CH618429A5 - - Google Patents

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Info

Publication number: CH618429A5
Authority: CH; Switzerland
Prior art keywords: group; tert; butyl; formula; atoms
Prior art date: 1974-12-20

Application number

CH1644375A

Other languages

German (de)

English (en)

Inventor

Hans Jorgen Petersen

Original Assignee

Leo Pharm Prod Ltd

Priority date (The priority date 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 date listed.)

1974-12-20

Filing date

1975-12-18

Publication date

1980-07-31

1975-12-18 Application filed by Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd

1980-07-31 Publication of CH618429A5 publication Critical patent/CH618429A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 83
238000000034 method Methods 0.000 claims description 58
-1 1-methyl-1-ethylpropyl group Chemical group 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
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
MDPHCIMOEKILTR-UHFFFAOYSA-N n'-pyridin-4-ylmethanediimine Chemical compound N=C=NC1=CC=NC=C1 MDPHCIMOEKILTR-UHFFFAOYSA-N 0.000 claims description 2
231100000331 toxic Toxicity 0.000 claims 1
230000002588 toxic effect Effects 0.000 claims 1
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 32
230000036772 blood pressure Effects 0.000 description 17
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 15
239000000203 mixture Substances 0.000 description 10
241000699670 Mus sp. Species 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
230000001077 hypotensive effect Effects 0.000 description 7
239000007858 starting material Substances 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
206010020772 Hypertension Diseases 0.000 description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
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 5
238000002474 experimental method Methods 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 4
241000700159 Rattus Species 0.000 description 4
230000003276 anti-hypertensive effect Effects 0.000 description 4
235000013877 carbamide Nutrition 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000003826 tablet Substances 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
150000003585 thioureas Chemical class 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 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
239000004480 active ingredient Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
150000001718 carbodiimides Chemical class 0.000 description 3
239000000969 carrier 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
239000007788 liquid Substances 0.000 description 3
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 2
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
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 2
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 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
244000025254 Cannabis sativa Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
230000001447 compensatory effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
210000003191 femoral vein Anatomy 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000001990 intravenous administration Methods 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
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
229960003632 minoxidil Drugs 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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 2
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 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
210000002700 urine Anatomy 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
VQLLQAHFCUODFW-UHFFFAOYSA-N 1-cyano-2-(1-methylcyclobutyl)-3-pyridin-3-ylguanidine Chemical compound C=1C=CN=CC=1NC(NC#N)=NC1(C)CCC1 VQLLQAHFCUODFW-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
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
MONUTWSAYFVBSJ-UHFFFAOYSA-N 2-butan-2-yl-1-cyano-3-pyridin-3-ylguanidine Chemical compound CCC(C)N=C(NC#N)NC1=CC=CN=C1 MONUTWSAYFVBSJ-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
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
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
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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
OUTVGVWQABKTSG-UHFFFAOYSA-N C(C(C)(C)C)N=C=NC1=NC=CC=C1 Chemical compound C(C(C)(C)C)N=C=NC1=NC=CC=C1 OUTVGVWQABKTSG-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
206010048964 Carotid artery occlusion Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
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125000003342 alkenyl group Chemical group 0.000 description 1
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
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230000002567 autonomic effect Effects 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
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235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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210000003169 central nervous system Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
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238000002425 crystallisation Methods 0.000 description 1
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XMYLSWOTJKUSHE-UHFFFAOYSA-N cyanamide;lead Chemical compound [Pb].NC#N XMYLSWOTJKUSHE-UHFFFAOYSA-N 0.000 description 1
150000001912 cyanamides Chemical class 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000007950 delayed release tablet Substances 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003925 fat Substances 0.000 description 1
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239000008273 gelatin Substances 0.000 description 1
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239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
VZVGEDRCVUKSEL-UHFFFAOYSA-N guancidine Chemical compound CCC(C)(C)N=C(N)NC#N VZVGEDRCVUKSEL-UHFFFAOYSA-N 0.000 description 1
229950007639 guancidine Drugs 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
XQTISGRJDQSYBN-UHFFFAOYSA-N n'-(1-methylcyclobutyl)-n-pyridin-3-ylmethanediimine Chemical compound 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
PTNIEGMSADHKLI-UHFFFAOYSA-N n'-butan-2-yl-n-pyridin-3-ylmethanediimine Chemical compound CCC(C)N=C=NC1=CC=CN=C1 PTNIEGMSADHKLI-UHFFFAOYSA-N 0.000 description 1
LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 1
MPXRMBZKHVPBDV-UHFFFAOYSA-N n'-propan-2-yl-n-pyridin-3-ylmethanediimine Chemical compound CC(C)N=C=NC1=CC=CN=C1 MPXRMBZKHVPBDV-UHFFFAOYSA-N 0.000 description 1
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 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
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
WWAYUWJCQDSADV-UHFFFAOYSA-N n-butyl-n'-pyridin-3-ylmethanediimine Chemical compound CCCCN=C=NC1=CC=CN=C1 WWAYUWJCQDSADV-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
XYOCBZBIBPISLH-UHFFFAOYSA-N n-cyclopentyl-n'-pyridin-2-ylmethanediimine Chemical compound C1CCCC1N=C=NC1=CC=CC=N1 XYOCBZBIBPISLH-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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
NXQBXAACCXYADT-UHFFFAOYSA-N n-phenyl-n'-pyridin-3-ylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CN=C1 NXQBXAACCXYADT-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 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
230000001376 precipitating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux 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
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)

CH1644375A 1974-12-20 1975-12-18 CH618429A5 (fr)

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
CH618429A5 true CH618429A5 (fr)	1980-07-31

Family

ID=10473276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1644375A CH618429A5 (fr)	1974-12-20	1975-12-18

Country Status (22)

Country	Link
US (2)	US4057636A (fr)
JP (1)	JPS6028819B2 (fr)
AT (1)	AT346357B (fr)
BE (1)	BE836885A (fr)
CA (1)	CA1067083A (fr)
CH (1)	CH618429A5 (fr)
DD (1)	DD122529A5 (fr)
DE (2)	DE2557438A1 (fr)
DK (1)	DK145341C (fr)
ES (1)	ES443725A1 (fr)
FI (1)	FI60560C (fr)
FR (1)	FR2294703A1 (fr)
GB (1)	GB1489879A (fr)
IE (1)	IE42141B1 (fr)
IT (1)	IT1062213B (fr)
LU (1)	LU74071A1 (fr)
NL (1)	NL184109C (fr)
PH (1)	PH12506A (fr)
SE (1)	SE424637B (fr)
SU (1)	SU683615A3 (fr)
YU (1)	YU39754B (fr)
ZA (1)	ZA757481B (fr)

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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
EP0302595B1 (fr) *	1987-07-07	1994-02-02	Beecham Group Plc	Pinacidil pour le traitement de l'hypertension pulmonaire ou de l'insuffisance ventriculaire droite
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
WO1989010757A1 (fr) *	1988-05-10	1989-11-16	Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis	Nouvelle preparation ophtalmique pour le traitement de glaucomes
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
NZ229828A (en) *	1988-08-09	1992-03-26	Squibb & Sons Inc	Aryl cyanoguanidine derivatives and pharmaceutical compositions
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
KR100220989B1 (ko) *	1989-02-03	1999-09-15	피터 지. 스트링거	구아니딘 유도체 및 이를 함유하는 약제학적 조성물
US5264445A (en) *	1989-02-03	1993-11-23	Eli Lilly And Company	(-)-N"-cyano-N-3-pyridyl-N'-1,2,2-trimethylpropylguanidine
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
JPH05294935A (ja) *	1991-03-15	1993-11-09	Green Cross Corp:The	アミノピリジン系化合物
US5371086A (en) *	1991-03-15	1994-12-06	The Green Cross Corporation	Aminopyridine compounds
FR2677019B1 (fr) *	1991-05-27	1994-11-25	Pf Medicament	Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique.
US5593993A (en) *	1991-08-02	1997-01-14	Medivir Ab	Method for inhibition of HIV related viruses
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
AU661747B2 (en) *	1991-12-23	1995-08-03	Pharmacia & Upjohn Company	Pyridylguanidine compounds for treatment of erectile dysfunction
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
AU4530693A (en) *	1992-08-13	1994-03-15	Upjohn Company, The	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
CA2179036A1 (fr) *	1994-01-28	1995-08-03	Stephen J. Humphrey	Cyanoguanidines utilisees comme agents bloquants des canaux 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
WO1998006399A1 (fr) *	1996-08-15	1998-02-19	Smithkline Beecham Corporation	Antagonistes du recepteur d'il-8
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
WO1999011621A2 (fr) *	1997-09-03	1999-03-11	American Home Products Corporation	Thiouree elevant les niveaux de hdl-cholesterol s'averant utilies comme agents antiatherosclereux
WO2000061561A1 (fr)	1999-04-09	2000-10-19	Shionogi Bioresearch Corp.	Composes a base de cyanoguanidine
GB9908410D0 (en)	1999-04-13	1999-06-09	Pfizer Ltd	Pyridines
US6417207B1 (en) *	1999-05-12	2002-07-09	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
US7589112B2 (en)	2002-10-24	2009-09-15	Merck Patent Gmbh	Methylene urea derivatives
WO2007022964A2 (fr) *	2005-08-24	2007-03-01	Abbott Gmbh & Co. Kg	Composes guanidine a substitution hetaryl et utilisation en tant que partenaires de liaison pour des recepteurs de 5-ht5
US20070250567A1 (en) *	2006-04-20	2007-10-25	Graham Philip R	System and method for controlling a telepresence system
WO2009089053A1 (fr) *	2008-01-11	2009-07-16	Nektar Therapeutics Al, Corporation	Conjugués de la classe des guanidines-oligomères
CA2820763A1 (fr)	2010-12-09	2012-06-14	Radikal Therapeutics Inc.	Derives de nitroxyde multifonctionnels et leurs utilisations
EP4025300A1 (fr) *	2019-09-03	2022-07-13	Salzman Group Ltd.	Agents d'ouverture des canaux potassiques régulés par l'atp comprenant de la guanidine et leurs utilisations
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

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* Cited by examiner, † Cited by third party
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/fr 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 SE SE7514153A patent/SE424637B/xx not_active IP Right Cessation
- 1975-12-15 YU YU3162/75A patent/YU39754B/xx unknown
- 1975-12-15 FR FR7538285A patent/FR2294703A1/fr active Granted
- 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 SU SU752198560A patent/SU683615A3/ru active
- 1975-12-19 LU LU74071A patent/LU74071A1/xx unknown
- 1975-12-19 JP JP50150732A patent/JPS6028819B2/ja not_active Expired
- 1975-12-19 DE DE19752557438 patent/DE2557438A1/de active Granted
- 1975-12-19 DE DE2560633A patent/DE2560633C2/de not_active Expired
- 1975-12-19 ES ES443725A patent/ES443725A1/es not_active Expired
- 1975-12-19 BE BE162952A patent/BE836885A/fr 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
1981
- 1981-10-22 US US06/314,023 patent/USRE31244E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
SU683615A3 (ru)	1979-08-30
DK145341C (da)	1983-03-28
LU74071A1 (fr)	1976-11-11
DE2560633C2 (fr)	1988-09-08
SE424637B (sv)	1982-08-02
DD122529A5 (fr)	1976-10-12
CA1067083A (fr)	1979-11-27
NL184109B (nl)	1988-11-16
FR2294703A1 (fr)	1976-07-16
BE836885A (fr)	1976-06-21
IE42141B1 (en)	1980-06-04
FR2294703B1 (fr)	1980-06-27
DK572975A (da)	1976-06-21
ZA757481B (en)	1977-01-26
NL184109C (nl)	1989-04-17
PH12506A (en)	1979-04-18
DE2557438A1 (de)	1976-06-24
US4057636A (en)	1977-11-08
SE7514153L (sv)	1976-06-21
FI60560C (fi)	1982-02-10
AU8712775A (en)	1977-06-09
YU39754B (en)	1985-04-30
ES443725A1 (es)	1977-04-16
FI60560B (fi)	1981-10-30
YU316275A (en)	1982-02-28
DK145341B (da)	1982-11-01
USRE31244E (en)	1983-05-17
IT1062213B (it)	1983-09-20
ATA936075A (de)	1978-03-15
DE2557438C2 (fr)	1989-01-05
AT346357B (de)	1978-11-10
JPS5186474A (fr)	1976-07-29
IE42141L (en)	1976-06-20
NL7514852A (nl)	1976-06-22
GB1489879A (en)	1977-10-26
FI753520A7 (fr)	1976-06-21
JPS6028819B2 (ja)	1985-07-06

Legal Events

Date	Code	Title	Description
1995-12-29	PL	Patent ceased

Publication	Publication Date	Title
DE2557438C2 (fr)	1989-01-05
EP0242851B1 (fr)	1990-06-13	Dérivés du N-(2'-aminophényl)-benzamide, procédé pour leur fabrication et leur utilisation dans la lutte contre les maladies néoplastiques
CH638520A5 (de)	1983-09-30	Verfahren zur herstellung von benzamid-verbindungen.
DE2012138C3 (de)	1978-08-10	N{4-(ß-Pyrazin- 2-carboxyamido-äthyl)benzolsulphonyl] -N' - cycloalkylharnstoffe und diese enthaltende pharmazeutische Präparate
EP0104423B1 (fr)	1986-05-21	Nitro-2-éthènediamines-1,1, procédé pour leur préparation ainsi que leur application comme médicaments
DE2847792C2 (fr)	1988-02-04
DE2461802C2 (de)	1985-01-03	Pyrazincarboxamidderivate
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DE1493672C3 (de)	1974-05-02	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE2238870C3 (de)	1978-09-28	Benzolsulfonylharnstoffe
DE2526795A1 (de)	1976-01-08	Sulfonamide
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DE1518816B2 (de)	1974-09-19	Benzolsulfony!harnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
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DE1670059A1 (de)	1970-08-13	Guanidinderivate und Verfahren zu ihrer Herstellung
DE1695565A1 (de)	1970-07-16	Neuartige Piperidinderivate und Verfahren zu ihrer Herstellung
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