CA1075240A - 4,5,6,7-tetrahydroimidazo-(4,5-c)-pyridine derivatives - Google Patents

4,5,6,7-tetrahydroimidazo-(4,5-c)-pyridine derivatives

Info

Publication number: CA1075240A
Authority: CA; Canada
Prior art keywords: pyridine; imidazo; carbon atoms; tetrahydro; hydrogen
Prior art date: 1976-01-07
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

Application number

CA269,126A

Other languages

English (en)

French (fr)

Inventor

Ugo Scarponi

Giorgio Palamidessi

Fulvio Luini

Giovanni Falconi

Luigi Bernardi

Giuliana Arcari

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Farmaceutici Italia SpA

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

1977-01-04

Publication date

1980-04-08

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

1977-01-04 Application filed by Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA

1980-04-08 Application granted granted Critical

1980-04-08 Publication of CA1075240A publication Critical patent/CA1075240A/en

Status Expired legal-status Critical Current

Links

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 abstract description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims abstract description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 9
239000002904 solvent Substances 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
125000001544 thienyl group Chemical group 0.000 claims abstract description 8
125000002541 furyl group Chemical group 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims abstract description 4
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 claims abstract description 4
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
239000012948 isocyanate Substances 0.000 claims abstract description 3
238000010992 reflux Methods 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 12
-1 alkyl isocyanate Chemical class 0.000 claims abstract 3
229910052760 oxygen Inorganic materials 0.000 claims abstract 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 3
150000002540 isothiocyanates Chemical class 0.000 claims description 3
BTMWJZPJQDYRFI-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound C1N=CC=C2NCNC21 BTMWJZPJQDYRFI-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
230000002496 gastric effect Effects 0.000 abstract description 6
208000025865 Ulcer Diseases 0.000 abstract description 4
230000028327 secretion Effects 0.000 abstract description 4
238000002560 therapeutic procedure Methods 0.000 abstract description 3
231100000397 ulcer Toxicity 0.000 abstract description 3
208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
150000007513 acids Chemical class 0.000 abstract description 2
238000010171 animal model Methods 0.000 abstract description 2
208000000718 duodenal ulcer Diseases 0.000 abstract description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
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 15
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 14
238000001704 evaporation Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
241000700159 Rattus Species 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000001078 anti-cholinergic effect Effects 0.000 description 5
230000001262 anti-secretory effect Effects 0.000 description 5
230000000767 anti-ulcer Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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 4
FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 4
LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 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
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 3
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002431 hydrogen Chemical group 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
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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 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
ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 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
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
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 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
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
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 2
LPEUHOWFPXLCQM-UHFFFAOYSA-N n-methyl-4-propan-2-yl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound CC(C)C1N(C(=S)NC)CCC2=C1N=CN2 LPEUHOWFPXLCQM-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 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
210000002784 stomach Anatomy 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
KKASGUHLXWAKEZ-UHFFFAOYSA-N 1-isothiocyanatopropane Chemical compound CCCN=C=S KKASGUHLXWAKEZ-UHFFFAOYSA-N 0.000 description 1
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
YIYHCYXLBKGXKF-UHFFFAOYSA-N 3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboximidamide;hydrochloride Chemical compound Cl.C1N(C(=N)N)CCC2=C1N=CN2 YIYHCYXLBKGXKF-UHFFFAOYSA-N 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
UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical compound C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-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
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
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
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
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
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
IZOGLMUTLGOAFW-UHFFFAOYSA-N 4-phenyl-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=CC=C1 IZOGLMUTLGOAFW-UHFFFAOYSA-N 0.000 description 1
OJQDVKRXYOZHRR-UHFFFAOYSA-N 4-propan-2-yl-4,5,6,7-tetrahydro-1h-imidazo[4,5-c]pyridine Chemical compound CC(C)C1NCCC2=C1N=CN2 OJQDVKRXYOZHRR-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
101100506034 Fibrobacter succinogenes (strain ATCC 19169 / S85) cel-3 gene Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
OOMXGFUBBBFWHR-UHFFFAOYSA-N O.SS Chemical compound O.SS OOMXGFUBBBFWHR-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000906446 Theraps Species 0.000 description 1
239000013543 active substance Substances 0.000 description 1
235000016720 allyl isothiocyanate Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000013305 food Nutrition 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
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
MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 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
MHGGQXIPBPGZFB-UHFFFAOYSA-N methyl n-cyano-n'-methylcarbamimidothioate Chemical compound CSC(=NC)NC#N MHGGQXIPBPGZFB-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
HEZPIEPFNYTNDI-UHFFFAOYSA-N n-butyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NCCCC)CCC2=C1N=CN2 HEZPIEPFNYTNDI-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
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
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
BSHMAXDSNXZRGH-UHFFFAOYSA-N n-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide;hydrochloride Chemical compound Cl.C1N(C(=S)NC(C)C)CCC2=C1N=CN2 BSHMAXDSNXZRGH-UHFFFAOYSA-N 0.000 description 1
XBCFFZCTNXKXCV-UHFFFAOYSA-N n-propan-2-yl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxamide;hydrochloride Chemical compound Cl.C1N(C(=O)NC(C)C)CCC2=C1N=CN2 XBCFFZCTNXKXCV-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
UZQUHBSNHZNDPZ-UHFFFAOYSA-N n-propyl-3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbothioamide Chemical compound C1N(C(=S)NCCC)CCC2=C1N=CN2 UZQUHBSNHZNDPZ-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000013049 sediment Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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)

CA269,126A 1976-01-07 1977-01-04 4,5,6,7-tetrahydroimidazo-(4,5-c)-pyridine derivatives Expired CA1075240A (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
CA1075240A true CA1075240A (en)	1980-04-08

Family

ID=26236032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA269,126A Expired CA1075240A (en)	1976-01-07	1977-01-04	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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2018078363A1 (en) *	2016-10-25	2018-05-03	Proximagen Limited	Process for the preparation of (3s,4s)-tetrahydrofuran-3-yl 4-isopropyl-6,7-dihydro-3h-imidazo[4,5-c]pyridine-5(4h)-carboxylate

Families Citing this family (2)

* 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

1976
- 1976-12-30 NL NL7614577A patent/NL7614577A/xx not_active Application Discontinuation
1977
- 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
- 1977-01-03 DE DE19772700012 patent/DE2700012A1/de not_active Withdrawn
- 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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2018078363A1 (en) *	2016-10-25	2018-05-03	Proximagen Limited	Process for the preparation of (3s,4s)-tetrahydrofuran-3-yl 4-isopropyl-6,7-dihydro-3h-imidazo[4,5-c]pyridine-5(4h)-carboxylate
US10988473B2 (en)	2016-10-25	2021-04-27	Benevolental Cambridge Limited	Process for the preparation of (3S,4S)-tetrahydrofuran-3-yl 4-isopropyl-6,7-dihydro-3H-imidazo[4,5-C]pyridine-5(4H)-carboxylate

Also Published As

Publication number	Publication date
DE2700012A1 (de)	1977-07-21
FR2337726A1 (fr)	1977-08-05
SE422062B (sv)	1982-02-15
SE7700041L (sv)	1977-07-08
DK146655C (da)	1984-05-07
ATA1877A (de)	1979-10-15
SU667136A3 (ru)	1979-06-05
DK177A (da)	1977-07-08
CH626084A5 (en)	1981-10-30
FR2337726B1 (da)	1980-03-14
DK146655B (da)	1983-11-28
AT356653B (de)	1980-05-12
NL7614577A (nl)	1977-07-11

Legal Events

Date	Code	Title	Description
1997-04-08	MKEX	Expiry

Publication	Publication Date	Title
DE2951675C2 (de)	1982-07-01	Guanidinothiazolverbindungen, Verfahren zu deren Herstellung und Arzneimittelzubereitungen
US4248880A (en)	1981-02-03	Treatment of gastric ulcers with naphthimidazole derivatives
US4687777A (en)	1987-08-18	Thiazolidinedione derivatives, useful as antidiabetic agents
US4375547A (en)	1983-03-01	N-Methyl-N'-2-([(2-dimethylaminomethyl)-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine
EP0003640B1 (en)	1982-01-27	Antisecretory guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them
US4362736A (en)	1982-12-07	Guanidinothiazole compounds, and medical compositions containing them
US4379158A (en)	1983-04-05	Antisecretory imidazole amidine compounds, composition and method of use
US4242350A (en)	1980-12-30	Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them
CS200546B2 (en)	1980-09-15	Method of producing derivatives of guanidine
PL102353B1 (pl)	1979-03-31	A method of producing new derivatives of 1,1-diaminoethylene
CS248750B2 (en)	1987-02-12	Production method of the 2-(n-subst.guanidino)-4-heteroarylthiazols
KR860001921B1 (ko)	1986-10-25	1,4-디하이드로피리딘의 제조방법
US4493840A (en)	1985-01-15	Antisecretory guanidine derivatives, and pharmaceutical compositions containing them
US4252819A (en)	1981-02-24	Antisecretory heterocyclic amidine compounds
US4141899A (en)	1979-02-27	4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridine derivatives
HU187478B (en)	1986-01-28	Process for preparing new imidazolyl-phenyl-amidines and pharmaceutical compositions containing thereof
US4293549A (en)	1981-10-06	Quinolinyl guanidines having antiinflammatory, analgesic or antipyretic activity
SE452884B (sv)	1987-12-21	Ergolinderivat, forfarande for deras framstellning och farmaceutiska kompositioner der de ingar
CA1201120A (en)	1986-02-25	Antiulcer 2-guanidino-4-(2-substituted-amino-4- imidazolyl) thiazoles and process therefor
CA1075240A (en)	1980-04-08	4,5,6,7-tetrahydroimidazo-(4,5-c)-pyridine derivatives
US4814341A (en)	1989-03-21	2-guanidino-4-(2-furyl) thiazoles as antiulcer agents
US4432990A (en)	1984-02-21	5-Aminoimidazoles as immunoregulants
KR870000912B1 (ko)	1987-05-06	디하이드로피리딘 유도체의 제조방법
US4735955A (en)	1988-04-05	2-substituted cycloheptoimidazole derivatives and anti-ulcerative agents containing the same
EP0074229B1 (en)	1986-04-09	Triazole gastric anti-secretory agents