JP3395912B2 - ヒドラゾアデノシン類 - Google Patents
ヒドラゾアデノシン類Info
- Publication number
- JP3395912B2 JP3395912B2 JP11666393A JP11666393A JP3395912B2 JP 3395912 B2 JP3395912 B2 JP 3395912B2 JP 11666393 A JP11666393 A JP 11666393A JP 11666393 A JP11666393 A JP 11666393A JP 3395912 B2 JP3395912 B2 JP 3395912B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- ribofuranosyl
- diazanyl
- purine
- methylene
- 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.)
- Expired - Lifetime
Links
- -1 nitro, amino Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 21
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Chemical group OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 21
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Chemical group OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 14
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 14
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical group OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical group OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 7
- 229930091371 Fructose Chemical group 0.000 claims description 7
- 239000005715 Fructose Chemical group 0.000 claims description 7
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical group OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229930182830 galactose Chemical group 0.000 claims description 7
- 150000002772 monosaccharides Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000003379 purinergic P1 receptor agonist Substances 0.000 claims description 3
- 239000003218 coronary vasodilator agent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229940122614 Adenosine receptor agonist Drugs 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 238000001953 recrystallisation Methods 0.000 description 18
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 16
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 8
- 229960005305 adenosine Drugs 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 230000024883 vasodilation Effects 0.000 description 7
- 102000009346 Adenosine receptors Human genes 0.000 description 6
- 108050000203 Adenosine receptors Proteins 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000010412 perfusion Effects 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- BAYFDGKAUSOEIS-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(6-amino-2-hydrazinylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(NN)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BAYFDGKAUSOEIS-UUOKFMHZSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UKEASMXMANFUQZ-LSCFUAHRSA-N C1=CC(OC)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 Chemical compound C1=CC(OC)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 UKEASMXMANFUQZ-LSCFUAHRSA-N 0.000 description 2
- ITFYSDWJXCEWHC-LSCFUAHRSA-N CC1=CC=CC(C=NNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](CO)O4)O)C=NC3=C(N)N=2)=C1 Chemical compound CC1=CC=CC(C=NNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](CO)O4)O)C=NC3=C(N)N=2)=C1 ITFYSDWJXCEWHC-LSCFUAHRSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PMMJCGFRGBDDQG-XNIJJKJLSA-N N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=C([N+]([O-])=O)C=C1 Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=C([N+]([O-])=O)C=C1 PMMJCGFRGBDDQG-XNIJJKJLSA-N 0.000 description 2
- QNEZIBAAJVBEHG-XNIJJKJLSA-N NC1=CC=CC(C=NNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](CO)O4)O)C=NC3=C(N)N=2)=C1 Chemical compound NC1=CC=CC(C=NNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](CO)O4)O)C=NC3=C(N)N=2)=C1 QNEZIBAAJVBEHG-XNIJJKJLSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 1
- QPZAPAYIOOBYAI-IDTAVKCVSA-N (2R,3R,4S,5R)-2-[6-amino-2-[2-(furan-3-ylmethylidene)hydrazinyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound NC1=C2N=CN(C2=NC(=N1)NN=CC1=COC=C1)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO QPZAPAYIOOBYAI-IDTAVKCVSA-N 0.000 description 1
- JPTATNMXNKQDSE-SCFUHWHPSA-N (2R,3R,4S,5R)-2-[6-amino-2-[2-(indolizin-3-ylmethylidene)hydrazinyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(NN=CC=3N4C=CC=CC4=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O JPTATNMXNKQDSE-SCFUHWHPSA-N 0.000 description 1
- VHMUQIWMOXQFBP-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-amino-2-(2-cyclohexylethoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1OCCC1CCCCC1 VHMUQIWMOXQFBP-LSCFUAHRSA-N 0.000 description 1
- DBFQHWKOYLSNEU-LSCFUAHRSA-N (2r,3r,4s,5r)-2-[6-amino-2-(2-phenylethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NCCC1=CC=CC=C1 DBFQHWKOYLSNEU-LSCFUAHRSA-N 0.000 description 1
- XJFMHMFFBSOEPR-XNIJJKJLSA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(cyclohexylmethylidene)hydrazinyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1CCCCC1 XJFMHMFFBSOEPR-XNIJJKJLSA-N 0.000 description 1
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- RZIYJWDNWCALSG-LSCFUAHRSA-N C1=CC(=CC=C1CC=NNC2=NC(=C3C(=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)N)F Chemical compound C1=CC(=CC=C1CC=NNC2=NC(=C3C(=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)N)F RZIYJWDNWCALSG-LSCFUAHRSA-N 0.000 description 1
- DUVUQYFYWUDDPW-LSCFUAHRSA-N C1=CC(C)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 Chemical compound C1=CC(C)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 DUVUQYFYWUDDPW-LSCFUAHRSA-N 0.000 description 1
- XAVFTXSMJCFSAS-SCFUHWHPSA-N C1=CC(CC)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 Chemical compound C1=CC(CC)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 XAVFTXSMJCFSAS-SCFUHWHPSA-N 0.000 description 1
- WYIXBSWZWJSNRL-XNIJJKJLSA-N C1=CC(N)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 Chemical compound C1=CC(N)=CC=C1C=NNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 WYIXBSWZWJSNRL-XNIJJKJLSA-N 0.000 description 1
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- JQZPCJAGIGKCNN-WVSUBDOOSA-N C1=NC=2C(N)=NC(NN=CC=3C=C4C=CC=CC4=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O Chemical compound C1=NC=2C(N)=NC(NN=CC=3C=C4C=CC=CC4=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O JQZPCJAGIGKCNN-WVSUBDOOSA-N 0.000 description 1
- LICQQKORWRFLFH-LSCFUAHRSA-N C=1C=CC=CC=1C(C)=NNC(N=C12)=NC(N)=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O Chemical compound C=1C=CC=CC=1C(C)=NNC(N=C12)=NC(N)=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O LICQQKORWRFLFH-LSCFUAHRSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
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- CEBYJLIWMBILKB-IDTAVKCVSA-N N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=CS1 Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=CS1 CEBYJLIWMBILKB-IDTAVKCVSA-N 0.000 description 1
- FPVAODOSBCIVHS-SDBHATRESA-N N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=NC=C1 Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=CC=NC=C1 FPVAODOSBCIVHS-SDBHATRESA-N 0.000 description 1
- KNQYGNKDZKWRPL-ZRFIDHNTSA-N N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=NC=CN1 Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C=NC=2C(N)=NC=1NN=CC1=NC=CN1 KNQYGNKDZKWRPL-ZRFIDHNTSA-N 0.000 description 1
- VGYLPYUAVODTOW-SCFUHWHPSA-N NC1=C2N=CN(C2=NC(=N1)NN=C(C)C1=CC=C(C=C1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO Chemical compound NC1=C2N=CN(C2=NC(=N1)NN=C(C)C1=CC=C(C=C1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO VGYLPYUAVODTOW-SCFUHWHPSA-N 0.000 description 1
- VTBBMINSOIYHBR-QTQZEZTPSA-N NC1=C2N=CN(C2=NC(=N1)NN=CC1=CC2=CC=C(C=C2C=C1)OC)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO Chemical compound NC1=C2N=CN(C2=NC(=N1)NN=CC1=CC2=CC=C(C=C2C=C1)OC)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO VTBBMINSOIYHBR-QTQZEZTPSA-N 0.000 description 1
- AKNMVSWRTZXKTC-QTQZEZTPSA-N NC1=C2N=CN(C2=NC(=N1)NN=CC1=CC=CC2=CC(=CC=C12)OC)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO Chemical compound NC1=C2N=CN(C2=NC(=N1)NN=CC1=CC=CC2=CC(=CC=C12)OC)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO AKNMVSWRTZXKTC-QTQZEZTPSA-N 0.000 description 1
- 102000000033 Purinergic Receptors Human genes 0.000 description 1
- 108010080192 Purinergic Receptors Proteins 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 230000008484 agonism Effects 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000001992 atrioventricular node Anatomy 0.000 description 1
- 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 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 230000000059 bradycardiac effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 210000005242 cardiac chamber Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004115 mitral valve Anatomy 0.000 description 1
- 101150104259 napC gene Proteins 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 238000000306 qrs interval Methods 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000002932 second-degree atrioventricular block Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/873,440 US5278150A (en) | 1992-04-24 | 1992-04-24 | 2-hydrazoadenosines and their utility for the treatmeat of vascular conditions |
| US873440 | 1992-04-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06128281A JPH06128281A (ja) | 1994-05-10 |
| JP3395912B2 true JP3395912B2 (ja) | 2003-04-14 |
Family
ID=25361637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11666393A Expired - Lifetime JP3395912B2 (ja) | 1992-04-24 | 1993-04-21 | ヒドラゾアデノシン類 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5278150A (enExample) |
| EP (1) | EP0567094B1 (enExample) |
| JP (1) | JP3395912B2 (enExample) |
| CA (1) | CA2093502C (enExample) |
| DE (1) | DE69323643T2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5477857A (en) * | 1993-09-10 | 1995-12-26 | Discovery Therapeutics, Inc. | Diagnostic uses of hydrazinoadenosines |
| US6448235B1 (en) | 1994-07-11 | 2002-09-10 | University Of Virginia Patent Foundation | Method for treating restenosis with A2A adenosine receptor agonists |
| US5877180A (en) * | 1994-07-11 | 1999-03-02 | University Of Virginia Patent Foundation | Method for treating inflammatory diseases with A2a adenosine receptor agonists |
| US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
| US5817641A (en) * | 1994-07-21 | 1998-10-06 | Thomas Jefferson University | Treatment of enterotoxigenic diarrhea with 2-substituted adenosine derivatives |
| AU740770B2 (en) | 1997-06-18 | 2001-11-15 | Aderis Pharmaceuticals, Inc. | Compositions and methods for preventing restenosis following revascularization procedures |
| US5972903A (en) * | 1997-10-07 | 1999-10-26 | Regents Of The University Of California Corporation | Method for promoting angiogenesis using heparin and adenosine |
| CA2305726A1 (en) | 1997-10-07 | 1999-04-15 | Regents Of The University Of California | Treating occlusive peripheral vascular disease and coronary disease with combinations of heparin and an adenoside a2 agonist, or with adenosine |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| DE10041478A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US6670334B2 (en) | 2001-01-05 | 2003-12-30 | University Of Virginia Patent Foundation | Method and compositions for treating the inflammatory response |
| GB2372741A (en) * | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,8-Disubstituted adenosine derivatives and their different uses |
| GB2372742A (en) * | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses |
| US20030027793A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal treatment of parkinson's disease |
| US20030026830A1 (en) * | 2001-05-08 | 2003-02-06 | Thomas Lauterback | Transdermal therapeutic system for parkinson's disease inducing high plasma levels of rotigotine |
| CA2460911C (en) * | 2001-10-01 | 2011-08-30 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
| WO2004016635A2 (en) * | 2002-08-15 | 2004-02-26 | Cv Therapeutics, Inc. | Partial and full agonists of a1 adenosine receptors |
| US20050033044A1 (en) * | 2003-05-19 | 2005-02-10 | Bristol-Myers Squibb Pharma Company | Methods for preparing 2-alkynyladenosine derivatives |
| EA011826B1 (ru) * | 2004-05-26 | 2009-06-30 | Инотек Фармасьютикалз Корпорейшн | Пуриновые производные в качестве агонистов аденозиновых арецепторов и способы их применения |
| US7576069B2 (en) * | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| WO2006023272A1 (en) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having a2a agonist activity |
| US7605143B2 (en) | 2004-08-02 | 2009-10-20 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5′-ribose groups having A2A agonist activity |
| CN101437526A (zh) * | 2004-09-20 | 2009-05-20 | 伊诺泰克制药公司 | 嘌呤衍生物及其用法 |
| US20060159621A1 (en) * | 2005-01-12 | 2006-07-20 | Barrett Richard J | Method of detecting myocardial dysfunction in patients having a history of asthma or bronchospasm |
| EP2218442A1 (en) | 2005-11-09 | 2010-08-18 | CombinatoRx, Inc. | Methods, compositions, and kits for the treatment of ophthalmic disorders |
| BRPI0619261A2 (pt) * | 2005-11-30 | 2011-09-27 | Inotek Pharmaceuticals Corp | derivados de purina e métodos de uso desses |
| WO2007092936A2 (en) * | 2006-02-08 | 2007-08-16 | University Of Virginia Patent Foundation | Method to treat gastric lesions |
| US8178509B2 (en) | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| JP2008285478A (ja) * | 2007-04-16 | 2008-11-27 | Santen Pharmaceut Co Ltd | アデノシンａ２ａ受容体アゴニストを有効成分として含有する緑内障治療剤 |
| US7558455B2 (en) * | 2007-06-29 | 2009-07-07 | Ethicon Endo-Surgery, Inc | Receiver aperture broadening for scanned beam imaging |
| US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| EP2257162A4 (en) * | 2008-02-29 | 2011-02-23 | King Pharmaceuticals Res & Dev | CRYSTALLIZED FORMS OF 2- {2-Ý (CYCLOHEXYL) METHYLENEHYDRAZINO} ADENOSINE |
| EP2274007B1 (en) | 2008-03-10 | 2016-12-14 | Cornell University | Modulation of blood brain barrier permeability |
| MX2012007661A (es) | 2010-01-11 | 2012-08-01 | Inotek Pharmaceuticals Corp | Combinacion, kit y metodo para reducir la presion intraocular. |
| EP2569325A4 (en) | 2010-03-26 | 2013-10-09 | Inotek Pharmaceuticals Corp | METHOD FOR REDUCING INNER EYE PRESSURE IN HUMANS USING N6-CYCLOPENTYLADENOSINE (CPA), CPA DERIVATIVES OR PRODRUGS THEREOF |
| EP3235825A1 (en) | 2012-01-26 | 2017-10-25 | Inotek Pharmaceuticals Corporation | Anhydrous polymorph a1 of [(2r,3s,4r,5r)-5-(6-(cyclopentylamino)-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)] methyl nitrate and processes of preparation thereof |
| NZ630759A (en) | 2013-03-15 | 2017-07-28 | Inotek Pharmaceuticals Corp | Ophthalmic formulations comprising an a1 agonist |
| EP3988559A4 (en) * | 2019-06-21 | 2023-07-19 | Academy of Military Medical Sciences | 2-BENZYLIDENE HYDRAZINOADENOSINE COMPOUNDS WITH A2A ADENOSINE RECEPTOR AGNOSTIC ACTIVITY |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990498A (en) | 1988-04-26 | 1991-02-05 | Temple University-Of The Commonwealth System Of Higher Education | 2- and 8-azido(2'-5')oligoadenylates and antiviral uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2034785A1 (de) * | 1970-07-14 | 1972-01-20 | Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof | Adenosin 5 carbonsäurederivate |
| US4224438A (en) * | 1970-07-14 | 1980-09-23 | Boehringer Mannheim Gmbh | Adenosine-5'-carboxylic acid amides |
| JPS4935635B1 (enExample) * | 1970-12-28 | 1974-09-25 | ||
| US4140851A (en) * | 1977-11-21 | 1979-02-20 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Synthesis and antitumor activity of 2,4,5-trisubstituted-pyrrolo2,3-d]-pyrimidine nucleosides |
| JP2619710B2 (ja) * | 1989-02-27 | 1997-06-11 | 日本製紙 株式会社 | ２′，３′−ジデオキシプリンヌクレオシド類の製造方法 |
| US5155098A (en) * | 1989-06-09 | 1992-10-13 | Hoechst-Roussel Pharmaceuticals Inc. | N-heteroaryl-purin-6-amines, and pharmaceutical compositions and methods employing them |
-
1992
- 1992-04-24 US US07/873,440 patent/US5278150A/en not_active Expired - Lifetime
-
1993
- 1993-04-06 CA CA002093502A patent/CA2093502C/en not_active Expired - Lifetime
- 1993-04-21 JP JP11666393A patent/JP3395912B2/ja not_active Expired - Lifetime
- 1993-04-21 DE DE69323643T patent/DE69323643T2/de not_active Expired - Lifetime
- 1993-04-21 EP EP93106460A patent/EP0567094B1/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990498A (en) | 1988-04-26 | 1991-02-05 | Temple University-Of The Commonwealth System Of Higher Education | 2- and 8-azido(2'-5')oligoadenylates and antiviral uses thereof |
Non-Patent Citations (4)
| Title |
|---|
| Ｃｏｌｌｅｃｔｉｏｎ Ｃｚｅｃｈｏｓｌｏｖ．Ｃｈｅｍ．Ｃｏｍｍｕｎ．，１９７８年，Ｖｏｌ．４３，ｐ．２３３０−２３４０ |
| Ｊ．Ｍｅｄ．Ｃｈｅｍ．，１９７２年，Ｖｏｌ．１５，Ｎｏ．７，ｐ．７３５−７３９ |
| Ｊ．Ｍｅｄ．Ｃｈｅｍ．，１９７７年，Ｖｏｌ．２０，Ｎｏ．３，ｐ．４０１−４０４ |
| Ｎｕｃｌｅｉｃ Ａｃｉｄｓ Ｒｅｓｅａｒｃｈ，１９８８年，Ｖｏｌ．１６，Ｎｏ．１，ｐ．２７９−２８９ |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2093502C (en) | 2004-06-22 |
| DE69323643T2 (de) | 1999-07-29 |
| EP0567094B1 (en) | 1999-03-03 |
| EP0567094A2 (en) | 1993-10-27 |
| EP0567094A3 (enExample) | 1994-03-30 |
| DE69323643D1 (de) | 1999-04-08 |
| US5278150A (en) | 1994-01-11 |
| JPH06128281A (ja) | 1994-05-10 |
| CA2093502A1 (en) | 1993-10-25 |
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