (en) * | 1997-07-15 | 2003-11-11 | Nicolaas M. J. Vermeulin | Polyamine analogues as therapeutic and diagnostic agents |
| JP4044728B2 (ja) | 1997-07-15 | 2008-02-06 | メディクエスト セラピューティックス インク | 治療および診断薬剤としての新規なポリアミンアナログ |
| US8198334B2 (en) | 1997-10-27 | 2012-06-12 | Pathologica Llc | Methods for modulating macrophage proliferation in ocular disease using polyamine analogs |
| US7087648B1 (en) | 1997-10-27 | 2006-08-08 | The Regents Of The University Of California | Methods for modulating macrophage proliferation using polyamine analogs |
| CA2355880A1 (en) * | 1998-12-16 | 2000-06-22 | Neal David Hone | Process for preparing polyamines |
| ATE308515T1 (de) * | 1999-02-05 | 2005-11-15 | Oridigm Corp | Antizymmodulatoren sowie deren verwendung |
| AU4678300A (en) * | 1999-04-30 | 2000-11-17 | Slil Biomedical Corporation | Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
| US7413536B1 (en) | 1999-09-14 | 2008-08-19 | Xenoport, Inc. | Substrates and screening methods for transport proteins |
| CA2318004A1 (en) * | 1999-09-15 | 2001-03-15 | Oridigm Corporation | Novel polyamine analogues as therapeutic and diagnostic agents |
| EP1088815A1 (en) * | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonyl amino acid derivatives |
| HUP0400494A3 (en) * | 2000-03-24 | 2004-08-30 | Mediquest Therapeutics Inc Sea | Polyamine analogues as cytotoxic agents and pharmaceutical compositions containing them |
| AU2008201086B2 (en) * | 2001-01-08 | 2011-06-09 | Aminex Theapeutics, Inc. | Hydrophobic Polyamine Analogs and Methods for their Use |
| CN100582084C (zh) * | 2001-01-08 | 2010-01-20 | 麦迪凯斯特治疗学股份有限公司 | 疏水性多胺类似物及其使用方法 |
| USRE43327E1 (en) * | 2001-01-08 | 2012-04-24 | Aminex Therapeutics, Inc. | Hydrophobic polyamine analogs and methods for their use |
| US7432302B2 (en) * | 2001-01-08 | 2008-10-07 | Mediquest Therapeutics, Inc. | Composition containing polyamine transport inhibitor and use thereof |
| US6645719B2 (en) * | 2001-06-05 | 2003-11-11 | Advanced Gene Technology Corporation | Herbal chip |
| WO2003013245A1 (en) * | 2001-08-07 | 2003-02-20 | Wisconsin Alumni Research Foundation | Polyamines and analogs for protecting cells during cancer chemotherapy and radiotherapy |
| EP1420786A2 (en) | 2001-08-23 | 2004-05-26 | The Government of the United States of America, as represented by the Secretary, Department of Health and Human Services | Methods of inhibiting formation of vascular channels and proliferation using pyridinone derivatives |
| US7030126B2 (en) * | 2001-11-16 | 2006-04-18 | Als Therapy Development Foundation, Inc. | Use of polyamine analogs for amyotrophic lateral sclerosis |
| US20030129208A1 (en) * | 2002-01-07 | 2003-07-10 | Alberts David S. | Topical application of alpha-DFMO and anti-inflammatory drug for treatment of actinic keratoses |
| GB0202645D0 (en) * | 2002-02-05 | 2002-03-20 | Univ Southampton | Treatment of chronic neurodegenerative diseases |
| US20050027016A1 (en) | 2002-02-07 | 2005-02-03 | Fahl Kathleen L | Polyamine compounds and compositions for use in conjection with cancer therapy |
| WO2004073701A1 (ja) * | 2003-02-19 | 2004-09-02 | Kuniyasu Soda | Lfa-1抑制剤、及びその用途 |
| WO2005014524A2 (en) * | 2003-08-07 | 2005-02-17 | Wisconsin Alumni Research Foundation | Amino thiol compounds and compositions for use in conjunction with cancer therapy |
| EP3175780A1 (en) | 2003-12-18 | 2017-06-07 | Metronom Health, Inc. | Implantable biosensor and methods of use thereof |
| EP1765272B1 (en) * | 2004-06-14 | 2009-12-16 | Unilever PLC | Method of decreasing sebum production and pore size |
| US7740875B2 (en) * | 2004-10-08 | 2010-06-22 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| US20060078580A1 (en) * | 2004-10-08 | 2006-04-13 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| US7199267B1 (en) * | 2005-10-21 | 2007-04-03 | Mediquest Therapeutics, Inc. | Recognition of oligiosaccaride molecular targets by polycationic small molecule inhibitors and treatment of immunological disorders and infectious diseases |
| US7411002B2 (en) | 2006-06-07 | 2008-08-12 | The University Of Kansas | Polycationic sulfonamides and use thereof |
| EP2096106B1 (en) * | 2006-11-15 | 2014-06-18 | Nihon University | Novel polyamine derivatives |
| US8497398B1 (en) * | 2007-05-02 | 2013-07-30 | University Of Central Florida Research Foundation, Inc. | Polyamine transporter selective compounds as anti-cancer agents |
| FR2919287B1 (fr) * | 2007-07-26 | 2012-10-12 | Pf Medicament | Nouveaux derives fluorescents de polyamines, leur procede de preparation et leurs applications en tant qu'outils de diagnostic dans le traitement des tumeurs cancereuses. |
| JP2010538072A (ja) * | 2007-09-06 | 2010-12-09 | ジェナエラ コーポレイション | 糖尿病を治療する方法 |
| US9285320B2 (en) * | 2008-05-01 | 2016-03-15 | University Of Central Florida Research Foundation, Inc. | Fluorescent cytotoxic compounds specific for the cellular polyamine transport system |
| GB0904842D0 (en) * | 2009-03-20 | 2009-05-06 | Univ Nottingham | Protein labelling |
| US8258186B2 (en) | 2009-07-16 | 2012-09-04 | Pathologica, Llc | Pharmaceutical for oral delivery comprising MGBG |
| FR2967675B1 (fr) * | 2010-11-24 | 2015-02-27 | Pf Medicament | Derives fluorescents de cyanines polyamines en tant que sonde de diagnostic |
| DK2943189T3 (da) | 2013-01-08 | 2021-04-06 | Pathologica Llc | Mitoguazon til behandling af progressiv multipel sklerose |
| WO2016047676A1 (ja) * | 2014-09-24 | 2016-03-31 | 国立大学法人弘前大学 | 生体由来細胞を用いたがん細胞の検出方法 |
| US10695000B2 (en) | 2015-09-02 | 2020-06-30 | Metronom Health, Inc. | Systems and methods for continuous health monitoring using an opto-enzymatic analyte sensor |
| MX2018010768A (es) | 2016-03-25 | 2018-11-29 | Aminex Therapeutics Inc | Poliaminas biodisponibles. |
| WO2018111934A1 (en) * | 2016-12-12 | 2018-06-21 | University Of South Florida | Polyamine compounds targeting the efflux pumps of multi-drug resistant bacterial pathogens and methods of using the same |
| EP3833352A4 (en) | 2018-08-10 | 2022-04-06 | University of Central Florida Research Foundation, Inc. | Non-polyamine based polyamine transport inhibitors and their use in the treatment of human cancers |
| US11865095B2 (en) | 2020-09-30 | 2024-01-09 | Aminex Therapeutics, Inc. | Combination drug substance of polyamine transport inhibitor and DFMO |
| CN115074118B (zh) * | 2022-06-27 | 2024-10-18 | 山东理工大学 | 一种基于芘基荧光探针分子的对硝基苯胺检测方法 |
| WO2024130693A1 (zh) * | 2022-12-23 | 2024-06-27 | 中国医学科学院基础医学研究所 | 精胺衍生物及其在疾病中的治疗用途 |
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| US4309442A (en) | 1977-07-11 | 1982-01-05 | Merrell Toraude Et Compagnie | Method for controlling fertility in mammals |
| HU200093B (en) * | 1983-12-20 | 1990-04-28 | Adam Kovacs | Process for production of medical compositions against tumour |
| US4818770A (en) | 1986-10-22 | 1989-04-04 | Boyce Thompson Institute For Plant Research | Prevention of a plant disease by specific inhibition of fungal polyamine biosynthesis |
| US5342945A (en) | 1986-12-02 | 1994-08-30 | University Of Florida Research Foundation, Inc. | Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives |
| US4774339A (en) | 1987-08-10 | 1988-09-27 | Molecular Probes, Inc. | Chemically reactive dipyrrometheneboron difluoride dyes |
| JP3072108B2 (ja) | 1988-12-09 | 2000-07-31 | ダイセル化学工業株式会社 | 新規なポリアミン化合物及びグルタミン酸レセプター遮断剤 |
| JPH02266858A (ja) | 1989-04-07 | 1990-10-31 | Hitachi Ltd | 直流機の固定子 |
| EP0597830A1 (en) | 1989-07-03 | 1994-05-25 | New York University Nyu Medical Center | Use of polyamines as ionic-channel regulating agents |
| US5274113A (en) | 1991-11-01 | 1993-12-28 | Molecular Probes, Inc. | Long wavelength chemically reactive dipyrrometheneboron difluoride dyes and conjugates |
| US5433896A (en) | 1994-05-20 | 1995-07-18 | Molecular Probes, Inc. | Dibenzopyrrometheneboron difluoride dyes |
| US5252714A (en) | 1990-11-28 | 1993-10-12 | The University Of Alabama In Huntsville | Preparation and use of polyethylene glycol propionaldehyde |
| US5248782A (en) | 1990-12-18 | 1993-09-28 | Molecular Probes, Inc. | Long wavelength heteroaryl-substituted dipyrrometheneboron difluoride dyes |
| US5312928A (en) * | 1991-02-11 | 1994-05-17 | Cambridge Neuroscience | Calcium channel antagonists and methodology for their identification |
| US5187288A (en) | 1991-05-22 | 1993-02-16 | Molecular Probes, Inc. | Ethenyl-substituted dipyrrometheneboron difluoride dyes and their synthesis |
| DK0743853T3 (da) * | 1994-02-08 | 2001-07-16 | Nps Pharma Inc | Forbindelser, der er aktive ved et nyt sted på receptorstyrede calciumkanaler, og som er nyttige til behandling af neurologiske tilstande og sygdomme |
| WO1996022962A1 (en) * | 1995-01-23 | 1996-08-01 | The Trustees Of Columbia University In The City Of New York | Butyryl-tyrosinyl spermine, analogs thereof and methods of preparing and using same |
| US5583239A (en) * | 1995-05-30 | 1996-12-10 | Lehigh University | Antimicrobial sterol conjugates |
| JPH09235271A (ja) * | 1996-02-29 | 1997-09-09 | Suntory Ltd | ポリアミン誘導体 |
| JP4044728B2 (ja) | 1997-07-15 | 2008-02-06 | メディクエスト セラピューティックス インク | 治療および診断薬剤としての新規なポリアミンアナログ |
| WO2000034226A1 (en) | 1998-12-10 | 2000-06-15 | Universite Laval | Polyamine transport inhibitors |
| ATE308515T1 (de) | 1999-02-05 | 2005-11-15 | Oridigm Corp | Antizymmodulatoren sowie deren verwendung |
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| WO1999003823A2 (en) | 1999-01-28 |
| JP4044728B2 (ja) | 2008-02-06 |
| AU8496898A (en) | 1999-02-10 |
| US6172261B1 (en) | 2001-01-09 |
| US7160923B1 (en) | 2007-01-09 |
| AU758570B2 (en) | 2003-03-27 |
| WO1999003823A3 (en) | 1999-04-08 |
| JP2001510181A (ja) | 2001-07-31 |
| EP1001927A2 (en) | 2000-05-24 |
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