JPS622590B2 - - Google Patents

Info

Publication number

JPS622590B2

JPS622590B2 JP58004631A JP463183A JPS622590B2 JP S622590 B2 JPS622590 B2 JP S622590B2 JP 58004631 A JP58004631 A JP 58004631A JP 463183 A JP463183 A JP 463183A JP S622590 B2 JPS622590 B2 JP S622590B2

Authority

JP

Japan

Prior art keywords

methyl

cimetidine

guanidine

cyano

reaction

Prior art date

1983-01-14

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

• Espacenet
• Global Dossier
• Discuss

• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
• 239000013078 crystal Substances 0.000 claims description 18
• 229960001380 cimetidine Drugs 0.000 claims description 17
• GCYDEHNKSNMNMN-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanethiol Chemical compound CC=1NC=NC=1CS GCYDEHNKSNMNMN-UHFFFAOYSA-N 0.000 claims description 5
• -1 N′-methyl-N′′-(2-substituted ethyl)-guanidine Chemical class 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims 1
• 150000002367 halogens Chemical group 0.000 claims 1
• 125000005905 mesyloxy group Chemical group 0.000 claims 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
• 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
• AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 14
• 238000000034 method Methods 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
• 229910052753 mercury Inorganic materials 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• GAIOTNZPXCFNJU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCCl GAIOTNZPXCFNJU-UHFFFAOYSA-N 0.000 description 2
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• 238000000862 absorption spectrum Methods 0.000 description 2
• 229940125904 compound 1 Drugs 0.000 description 2
• 229940125782 compound 2 Drugs 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
• 150000002460 imidazoles Chemical class 0.000 description 2
• 230000001678 irradiating effect Effects 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• KWULCRGWFZACSD-UHFFFAOYSA-N 2-(2-chloroethyl)guanidine Chemical compound NC(N)=NCCCl KWULCRGWFZACSD-UHFFFAOYSA-N 0.000 description 1
• XTNKKKZZEGJQDP-UHFFFAOYSA-N 2-[(n-cyano-n'-methylcarbamimidoyl)amino]ethyl 4-methylbenzenesulfonate Chemical compound N#CNC(=NC)NCCOS(=O)(=O)C1=CC=C(C)C=C1 XTNKKKZZEGJQDP-UHFFFAOYSA-N 0.000 description 1
• FOWRNONMFJXAJD-UHFFFAOYSA-N 2-[(n-cyano-n'-methylcarbamimidoyl)amino]ethyl methanesulfonate Chemical compound N#CNC(=NC)NCCOS(C)(=O)=O FOWRNONMFJXAJD-UHFFFAOYSA-N 0.000 description 1
• OFFPEAOWWDXZOY-UHFFFAOYSA-N 2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CN=C(N)NCCSCC=1N=CNC=1C OFFPEAOWWDXZOY-UHFFFAOYSA-N 0.000 description 1
• 230000000767 anti-ulcer Effects 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 229960001340 histamine Drugs 0.000 description 1
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1