CA1067083A - Anti-hypertensive n"-cyano-pyridyl guanidines - Google Patents
Anti-hypertensive n"-cyano-pyridyl guanidinesInfo
- Publication number
- CA1067083A CA1067083A CA241,325A CA241325A CA1067083A CA 1067083 A CA1067083 A CA 1067083A CA 241325 A CA241325 A CA 241325A CA 1067083 A CA1067083 A CA 1067083A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pyridyl
- cyano
- formula
- radical
- 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
Links
- 230000003276 anti-hypertensive effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 238000000034 method Methods 0.000 claims abstract description 89
- 230000008569 process Effects 0.000 claims abstract description 37
- -1 pyridyl carbodiimides Chemical class 0.000 claims abstract description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 7
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- VNDMHLAEEQWFEV-UHFFFAOYSA-N n'-tert-butyl-n-pyridin-3-ylmethanediimine Chemical compound CC(C)(C)N=C=NC1=CC=CN=C1 VNDMHLAEEQWFEV-UHFFFAOYSA-N 0.000 claims description 21
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- TXXOFXVEUPZZHB-UHFFFAOYSA-N 2-tert-butyl-1-cyano-3-pyridin-3-ylguanidine Chemical compound CC(C)(C)N=C(NC#N)NC1=CC=CN=C1 TXXOFXVEUPZZHB-UHFFFAOYSA-N 0.000 claims description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- HKZNADVVGXKQDL-UHFFFAOYSA-N 1-cyano-2-(2-methylbutan-2-yl)-3-(3-pyridinyl)guanidine Chemical compound CCC(C)(C)N=C(NC#N)NC1=CC=CN=C1 HKZNADVVGXKQDL-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- DVFDIUYWCJGOOJ-UHFFFAOYSA-N 1-cyano-2-(2,2-dimethylpropyl)-3-pyridin-3-ylguanidine Chemical compound CC(C)(C)CN=C(NC#N)NC1=CC=CN=C1 DVFDIUYWCJGOOJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- SDYSNRRRDUJUAS-UHFFFAOYSA-N 2-(3,3-dimethylbutyl)guanidine Chemical compound CC(C)(C)CCN=C(N)N SDYSNRRRDUJUAS-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- MDPHCIMOEKILTR-UHFFFAOYSA-N n'-pyridin-4-ylmethanediimine Chemical compound N=C=NC1=CC=NC=C1 MDPHCIMOEKILTR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- QOYJKSTXGPEIDB-UHFFFAOYSA-N n'-(2-methylbutan-2-yl)-n-pyridin-3-ylmethanediimine Chemical compound CCC(C)(C)N=C=NC1=CC=CN=C1 QOYJKSTXGPEIDB-UHFFFAOYSA-N 0.000 claims description 2
- BPSDCBNFPAYLCU-UHFFFAOYSA-N n'-(3-methylpentan-3-yl)-n-pyridin-3-ylmethanediimine Chemical compound CCC(C)(CC)N=C=NC1=CC=CN=C1 BPSDCBNFPAYLCU-UHFFFAOYSA-N 0.000 claims description 2
- UWEMVHJIUZWPBX-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-n'-pyridin-3-ylmethanediimine Chemical compound CC(C)(C)CN=C=NC1=CC=CN=C1 UWEMVHJIUZWPBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- DUHKVGCSEPEJRY-UHFFFAOYSA-N 1-cyano-2-(3-ethylpentan-3-yl)-3-pyridin-3-ylguanidine Chemical compound CCC(CC)(CC)N=C(NC#N)NC1=CC=CN=C1 DUHKVGCSEPEJRY-UHFFFAOYSA-N 0.000 claims 2
- DVBZYBSNXKAJHX-UHFFFAOYSA-N 1-cyano-2-(3-methylpentan-3-yl)-3-pyridin-3-ylguanidine Chemical compound CCC(C)(CC)N=C(NC#N)NC1=CC=CN=C1 DVBZYBSNXKAJHX-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- QLZDQAYRCYLCDS-UHFFFAOYSA-N n'-(3-ethylpentan-3-yl)-n-pyridin-3-ylmethanediimine Chemical compound CCC(CC)(CC)N=C=NC1=CC=CN=C1 QLZDQAYRCYLCDS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- 230000001077 hypotensive effect Effects 0.000 abstract description 6
- 230000036772 blood pressure Effects 0.000 abstract description 5
- 208000001953 Hypotension Diseases 0.000 abstract description 3
- 208000021822 hypotensive Diseases 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 3
- 231100001274 therapeutic index Toxicity 0.000 abstract description 3
- 230000008018 melting Effects 0.000 description 49
- 238000002844 melting Methods 0.000 description 49
- 238000010521 absorption reaction Methods 0.000 description 13
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 150000003585 thioureas Chemical class 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 150000001718 carbodiimides Chemical class 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000674 adrenergic antagonist Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 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 3
- 239000003814 drug Substances 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
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- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- 125000004414 alkyl thio group Chemical group 0.000 description 2
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
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- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
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- 230000002526 effect on cardiovascular system Effects 0.000 description 1
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- 229950007639 guancidine Drugs 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 125000005394 methallyl group Chemical group 0.000 description 1
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- NVNNBNRPKLNWDJ-UHFFFAOYSA-N methyl n-pyridin-2-ylcarbamodithioate Chemical compound CSC(=S)NC1=CC=CC=N1 NVNNBNRPKLNWDJ-UHFFFAOYSA-N 0.000 description 1
- 229960003632 minoxidil Drugs 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- MJGSUXJFWQPDAK-UHFFFAOYSA-N n'-(2-methylbutan-2-yl)-n-pyridin-4-ylmethanediimine Chemical compound CCC(C)(C)N=C=NC1=CC=NC=C1 MJGSUXJFWQPDAK-UHFFFAOYSA-N 0.000 description 1
- NZHJRKIZENYXSI-UHFFFAOYSA-N n'-tert-butyl-n-pyridin-2-ylmethanediimine Chemical group CC(C)(C)N=C=NC1=CC=CC=N1 NZHJRKIZENYXSI-UHFFFAOYSA-N 0.000 description 1
- CELHWLWSQBTZII-UHFFFAOYSA-N n'-tert-butyl-n-pyridin-4-ylmethanediimine Chemical compound CC(C)(C)N=C=NC1=CC=NC=C1 CELHWLWSQBTZII-UHFFFAOYSA-N 0.000 description 1
- BQNUIPPUWFUEOC-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-n'-pyridin-4-ylmethanediimine Chemical compound CC(C)(C)CN=C=NC1=CC=NC=C1 BQNUIPPUWFUEOC-UHFFFAOYSA-N 0.000 description 1
- RTJSAEAGHXVRMH-UHFFFAOYSA-N n-benzyl-n'-pyridin-4-ylmethanediimine Chemical compound C=1C=CC=CC=1CN=C=NC1=CC=NC=C1 RTJSAEAGHXVRMH-UHFFFAOYSA-N 0.000 description 1
- AKQKMGYJEPIIRN-UHFFFAOYSA-N n-ethyl-n'-(2-propylpyridin-3-yl)methanediimine Chemical group CCCC1=NC=CC=C1N=C=NCC AKQKMGYJEPIIRN-UHFFFAOYSA-N 0.000 description 1
- VZLQJNMOLQROHR-UHFFFAOYSA-N n-ethyl-n'-(2-propylpyridin-4-yl)methanediimine Chemical compound CCCC1=CC(N=C=NCC)=CC=N1 VZLQJNMOLQROHR-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229960003147 reserpine Drugs 0.000 description 1
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- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB55209/74A GB1489879A (en) | 1974-12-20 | 1974-12-20 | N'-cyano-n'-3-pyridylguanidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067083A true CA1067083A (en) | 1979-11-27 |
Family
ID=10473276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,325A Expired CA1067083A (en) | 1974-12-20 | 1975-12-09 | Anti-hypertensive n"-cyano-pyridyl guanidines |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4057636A (en, 2012) |
| JP (1) | JPS6028819B2 (en, 2012) |
| AT (1) | AT346357B (en, 2012) |
| BE (1) | BE836885A (en, 2012) |
| CA (1) | CA1067083A (en, 2012) |
| CH (1) | CH618429A5 (en, 2012) |
| DD (1) | DD122529A5 (en, 2012) |
| DE (2) | DE2557438A1 (en, 2012) |
| DK (1) | DK145341C (en, 2012) |
| ES (1) | ES443725A1 (en, 2012) |
| FI (1) | FI60560C (en, 2012) |
| FR (1) | FR2294703A1 (en, 2012) |
| GB (1) | GB1489879A (en, 2012) |
| IE (1) | IE42141B1 (en, 2012) |
| IT (1) | IT1062213B (en, 2012) |
| LU (1) | LU74071A1 (en, 2012) |
| NL (1) | NL184109C (en, 2012) |
| PH (1) | PH12506A (en, 2012) |
| SE (1) | SE424637B (en, 2012) |
| SU (1) | SU683615A3 (en, 2012) |
| YU (1) | YU39754B (en, 2012) |
| ZA (1) | ZA757481B (en, 2012) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5562066A (en) * | 1978-11-03 | 1980-05-10 | Toshihiko Okamoto | N-(2-substituted-4-pyridyl)-urea and thio urea, their preparation and plant growth regulator |
| US4490533A (en) * | 1980-12-22 | 1984-12-25 | Merck & Co., Inc. | Aminoalkyl pyridine derivatives |
| IE52935B1 (en) * | 1981-04-15 | 1988-04-13 | Leo Pharm Prod Ltd | Pharmaceutical preparation |
| IE54196B1 (en) * | 1981-09-10 | 1989-07-19 | Leo Pharm Prod Ltd | Chemical compounds |
| DK58983D0 (da) * | 1983-02-11 | 1983-02-11 | Leo Pharm Prod Ltd | Farmaceutisk praeparat |
| JPS604120A (ja) * | 1983-06-22 | 1985-01-10 | Shionogi & Co Ltd | 作用持続型ピナシジル製剤 |
| US4617311A (en) * | 1985-05-17 | 1986-10-14 | Eli Lilly And Company | Antiasthmatic method |
| GB8617623D0 (en) | 1986-07-18 | 1986-08-28 | Beecham Group Plc | Treatment |
| DE3887591T2 (de) * | 1987-07-07 | 1994-05-19 | Beecham Group Plc | Pinacidil zur Behandlung von pulmonaler Hypertonie oder Rechtsversagen. |
| GB8800199D0 (en) * | 1988-01-06 | 1988-02-10 | Beecham Group Plc | Pharmaceutical preparation |
| US5244664A (en) * | 1988-01-21 | 1993-09-14 | Leo Pharmaceutical Products Ltd. | Topical preparation for treatment of alopecia |
| GB8801318D0 (en) * | 1988-01-21 | 1988-02-17 | Leo Pharm Prod Ltd | Pharmaceutical preparations |
| AU3693789A (en) * | 1988-05-10 | 1989-11-29 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | New ophthalmic preparation for treating glaucoma |
| NZ229828A (en) * | 1988-08-09 | 1992-03-26 | Squibb & Sons Inc | Aryl cyanoguanidine derivatives and pharmaceutical compositions |
| US5278169A (en) * | 1988-08-09 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Method of treating or prevention of fibrillation of the heart |
| US5011837A (en) * | 1988-08-09 | 1991-04-30 | E. R. Squibb & Sons, Inc. | Aryl cyanoguanidines: potassium channel activators and method of making same |
| JP2884412B2 (ja) * | 1988-10-21 | 1999-04-19 | 日本バイエルアグロケム株式会社 | 殺虫性シアノ化合物 |
| US5264445A (en) * | 1989-02-03 | 1993-11-23 | Eli Lilly And Company | (-)-N"-cyano-N-3-pyridyl-N'-1,2,2-trimethylpropylguanidine |
| KR100220989B1 (ko) * | 1989-02-03 | 1999-09-15 | 피터 지. 스트링거 | 구아니딘 유도체 및 이를 함유하는 약제학적 조성물 |
| EP0407346A3 (en) * | 1989-07-07 | 1991-10-02 | Ciba-Geigy Ag | Aminopyridines |
| US5006523A (en) * | 1989-10-26 | 1991-04-09 | E. R. Squibb & Sons, Inc. | Antiarrhythmic agents: aryl cyanoguanidine potassium channel blockers |
| US5217982A (en) * | 1990-09-25 | 1993-06-08 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive properties |
| US5371086A (en) * | 1991-03-15 | 1994-12-06 | The Green Cross Corporation | Aminopyridine compounds |
| JPH05294935A (ja) * | 1991-03-15 | 1993-11-09 | Green Cross Corp:The | アミノピリジン系化合物 |
| FR2677019B1 (fr) * | 1991-05-27 | 1994-11-25 | Pf Medicament | Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique. |
| IL102548A (en) * | 1991-08-02 | 1998-08-16 | Medivir Ab | Thiourea derivatives for use in the preparation of medicaments for the inhibition of hiv and the treatment of aids and some such novel compounds |
| US5593993A (en) * | 1991-08-02 | 1997-01-14 | Medivir Ab | Method for inhibition of HIV related viruses |
| ES2099293T3 (es) * | 1991-12-23 | 1997-05-16 | Upjohn Co | Compuestos de piridilguanidina para el tratamiento de la disfuncion erectil. |
| US5262419A (en) * | 1992-06-11 | 1993-11-16 | E. R. Squibb & Sons, Inc. | Method for the prophylaxis and/or treatment of ulcerative gastrointestinal conditions using a potassium channel activator |
| WO1994004499A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
| GB9219472D0 (en) * | 1992-09-15 | 1992-10-28 | Leo Pharm Prod Ltd | Chemical compounds |
| JPH06228100A (ja) * | 1992-12-07 | 1994-08-16 | Green Cross Corp:The | 光学活性アミノピリジン誘導体およびその用途 |
| JPH08511264A (ja) * | 1993-06-11 | 1996-11-26 | ジ・アップジョン・カンパニー | Ｋ−チャンネル遮断剤としてのピリミジン，シアノグアニジン |
| US5547966A (en) * | 1993-10-07 | 1996-08-20 | Bristol-Myers Squibb Company | Aryl urea and related compounds |
| US5633374A (en) * | 1993-11-26 | 1997-05-27 | The Upjohn Company | Pyrimidine, cyanoguanidines as K-channel blockers |
| MX9603051A (es) * | 1994-01-28 | 1997-06-28 | Upjohn Co | Cianoguanidinas como bloqueadores del canal-k. |
| US5525742A (en) * | 1994-06-10 | 1996-06-11 | The Upjohn Company | Azidophenylcyanoguanidines as photoaffinity probes |
| US5856449A (en) * | 1994-11-17 | 1999-01-05 | Pharmacia & Upjohn Company | Protein affecting KATP channels |
| JP2000516621A (ja) * | 1996-08-15 | 2000-12-12 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| US5972894A (en) * | 1997-08-07 | 1999-10-26 | Cytran, Inc. | Peptides having potassium channel opener activity |
| US6458835B2 (en) | 1997-08-13 | 2002-10-01 | Bristol-Myers Squibb Company | Method of inhibiting or treating chemotherapy-induced hair loss |
| US6013668A (en) | 1997-08-13 | 2000-01-11 | Bristol-Myers Squibb Company | Enantiomers of 4-[[(cyanoimino) [(1,2,2-trimethylpropyl) amino]methyl]amino]benzonitrile |
| AU9211098A (en) * | 1997-09-03 | 1999-03-22 | American Home Products Corporation | Thiourea for increasing hdl-cholesterol levels, which are useful as anti-atherosclerotic agents |
| US6255323B1 (en) | 1999-04-09 | 2001-07-03 | Shionogi Bioresearch Corp. | Cyanoguanidine compounds |
| GB9908410D0 (en) | 1999-04-13 | 1999-06-09 | Pfizer Ltd | Pyridines |
| WO2000067754A1 (en) * | 1999-05-12 | 2000-11-16 | Nitromed, Inc. | Nitrosated and nitrosylated potassium channel activators, compositions and methods of use |
| US6645968B2 (en) | 1999-08-03 | 2003-11-11 | Abbott Laboratories | Potassium channel openers |
| AU2003268926B2 (en) * | 2002-10-24 | 2010-06-17 | Merck Patent Gmbh | Methylene urea derivatives as raf-kinase inhibitors |
| US9296697B2 (en) * | 2005-08-24 | 2016-03-29 | Abbott Laboratories | Hetaryl-substituted guanidine compounds and use thereof as binding partners for 5-HT5-receptors |
| US20070250567A1 (en) * | 2006-04-20 | 2007-10-25 | Graham Philip R | System and method for controlling a telepresence system |
| WO2009089053A1 (en) * | 2008-01-11 | 2009-07-16 | Nektar Therapeutics Al, Corporation | Oligomer-guanidine class conjugates |
| CA2820763A1 (en) | 2010-12-09 | 2012-06-14 | Radikal Therapeutics Inc. | Multifunctional nitroxide derivatives and uses thereof |
| EP4025300A1 (en) * | 2019-09-03 | 2022-07-13 | Salzman Group Ltd. | Atp-regulated potassium channel openers comprising guanidine and uses thereof |
| JP2025066196A (ja) * | 2022-03-14 | 2025-04-23 | 国立大学法人東北大学 | 認知機能改善剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036083A (en) * | 1959-05-15 | 1962-05-22 | Ciba Geigy Corp | Certain 2-pyridyl lower alkyl guanidines |
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
-
1974
- 1974-12-20 GB GB55209/74A patent/GB1489879A/en not_active Expired
-
1975
- 1975-11-24 IE IE2554/75A patent/IE42141B1/en unknown
- 1975-11-27 ZA ZA7481A patent/ZA757481B/xx unknown
- 1975-12-01 US US05/636,747 patent/US4057636A/en not_active Expired - Lifetime
- 1975-12-09 CA CA241,325A patent/CA1067083A/en not_active Expired
- 1975-12-10 AT AT936075A patent/AT346357B/de not_active IP Right Cessation
- 1975-12-12 PH PH17861A patent/PH12506A/en unknown
- 1975-12-12 FI FI753520A patent/FI60560C/fi not_active IP Right Cessation
- 1975-12-15 FR FR7538285A patent/FR2294703A1/fr active Granted
- 1975-12-15 YU YU3162/75A patent/YU39754B/xx unknown
- 1975-12-15 SE SE7514153A patent/SE424637B/xx not_active IP Right Cessation
- 1975-12-17 DK DK572975A patent/DK145341C/da not_active IP Right Cessation
- 1975-12-18 DD DD190290A patent/DD122529A5/xx unknown
- 1975-12-18 CH CH1644375A patent/CH618429A5/de not_active IP Right Cessation
- 1975-12-19 IT IT70152/75A patent/IT1062213B/it active
- 1975-12-19 NL NLAANVRAGE7514852,A patent/NL184109C/xx not_active IP Right Cessation
- 1975-12-19 DE DE19752557438 patent/DE2557438A1/de active Granted
- 1975-12-19 LU LU74071A patent/LU74071A1/xx unknown
- 1975-12-19 DE DE2560633A patent/DE2560633C2/de not_active Expired
- 1975-12-19 JP JP50150732A patent/JPS6028819B2/ja not_active Expired
- 1975-12-19 BE BE162952A patent/BE836885A/xx not_active IP Right Cessation
- 1975-12-19 SU SU752198560A patent/SU683615A3/ru active
- 1975-12-19 ES ES443725A patent/ES443725A1/es not_active Expired
-
1981
- 1981-10-22 US US06/314,023 patent/USRE31244E/en not_active Expired - Lifetime
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