JPS6028819B2 - 新規なるグアニジン誘導体の製造方法 - Google Patents
新規なるグアニジン誘導体の製造方法Info
- Publication number
- JPS6028819B2 JPS6028819B2 JP50150732A JP15073275A JPS6028819B2 JP S6028819 B2 JPS6028819 B2 JP S6028819B2 JP 50150732 A JP50150732 A JP 50150732A JP 15073275 A JP15073275 A JP 15073275A JP S6028819 B2 JPS6028819 B2 JP S6028819B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- compound
- butyl
- pyridylcarbodiimide
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000002357 guanidines Chemical class 0.000 title 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 8
- 230000008018 melting Effects 0.000 description 53
- 238000002844 melting Methods 0.000 description 53
- -1 neobentyl Chemical group 0.000 description 27
- VNDMHLAEEQWFEV-UHFFFAOYSA-N n'-tert-butyl-n-pyridin-3-ylmethanediimine Chemical group CC(C)(C)N=C=NC1=CC=CN=C1 VNDMHLAEEQWFEV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000000862 absorption spectrum Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
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- NZHJRKIZENYXSI-UHFFFAOYSA-N n'-tert-butyl-n-pyridin-2-ylmethanediimine Chemical compound CC(C)(C)N=C=NC1=CC=CC=N1 NZHJRKIZENYXSI-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
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- 230000036772 blood pressure Effects 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- WWAYUWJCQDSADV-UHFFFAOYSA-N n-butyl-n'-pyridin-3-ylmethanediimine Chemical compound CCCCN=C=NC1=CC=CN=C1 WWAYUWJCQDSADV-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 150000003585 thioureas Chemical class 0.000 description 4
- 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 description 3
- 101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- SDYSNRRRDUJUAS-UHFFFAOYSA-N 2-(3,3-dimethylbutyl)guanidine Chemical compound CC(C)(C)CCN=C(N)N SDYSNRRRDUJUAS-UHFFFAOYSA-N 0.000 description 2
- WFJPRCMYUOOTNS-UHFFFAOYSA-N 2-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CC=N1 WFJPRCMYUOOTNS-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- IAOODFPJRUTMSC-UHFFFAOYSA-N 3-cyano-1-ethyl-1-propyl-2-pyridin-3-ylguanidine Chemical compound CCCN(CC)C(NC#N)=NC1=CC=CN=C1 IAOODFPJRUTMSC-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 206010048964 Carotid artery occlusion Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NAIKTOIXSPSWRI-UHFFFAOYSA-N N=C=NC1=CC=CN=C1 Chemical compound N=C=NC1=CC=CN=C1 NAIKTOIXSPSWRI-UHFFFAOYSA-N 0.000 description 2
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- SSGODMHQNTWPOX-UHFFFAOYSA-N cyanothiourea Chemical compound NC(=S)NC#N SSGODMHQNTWPOX-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical compound N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- MDPHCIMOEKILTR-UHFFFAOYSA-N n'-pyridin-4-ylmethanediimine Chemical compound N=C=NC1=CC=NC=C1 MDPHCIMOEKILTR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 238000002347 injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VVZJCIJTYJBLFZ-UHFFFAOYSA-N methyl n'-tert-butyl-n-cyanocarbamimidothioate Chemical compound CC(C)(C)NC(SC)=NC#N VVZJCIJTYJBLFZ-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- XQTISGRJDQSYBN-UHFFFAOYSA-N n'-(1-methylcyclobutyl)-n-pyridin-3-ylmethanediimine Chemical group C=1C=CN=CC=1N=C=NC1(C)CCC1 XQTISGRJDQSYBN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IVSYYJGSFMXYJH-UHFFFAOYSA-N n'-tert-butyl-n-quinolin-3-ylmethanediimine Chemical group C1=CC=CC2=CC(N=C=NC(C)(C)C)=CN=C21 IVSYYJGSFMXYJH-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
- XPQARCWBXJELJL-UHFFFAOYSA-N n-cyclobutyl-n'-pyridin-3-ylmethanediimine Chemical compound C1CCC1N=C=NC1=CC=CN=C1 XPQARCWBXJELJL-UHFFFAOYSA-N 0.000 description 1
- ZYBMQJFKYYRYAV-UHFFFAOYSA-N n-cyclooctyl-n'-pyridin-4-ylmethanediimine Chemical compound C1CCCCCCC1N=C=NC1=CC=NC=C1 ZYBMQJFKYYRYAV-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
- 210000000826 nictitating membrane Anatomy 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB55209/74 | 1974-12-20 | ||
| GB55209/74A GB1489879A (en) | 1974-12-20 | 1974-12-20 | N'-cyano-n'-3-pyridylguanidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5186474A JPS5186474A (en, 2012) | 1976-07-29 |
| JPS6028819B2 true JPS6028819B2 (ja) | 1985-07-06 |
Family
ID=10473276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50150732A Expired JPS6028819B2 (ja) | 1974-12-20 | 1975-12-19 | 新規なるグアニジン誘導体の製造方法 |
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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