CA1145751A - Cyanoguanidine derivatives and process for the preparation thereof - Google Patents
Cyanoguanidine derivatives and process for the preparation thereofInfo
- Publication number
- CA1145751A CA1145751A CA000345777A CA345777A CA1145751A CA 1145751 A CA1145751 A CA 1145751A CA 000345777 A CA000345777 A CA 000345777A CA 345777 A CA345777 A CA 345777A CA 1145751 A CA1145751 A CA 1145751A
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- cyano
- methyl
- group
- formula
- 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
- 238000000034 method Methods 0.000 title claims abstract description 77
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- -1 amine compound Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 17
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002541 isothioureas Chemical class 0.000 claims description 5
- 150000002542 isoureas Chemical class 0.000 claims description 5
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 15
- 238000010438 heat treatment Methods 0.000 claims 14
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 8
- MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-UHFFFAOYSA-N 0.000 claims 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims 4
- ZJWYEBFUZYOBGI-UHFFFAOYSA-N (2-methoxyphenyl)-pyridin-2-ylmethanamine Chemical compound COC1=CC=CC=C1C(N)C1=CC=CC=N1 ZJWYEBFUZYOBGI-UHFFFAOYSA-N 0.000 claims 3
- YASIJBZPJZUSNT-UHFFFAOYSA-N (2-methylphenyl)-pyridin-2-ylmethanamine Chemical compound CC1=CC=CC=C1C(N)C1=CC=CC=N1 YASIJBZPJZUSNT-UHFFFAOYSA-N 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- AHGHYTLHTMRGLP-UHFFFAOYSA-N (3-chlorophenyl)-pyridin-2-ylmethanamine Chemical compound C=1C=CC=NC=1C(N)C1=CC=CC(Cl)=C1 AHGHYTLHTMRGLP-UHFFFAOYSA-N 0.000 claims 2
- QMZJADVJDRSQAP-UHFFFAOYSA-N (4-methylphenyl)-pyridin-2-ylmethanamine Chemical compound C1=CC(C)=CC=C1C(N)C1=CC=CC=N1 QMZJADVJDRSQAP-UHFFFAOYSA-N 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- MVQKNMZGVHGNKF-UHFFFAOYSA-N (2-chlorophenyl)-pyridin-2-ylmethanamine Chemical compound C=1C=CC=C(Cl)C=1C(N)C1=CC=CC=N1 MVQKNMZGVHGNKF-UHFFFAOYSA-N 0.000 claims 1
- WVFDOYUFYUNJTM-UHFFFAOYSA-N (3-methylphenyl)-pyridin-2-ylmethanamine Chemical compound CC1=CC=CC(C(N)C=2N=CC=CC=2)=C1 WVFDOYUFYUNJTM-UHFFFAOYSA-N 0.000 claims 1
- YDPKXALAYGLYAZ-UHFFFAOYSA-N (4-methoxyphenyl)-pyridin-2-ylmethanamine Chemical compound C1=CC(OC)=CC=C1C(N)C1=CC=CC=N1 YDPKXALAYGLYAZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 claims 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- RTVNATIYZXTCHK-UHFFFAOYSA-N methyl n-cyano-n'-[3-(dimethylamino)propyl]carbamimidothioate Chemical compound N#CNC(SC)=NCCCN(C)C RTVNATIYZXTCHK-UHFFFAOYSA-N 0.000 claims 1
- RHRLUGZOQWPHFA-UHFFFAOYSA-N pyridin-2-yl-[3-(trifluoromethyl)phenyl]methanamine Chemical compound C=1C=CC=NC=1C(N)C1=CC=CC(C(F)(F)F)=C1 RHRLUGZOQWPHFA-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 6
- 230000001262 anti-secretory effect Effects 0.000 abstract description 3
- 229960004198 guanidine Drugs 0.000 description 28
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 27
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 230000001142 anti-diarrhea Effects 0.000 description 2
- 230000003501 anti-edematous effect Effects 0.000 description 2
- 230000002467 anti-pepsin effect Effects 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 238000002690 local anesthesia Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 101100536893 Schizosaccharomyces pombe (strain 972 / ATCC 24843) thi9 gene Proteins 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 229960000905 indomethacin Drugs 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940095050 propylene Drugs 0.000 description 1
- 230000002040 relaxant effect Effects 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
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003639 vasoconstrictive effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
-
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000410453A CA1158648A (en) | 1979-02-16 | 1982-08-30 | Cyanoguanidine derivatives and process for the preparation thereof |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54015990A JPS6016940B2 (ja) | 1979-02-16 | 1979-02-16 | シアノグアニジン誘導体およびその製造法 |
| JP1598979A JPS568357A (en) | 1979-02-16 | 1979-02-16 | Cyanoguanidine derivative and its production |
| JP15,990/79 | 1979-02-16 | ||
| JP15,989/79 | 1979-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145751A true CA1145751A (en) | 1983-05-03 |
Family
ID=26352224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345777A Expired CA1145751A (en) | 1979-02-16 | 1980-02-15 | Cyanoguanidine derivatives and process for the preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (5) | US4287346A (enExample) |
| CA (1) | CA1145751A (enExample) |
| CH (1) | CH641772A5 (enExample) |
| DE (1) | DE3005786A1 (enExample) |
| FR (1) | FR2453155A1 (enExample) |
| GB (2) | GB2107306B (enExample) |
| IT (1) | IT1141214B (enExample) |
| NL (1) | NL8000869A (enExample) |
| SE (2) | SE8001216L (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287346A (en) * | 1979-02-16 | 1981-09-01 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
| EP0072926B1 (de) * | 1981-08-19 | 1986-09-24 | MERCK PATENT GmbH | 2-Aryl-imidazopyridine |
| IE54196B1 (en) * | 1981-09-10 | 1989-07-19 | Leo Pharm Prod Ltd | Chemical compounds |
| IT1190793B (it) * | 1982-04-27 | 1988-02-24 | Magis Farmaceutici | Composti attivi nel trattamento dell'ulcera e sintomi allergici della pelle |
| US4496573A (en) * | 1982-08-24 | 1985-01-29 | William H. Rorer, Inc. | 1-Pyridylmethyl-3-acyl guanidines |
| US4529723A (en) * | 1983-04-29 | 1985-07-16 | William H. Rorer, Inc. | Bicyclic benzenoid aminoalkylene ethers and thioethers, pharmaceutical compositions and use |
| US4689348A (en) * | 1984-08-17 | 1987-08-25 | Dow Chemical Company | Cyanoguanidines useful as animal growth promoting agents |
| US4661520A (en) * | 1984-08-17 | 1987-04-28 | The Dow Chemical Company | Cyanoguanidine useful as an animal growth promoting agent |
| FR2579201B1 (fr) * | 1985-03-19 | 1987-05-07 | Bernard Lyon I Universite Clau | Composes chimiques perfectionnes, utilisation comme agents edulcorants et compositions contenant de tels agents |
| US4921939A (en) * | 1985-03-19 | 1990-05-01 | Universite Claude Bernard -Lyon 1 | Sweetening agents |
| FR2579202B1 (fr) * | 1985-03-19 | 1988-04-29 | Univ Claude Bernard Lyon | Nouveaux composes chimiques, utilisation comme agents edulcorants et compositions contenant de tels agents |
| US4963573A (en) * | 1985-11-04 | 1990-10-16 | Janssen Pharmaceutica N.V. | [[[(3-pyridinyl)methylen]amino]oxy]alkanoic acids and esters |
| US4746671A (en) * | 1985-11-04 | 1988-05-24 | Janssen Pharmaceutica N.V. | Pharmaceutical use of [[[(3-pyridinyl)methylen]amino]oxy]alkanoic acids and esters |
| US4895840A (en) * | 1987-06-10 | 1990-01-23 | A. H. Robins Company, Incorporated | N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines |
| GB8722776D0 (en) * | 1987-09-28 | 1987-11-04 | Smith Kline French Lab | Chemical compounds |
| US4900740A (en) * | 1987-10-02 | 1990-02-13 | The Nutrasweet Company | N,N'-disubstituted guanidines containing a carboxyl or a tetrazolyl moiety |
| FR2624699B1 (fr) * | 1987-12-18 | 1990-04-13 | Bernard Lyon I Universite Clau | Derives heterocycliques de n-carbamoyl-, n-thiocarbamoyl- ou n-amidino-glycine ou beta-alanine utiles comme agents edulcorants |
| US5272164A (en) * | 1988-12-27 | 1993-12-21 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| FI95244C (fi) * | 1988-12-27 | 1996-01-10 | Kirin Brewery | Analogiamenetelmä valmistaa lääkeaineina käyttökelpoisia uusia karboksimidiamidijohdannaisia tai niiden farmaseuttisesti sopivia happoadditiosuoloja |
| JPH0662567B2 (ja) * | 1988-12-27 | 1994-08-17 | 麒麟麦酒株式会社 | ピリジンカルボキシイミダミド誘導体、その製造中間体、製造法および用途 |
| IE911168A1 (en) * | 1990-04-13 | 1991-10-23 | Takeda Chemical Industries Ltd | Novel intermediates for preparing guanidine derivatives,¹their preparation and use |
| WO1994004499A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
| AU673785B2 (en) * | 1993-06-11 | 1996-11-21 | Upjohn Company, The | Pyrimidine cyanoguanidines as K-channel blockers |
| US6022984A (en) * | 1998-07-27 | 2000-02-08 | Pfizer Inc. | Efficient synthesis of furan sulfonamide compounds useful in the synthesis of new IL-1 inhibitors |
| US7700561B2 (en) * | 2002-02-22 | 2010-04-20 | Shire Llc | Abuse-resistant amphetamine prodrugs |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3128280A (en) * | 1959-10-23 | 1964-04-07 | Searle & Co | 1-(alkoxylated/halogenated phenyl)-3-pyridylmethylureas |
| US3028391A (en) * | 1960-03-30 | 1962-04-03 | Searle & Co | 1-alkyl-3-(alpha-phenyl-4-pyridylmethyl) ureas and thioureas |
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
| US4156727A (en) * | 1975-07-31 | 1979-05-29 | Smith Kline & French Laboratories Limited | Alkoxy pyridine compounds |
| GB1564502A (en) * | 1975-07-31 | 1980-04-10 | Smith Kline French Lab | Guanidines thioureas and 1,1-diamino-2-nitroethylene derivatives |
| JPS5444660A (en) * | 1977-08-29 | 1979-04-09 | Yamanouchi Pharmaceut Co Ltd | Heterocyclic compound and its preparation |
| US4287346A (en) * | 1979-02-16 | 1981-09-01 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
-
1980
- 1980-02-12 US US06/120,876 patent/US4287346A/en not_active Expired - Lifetime
- 1980-02-12 NL NL8000869A patent/NL8000869A/nl not_active Application Discontinuation
- 1980-02-14 CH CH123280A patent/CH641772A5/de not_active IP Right Cessation
- 1980-02-15 IT IT19938/80A patent/IT1141214B/it active
- 1980-02-15 DE DE19803005786 patent/DE3005786A1/de not_active Withdrawn
- 1980-02-15 CA CA000345777A patent/CA1145751A/en not_active Expired
- 1980-02-15 SE SE8001216A patent/SE8001216L/xx not_active Application Discontinuation
- 1980-02-18 FR FR8003470A patent/FR2453155A1/fr active Granted
- 1980-02-18 GB GB08211155A patent/GB2107306B/en not_active Expired
- 1980-02-18 GB GB8005465A patent/GB2046736B/en not_active Expired
- 1980-08-13 US US06/178,017 patent/US4327217A/en not_active Expired - Lifetime
-
1981
- 1981-04-13 US US06/253,276 patent/US4363921A/en not_active Expired - Fee Related
- 1981-09-15 US US06/302,360 patent/US4396764A/en not_active Expired - Fee Related
-
1982
- 1982-01-28 US US06/344,079 patent/US4426521A/en not_active Expired - Fee Related
-
1984
- 1984-07-26 SE SE8403871A patent/SE8403871L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4426521A (en) | 1984-01-17 |
| IT1141214B (it) | 1986-10-01 |
| FR2453155B1 (enExample) | 1983-07-08 |
| CH641772A5 (de) | 1984-03-15 |
| GB2046736B (en) | 1983-05-18 |
| SE8403871D0 (sv) | 1984-07-26 |
| DE3005786A1 (de) | 1980-08-28 |
| SE8403871L (sv) | 1984-07-26 |
| US4327217A (en) | 1982-04-27 |
| SE8001216L (sv) | 1980-08-17 |
| US4287346A (en) | 1981-09-01 |
| IT8019938A0 (it) | 1980-02-15 |
| GB2107306A (en) | 1983-04-27 |
| FR2453155A1 (fr) | 1980-10-31 |
| US4363921A (en) | 1982-12-14 |
| GB2046736A (en) | 1980-11-19 |
| US4396764A (en) | 1983-08-02 |
| GB2107306B (en) | 1983-09-01 |
| NL8000869A (nl) | 1980-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1145751A (en) | Cyanoguanidine derivatives and process for the preparation thereof | |
| Brzozowski et al. | Synthesis, structural characterization and antitumor activity of novel 2, 4-diamino-1, 3, 5-triazine derivatives | |
| CA2223307A1 (en) | Amino-substituted thiadiazoles, pyrimidines, triazines or triazoles useful as ctf receptor antagonists | |
| US4968804A (en) | Bipyridine compounds | |
| FI73209B (fi) | Foerfarande foer framstaellning av nya imidazolylfenylamidiner, vilka har histamin h2-reseptorantagonist-aktivitet, som inhiberar utsoendring av magsyra. | |
| US20040138257A1 (en) | Chemical derivatives and their application as antitelomerase agent | |
| NZ243959A (en) | Substituted pyrazine derivatives and pharmaceutical compositions thereof | |
| CZ9497A3 (en) | Use of thiazole and thiadiazole derivatives as dopamine d3 receptor ligands | |
| US5164397A (en) | 2-aminopyrimidine-4-carboxamide derivatives, their preparation and their application in urinary therapeutics | |
| CA1062263A (en) | Histamine h-2 receptor antagonists | |
| KR930011491B1 (ko) | 이미다졸릴 알킬 구아니딘 유도체의 제조방법 | |
| US3935209A (en) | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity | |
| KR101130913B1 (ko) | 헤테로시클릭 화합물 및 이를 활성 성분으로서 포함하는항악성종양제 | |
| Braña et al. | Benzimidazo [1, 2‐c] quinazoline dimers as potential antitumor agents | |
| US5212187A (en) | Pyridyl alkylamine compounds which are useful against histamine h1 and h2 receptors | |
| Yamada et al. | Pyridazinones. 3. Synthesis, antisecretory, and antiulcer activities of 2-cyanoguanidine derivatives | |
| CA1244827A (en) | Process for preparing 4,5,6,7-tetrahydro-thiazolo ¬5,4-c|-pyridine derivatives | |
| US4157347A (en) | N-cyano isothioureas | |
| NO781572L (no) | Fremgangsmaate for fremstilling av bisamidiner | |
| US4550118A (en) | Heterocyclic compounds | |
| US4415582A (en) | Method of treating ulcers or hypersecretion | |
| Krezel et al. | New mitoguazone analogues with anticancer activity | |
| KATSURA et al. | Studies on antiulcer drugs. VI. 4-Furyl-2-guanidinothiazoles and related compounds as potent histamine H2-receptor antagonists | |
| Küçükgüzel et al. | Synthesis and characterization of some thiourea derivatives from 1, 2, 4-triazolin3-3-thiones | |
| DE3044566A1 (de) | N-substituierte imidazol-derivate, ihre herstellung, diese enthaltende arzneimittel und ihre verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |