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)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic 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 |
| 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 |
| US6448235B1 (en) | 1994-07-11 | 2002-09-10 | University Of Virginia Patent Foundation | Method for treating restenosis with A2A adenosine receptor agonists |
| US5817641A (en) * | 1994-07-21 | 1998-10-06 | Thomas Jefferson University | Treatment of enterotoxigenic diarrhea with 2-substituted adenosine derivatives |
| JP2002505687A (ja) | 1997-06-18 | 2002-02-19 | ディスカバリー セラピューティクス，インコーポレイテッド | 脈管再生手順の後の再狭窄を防止するための組成物および方法 |
| US6440947B1 (en) | 1997-10-07 | 2002-08-27 | The Regents Of The University Of California | Method for treating occlusive peripheral vascular disease and coronary disease |
| US5972903A (en) * | 1997-10-07 | 1999-10-26 | Regents Of The University Of California Corporation | Method for promoting angiogenesis using heparin and adenosine |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| 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 |
| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| 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 |
| GB2372742A (en) * | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses |
| GB2372741A (en) * | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,8-Disubstituted 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 |
| RU2340623C2 (ru) * | 2002-08-15 | 2008-12-10 | Си Ви Терапьютикс, Инк. | Частичные и полные агонисты аденозиновых рецепторов a1 |
| US20050033044A1 (en) | 2003-05-19 | 2005-02-10 | Bristol-Myers Squibb Pharma Company | Methods for preparing 2-alkynyladenosine derivatives |
| PT1758596E (pt) | 2004-05-26 | 2010-06-23 | Inotek Pharmaceuticals Corp | Derivados de purina como agonistas do receptor de adenosina a1 e processos para a sua utilização |
| US7442687B2 (en) * | 2004-08-02 | 2008-10-28 | The University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| SG155182A1 (en) | 2004-08-02 | 2009-09-30 | Univ Virginia | 2-propynyl adenosine analogs with modified 5æ-ribose groups having a2a agonist activity |
| WO2006028618A1 (en) * | 2004-08-02 | 2006-03-16 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity |
| NZ554506A (en) * | 2004-09-20 | 2011-01-28 | Inotek Pharmaceuticals Corp | Purine derivatives and methods of use thereof |
| MX2007008412A (es) * | 2005-01-12 | 2007-09-04 | King Pharmaceuticals Res & Dev | Metodo para detectar disfuncion miocardica en pacientes que cuentan con un historial de asma y broncoespasmos. |
| EP1956906A4 (en) | 2005-11-09 | 2009-12-30 | Combinatorx Inc | METHODS, COMPOSITIONS AND KITS FOR THE TREATMENT OF PATHOLOGIES |
| AU2006320578B2 (en) * | 2005-11-30 | 2013-01-31 | Inotek Pharmaceuticals Corporation | Purine derivatives and methods of use thereof |
| US20080027022A1 (en) * | 2006-02-08 | 2008-01-31 | Linden Joel M | Method to treat gastric lesions |
| WO2007120972A2 (en) | 2006-02-10 | 2007-10-25 | 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 |
| WO2009108829A2 (en) * | 2008-02-29 | 2009-09-03 | King Pharmaceuticals Research And Development, Inc. | Crystal forms of 2-{2-[(cyclohexyl)methylene]hydrazino}adenosine |
| US20110064671A1 (en) | 2008-03-10 | 2011-03-17 | Cornell University | Modulation of blood brain barrier permeability |
| BR112012017106A2 (pt) | 2010-01-11 | 2018-05-29 | Inotek Pharmaceuticals Corp | combinação, kit e método de redução de pressão intraocular. |
| JP2013523739A (ja) | 2010-03-26 | 2013-06-17 | イノテック ファーマシューティカルズ コーポレイション | Ｎ６−シクロペンチルアデノシン（ｃｐａ）、ｃｐａ誘導体またはそれらのプロドラッグを用いてヒトにおける眼内圧を低下させる方法 |
| NZ627778A (en) | 2012-01-26 | 2017-01-27 | Inotek Pharmaceuticals Corp | Anhydrous polymorphs of (2r,3s,4r,5r)-5-(6-(cyclopentylamino)-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)} methyl nitrate and processes of preparation thereof |
| AU2014239222A1 (en) | 2013-03-15 | 2015-10-01 | Inotek Pharmaceuticals Corporation | Ophthalmic formulations |
| WO2020253872A1 (zh) * | 2019-06-21 | 2020-12-24 | 中国人民解放军军事科学院军事医学研究院 | 具有a2a腺苷受体激动活性的2-苄叉肼基腺苷类化合物 |
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 |
|---|---|
| CA2093502A1 (en) | 1993-10-25 |
| DE69323643T2 (de) | 1999-07-29 |
| JPH06128281A (ja) | 1994-05-10 |
| US5278150A (en) | 1994-01-11 |
| DE69323643D1 (de) | 1999-04-08 |
| EP0567094A2 (en) | 1993-10-27 |
| EP0567094A3 (enExample) | 1994-03-30 |
| CA2093502C (en) | 2004-06-22 |
| EP0567094B1 (en) | 1999-03-03 |
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