JP2005502681A5 - - Google Patents
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- JP2005502681A5 JP2005502681A5 JP2003524971A JP2003524971A JP2005502681A5 JP 2005502681 A5 JP2005502681 A5 JP 2005502681A5 JP 2003524971 A JP2003524971 A JP 2003524971A JP 2003524971 A JP2003524971 A JP 2003524971A JP 2005502681 A5 JP2005502681 A5 JP 2005502681A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- substituted
- atoms
- aromatic
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims description 95
- 239000008194 pharmaceutical composition Substances 0.000 claims description 53
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- -1 mesylate salt Chemical class 0.000 claims description 19
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims 440
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 387
- 229910052760 oxygen Inorganic materials 0.000 claims 252
- 125000004432 carbon atom Chemical group C* 0.000 claims 242
- 125000004430 oxygen atom Chemical group O* 0.000 claims 241
- 125000004434 sulfur atom Chemical group 0.000 claims 241
- 125000000217 alkyl group Chemical group 0.000 claims 182
- 125000001475 halogen functional group Chemical group 0.000 claims 168
- 229910052757 nitrogen Inorganic materials 0.000 claims 147
- 150000001875 compounds Chemical class 0.000 claims 105
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 91
- 208000027866 inflammatory disease Diseases 0.000 claims 69
- 229910052739 hydrogen Inorganic materials 0.000 claims 67
- 238000000034 method Methods 0.000 claims 63
- 208000002249 Diabetes Complications Diseases 0.000 claims 55
- 201000010099 disease Diseases 0.000 claims 52
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 52
- 230000010410 reperfusion Effects 0.000 claims 42
- 208000018737 Parkinson disease Diseases 0.000 claims 35
- 208000027418 Wounds and injury Diseases 0.000 claims 35
- 229910052799 carbon Inorganic materials 0.000 claims 35
- 230000006378 damage Effects 0.000 claims 35
- 208000014674 injury Diseases 0.000 claims 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 33
- 206010012655 Diabetic complications Diseases 0.000 claims 29
- 229910052717 sulfur Inorganic materials 0.000 claims 22
- 208000037976 chronic inflammation Diseases 0.000 claims 20
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 20
- 230000002757 inflammatory effect Effects 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 210000000056 organ Anatomy 0.000 claims 19
- 125000003282 alkyl amino group Chemical group 0.000 claims 13
- 206010012601 diabetes mellitus Diseases 0.000 claims 13
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 12
- 208000019693 Lung disease Diseases 0.000 claims 12
- 210000003169 central nervous system Anatomy 0.000 claims 12
- 210000004195 gingiva Anatomy 0.000 claims 11
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 10
- 238000002054 transplantation Methods 0.000 claims 10
- 206010061218 Inflammation Diseases 0.000 claims 8
- 230000004054 inflammatory process Effects 0.000 claims 8
- 230000009885 systemic effect Effects 0.000 claims 8
- 206010008118 cerebral infarction Diseases 0.000 claims 4
- 208000026106 cerebrovascular disease Diseases 0.000 claims 4
- 208000010125 myocardial infarction Diseases 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 230000017531 blood circulation Effects 0.000 claims 2
- 210000004204 blood vessel Anatomy 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000002831 pharmacologic agent Substances 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1c(*)c(*)c(*)c2c1*C(c1c(*)c(*)c(*)c(I)c11)=C2N(*)C1=* Chemical compound *c1c(*)c(*)c(*)c2c1*C(c1c(*)c(*)c(*)c(I)c11)=C2N(*)C1=* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 2
- 229950002757 teoclate Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- CVBPOLXDFLTAGK-UHFFFAOYSA-N 11h-indeno[1,2-c]isoquinoline Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=NC=C21 CVBPOLXDFLTAGK-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
- VERUFXOALATMPS-UHFFFAOYSA-N 5,5-diamino-2-(2-phenylethenyl)cyclohex-3-ene-1,1-disulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)(S(O)(=O)=O)C1C=CC1=CC=CC=C1 VERUFXOALATMPS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MOPKKHSEOPGEBJ-UHFFFAOYSA-N O=C1NC(c2c(C3)cccc2)=C3c2ccccc12 Chemical compound O=C1NC(c2c(C3)cccc2)=C3c2ccccc12 MOPKKHSEOPGEBJ-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229950003153 amsonate Drugs 0.000 description 1
- OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940090805 clavulanate Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 229950000206 estolate Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/944,524 US20030096833A1 (en) | 2001-08-31 | 2001-08-31 | Substituted ideno[1,2-c]isoquinoline derivatives and methods of use thereof |
| PCT/US2002/027585 WO2003020700A2 (en) | 2001-08-31 | 2002-08-30 | SUBSTITUTED INDENO[1,2-c]ISOQUINOLINE DERIVATIVES AND METHODS OF USE THEREOF |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005502681A JP2005502681A (ja) | 2005-01-27 |
| JP2005502681A5 true JP2005502681A5 (https=) | 2007-03-22 |
Family
ID=25481570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003524971A Pending JP2005502681A (ja) | 2001-08-31 | 2002-08-30 | 置換インデノ［１，２−ｃ］イソキノリン誘導体及びその使用方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US20030096833A1 (https=) |
| EP (2) | EP2174659A1 (https=) |
| JP (1) | JP2005502681A (https=) |
| KR (1) | KR100922825B1 (https=) |
| CN (2) | CN100503574C (https=) |
| AT (1) | ATE465733T1 (https=) |
| AU (1) | AU2002329920B2 (https=) |
| BR (1) | BR0212225A (https=) |
| CA (1) | CA2457534A1 (https=) |
| CO (1) | CO5560543A2 (https=) |
| DE (1) | DE60236170D1 (https=) |
| EC (1) | ECSP044997A (https=) |
| ES (1) | ES2345436T3 (https=) |
| IL (1) | IL160437A0 (https=) |
| MX (1) | MXPA04001887A (https=) |
| NO (1) | NO20040845L (https=) |
| NZ (1) | NZ531218A (https=) |
| RU (1) | RU2300523C2 (https=) |
| WO (1) | WO2003020700A2 (https=) |
| ZA (1) | ZA200401376B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2362662A1 (en) * | 1999-02-12 | 2000-08-17 | Glaxo Group Limited | Phosphoramidate, and mono-, di-, and tri-phosphate esters of (1r, cis)-4-(6-amino-9h-purin-9-yl)-2-cyclopentene-1-methanol as antiviral agents |
| US6956035B2 (en) * | 2001-08-31 | 2005-10-18 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| US20030096833A1 (en) * | 2001-08-31 | 2003-05-22 | Jagtap Prakash G. | Substituted ideno[1,2-c]isoquinoline derivatives and methods of use thereof |
| EP1603567A4 (en) * | 2003-02-28 | 2006-10-18 | Inotek Pharmaceuticals Corp | TETRACYCLIC BENZAMIDE DERIVATIVES AND METHOD OF USE THEREOF |
| WO2004100891A2 (en) * | 2003-05-12 | 2004-11-25 | Purdue Research Foundation | Cytotoxic indeno and isoindoloisoquinolones |
| US20050228007A1 (en) * | 2004-02-26 | 2005-10-13 | Prakash Jagtap | Isoquinoline derivatives and methods of use thereof |
| EP1722796A4 (en) * | 2004-02-26 | 2008-01-23 | Inotek Pharmaceuticals Corp | TETRACYCLIC LACTAM DERIVATIVES AND USES THEREOF |
| CA2564027A1 (en) * | 2004-05-17 | 2005-11-24 | Tibotec Pharmaceuticals Ltd. | 1-heterocyclyl-1,5-dihydro-pyrido[3,2-b]indol-2-ones |
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-
2001
- 2001-08-31 US US09/944,524 patent/US20030096833A1/en not_active Abandoned
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2002
- 2002-08-30 CN CNB028213254A patent/CN100503574C/zh not_active Expired - Fee Related
- 2002-08-30 NZ NZ531218A patent/NZ531218A/en not_active IP Right Cessation
- 2002-08-30 US US10/233,198 patent/US6828319B2/en not_active Expired - Fee Related
- 2002-08-30 JP JP2003524971A patent/JP2005502681A/ja active Pending
- 2002-08-30 CA CA002457534A patent/CA2457534A1/en not_active Abandoned
- 2002-08-30 EP EP10152431A patent/EP2174659A1/en not_active Withdrawn
- 2002-08-30 BR BR0212225-1A patent/BR0212225A/pt not_active IP Right Cessation
- 2002-08-30 AU AU2002329920A patent/AU2002329920B2/en not_active Ceased
- 2002-08-30 DE DE60236170T patent/DE60236170D1/de not_active Expired - Lifetime
- 2002-08-30 CN CNA2006100924325A patent/CN1880306A/zh active Pending
- 2002-08-30 IL IL16043702A patent/IL160437A0/xx unknown
- 2002-08-30 MX MXPA04001887A patent/MXPA04001887A/es active IP Right Grant
- 2002-08-30 EP EP02766175A patent/EP1420785B1/en not_active Expired - Lifetime
- 2002-08-30 AT AT02766175T patent/ATE465733T1/de not_active IP Right Cessation
- 2002-08-30 ES ES02766175T patent/ES2345436T3/es not_active Expired - Lifetime
- 2002-08-30 WO PCT/US2002/027585 patent/WO2003020700A2/en not_active Ceased
- 2002-08-30 KR KR1020047002771A patent/KR100922825B1/ko not_active Expired - Fee Related
- 2002-08-30 RU RU2004109141/04A patent/RU2300523C2/ru not_active IP Right Cessation
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2004
- 2004-02-19 ZA ZA200401376A patent/ZA200401376B/en unknown
- 2004-02-25 CO CO04016685A patent/CO5560543A2/es not_active Application Discontinuation
- 2004-02-26 NO NO20040845A patent/NO20040845L/no unknown
- 2004-02-27 EC EC2004004997A patent/ECSP044997A/es unknown
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2008
- 2008-06-16 US US12/140,120 patent/US20080262016A1/en not_active Abandoned
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