NO802069L - Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazopyridiner. - Google Patents

Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazopyridiner.

Info

Publication number: NO802069L
Authority: NO; Norway
Prior art keywords: ethoxy; pyridine; methoxyphenyl; imidazo; carbon atoms
Prior art date: 1979-07-11

Application number

NO802069A

Other languages

English (en)

Norwegian (no)

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

1980-07-10

Publication date

1981-01-12

1980-07-10 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1981-01-12 Publication of NO802069L publication Critical patent/NO802069L/no

Links

238000000034 method Methods 0.000 title claims 6
150000005232 imidazopyridines Chemical class 0.000 title 1
230000001225 therapeutic effect Effects 0.000 title 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 61
-1 phenylsulfinyl group Chemical group 0.000 claims description 44
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 7
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
235000005985 organic acids Nutrition 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
150000003222 pyridines Chemical class 0.000 claims 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 claims description 3
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 claims description 3
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 claims description 3
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
230000008018 melting Effects 0.000 description 10
238000002844 melting Methods 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
229960000583 acetic acid Drugs 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
230000009090 positive inotropic effect Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
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
230000000144 pharmacologic effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000282326 Felis catus Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
229940093915 gynecological organic acid Drugs 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 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
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
230000001965 increasing effect Effects 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
239000002904 solvent 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
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
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
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
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 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
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
LYCOMKLHJHRKSY-UHFFFAOYSA-N 2-[4-methoxy-2-[2-(4-nitrophenyl)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([N+]([O-])=O)C=C1 LYCOMKLHJHRKSY-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
206010007556 Cardiac failure acute Diseases 0.000 description 1
206010007559 Cardiac failure congestive Diseases 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
241001465754 Metazoa Species 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
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 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
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000036772 blood pressure 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
210000005242 cardiac chamber Anatomy 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
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 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
238000010438 heat treatment Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 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
238000005259 measurement Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository 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

Landscapes

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

NO802069A 1979-07-11 1980-07-10 Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazopyridiner. NO802069L (no)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
NO802069L true NO802069L (no)	1981-01-12

Family

ID=6075441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO802069A NO802069L (no)	1979-07-11	1980-07-10	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazopyridiner.

Country Status (17)

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

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
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"
EP0072926B1 (de) *	1981-08-19	1986-09-24	MERCK PATENT GmbH	2-Aryl-imidazopyridine
ES517193A0 (es) *	1981-11-10	1983-12-01	Wellcome Found	Un procedimiento para la preparacion de nuevos derivados de imidazo (4,5-c)piridina.
US4758574A (en) *	1982-05-03	1988-07-19	Eli Lilly And Company	2-phenylimidazio (4,5-c) pyridines
US4904785A (en) *	1982-05-03	1990-02-27	Eli Lilly And Company	2-phenylimidazo[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
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
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1979
- 1979-07-11 DE DE19792927987 patent/DE2927987A1/de not_active Withdrawn
1980
- 1980-06-26 DE DE8080103613T patent/DE3060551D1/de not_active Expired
- 1980-06-26 AT AT80103613T patent/ATE1194T1/de not_active IP Right Cessation
- 1980-06-26 EP EP80103613A patent/EP0022495B1/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 PT PT71525A patent/PT71525B/pt unknown
- 1980-07-09 IL IL60532A patent/IL60532A/xx unknown
- 1980-07-09 FI FI802203A patent/FI67218C/fi not_active IP Right Cessation
- 1980-07-10 CA CA000355892A patent/CA1146555A/en not_active Expired
- 1980-07-10 ES ES493275A patent/ES493275A0/es active Granted
- 1980-07-10 NZ NZ194303A patent/NZ194303A/xx unknown
- 1980-07-10 AU AU60308/80A patent/AU537819B2/en not_active Ceased
- 1980-07-10 ZA ZA00804146A patent/ZA804146B/xx unknown
- 1980-07-10 NO NO802069A patent/NO802069L/no unknown

Also Published As

Publication number	Publication date
IL60532A0 (en)	1980-09-16
EP0022495B1 (de)	1982-06-16
FI67218B (fi)	1984-10-31
DE3060551D1 (en)	1982-08-05
PH17337A (en)	1984-08-01
JPS5625179A (en)	1981-03-10
DK295880A (da)	1981-01-12
ATE1194T1 (de)	1982-07-15
ES8106904A1 (es)	1981-09-01
US4327100A (en)	1982-04-27
PT71525A (de)	1980-08-01
DE2927987A1 (de)	1981-02-05
IL60532A (en)	1983-07-31
AU537819B2 (en)	1984-07-12
FI802203A (fi)	1981-01-12
CA1146555A (en)	1983-05-17
GR69622B (xx)	1982-07-06
ES493275A0 (es)	1981-09-01
FI67218C (fi)	1985-02-11
ZA804146B (en)	1982-03-31
AU6030880A (en)	1981-01-15
EP0022495A1 (de)	1981-01-21
NZ194303A (en)	1982-05-31
PT71525B (de)	1981-12-11

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NO862477L (no)	1986-12-22	Analogifremgangsmaate for fremstilling av terapeutisk aktive 2-arylimidazol-derivater.
NO814239L (no)	1982-06-14	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrimidinon-derivater
EP0263352A1 (de)	1988-04-13	Neue Imidazo-benzoxazinone, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel
NO842684L (no)	1985-01-07	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazol-derivater
IE47139B1 (en)	1983-12-28	4-substituted-pyrazoles
US5635511A (en)	1997-06-03	Treatment of heart rhythm disorders by administration of 3-phenylsulfonyl-3,7-diazabicyclo[3.3.1]nonane compounds.
HU193073B (en)	1987-08-28	Process for producing new benzimidazoles
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US4055650A (en)	1977-10-25	Certain 4-phenoxy(or phenylthio)-3-n-acylated-sulfonamido-pyridines
SE455701B (sv)	1988-08-01	Svavelhaltiga isokinolinderivat samt farmaceutiska beredningar innehalllande dem
HU193072B (en)	1987-08-28	Process for preparing new 2-phenyl-imidazo/4,5-c/pyridinone derivatives
US4596830A (en)	1986-06-24	Novel derivatives of 2-(2-thienyl)-imidazo[4,5-b]-pyridines and their pharmaceutically acceptable salts
SU1331430A3 (ru)	1987-08-15	Способ получени карбостирильных соединений или их фармацевтически приемлемых солей
KR840000323B1 (ko)	1984-03-19	2-알콕시페닐-이미다조[4,5-b] 피리딘의 제조방법
NO844371L (no)	1985-05-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive purinderivater
JPS59104378A (ja)	1984-06-16	カルボスチリル誘導体
CS231491A3 (en)	1992-02-19	Process for preparing 6-(3-substituted amino)propionyl)-7-deacetyl forskolin derivatives
JPS62226982A (ja)	1987-10-05	２−ピペリジノアミノ置換ピリミドピリミジン誘導体
CS228544B2 (cs)	1984-05-14	Způsob výroby nových chinolonů
MXPA95000679A (en)	1998-10-15	New drugs containing compounds of 3-phenilsulfonil-3,7-diazabiciclo (3,3,1) non