FI67218C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-alkoxifenyl-imidazo(4,5-b)pyridiner - Google Patents

Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-alkoxifenyl-imidazo(4,5-b)pyridiner Download PDF

Info

Publication number: FI67218C
Authority: FI; Finland
Prior art keywords: imidazo; pyridine; ethoxy; methoxyphenyl; carbon atoms
Prior art date: 1979-07-11

Application number

FI802203A

Other languages

English (en)

Finnish (fi)

Other versions

FI802203A (fi

FI67218B (fi

Inventor

Volkhard Austel

Manfred Reiffen

Joachim Heider

Willi Diederen

Original Assignee

Thomae Gmbh Dr K

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.)

1979-07-11

Filing date

1980-07-09

Publication date

1985-02-11

1980-07-09 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1981-01-12 Publication of FI802203A publication Critical patent/FI802203A/fi

1984-10-31 Publication of FI67218B publication Critical patent/FI67218B/fi

1985-02-11 Application granted granted Critical

1985-02-11 Publication of FI67218C publication Critical patent/FI67218C/fi

Links

238000002360 preparation method Methods 0.000 title claims description 4
230000000144 pharmacologic effect Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
-1 phenyl-substituted phenyl Chemical group 0.000 claims description 10
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 8
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
235000005985 organic acids Nutrition 0.000 claims description 6
238000000034 method Methods 0.000 claims description 4
150000003222 pyridines Chemical class 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 abstract 1
239000000496 cardiotonic agent Substances 0.000 abstract 1
230000003177 cardiotonic effect Effects 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
239000005555 hypertensive agent Substances 0.000 abstract 1
230000001631 hypertensive effect Effects 0.000 abstract 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
231100000252 nontoxic Toxicity 0.000 abstract 1
230000003000 nontoxic effect Effects 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CIGPWXUOWOGBDU-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.ClCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 CIGPWXUOWOGBDU-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
230000009090 positive inotropic effect Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
239000000126 substance Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WMNJIIKPYJDRTP-UHFFFAOYSA-N 2-[2-[2-(4-chlorophenyl)sulfinylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC=C(Cl)C=C1 WMNJIIKPYJDRTP-UHFFFAOYSA-N 0.000 description 3
ASNSQXXPEMXRIC-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-methoxyphenyl)sulfinylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1S(=O)CCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 ASNSQXXPEMXRIC-UHFFFAOYSA-N 0.000 description 3
LYCOMKLHJHRKSY-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-nitrophenyl)sulfinylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical group C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC=C([N+]([O-])=O)C=C1 LYCOMKLHJHRKSY-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
238000000746 purification Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
YWYAIQGWEIWYLP-UHFFFAOYSA-N 2-[2-[2-(2,4-dimethoxyphenyl)sulfinylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC(OC)=CC=C1S(=O)CCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 YWYAIQGWEIWYLP-UHFFFAOYSA-N 0.000 description 2
QOSGFVQLQJNBNZ-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-methoxyphenyl)sulfanylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1SCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 QOSGFVQLQJNBNZ-UHFFFAOYSA-N 0.000 description 2
125000006012 2-chloroethoxy group Chemical group 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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000829 suppository Substances 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
FRZIFMKSYWAOSE-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.C1=CC=C2NC=NC2=N1 FRZIFMKSYWAOSE-UHFFFAOYSA-N 0.000 description 1
WHVJOUCNIARNDA-UHFFFAOYSA-N 2-[2-(2-benzylsulfanylethoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSCC1=CC=CC=C1 WHVJOUCNIARNDA-UHFFFAOYSA-N 0.000 description 1
ILVKENBRORQHHE-UHFFFAOYSA-N 2-[2-(2-benzylsulfinylethoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)CC1=CC=CC=C1 ILVKENBRORQHHE-UHFFFAOYSA-N 0.000 description 1
XTGRSUBVYROTAS-UHFFFAOYSA-N 2-[2-(3-ethylsulfinylpropoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound CCS(=O)CCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 XTGRSUBVYROTAS-UHFFFAOYSA-N 0.000 description 1
JJGJMZQTKXBOKI-UHFFFAOYSA-N 2-[2-[2-(2,4-dimethoxyphenyl)sulfanylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC(OC)=CC=C1SCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 JJGJMZQTKXBOKI-UHFFFAOYSA-N 0.000 description 1
YXJTUDWNLVAYRS-UHFFFAOYSA-N 2-[2-[2-(3,4-dimethoxyphenyl)sulfanylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC=C(OC)C(OC)=C1 YXJTUDWNLVAYRS-UHFFFAOYSA-N 0.000 description 1
XUUGYJLATKPKCA-UHFFFAOYSA-N 2-[2-[2-(4,5-dimethoxy-2-methylphenyl)sulfanylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC(OC)=C(OC)C=C1C XUUGYJLATKPKCA-UHFFFAOYSA-N 0.000 description 1
FVKDXHFGGAZCCR-UHFFFAOYSA-N 2-[2-[2-(4,5-dimethoxy-2-methylphenyl)sulfinylethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC(OC)=C(OC)C=C1C FVKDXHFGGAZCCR-UHFFFAOYSA-N 0.000 description 1
ISJUCPCQEGBUTH-UHFFFAOYSA-N 2-[2-[2-(benzenesulfinyl)ethoxy]-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC=CC=C1 ISJUCPCQEGBUTH-UHFFFAOYSA-N 0.000 description 1
JETXMGAQENYUSZ-UHFFFAOYSA-N 2-[4-methoxy-2-(2-phenylsulfanylethoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC=CC=C1 JETXMGAQENYUSZ-UHFFFAOYSA-N 0.000 description 1
MBHHDFJBODIOEI-UHFFFAOYSA-N 2-[4-methoxy-2-(3-methylsulfinylpropoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound CS(=O)CCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 MBHHDFJBODIOEI-UHFFFAOYSA-N 0.000 description 1
BAJAJLHZTDYRRF-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(2-methoxyphenyl)sulfanylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC=CC=C1OC BAJAJLHZTDYRRF-UHFFFAOYSA-N 0.000 description 1
ZOPVDLZKCIBUSF-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(2-methoxyphenyl)sulfinylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC=CC=C1OC ZOPVDLZKCIBUSF-UHFFFAOYSA-N 0.000 description 1
BYYJYJVIDWOGQH-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-methylphenyl)sulfanylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC=C(C)C=C1 BYYJYJVIDWOGQH-UHFFFAOYSA-N 0.000 description 1
CRRXXKQMOUYJRX-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-methylphenyl)sulfinylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCS(=O)C1=CC=C(C)C=C1 CRRXXKQMOUYJRX-UHFFFAOYSA-N 0.000 description 1
GFFJAROYOOZQRO-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-nitrophenyl)sulfanylethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C(OC)=CC=C(C=2NC3=CC=CN=C3N=2)C=1OCCSC1=CC=C([N+]([O-])=O)C=C1 GFFJAROYOOZQRO-UHFFFAOYSA-N 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
VOLKQGYDJGFFJQ-UHFFFAOYSA-N COC1=CC(=C(C=C1)C2=NC3=C(N2)CCN3)OCCS(=O)C4=CC(=C(C=C4)OC)OC Chemical compound COC1=CC(=C(C=C1)C2=NC3=C(N2)CCN3)OCCS(=O)C4=CC(=C(C=C4)OC)OC VOLKQGYDJGFFJQ-UHFFFAOYSA-N 0.000 description 1
206010007558 Cardiac failure chronic Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000003187 abdominal effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000004071 biological effect Effects 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
230000003683 cardiac damage Effects 0.000 description 1
206010007625 cardiogenic shock Diseases 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
210000005240 left ventricle Anatomy 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
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Hospice & Palliative Care (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

FI802203A 1979-07-11 1980-07-09 Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-alkoxifenyl-imidazo(4,5-b)pyridiner FI67218C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19792927987 DE2927987A1 (de)	1979-07-11	1979-07-11	Neue 2-alkoxyphenyl-imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine, deren herstellung und deren verwendung als arzneimittel
DE2927987		1979-07-11

Publications (3)

Publication Number	Publication Date
FI802203A FI802203A (fi)	1981-01-12
FI67218B FI67218B (fi)	1984-10-31
FI67218C true FI67218C (fi)	1985-02-11

Family

ID=6075441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI802203A FI67218C (fi)	1979-07-11	1980-07-09	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-alkoxifenyl-imidazo(4,5-b)pyridiner

Country Status (17)

Country	Link
US (1)	US4327100A (da)
EP (1)	EP0022495B1 (da)
JP (1)	JPS5625179A (da)
AT (1)	ATE1194T1 (da)
AU (1)	AU537819B2 (da)
CA (1)	CA1146555A (da)
DE (2)	DE2927987A1 (da)
DK (1)	DK295880A (da)
ES (1)	ES493275A0 (da)
FI (1)	FI67218C (da)
GR (1)	GR69622B (da)
IL (1)	IL60532A (da)
NO (1)	NO802069L (da)
NZ (1)	NZ194303A (da)
PH (1)	PH17337A (da)
PT (1)	PT71525B (da)
ZA (1)	ZA804146B (da)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3037464A1 (de) *	1980-10-03	1982-05-19	Dr. Karl Thomae Gmbh, 7950 Biberach	6-hydroxy-2-phenyl-imidazo 4,5-b zu pyridine, ihre herstellung und diese sie enthaltende arzneimittel
EP0072926B1 (de) *	1981-08-19	1986-09-24	MERCK PATENT GmbH	2-Aryl-imidazopyridine
DE3132754A1 (de) *	1981-08-19	1983-03-03	Merck Patent Gmbh, 6100 Darmstadt	"2-aryl-imidazo(4,5-b)pyridine, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung"
ES8401486A1 (es) *	1981-11-10	1983-12-01	Wellcome Found	Un procedimiento para la preparacion de nuevos derivados de imidazo (4,5-c)piridina.
US4904785A (en) *	1982-05-03	1990-02-27	Eli Lilly And Company	2-phenylimidazo[4,5-c]pyridines
US4758574A (en) *	1982-05-03	1988-07-19	Eli Lilly And Company	2-phenylimidazio (4,5-c) pyridines
DE3217583A1 (de) *	1982-05-11	1983-11-17	Merck Patent Gmbh, 6100 Darmstadt	2-aryl-tetraazaindene
AT384809B (de) *	1982-05-28	1988-01-11	Sandoz Ag	Verfahren zur herstellung von neuen imidazopyridin-derivaten
DE3224512A1 (de) *	1982-07-01	1984-01-05	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel
US4636502A (en) *	1982-12-27	1987-01-13	Eli Lilly And Company	Methods of producing a positive inotropic effect or vasodilation by administration of 2-phenyl imidazo pyrimidines and pyrazines
US4537889A (en) *	1982-12-27	1985-08-27	Eli Lilly And Company	Inotropic agents
DE3324115A1 (de) *	1983-07-05	1985-01-17	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel
US4515796A (en) *	1983-09-08	1985-05-07	Eli Lilly And Company	Certain naphthalenyl imidazo compounds and their pharmaceutical use
US4533734A (en) *	1983-11-10	1985-08-06	Eli Lilly And Company	Inotropic agents
DE3346575A1 (de) *	1983-12-23	1985-07-04	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue benzimidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel
DE3347290A1 (de) *	1983-12-28	1985-07-11	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue 2-phenyl-imidazole, ihre herstellung und diese verbindungen enthaltende arzneimittel
AU581894B2 (en) *	1984-06-05	1989-03-09	Lockwood Security Products Pty Limited	Lock assembly
DE3445299A1 (de) *	1984-12-12	1986-06-19	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue imidazoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3522230A1 (de) *	1985-06-21	1987-01-02	Thomae Gmbh Dr K	Neue 2-arylimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
JP2577222B2 (ja) *	1987-04-10	1997-01-29	興和株式会社	新規な置換アニリド誘導体
US5227384A (en) *	1988-03-14	1993-07-13	G. D. Searle & Co.	5-substituted [4,5-c] imidazopyridines and pharmaceutical use thereof
US5302601A (en) *	1988-03-14	1994-04-12	G. D. Searle & Co.	5-substituted imidazo[4,5-c]pyridines
US4914108A (en) *	1988-03-14	1990-04-03	G. D. Searle & Co.	5-substituted(4,5-c)imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US5019581A (en) *	1988-03-14	1991-05-28	G. D. Searle & Co.	5-substituted (4,5-c) imidazopyridine compounds which have useful platelet activating factor antagonistic activity
US4990518A (en) *	1989-09-13	1991-02-05	G. D. Searle & Co.	Pharmacologically active heteroaryl substituted imidazo (4,5-c) pyridines
US4988707A (en) *	1989-09-13	1991-01-29	G. D. Searle & Co.	Pharmacologically active phenylalkanoyl substituted imidazo (4,5-C) pyridines
US5066654A (en) *	1990-10-22	1991-11-19	A. H. Robins Company, Incorporated	2-aryl-3-heterocyclicmethyl-3H-imidazo[4,5-b]pyridines as anxiolytics and anticonvulsants
US5208242A (en) *	1992-08-26	1993-05-04	G. D. Searle & Co.	5-substituted-4-phenyl-5H-imidazo[4,5-c]pyridine derivatives
US9474109B2 (en)	2012-08-13	2016-10-18	Tokuden Co., Ltd.	Induction heating apparatus

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH373392A (de) *	1958-12-10	1963-11-30	Ciba Geigy	Verfahren zur Herstellung neuer Azaverbindungen
DE2361757A1 (de) *	1973-12-12	1975-06-26	Thomae Gmbh Dr K	Neue imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine
US3985891A (en) *	1973-02-03	1976-10-12	Boehringer Ingelheim Gmbh	2-Phenyl-imidazo (4,5-b)pyridines and salts thereof
DE2305339C3 (de)	1973-02-03	1980-05-08	Dr. Karl Thomae Gmbh, 7950 Biberach	Imidazo [4,5-b] pyridine, ihre Herstellung und ihre Verwendung als Cardiötonica
US3996233A (en) *	1975-02-10	1976-12-07	E. R. Squibb & Sons, Inc.	Amino derivatives of imidazo[4,5-b]pyridines

1979
- 1979-07-11 DE DE19792927987 patent/DE2927987A1/de not_active Withdrawn
1980
- 1980-06-26 EP EP80103613A patent/EP0022495B1/de not_active Expired
- 1980-06-26 AT AT80103613T patent/ATE1194T1/de not_active IP Right Cessation
- 1980-06-26 DE DE8080103613T patent/DE3060551D1/de not_active Expired
- 1980-06-30 US US06/163,970 patent/US4327100A/en not_active Expired - Lifetime
- 1980-07-01 JP JP8992580A patent/JPS5625179A/ja active Pending
- 1980-07-07 GR GR62396A patent/GR69622B/el unknown
- 1980-07-08 PH PH24257A patent/PH17337A/en unknown
- 1980-07-09 DK DK295880A patent/DK295880A/da not_active Application Discontinuation
- 1980-07-09 FI FI802203A patent/FI67218C/fi not_active IP Right Cessation
- 1980-07-09 PT PT71525A patent/PT71525B/pt unknown
- 1980-07-09 IL IL60532A patent/IL60532A/xx unknown
- 1980-07-10 ES ES493275A patent/ES493275A0/es active Granted
- 1980-07-10 ZA ZA00804146A patent/ZA804146B/xx unknown
- 1980-07-10 NZ NZ194303A patent/NZ194303A/xx unknown
- 1980-07-10 CA CA000355892A patent/CA1146555A/en not_active Expired
- 1980-07-10 NO NO802069A patent/NO802069L/no unknown
- 1980-07-10 AU AU60308/80A patent/AU537819B2/en not_active Ceased

Also Published As

Publication number	Publication date
US4327100A (en)	1982-04-27
PT71525B (de)	1981-12-11
PT71525A (de)	1980-08-01
IL60532A0 (en)	1980-09-16
FI802203A (fi)	1981-01-12
PH17337A (en)	1984-08-01
IL60532A (en)	1983-07-31
EP0022495B1 (de)	1982-06-16
FI67218B (fi)	1984-10-31
DE3060551D1 (en)	1982-08-05
AU537819B2 (en)	1984-07-12
NO802069L (no)	1981-01-12
AU6030880A (en)	1981-01-15
DE2927987A1 (de)	1981-02-05
ES8106904A1 (es)	1981-09-01
DK295880A (da)	1981-01-12
GR69622B (da)	1982-07-06
NZ194303A (en)	1982-05-31
CA1146555A (en)	1983-05-17
ZA804146B (en)	1982-03-31
ATE1194T1 (de)	1982-07-15
JPS5625179A (en)	1981-03-10
ES493275A0 (es)	1981-09-01
EP0022495A1 (de)	1981-01-21

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: DR. KARL THOMAE GESELLSCHAFT MIT

Publication	Publication Date	Title
FI67218C (fi)	1985-02-11	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-alkoxifenyl-imidazo(4,5-b)pyridiner
US4256748A (en)	1981-03-17	Imidazo[2,1-b]quinazolin-2(3H)-ones and pharmaceutical compositions for treatment and prophylaxis of cardiac insufficiency and cardiac failure
SU1681728A3 (ru)	1991-09-30	Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты
US3632645A (en)	1972-01-04	Substituted phenylacetyl derivatives of guanidine o-alkylisoureas s-alkylisothioureas and p-nitrobenzylisothiourea
CS254319B2 (en)	1988-01-15	Method of imidazole derivatives production
US4299834A (en)	1981-11-10	8-Phenyl-purines and pharmaceutical compositions containing same
FI106856B (fi)	2001-04-30	Menetelmä terapeuttisesti aktiivisten heterosyklisellä ryhmällä substituoitujen bentsoyyliguanidiinijohdannaisten valmistamiseksi
IL187421A (en)	2011-11-30	Process for the synthesis of 5-(methyl-1h-imidazol-1-yl)-3-(tri fluoromethyl)-benzeneamine
US4639463A (en)	1987-01-27	Substituted phenylsulfonyloxybenzimidazolecarbamates and anthelmintic compositions
GB2119377A (en)	1983-11-16	Imidazo pyridines
FI64144C (fi)	1983-10-10	Foerfarande foer framstaellning av 2-arylamino-2-imidazolinderivat
CA1092111A (en)	1980-12-23	Sulfonamido-benzoic acid derivatives and process for the preparation thereof
US4259344A (en)	1981-03-31	Sulfur-containing benzimidazole derivatives
FI89267C (fi)	1993-09-10	Foerfarande foer framstaellning av terapeutiskt aktiva 4,5-dihydro-oxazoler
EP0998466B1 (en)	2002-10-16	A process for the preparation of tetraazamacrocycles
HU193073B (en)	1987-08-28	Process for producing new benzimidazoles
AU624406B2 (en)	1992-06-11	2-aminobenzyl (thiosulfinyl) imidazole derivatives
RU2039051C1 (ru)	1995-07-09	Производные триазолилгидразида и их фармацевтически пригодные соли
IE46605B1 (en)	1983-07-27	Benzimidazole-2-thiones useful as anthelmintics
SU1179927A3 (ru)	1985-09-15	Способ получени производных бензтриазола
GB2126225A (en)	1984-03-21	Benzamide derivatives
CS273338B2 (en)	1991-03-12	Method of carboxyl acid's derivative preparation
EP0116628B1 (en)	1989-01-18	1-acyl-3-pyridylmethylguanidines and their use as antihypertensive agents
DK153942B (da)	1988-09-26	Analogifremgangsmaade til fremstilling af cyclohexylpenylethylsulfonyl- eller -sulfinylderivater
FI62095B (fi)	1982-07-30	Foerfarande foer framstaellning av nya 1- och d1-6-(m-(isoxazol-3-karboxiamido)-fenyl)-2,3,5,6-tetrahydroimidazo(2,1-b)tiazolderivat vilka anvaends som maskmedel