JP2004532251A5 - - Google Patents
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- JP2004532251A5 JP2004532251A5 JP2002592879A JP2002592879A JP2004532251A5 JP 2004532251 A5 JP2004532251 A5 JP 2004532251A5 JP 2002592879 A JP2002592879 A JP 2002592879A JP 2002592879 A JP2002592879 A JP 2002592879A JP 2004532251 A5 JP2004532251 A5 JP 2004532251A5
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- Japan
- Prior art keywords
- mono
- residues
- alkyl
- aryl
- group
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 329
- 125000003118 aryl group Chemical group 0.000 claims 320
- -1 gallium porphyrin Chemical class 0.000 claims 256
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 214
- 125000004404 heteroalkyl group Chemical group 0.000 claims 208
- 125000001072 heteroaryl group Chemical group 0.000 claims 195
- 125000000524 functional group Chemical group 0.000 claims 194
- 125000001188 haloalkyl group Chemical group 0.000 claims 190
- 125000000623 heterocyclic group Chemical group 0.000 claims 180
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 160
- 150000001413 amino acids Chemical class 0.000 claims 121
- 229920000570 polyether Polymers 0.000 claims 113
- 239000004721 Polyphenylene oxide Substances 0.000 claims 105
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 92
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 86
- 238000000034 method Methods 0.000 claims 84
- 150000002500 ions Chemical class 0.000 claims 67
- 229910052736 halogen Inorganic materials 0.000 claims 64
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 61
- 229910052733 gallium Inorganic materials 0.000 claims 57
- 125000005843 halogen group Chemical group 0.000 claims 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 49
- 150000001408 amides Chemical class 0.000 claims 39
- 150000002148 esters Chemical class 0.000 claims 35
- 125000003107 substituted aryl group Chemical group 0.000 claims 35
- 125000004429 atom Chemical group 0.000 claims 31
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 26
- 101150065749 Churc1 gene Proteins 0.000 claims 26
- 102100038239 Protein Churchill Human genes 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 24
- 229910021645 metal ion Inorganic materials 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- QGKVXWDADKTZHW-UHFFFAOYSA-N azaporphyrin Chemical compound C1=C(N=2)C=CC=2C=C(N=2)C=CC=2C=C(N2)C=CC2=CC2=CNC1=N2 QGKVXWDADKTZHW-UHFFFAOYSA-N 0.000 claims 15
- 125000004122 cyclic group Chemical group 0.000 claims 15
- 125000006239 protecting group Chemical group 0.000 claims 15
- 230000001225 therapeutic effect Effects 0.000 claims 15
- 210000001519 tissue Anatomy 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 13
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 13
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 13
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000003277 amino group Chemical group 0.000 claims 13
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 13
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 13
- 125000004104 aryloxy group Chemical group 0.000 claims 13
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 13
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 13
- 150000004820 halides Chemical class 0.000 claims 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 13
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims 13
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims 13
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 13
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 13
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 13
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000000539 amino acid group Chemical group 0.000 claims 9
- 230000007935 neutral effect Effects 0.000 claims 9
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 230000001678 irradiating effect Effects 0.000 claims 8
- 229910052751 metal Inorganic materials 0.000 claims 8
- 239000002184 metal Substances 0.000 claims 8
- 150000004032 porphyrins Chemical class 0.000 claims 8
- NCAJWYASAWUEBY-UHFFFAOYSA-N 3-[20-(2-carboxyethyl)-9,14-diethyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid Chemical compound N1C2=C(C)C(CC)=C1C=C(N1)C(C)=C(CC)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 NCAJWYASAWUEBY-UHFFFAOYSA-N 0.000 claims 7
- 208000037803 restenosis Diseases 0.000 claims 7
- VAJVGAQAYOAJQI-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-3,8,13,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical compound N1C(C=C2C(C)=CC(N2)=CC=2C(=C(CCC(O)=O)C(=C3)N=2)C)=CC(C)=C1C=C1C(C)=C(CCC(O)=O)C3=N1 VAJVGAQAYOAJQI-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- KNYADCQFKXFMEI-UHFFFAOYSA-N [N]1C2=CC=C1C=C(N1)C=C(Cl)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 Chemical compound [N]1C2=CC=C1C=C(N1)C=C(Cl)C1=CC([N]1)=CC=C1C=C(N1)C=CC1=C2 KNYADCQFKXFMEI-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 238000001514 detection method Methods 0.000 claims 6
- 238000002560 therapeutic procedure Methods 0.000 claims 6
- 201000001320 Atherosclerosis Diseases 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 5
- 229910052763 palladium Inorganic materials 0.000 claims 5
- 150000004033 porphyrin derivatives Chemical class 0.000 claims 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims 5
- 230000002792 vascular Effects 0.000 claims 5
- 229910052725 zinc Inorganic materials 0.000 claims 5
- 230000006378 damage Effects 0.000 claims 4
- 230000005292 diamagnetic effect Effects 0.000 claims 4
- 150000002170 ethers Chemical class 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 229910052738 indium Inorganic materials 0.000 claims 4
- 230000005298 paramagnetic effect Effects 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 229910052718 tin Inorganic materials 0.000 claims 4
- 229910052727 yttrium Inorganic materials 0.000 claims 4
- 201000004624 Dermatitis Diseases 0.000 claims 3
- 229910052782 aluminium Inorganic materials 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052742 iron Inorganic materials 0.000 claims 3
- 230000005291 magnetic effect Effects 0.000 claims 3
- 210000004509 vascular smooth muscle cell Anatomy 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims 2
- NKCPOFKWOHNOHZ-UHFFFAOYSA-N 23H-porphyrin-2,3,5,7,21-pentacarboxylic acid Chemical class N1C(C=C2N=C(C=C3N(C(=C4C(O)=O)C(C(O)=O)=C3C(O)=O)C(O)=O)C=C2)=CC=C1C=C1C=C(C(=O)O)C4=N1 NKCPOFKWOHNOHZ-UHFFFAOYSA-N 0.000 claims 2
- VXISDLXPDHAQEK-UHFFFAOYSA-N 23h-porphyrin-2,3,5,7,8,21-hexacarboxylic acid Chemical class N1C(C=C2N=C(C=C3N(C(=C4C(O)=O)C(C(O)=O)=C3C(O)=O)C(O)=O)C=C2)=CC=C1C=C1C(C(=O)O)=C(C(O)=O)C4=N1 VXISDLXPDHAQEK-UHFFFAOYSA-N 0.000 claims 2
- MOTVYDVWODTRDF-UHFFFAOYSA-N 3-[7,12,17-tris(2-carboxyethyl)-3,8,13,18-tetrakis(carboxymethyl)-21,22-dihydroporphyrin-2-yl]propanoic acid Chemical class N1C(C=C2C(=C(CC(O)=O)C(=CC=3C(=C(CC(O)=O)C(=C4)N=3)CCC(O)=O)N2)CCC(O)=O)=C(CC(O)=O)C(CCC(O)=O)=C1C=C1C(CC(O)=O)=C(CCC(=O)O)C4=N1 MOTVYDVWODTRDF-UHFFFAOYSA-N 0.000 claims 2
- UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical class CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 claims 2
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical class CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 2
- 108010035532 Collagen Proteins 0.000 claims 2
- 102000008186 Collagen Human genes 0.000 claims 2
- 229910052691 Erbium Inorganic materials 0.000 claims 2
- 229910052693 Europium Inorganic materials 0.000 claims 2
- 229910052689 Holmium Inorganic materials 0.000 claims 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 2
- 229910052765 Lutetium Inorganic materials 0.000 claims 2
- JGQGDUURWUDSDW-UHFFFAOYSA-N N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=NN=C1C=C1C=CC4=N1 Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=NN=C1C=C1C=CC4=N1 JGQGDUURWUDSDW-UHFFFAOYSA-N 0.000 claims 2
- 229910052779 Neodymium Inorganic materials 0.000 claims 2
- 229910052772 Samarium Inorganic materials 0.000 claims 2
- 229910052771 Terbium Inorganic materials 0.000 claims 2
- 229910052776 Thorium Inorganic materials 0.000 claims 2
- 229910052775 Thulium Inorganic materials 0.000 claims 2
- 229910052770 Uranium Inorganic materials 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 238000002399 angioplasty Methods 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 210000001772 blood platelet Anatomy 0.000 claims 2
- 229910052793 cadmium Inorganic materials 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 229910052804 chromium Inorganic materials 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229920001436 collagen Polymers 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
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- 230000001747 exhibiting effect Effects 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 229910052735 hafnium Inorganic materials 0.000 claims 2
- 125000005027 hydroxyaryl group Chemical group 0.000 claims 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 238000012977 invasive surgical procedure Methods 0.000 claims 2
- 229910052741 iridium Inorganic materials 0.000 claims 2
- 229910052746 lanthanum Inorganic materials 0.000 claims 2
- 229910052745 lead Inorganic materials 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 229910052748 manganese Inorganic materials 0.000 claims 2
- 238000013507 mapping Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 229940055577 oleyl alcohol Drugs 0.000 claims 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims 2
- 229940067082 pentetate Drugs 0.000 claims 2
- 229960003330 pentetic acid Drugs 0.000 claims 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 230000035479 physiological effects, processes and functions Effects 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 230000008569 process Effects 0.000 claims 2
- 229910052703 rhodium Inorganic materials 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 229910052709 silver Inorganic materials 0.000 claims 2
- 210000002027 skeletal muscle Anatomy 0.000 claims 2
- 210000003491 skin Anatomy 0.000 claims 2
- 230000006641 stabilisation Effects 0.000 claims 2
- 238000011105 stabilization Methods 0.000 claims 2
- 229910052713 technetium Inorganic materials 0.000 claims 2
- 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 2
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical group C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 claims 2
- 229910052721 tungsten Inorganic materials 0.000 claims 2
- 229910052720 vanadium Inorganic materials 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 229910052726 zirconium Inorganic materials 0.000 claims 2
- HMSMOZAIMDNRBW-UHFFFAOYSA-N 100572-96-1 Chemical compound C1=CC2=NC1=CC=C(N1)C=CC1=C(N1)C=CC1=CC=C1C=CC2=N1 HMSMOZAIMDNRBW-UHFFFAOYSA-N 0.000 claims 1
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- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 1
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
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- 2002-05-31 US US10/159,005 patent/US6827926B2/en not_active Expired - Fee Related
- 2002-05-31 CA CA002448562A patent/CA2448562A1/en not_active Abandoned
- 2002-05-31 JP JP2002592879A patent/JP2004532251A/ja active Pending
- 2002-05-31 WO PCT/US2002/017180 patent/WO2002096366A2/en not_active Ceased
- 2002-05-31 AU AU2002344234A patent/AU2002344234B2/en not_active Ceased
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2004
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