CH626084A5 - Process for the preparation of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine derivatives - Google Patents

Process for the preparation of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine derivatives Download PDF

Info

Publication number: CH626084A5
Authority: CH; Switzerland
Prior art keywords: pyridine; tetrahydroimidazo; title; compound mentioned; procedure
Prior art date: 1976-01-07

Application number

CH15377A

Other languages

German (de)

English (en)

Inventor

Giuliana Arcari

Luigi Bernardi

Giovanni Falconi

Fulvio Luini

Giorgio Paiamidessi

Ugo Scarponi

Original Assignee

Farmaceutici Italia

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.)

1976-01-07

Filing date

1977-01-06

Publication date

1981-10-30

1976-01-07 Priority claimed from GB573/76A external-priority patent/GB1524481A/en

1977-01-06 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1981-10-30 Publication of CH626084A5 publication Critical patent/CH626084A5/de

Links

238000000034 method Methods 0.000 title claims description 43
URMVFILWXLQJIP-UHFFFAOYSA-N 4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridine Chemical class C1NCCC2=C1NC=N2 URMVFILWXLQJIP-UHFFFAOYSA-N 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 58
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
-1 alkyl isocyanate Chemical class 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 2
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 4
229910052739 hydrogen Inorganic materials 0.000 claims 4
239000001257 hydrogen Substances 0.000 claims 4
150000002431 hydrogen Chemical group 0.000 claims 3
125000000753 cycloalkyl group Chemical group 0.000 claims 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
125000004442 acylamino group Chemical group 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002540 isothiocyanates Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000011593 sulfur Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 10
238000001704 evaporation Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
230000008020 evaporation Effects 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
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 6
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 5
QYCAPCVZIYWAAR-UHFFFAOYSA-N 4-cyclohexyl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound C1CCCCC1C1C(N=CN2)=C2CCN1 QYCAPCVZIYWAAR-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000001078 anti-cholinergic effect Effects 0.000 description 5
230000000767 anti-ulcer Effects 0.000 description 5
230000002496 gastric effect Effects 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
RATNHEJNTDOUKB-UHFFFAOYSA-N 4-(furan-2-yl)-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound N1CCC=2NC=NC=2C1C1=CC=CO1 RATNHEJNTDOUKB-UHFFFAOYSA-N 0.000 description 4
RVRGWEYCNVKOQT-UHFFFAOYSA-N 4-ethyl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound CCC1NCCC2=C1N=CN2 RVRGWEYCNVKOQT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000002541 furyl group Chemical group 0.000 description 4
229960004931 histamine dihydrochloride Drugs 0.000 description 4
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 4
238000006386 neutralization reaction Methods 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
FYUSKUJSMSAABJ-UHFFFAOYSA-N 4-thiophen-2-yl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound N1CCC=2NC=NC=2C1C1=CC=CS1 FYUSKUJSMSAABJ-UHFFFAOYSA-N 0.000 description 3
FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000028327 secretion Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
SHIJOLLBBCZWON-UHFFFAOYSA-N 4-phenyl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound N1CCC=2NC=NC=2C1C1=CC=CC=C1 SHIJOLLBBCZWON-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229930003347 Atropine Natural products 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
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 2
229960000396 atropine Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
239000003480 eluent Substances 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
210000001187 pylorus Anatomy 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
238000005303 weighing Methods 0.000 description 2
SKWDIXBVQATQSG-UHFFFAOYSA-N 2-chloro-5-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(C(O)=O)=C1 SKWDIXBVQATQSG-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
WETQXNKTCDDFSL-UHFFFAOYSA-N 3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound C1N(C(=N)N)CCC2=C1N=CN2 WETQXNKTCDDFSL-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
ZLEYOATWOLMVOE-UHFFFAOYSA-N 3-methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine Chemical compound C1CNCC2=C1N=CN2C ZLEYOATWOLMVOE-UHFFFAOYSA-N 0.000 description 1
BVJUYSBEKLVVMA-UHFFFAOYSA-N 3-methyl-n-propan-2-yl-6,7-dihydro-4h-imidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)C)CCC2=C1N(C)C=N2 BVJUYSBEKLVVMA-UHFFFAOYSA-N 0.000 description 1
CHLFJSVTUQAGSC-UHFFFAOYSA-N 4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridine;hydrochloride Chemical compound Cl.C1NCCC2=C1N=CN2 CHLFJSVTUQAGSC-UHFFFAOYSA-N 0.000 description 1
ZSDLRZIJPYHXKE-UHFFFAOYSA-N 4-(furan-2-yl)-N-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound O1C(=CC=C1)C1N(CCC2=C1N=CN2)C(NC(C)C)=S ZSDLRZIJPYHXKE-UHFFFAOYSA-N 0.000 description 1
YPAQUVNTWSYBHD-UHFFFAOYSA-N 4-(furan-2-yl)-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CNC(=S)N1CCC=2NC=NC=2C1C1=CC=CO1 YPAQUVNTWSYBHD-UHFFFAOYSA-N 0.000 description 1
CNJGUYMFNPGVMZ-UHFFFAOYSA-N 4-(furan-2-yl)-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CNC(=O)N1CCC=2NC=NC=2C1C1=CC=CO1 CNJGUYMFNPGVMZ-UHFFFAOYSA-N 0.000 description 1
OTVJIRREMFTLJS-UHFFFAOYSA-N 4-(furan-2-yl)-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CC(C)NC(=O)N1CCC=2NC=NC=2C1C1=CC=CO1 OTVJIRREMFTLJS-UHFFFAOYSA-N 0.000 description 1
FTEVPXYHUWQJQB-UHFFFAOYSA-N 4-cyclohexyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound NC(=N)N1CCC=2NC=NC=2C1C1CCCCC1 FTEVPXYHUWQJQB-UHFFFAOYSA-N 0.000 description 1
PNQGCAJOFLMSIH-UHFFFAOYSA-N 4-cyclohexyl-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CNC(=S)N1CCC=2NC=NC=2C1C1CCCCC1 PNQGCAJOFLMSIH-UHFFFAOYSA-N 0.000 description 1
MEMSYHRDHOZLJH-UHFFFAOYSA-N 4-cyclohexyl-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CNC(=O)N1CCC=2NC=NC=2C1C1CCCCC1 MEMSYHRDHOZLJH-UHFFFAOYSA-N 0.000 description 1
XUPAAIZGKMYPND-UHFFFAOYSA-N 4-cyclohexyl-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CC(C)NC(=S)N1CCC=2NC=NC=2C1C1CCCCC1 XUPAAIZGKMYPND-UHFFFAOYSA-N 0.000 description 1
RBTRAKAAPVTKIF-UHFFFAOYSA-N 4-cyclohexyl-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CC(C)NC(=O)N1CCC=2NC=NC=2C1C1CCCCC1 RBTRAKAAPVTKIF-UHFFFAOYSA-N 0.000 description 1
DBBTUQGDCPIXRD-UHFFFAOYSA-N 4-ethyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound CCC1N(C(N)=N)CCC2=C1N=CN2 DBBTUQGDCPIXRD-UHFFFAOYSA-N 0.000 description 1
CKJIMCWELNMHRJ-UHFFFAOYSA-N 4-ethyl-3-methyl-n-propan-2-yl-6,7-dihydro-4h-imidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CCC1N(C(=S)NC(C)C)CCC2=C1N(C)C=N2 CKJIMCWELNMHRJ-UHFFFAOYSA-N 0.000 description 1
QVBCCEOWBGATEV-UHFFFAOYSA-N 4-ethyl-n'-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound CCC1N(C(=N)NC(C)C)CCC2=C1N=CN2 QVBCCEOWBGATEV-UHFFFAOYSA-N 0.000 description 1
WSUXMDMWCSWUBD-UHFFFAOYSA-N 4-ethyl-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CCC1N(C(=S)NC)CCC2=C1N=CN2 WSUXMDMWCSWUBD-UHFFFAOYSA-N 0.000 description 1
SMXQRQWHULRAEG-UHFFFAOYSA-N 4-ethyl-n-methyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CCC1N(C(=O)NC)CCC2=C1N=CN2 SMXQRQWHULRAEG-UHFFFAOYSA-N 0.000 description 1
OJVWLNGLABMLOE-UHFFFAOYSA-N 4-ethyl-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CCC1N(C(=S)NC(C)C)CCC2=C1N=CN2 OJVWLNGLABMLOE-UHFFFAOYSA-N 0.000 description 1
UIMSUQBDEAHIJS-UHFFFAOYSA-N 4-ethyl-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CCC1N(C(=O)NC(C)C)CCC2=C1N=CN2 UIMSUQBDEAHIJS-UHFFFAOYSA-N 0.000 description 1
ZHIOCPMLUAICJZ-UHFFFAOYSA-N 4-phenyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound NC(=N)N1CCC=2NC=NC=2C1C1=CC=CC=C1 ZHIOCPMLUAICJZ-UHFFFAOYSA-N 0.000 description 1
MCBFETZWABNQDI-UHFFFAOYSA-N 4-phenyl-n-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CC(C)NC(=S)N1CCC=2NC=NC=2C1C1=CC=CC=C1 MCBFETZWABNQDI-UHFFFAOYSA-N 0.000 description 1
HVBRWZCJNYIZOG-UHFFFAOYSA-N 4-propan-2-yl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine;dihydrochloride Chemical compound Cl.Cl.CC(C)C1NCCC2=C1N=CN2 HVBRWZCJNYIZOG-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
206010022714 Intestinal ulcer Diseases 0.000 description 1
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
KAZVJVSIJWIMDA-UHFFFAOYSA-N N-propan-2-yl-4-thiophen-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound S1C(=CC=C1)C1N(CCC2=C1N=CN2)C(NC(C)C)=S KAZVJVSIJWIMDA-UHFFFAOYSA-N 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
241000906446 Theraps Species 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001262 anti-secretory effect Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
HRDFVQLHRAQAKQ-UHFFFAOYSA-N methyl n'-ethylcarbamimidothioate Chemical compound CCNC(=N)SC HRDFVQLHRAQAKQ-UHFFFAOYSA-N 0.000 description 1
YQSVTOWNQBRXDG-UHFFFAOYSA-N methyl n'-propan-2-ylcarbamimidothioate Chemical compound CSC(=N)NC(C)C YQSVTOWNQBRXDG-UHFFFAOYSA-N 0.000 description 1
ADYLVPJKNVHFQR-UHFFFAOYSA-N n',4-diethyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound CCC1N(C(=N)NCC)CCC2=C1N=CN2 ADYLVPJKNVHFQR-UHFFFAOYSA-N 0.000 description 1
MVCHBRBPJQFEAP-UHFFFAOYSA-N n'-ethyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide Chemical compound C1N(C(=N)NCC)CCC2=C1N=CN2 MVCHBRBPJQFEAP-UHFFFAOYSA-N 0.000 description 1
VTOYNTSJQJDUHY-UHFFFAOYSA-N n,3-dimethyl-6,7-dihydro-4h-imidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC)CCC2=C1N(C)C=N2 VTOYNTSJQJDUHY-UHFFFAOYSA-N 0.000 description 1
KXKUKWNSXXATOJ-UHFFFAOYSA-N n,4-di(propan-2-yl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CC(C)C1N(C(=S)NC(C)C)CCC2=C1N=CN2 KXKUKWNSXXATOJ-UHFFFAOYSA-N 0.000 description 1
IEGZMKUJFUOZHA-UHFFFAOYSA-N n,4-di(propan-2-yl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CC(C)C1N(C(=O)NC(C)C)CCC2=C1N=CN2 IEGZMKUJFUOZHA-UHFFFAOYSA-N 0.000 description 1
DEROUHNJUYTPQV-UHFFFAOYSA-N n-butyl-4-ethyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CCC1N(C(=S)NCCCC)CCC2=C1N=CN2 DEROUHNJUYTPQV-UHFFFAOYSA-N 0.000 description 1
IDPNDFFGOBLKAQ-UHFFFAOYSA-N n-cyclohexyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1CC=2NC=NC=2CN1C(=S)NC1CCCCC1 IDPNDFFGOBLKAQ-UHFFFAOYSA-N 0.000 description 1
FCLGBEQJYURSQQ-UHFFFAOYSA-N n-cyclopentyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound C1CC=2NC=NC=2CN1C(=O)NC1CCCC1 FCLGBEQJYURSQQ-UHFFFAOYSA-N 0.000 description 1
WZTKUNYRXNOMLV-UHFFFAOYSA-N n-cyclopropyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1CC=2NC=NC=2CN1C(=S)NC1CC1 WZTKUNYRXNOMLV-UHFFFAOYSA-N 0.000 description 1
QCCDCLAGJXNZBF-UHFFFAOYSA-N n-cyclopropyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound C1CC=2NC=NC=2CN1C(=O)NC1CC1 QCCDCLAGJXNZBF-UHFFFAOYSA-N 0.000 description 1
YFWDCUUYHBMZMK-UHFFFAOYSA-N n-ethyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NCC)CCC2=C1N=CN2 YFWDCUUYHBMZMK-UHFFFAOYSA-N 0.000 description 1
UCMZPBLRPQBJKS-UHFFFAOYSA-N n-methyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC)CCC2=C1N=CN2 UCMZPBLRPQBJKS-UHFFFAOYSA-N 0.000 description 1
DHIKRKWROKNFIU-UHFFFAOYSA-N n-methyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound C1N(C(=O)NC)CCC2=C1N=CN2 DHIKRKWROKNFIU-UHFFFAOYSA-N 0.000 description 1
IXDUVRDDMJICAH-UHFFFAOYSA-N n-methyl-4-phenyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CNC(=S)N1CCC=2NC=NC=2C1C1=CC=CC=C1 IXDUVRDDMJICAH-UHFFFAOYSA-N 0.000 description 1
OKSWHQKGWUDNSW-UHFFFAOYSA-N n-methyl-4-phenyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CNC(=O)N1CCC=2NC=NC=2C1C1=CC=CC=C1 OKSWHQKGWUDNSW-UHFFFAOYSA-N 0.000 description 1
GPSLKRCNZKUCAS-UHFFFAOYSA-N n-methyl-4-thiophen-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CNC(=S)N1CCC=2NC=NC=2C1C1=CC=CS1 GPSLKRCNZKUCAS-UHFFFAOYSA-N 0.000 description 1
WZSHQCSZCHZAFR-UHFFFAOYSA-N n-methyl-4-thiophen-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CNC(=O)N1CCC=2NC=NC=2C1C1=CC=CS1 WZSHQCSZCHZAFR-UHFFFAOYSA-N 0.000 description 1
WZIKKZZXJQSSFQ-UHFFFAOYSA-N n-phenyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1CC=2NC=NC=2CN1C(=S)NC1=CC=CC=C1 WZIKKZZXJQSSFQ-UHFFFAOYSA-N 0.000 description 1
WKIJBHOYFVOWMW-UHFFFAOYSA-N n-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NC(C)C)CCC2=C1N=CN2 WKIJBHOYFVOWMW-UHFFFAOYSA-N 0.000 description 1
LFWOUMMPXLIRRU-UHFFFAOYSA-N n-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound C1N(C(=O)NC(C)C)CCC2=C1N=CN2 LFWOUMMPXLIRRU-UHFFFAOYSA-N 0.000 description 1
IPAAAMHZVFOYCV-UHFFFAOYSA-N n-propan-2-yl-4-thiophen-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide Chemical compound CC(C)NC(=O)N1CCC=2NC=NC=2C1C1=CC=CS1 IPAAAMHZVFOYCV-UHFFFAOYSA-N 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH15377A 1976-01-07 1977-01-06 Process for the preparation of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine derivatives CH626084A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB573/76A GB1524481A (en)	1976-01-07	1976-01-07	Tetrahydo - imidazopyridine derivatives
GB2707176		1976-06-29

Publications (1)

Publication Number	Publication Date
CH626084A5 true CH626084A5 (en)	1981-10-30

Family

ID=26236032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH15377A CH626084A5 (en)	1976-01-07	1977-01-06	Process for the preparation of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine derivatives

Country Status (9)

Country	Link
AT (1)	AT356653B (da)
CA (1)	CA1075240A (da)
CH (1)	CH626084A5 (da)
DE (1)	DE2700012A1 (da)
DK (1)	DK146655C (da)
FR (1)	FR2337726A1 (da)
NL (1)	NL7614577A (da)
SE (1)	SE422062B (da)
SU (1)	SU667136A3 (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1098015B (it) *	1978-08-07	1985-08-31	Farmaceutici Italia	Nuovi 4,5,6,7,-tetraidroimidazo-aperta par.quadrata 4,5-c chiusa par.quadrata-piridin-derivati
US6908926B1 (en)	1999-04-16	2005-06-21	Novo Nordisk A/S	Substituted imidazoles, their preparation and use
GB201618029D0 (en) *	2016-10-25	2016-12-07	Proximagen Ltd	New process

1976
- 1976-12-30 NL NL7614577A patent/NL7614577A/xx not_active Application Discontinuation
1977
- 1977-01-03 DE DE19772700012 patent/DE2700012A1/de not_active Withdrawn
- 1977-01-03 SE SE7700041A patent/SE422062B/xx not_active IP Right Cessation
- 1977-01-03 DK DK177A patent/DK146655C/da not_active IP Right Cessation
- 1977-01-04 AT AT1877A patent/AT356653B/de not_active IP Right Cessation
- 1977-01-04 CA CA269,126A patent/CA1075240A/en not_active Expired
- 1977-01-05 FR FR7700162A patent/FR2337726A1/fr active Granted
- 1977-01-06 CH CH15377A patent/CH626084A5/de not_active IP Right Cessation
- 1977-01-06 SU SU772435956A patent/SU667136A3/ru active

Also Published As

Publication number	Publication date
NL7614577A (nl)	1977-07-11
ATA1877A (de)	1979-10-15
DK177A (da)	1977-07-08
DK146655C (da)	1984-05-07
FR2337726A1 (fr)	1977-08-05
FR2337726B1 (da)	1980-03-14
AT356653B (de)	1980-05-12
DE2700012A1 (de)	1977-07-21
CA1075240A (en)	1980-04-08
DK146655B (da)	1983-11-28
SU667136A3 (ru)	1979-06-05
SE7700041L (sv)	1977-07-08
SE422062B (sv)	1982-02-15

Legal Events

Date	Code	Title	Description
1987-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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DE3001328C2 (da)	1989-06-08
CH649527A5 (de)	1985-05-31	1,2-diaminocyclobuten-3,4-dione, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten.
EP0528922B1 (de)	1999-06-16	Neue sulfonylverbindungen
DE2905811C2 (da)	1988-10-13
DD213920A5 (de)	1984-09-26	Verfahren zur herstellung von dihydropyridinen
DE2847792C2 (da)	1988-02-04
DE3240727A1 (de)	1983-05-19	Ergolinderivate, verfahren zu deren herstellung sowie pharmazeutische zubereitungen, die diese enthalten
DE2112349A1 (de)	1971-10-14	Di- und tri-substituierte Imidazole
DE1914571C3 (de)	1978-09-28	L-SHydroxy-e-oxomorphinan-Verbindungen
DE3216843C2 (de)	1986-10-23	3-Thiomethyl-pyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH509318A (de)	1971-06-30	Verfahren zur Herstellung von substituierten Benzimidazolen
DE2720545A1 (de)	1977-11-10	Neue chinazolinderivate, ihre herstellung und pharmazeutische mittel
CH626084A5 (en)	1981-10-30	Process for the preparation of 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine derivatives
DE3445192C2 (da)	1993-02-18
DE2819874A1 (de)	1978-11-09	Bisamidine, verfahren zu ihrer herstellung und ihre verwendung als histamin- h tief 2 - receptor-antagonisten
DE2913295C2 (da)	1988-09-22
DE2045049A1 (de)	1972-03-23	Neue Nitrofurandenvate und Ver fahren zu ihrer Herstellung
DE68918651T2 (de)	1995-05-24	Verwendung von Imidazopyrazolderivaten als analgesische und antiinflammatorische Mittel.
DE2605824C3 (de)	1981-04-23	N-Acylaniline, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
DE602004011773T2 (de)	2009-02-05	Neue imidazopyridinverbindung ii mit therapeutischer wirkung
DE1934392B2 (de)	1973-10-18	Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung
EP0037471B1 (de)	1984-05-30	1-Aroyl-2-phenylamino-2-imidazoline, ihre Herstellung und diese enthaltende Arzneimittel
EP0049853B1 (de)	1985-02-13	Neue Prostaglandine, ihre Herstellung und pharmazeutische Kompositionen
EP0111205B1 (de)	1987-04-01	Acridanon-Derivate