JPS6125712B2 - - Google Patents
Info
- Publication number
- JPS6125712B2 JPS6125712B2 JP2751185A JP2751185A JPS6125712B2 JP S6125712 B2 JPS6125712 B2 JP S6125712B2 JP 2751185 A JP2751185 A JP 2751185A JP 2751185 A JP2751185 A JP 2751185A JP S6125712 B2 JPS6125712 B2 JP S6125712B2
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- butyl
- tert
- pyridylcarbodiimide
- procedure
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 89
- 238000000034 method Methods 0.000 description 70
- 238000002844 melting Methods 0.000 description 51
- 230000008018 melting Effects 0.000 description 51
- -1 1-methyl-1-ethylpropyl Chemical group 0.000 description 30
- 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 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 13
- 238000000862 absorption spectrum Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000003276 anti-hypertensive effect Effects 0.000 description 10
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
- 150000001718 carbodiimides Chemical class 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- 150000003585 thioureas Chemical class 0.000 description 5
- 150000003672 ureas Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ADAMEOZKZQRNKP-UHFFFAOYSA-N n'-propylmethanediimine Chemical compound CCCN=C=N ADAMEOZKZQRNKP-UHFFFAOYSA-N 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
- 238000001308 synthesis method Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 239000003795 chemical substances by application 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
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 3
- MDPHCIMOEKILTR-UHFFFAOYSA-N n'-pyridin-4-ylmethanediimine Chemical compound N=C=NC1=CC=NC=C1 MDPHCIMOEKILTR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 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 description 2
- UYUQONVPLCYBAX-UHFFFAOYSA-N 1-cyano-2-(2-methylpentan-2-yl)-3-pyridin-3-ylguanidine Chemical compound CCCC(C)(C)N=C(NC#N)NC1=CC=CN=C1 UYUQONVPLCYBAX-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- 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
- UHLKYVNSNIWKGX-UHFFFAOYSA-N 2-pyridin-3-ylguanidine Chemical compound NC(=N)NC1=CC=CN=C1 UHLKYVNSNIWKGX-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- SFOZWPZYXCDPJW-UHFFFAOYSA-N CC(C(N=C=N)(C)C)(CC)C Chemical compound CC(C(N=C=N)(C)C)(CC)C SFOZWPZYXCDPJW-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 206010010356 Congenital anomaly Diseases 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 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
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- VZVGEDRCVUKSEL-UHFFFAOYSA-N guancidine Chemical compound CCC(C)(C)N=C(N)NC#N VZVGEDRCVUKSEL-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VVZJCIJTYJBLFZ-UHFFFAOYSA-N methyl n'-tert-butyl-n-cyanocarbamimidothioate Chemical compound CC(C)(C)NC(SC)=NC#N VVZJCIJTYJBLFZ-UHFFFAOYSA-N 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 239000007939 sustained release tablet Substances 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- ROBGTOPHXVNLTK-UHFFFAOYSA-N 1-cyano-2-(2,2-dimethylpropyl)-3-pyridin-4-ylguanidine Chemical compound CC(C)(C)CN=C(NC#N)NC1=CC=NC=C1 ROBGTOPHXVNLTK-UHFFFAOYSA-N 0.000 description 1
- FGPMFMZQHRFFLZ-UHFFFAOYSA-N 1-cyano-2-(2-methylbutan-2-yl)-3-pyridin-2-ylguanidine Chemical compound CCC(C)(C)NC(NC#N)=NC1=CC=CC=N1 FGPMFMZQHRFFLZ-UHFFFAOYSA-N 0.000 description 1
- YCIUNWKLRAIFJN-UHFFFAOYSA-N 1-cyano-2-(2-methylbutan-2-yl)-3-pyridin-4-ylguanidine Chemical compound CCC(C)(C)N=C(NC#N)NC1=CC=NC=C1 YCIUNWKLRAIFJN-UHFFFAOYSA-N 0.000 description 1
- WUEVGUGUDMCZSY-UHFFFAOYSA-N 1-cyano-2-(2-methylpropyl)-3-pyridin-3-ylguanidine Chemical compound CC(C)CN=C(NC#N)NC1=CC=CN=C1 WUEVGUGUDMCZSY-UHFFFAOYSA-N 0.000 description 1
- IIKZPEBRTNYSJD-UHFFFAOYSA-N 1-cyano-2-(2-phenylethyl)-3-pyridin-3-ylguanidine Chemical compound C=1C=CC=CC=1CCN=C(NC#N)NC1=CC=CN=C1 IIKZPEBRTNYSJD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- UBLLTWXDTMLVSQ-UHFFFAOYSA-N 1-cyano-2-(3-methylbutyl)-3-pyridin-3-ylguanidine Chemical compound CC(C)CCN=C(NC#N)NC1=CC=CN=C1 UBLLTWXDTMLVSQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AMIPMYBJQDRKHK-UHFFFAOYSA-N 1-cyano-2-cyclohexyl-3-pyridin-3-ylguanidine Chemical compound C1CCCCC1N=C(NC#N)NC1=CC=CN=C1 AMIPMYBJQDRKHK-UHFFFAOYSA-N 0.000 description 1
- CTKDDIUHAMTXOQ-UHFFFAOYSA-N 1-cyano-2-cyclooctyl-3-pyridin-4-ylguanidine Chemical compound C1CCCCCCC1N=C(NC#N)NC1=CC=NC=C1 CTKDDIUHAMTXOQ-UHFFFAOYSA-N 0.000 description 1
- MMDTYIREYCRUJE-UHFFFAOYSA-N 1-cyano-2-cyclopropyl-3-pyridin-3-ylguanidine Chemical compound C1CC1N=C(NC#N)NC1=CC=CN=C1 MMDTYIREYCRUJE-UHFFFAOYSA-N 0.000 description 1
- YQCMJXODNUFPHT-UHFFFAOYSA-N 1-cyano-2-heptyl-3-pyridin-3-ylguanidine Chemical compound CCCCCCCN=C(NC#N)NC1=CC=CN=C1 YQCMJXODNUFPHT-UHFFFAOYSA-N 0.000 description 1
- NFMOPFYCTMVRGT-UHFFFAOYSA-N 1-cyano-2-pentyl-3-pyridin-3-ylguanidine Chemical compound CCCCCN=C(NC#N)NC1=CC=CN=C1 NFMOPFYCTMVRGT-UHFFFAOYSA-N 0.000 description 1
- PMHWHMPEEVACQW-UHFFFAOYSA-N 1-cyano-2-phenyl-3-pyridin-3-ylguanidine Chemical compound C=1C=CC=CC=1N=C(NC#N)NC1=CC=CN=C1 PMHWHMPEEVACQW-UHFFFAOYSA-N 0.000 description 1
- CLHNOAUGSNXENE-UHFFFAOYSA-N 1-cyano-2-propan-2-yl-3-pyridin-3-ylguanidine Chemical compound CC(C)N=C(NC#N)NC1=CC=CN=C1 CLHNOAUGSNXENE-UHFFFAOYSA-N 0.000 description 1
- BOSGAOAGCGYYOH-UHFFFAOYSA-N 1-cyano-2-propyl-3-pyridin-3-ylguanidine Chemical compound CCCN=C(NC#N)NC1=CC=CN=C1 BOSGAOAGCGYYOH-UHFFFAOYSA-N 0.000 description 1
- NAMHJZDHCHSGAX-UHFFFAOYSA-N 1-tert-butyl-3-pyridin-3-ylthiourea Chemical compound CC(C)(C)NC(=S)NC1=CC=CN=C1 NAMHJZDHCHSGAX-UHFFFAOYSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- VENDSKJUGASHGJ-UHFFFAOYSA-N 2-benzyl-1-cyano-3-pyridin-3-ylguanidine Chemical compound C=1C=CC=CC=1CN=C(NC#N)NC1=CC=CN=C1 VENDSKJUGASHGJ-UHFFFAOYSA-N 0.000 description 1
- HKCIAYNSNFLSIC-UHFFFAOYSA-N 2-benzyl-1-cyano-3-pyridin-4-ylguanidine Chemical compound C=1C=CC=CC=1CN=C(NC#N)NC1=CC=NC=C1 HKCIAYNSNFLSIC-UHFFFAOYSA-N 0.000 description 1
- YBNIJHZRKKIBOT-UHFFFAOYSA-N 2-butyl-1-cyano-3-pyridin-3-ylguanidine Chemical compound CCCCN=C(NC#N)NC1=CC=CN=C1 YBNIJHZRKKIBOT-UHFFFAOYSA-N 0.000 description 1
- MHDCDPXQCUJWCH-UHFFFAOYSA-N 2-butyl-1-cyanoguanidine Chemical compound CCCCN=C(N)NC#N MHDCDPXQCUJWCH-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 1
- VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 description 1
- WMBJNBSNCYQXKN-UHFFFAOYSA-N 2-tert-butyl-1-cyano-3-pyridin-2-ylguanidine Chemical compound CC(C)(C)N=C(NC#N)NC1=CC=CC=N1 WMBJNBSNCYQXKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JLILGSIKDCNUNZ-UHFFFAOYSA-N 2-tert-butyl-1-cyano-3-pyridin-4-ylguanidine Chemical compound CC(C)(C)N=C(NC#N)NC1=CC=NC=C1 JLILGSIKDCNUNZ-UHFFFAOYSA-N 0.000 description 1
- MQURPTKTYDZFKO-UHFFFAOYSA-N 2-tert-butyl-1-cyano-3-quinolin-3-ylguanidine Chemical compound C1=CC=CC2=CC(NC(NC#N)=NC(C)(C)C)=CN=C21 MQURPTKTYDZFKO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VMSZFBSYWXMXRF-UHFFFAOYSA-N 3-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CN=C1 VMSZFBSYWXMXRF-UHFFFAOYSA-N 0.000 description 1
- LNBCGLZYLJMGKP-JZGIKJSDSA-N 4-[(1r)-2-amino-1-hydroxyethyl]benzene-1,2-diol;2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.OC(=O)C(O)C(O)C(O)=O.NC[C@H](O)C1=CC=C(O)C(O)=C1 LNBCGLZYLJMGKP-JZGIKJSDSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 206010048964 Carotid artery occlusion Diseases 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
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- ZHHXBBLJRQSVFX-UHFFFAOYSA-N methyl n-cyano-n'-pyridin-3-ylcarbamimidothioate Chemical compound N#CNC(SC)=NC1=CC=CN=C1 ZHHXBBLJRQSVFX-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- IVSYYJGSFMXYJH-UHFFFAOYSA-N n'-tert-butyl-n-quinolin-3-ylmethanediimine Chemical compound C1=CC=CC2=CC(N=C=NC(C)(C)C)=CN=C21 IVSYYJGSFMXYJH-UHFFFAOYSA-N 0.000 description 1
- 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 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
- AKQKMGYJEPIIRN-UHFFFAOYSA-N n-ethyl-n'-(2-propylpyridin-3-yl)methanediimine Chemical compound 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000011886 peripheral blood Substances 0.000 description 1
- 230000002085 persistent effect Effects 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
- 238000002360 preparation method Methods 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- CFOJQUGXHMGMOT-UHFFFAOYSA-N pyridin-3-ylthiourea Chemical compound NC(=S)NC1=CC=CN=C1 CFOJQUGXHMGMOT-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 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
- 238000001228 spectrum Methods 0.000 description 1
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- 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
- 239000005526 vasoconstrictor agent Substances 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
Landscapes
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2751185A JPS60190763A (ja) | 1985-02-13 | 1985-02-13 | ピリジルカルボジイミド誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2751185A JPS60190763A (ja) | 1985-02-13 | 1985-02-13 | ピリジルカルボジイミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60190763A JPS60190763A (ja) | 1985-09-28 |
| JPS6125712B2 true JPS6125712B2 (is) | 1986-06-17 |
Family
ID=12223154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2751185A Granted JPS60190763A (ja) | 1985-02-13 | 1985-02-13 | ピリジルカルボジイミド誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60190763A (is) |
-
1985
- 1985-02-13 JP JP2751185A patent/JPS60190763A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60190763A (ja) | 1985-09-28 |
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