CA2213420A1 - Purine compounds and xanthine oxidase inhibitors - Google Patents
Purine compounds and xanthine oxidase inhibitorsInfo
- Publication number
- CA2213420A1 CA2213420A1 CA002213420A CA2213420A CA2213420A1 CA 2213420 A1 CA2213420 A1 CA 2213420A1 CA 002213420 A CA002213420 A CA 002213420A CA 2213420 A CA2213420 A CA 2213420A CA 2213420 A1 CA2213420 A1 CA 2213420A1
- Authority
- CA
- Canada
- Prior art keywords
- purine
- group
- compound
- mmol
- crystals
- 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
- 239000003064 xanthine oxidase inhibitor Substances 0.000 title claims description 9
- 150000003212 purines Chemical class 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000005843 halogen group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 20
- -1 hydroxy, mercapto Chemical class 0.000 claims abstract description 19
- 201000001431 Hyperuricemia Diseases 0.000 claims abstract description 12
- 201000005569 Gout Diseases 0.000 claims abstract description 9
- 230000003449 preventive effect Effects 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229940123769 Xanthine oxidase inhibitor Drugs 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 63
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 16
- LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Natural products O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 102000004316 Oxidoreductases Human genes 0.000 abstract 1
- 108090000854 Oxidoreductases Proteins 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 106
- 230000015572 biosynthetic process Effects 0.000 description 105
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 97
- 239000013078 crystal Substances 0.000 description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000007787 solid Substances 0.000 description 35
- 230000002829 reductive effect Effects 0.000 description 30
- 235000019441 ethanol Nutrition 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- DQPYBDVXNBBRJD-UHFFFAOYSA-N 6-hydrazinyl-1,7-dihydropurin-2-one Chemical compound NNC1=NC(=O)NC2=C1N=CN2 DQPYBDVXNBBRJD-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XVNUBRNZEFYAHQ-UHFFFAOYSA-N 6-hydrazinyl-1,7-dihydropurine-2-thione Chemical compound NNC1=NC(=S)NC2=C1N=CN2 XVNUBRNZEFYAHQ-UHFFFAOYSA-N 0.000 description 15
- 108010093894 Xanthine oxidase Proteins 0.000 description 14
- 102100033220 Xanthine oxidase Human genes 0.000 description 14
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 12
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 11
- LGVZYOTZCIMBEV-UHFFFAOYSA-N 6-[amino(methyl)amino]-3,7-dihydropurin-2-one Chemical compound CN(N)C1=NC(=O)NC2=C1N=CN2 LGVZYOTZCIMBEV-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- QCFNQRYMMJROEN-UHFFFAOYSA-N (2-chloro-7h-purin-6-yl)hydrazine Chemical compound NNC1=NC(Cl)=NC2=C1NC=N2 QCFNQRYMMJROEN-UHFFFAOYSA-N 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 8
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 6
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 5
- FABHPBUKYDZYNQ-UHFFFAOYSA-N 6-[amino(methyl)amino]-3,7-dihydropurine-2-thione Chemical compound CN(N)C1=NC(=S)NC2=C1N=CN2 FABHPBUKYDZYNQ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 5
- 229960003459 allopurinol Drugs 0.000 description 5
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 4
- KNOLGURLPMQDCC-UHFFFAOYSA-N 6-hydrazinyl-7h-purin-2-amine Chemical compound NNC1=NC(N)=NC2=C1NC=N2 KNOLGURLPMQDCC-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
- 229940075420 xanthine Drugs 0.000 description 4
- MVOLONKPBYDCBY-UHFFFAOYSA-N 2-chloro-n-[(4-methoxyphenyl)methylideneamino]-7h-purin-6-amine Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(Cl)=NC2=C1N=CN2 MVOLONKPBYDCBY-UHFFFAOYSA-N 0.000 description 3
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 3
- ALCXNSKCLNEYQV-UHFFFAOYSA-N 6-[2-[(4-methoxyphenyl)methylidene]hydrazinyl]-1,7-dihydropurine-2-thione Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(=S)NC2=C1N=CN2 ALCXNSKCLNEYQV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229940081310 piperonal Drugs 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
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- 229910052623 talc Inorganic materials 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- LBBZMBBDCZIGTI-UHFFFAOYSA-N 2-chloro-n-[(4-fluorophenyl)methylideneamino]-7h-purin-6-amine Chemical compound C1=CC(F)=CC=C1C=NNC1=NC(Cl)=NC2=C1N=CN2 LBBZMBBDCZIGTI-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- FAEPWEARBQUGAU-UHFFFAOYSA-N 6-[2-[(4-chlorophenyl)methylidene]hydrazinyl]-1,7-dihydropurin-2-one Chemical compound C1=CC(Cl)=CC=C1C=NNC1=NC(=O)NC2=C1N=CN2 FAEPWEARBQUGAU-UHFFFAOYSA-N 0.000 description 2
- UNIGLJQRLNEZAY-UHFFFAOYSA-N 6-[2-[(4-methoxyphenyl)methylidene]hydrazinyl]-1,7-dihydropurin-2-one Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(=O)NC2=C1N=CN2 UNIGLJQRLNEZAY-UHFFFAOYSA-N 0.000 description 2
- PCVSBCXIXDVPBZ-UHFFFAOYSA-N 6-[[(2-methoxyphenyl)methylideneamino]-methylamino]-3,7-dihydropurin-2-one Chemical compound COC1=CC=CC=C1C=NN(C)C1=NC(=O)NC2=C1N=CN2 PCVSBCXIXDVPBZ-UHFFFAOYSA-N 0.000 description 2
- HUFMVHQBTYPYGW-UHFFFAOYSA-N 6-n-[(4-methoxyphenyl)methylideneamino]-7h-purine-2,6-diamine Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(N)=NC2=C1N=CN2 HUFMVHQBTYPYGW-UHFFFAOYSA-N 0.000 description 2
- RJOXFJDOUQJOMQ-UHFFFAOYSA-N 6-sulfanylidene-3,7-dihydropurin-2-one Chemical compound S=C1NC(=O)NC2=C1NC=N2 RJOXFJDOUQJOMQ-UHFFFAOYSA-N 0.000 description 2
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- 101100460387 Caenorhabditis elegans nhx-3 gene Proteins 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- UVZBXXXXIRYACB-UHFFFAOYSA-N N12C(=S)NC=3NC=NC=3C2=NN=C1C1=CC=CC=C1 Chemical compound N12C(=S)NC=3NC=NC=3C2=NN=C1C1=CC=CC=C1 UVZBXXXXIRYACB-UHFFFAOYSA-N 0.000 description 1
- GYCSGXAKECWSJP-UHFFFAOYSA-N N1C(=S)N2C(C)=NN=C2C2=C1NC=N2 Chemical compound N1C(=S)N2C(C)=NN=C2C2=C1NC=N2 GYCSGXAKECWSJP-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- LURQBQNWDYASPJ-UHFFFAOYSA-N hydrazinyl Chemical compound N[NH] LURQBQNWDYASPJ-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZJJZWNDBAONXPX-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethylideneamino)-2-chloro-7h-purin-6-amine Chemical compound C1=C2OCOC2=CC(C=NNC=2N=C(N=C3NC=NC3=2)Cl)=C1 ZJJZWNDBAONXPX-UHFFFAOYSA-N 0.000 description 1
- GTGGCIQWJDNVDC-UHFFFAOYSA-N n-(butylideneamino)-2-chloro-7h-purin-6-amine Chemical compound CCCC=NNC1=NC(Cl)=NC2=C1N=CN2 GTGGCIQWJDNVDC-UHFFFAOYSA-N 0.000 description 1
- VCVLJCHFJSSEDG-UHFFFAOYSA-N n-[(4-nitrophenyl)methylideneamino]-7h-purin-6-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=NNC1=NC=NC2=C1NC=N2 VCVLJCHFJSSEDG-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5653795 | 1995-02-21 | ||
| JP5653695 | 1995-02-21 | ||
| JP56537/1995 | 1995-02-21 | ||
| JP56536/1995 | 1995-02-21 | ||
| JP6337795 | 1995-02-27 | ||
| JP6337895 | 1995-02-27 | ||
| JP63378/1995 | 1995-02-27 | ||
| JP63377/1995 | 1995-02-27 | ||
| JP248739/1995 | 1995-09-01 | ||
| JP24874095 | 1995-09-01 | ||
| JP248740/1995 | 1995-09-01 | ||
| JP24873995 | 1995-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2213420A1 true CA2213420A1 (en) | 1996-08-29 |
Family
ID=27550642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002213420A Abandoned CA2213420A1 (en) | 1995-02-21 | 1996-02-21 | Purine compounds and xanthine oxidase inhibitors |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5990118A (enExample) |
| EP (1) | EP0811624A1 (enExample) |
| CA (1) | CA2213420A1 (enExample) |
| WO (1) | WO1996026208A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ329798A (en) * | 1996-07-03 | 1999-04-29 | Japan Energy Corp | Purine derivatives their tautomers and salts thereof and interferon secretion inducers, antiviral agents and anticancer drugs containing the same |
| ES2166270B1 (es) * | 1999-07-27 | 2003-04-01 | Almirall Prodesfarma Sa | Derivados de 8-fenil-6,9-dihidro-(1,2,4,)triazolo(3,4-i)purin-5-ona. |
| WO2006121995A2 (en) | 2005-05-09 | 2006-11-16 | Tap Pharmaceutical Products, Inc. | Methods for treating nephrolithiasis |
| KR101797936B1 (ko) | 2010-09-10 | 2017-11-15 | 다케다 파마슈티칼스 유에스에이, 인코포레이티드 | 테오필린과 페북소스타트의 병용 치료 방법 |
| CN112912378B (zh) * | 2018-08-30 | 2023-09-12 | 泰拉强石株式会社 | 用于抑制黄嘌呤氧化酶的肼基嘌呤化合物以及三唑并嘌呤化合物 |
| EP3950064A4 (en) * | 2019-04-03 | 2023-01-04 | Tera Stone Co., Ltd | THYMINE NUCLEOBASE BASED TRIAZOLOPYRIMIDINES AND PROCESS FOR THEIR PRODUCTION |
| CN114796170A (zh) * | 2022-06-01 | 2022-07-29 | 集美大学 | 对羟基苯甲醛在制备改善或治疗高尿酸血症的药物中的应用 |
-
1996
- 1996-02-21 US US08/894,474 patent/US5990118A/en not_active Expired - Fee Related
- 1996-02-21 CA CA002213420A patent/CA2213420A1/en not_active Abandoned
- 1996-02-21 EP EP96903203A patent/EP0811624A1/en not_active Withdrawn
- 1996-02-21 WO PCT/JP1996/000391 patent/WO1996026208A1/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0811624A1 (en) | 1997-12-10 |
| WO1996026208A1 (en) | 1996-08-29 |
| US5990118A (en) | 1999-11-23 |
| EP0811624A4 (enExample) | 1998-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |