DE3005786A1 - Cyanoguanidinderivate und verfahren zu deren herstellung - Google Patents
Cyanoguanidinderivate und verfahren zu deren herstellungInfo
- Publication number
- DE3005786A1 DE3005786A1 DE19803005786 DE3005786A DE3005786A1 DE 3005786 A1 DE3005786 A1 DE 3005786A1 DE 19803005786 DE19803005786 DE 19803005786 DE 3005786 A DE3005786 A DE 3005786A DE 3005786 A1 DE3005786 A1 DE 3005786A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- pyridyl
- ncn
- acid addition
- addition salt
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 21
- -1 puryl Chemical group 0.000 claims description 19
- 239000002253 acid Substances 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
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000002541 isothioureas Chemical class 0.000 claims description 7
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000002542 isoureas Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 98
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 28
- 239000000460 chlorine Substances 0.000 description 21
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 18
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 210000003608 fece Anatomy 0.000 description 7
- 239000010871 livestock manure Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 210000003298 dental enamel Anatomy 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 230000003501 anti-edematous effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 230000001078 anti-cholinergic effect Effects 0.000 description 2
- 230000001142 anti-diarrhea Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 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
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000002467 anti-pepsin effect Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 229940125714 antidiarrheal agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- PUFQVTATUTYEAL-UHFFFAOYSA-N cinchocaine Chemical compound C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCCN(CC)CC)=C21 PUFQVTATUTYEAL-UHFFFAOYSA-N 0.000 description 1
- 229960001747 cinchocaine Drugs 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 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
- 229960005015 local anesthetics Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000005394 methallyl 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 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 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 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
- 125000001424 substituent group Chemical group 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
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 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)
Applications Claiming Priority (2)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3005786A1 true DE3005786A1 (de) | 1980-08-28 |
Family
ID=26352224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803005786 Withdrawn DE3005786A1 (de) | 1979-02-16 | 1980-02-15 | Cyanoguanidinderivate und verfahren zu deren herstellung |
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) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2512447A1 (fr) * | 1981-09-10 | 1983-03-11 | Rech Applications Therap | Nouveaux derives de n''-cyano n-oxydo-1 pyridinio-4 guanidine n'-substituee utiles comme medicaments antihypertenseurs et procede de leur preparation |
| EP0116628A4 (en) * | 1982-08-24 | 1985-02-18 | Rorer Internat Overseas Inc | 1-ACYL-3-PYRIDYLMETHYLGUANIDINE AND THEIR USE AS AN ANI-HYPERTENSIVE. |
| EP0388528A3 (en) * | 1988-12-27 | 1991-06-05 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| US5166347A (en) * | 1988-12-27 | 1992-11-24 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| US5272164A (en) * | 1988-12-27 | 1993-12-21 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| WO1994004499A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
| WO1994029280A1 (en) * | 1993-06-11 | 1994-12-22 | The Upjohn Company | Pyrimidine cyanoguanidines as k-channel blockers |
Families Citing this family (18)
| 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 |
| IT1190793B (it) * | 1982-04-27 | 1988-02-24 | Magis Farmaceutici | Composti attivi nel trattamento dell'ulcera e sintomi allergici della pelle |
| 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 |
| IE911168A1 (en) * | 1990-04-13 | 1991-10-23 | Takeda Chemical Industries Ltd | Novel intermediates for preparing guanidine derivatives,¹their preparation and use |
| 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
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2512447A1 (fr) * | 1981-09-10 | 1983-03-11 | Rech Applications Therap | Nouveaux derives de n''-cyano n-oxydo-1 pyridinio-4 guanidine n'-substituee utiles comme medicaments antihypertenseurs et procede de leur preparation |
| EP0116628A4 (en) * | 1982-08-24 | 1985-02-18 | Rorer Internat Overseas Inc | 1-ACYL-3-PYRIDYLMETHYLGUANIDINE AND THEIR USE AS AN ANI-HYPERTENSIVE. |
| EP0388528A3 (en) * | 1988-12-27 | 1991-06-05 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| US5166347A (en) * | 1988-12-27 | 1992-11-24 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| US5272164A (en) * | 1988-12-27 | 1993-12-21 | Kirin Beer Kabushiki Kaisha | Carboximidamide derivatives |
| WO1994004499A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
| WO1994004500A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
| CN1039997C (zh) * | 1992-08-13 | 1998-09-30 | 法马西亚及厄普约翰公司 | 氰基胍类及其盐和含有它们的药物组合物 |
| WO1994029280A1 (en) * | 1993-06-11 | 1994-12-22 | The Upjohn Company | Pyrimidine cyanoguanidines as k-channel blockers |
Also Published As
| Publication number | Publication date |
|---|---|
| US4426521A (en) | 1984-01-17 |
| IT1141214B (it) | 1986-10-01 |
| FR2453155B1 (enExample) | 1983-07-08 |
| CA1145751A (en) | 1983-05-03 |
| CH641772A5 (de) | 1984-03-15 |
| GB2046736B (en) | 1983-05-18 |
| SE8403871D0 (sv) | 1984-07-26 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
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| 8141 | Disposal/no request for examination |