DD298781A5 - Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden - Google Patents

Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden Download PDF

Info

Publication number: DD298781A5
Authority: DD; German Democratic Republic
Prior art keywords: cyano; bipyridine; formula; oxides; acid
Prior art date: 1990-03-09

Application number

DD90338543A

Other languages

German (de)

English (en)

Inventor

Erhard Klauschenz

Volker Hagen

Angela Hagen

Peter Muschick

Brigitte Schlegel

Sabine Heer

Gottfried Faust

Hans-Joachim Jaensch

Original Assignee

Inst Wirkstofforschung

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.)

1990-03-09

Filing date

1990-03-09

Publication date

1992-03-12

1990-03-09 Application filed by Inst Wirkstofforschung filed Critical Inst Wirkstofforschung

1990-03-09 Priority to DD90338543A priority Critical patent/DD298781A5/de

1991-02-13 Priority to EP91101972A priority patent/EP0445552A1/fr

1991-03-07 Priority to US07/665,682 priority patent/US5162533A/en

1991-03-07 Priority to UA4894774A priority patent/UA18260A1/uk

1991-03-07 Priority to SU914894774A priority patent/RU2015968C1/ru

1991-03-07 Priority to PL28933491A priority patent/PL289334A1/xx

1991-03-08 Priority to HU91764A priority patent/HUT58055A/hu

1991-03-08 Priority to JP3069280A priority patent/JPH06287178A/ja

1992-03-12 Publication of DD298781A5 publication Critical patent/DD298781A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims abstract description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 10
239000002904 solvent Substances 0.000 claims abstract description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 6
229960000583 acetic acid Drugs 0.000 claims abstract description 6
150000001298 alcohols Chemical class 0.000 claims abstract description 5
229910021529 ammonia Inorganic materials 0.000 claims abstract description 5
239000002585 base Substances 0.000 claims abstract description 5
239000012362 glacial acetic acid Substances 0.000 claims abstract description 5
150000004965 peroxy acids Chemical class 0.000 claims abstract description 5
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
150000001340 alkali metals Chemical class 0.000 claims abstract description 4
150000001412 amines Chemical class 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
-1 amino, substituted amino, morpholino Chemical group 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
QLJNHAQMRLVCLS-UHFFFAOYSA-N 2-chloro-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carbonitrile Chemical class C1=C[N+]([O-])=CC=C1C1=CN=C(Cl)C(C#N)=C1 QLJNHAQMRLVCLS-UHFFFAOYSA-N 0.000 claims description 11
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 8
QLANKOLWRZJCIO-UHFFFAOYSA-N 5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carbonitrile Chemical class C1=C[N+]([O-])=CC=C1C1=CN=CC(C#N)=C1 QLANKOLWRZJCIO-UHFFFAOYSA-N 0.000 claims description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 4
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 3
MKAWYORPNLOIRQ-UHFFFAOYSA-N 5-pyridin-4-ylpyridine-3-carbonitrile Chemical class N#CC1=CN=CC(C=2C=CN=CC=2)=C1 MKAWYORPNLOIRQ-UHFFFAOYSA-N 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 claims description 2
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
PZRHRDRVRGEVNW-UHFFFAOYSA-N milrinone Chemical compound N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C PZRHRDRVRGEVNW-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical class N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 6
229960003574 milrinone Drugs 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
229960002105 amrinone Drugs 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
230000003177 cardiotonic effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
WNXSIPLQLUDQDP-UHFFFAOYSA-N 2-morpholin-4-yl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound N#CC1=CC(C=2C=CN=CC=2)=CN=C1N1CCOCC1 WNXSIPLQLUDQDP-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
230000003182 bronchodilatating effect Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000009090 positive inotropic effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000000304 vasodilatating effect Effects 0.000 description 3
IKYMHZPIRGEEDR-UHFFFAOYSA-N 1-oxido-4-pyridin-3-ylpyridin-1-ium Chemical class C1=C[N+]([O-])=CC=C1C1=CC=CN=C1 IKYMHZPIRGEEDR-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
BLNLFSSXWDYPFM-UHFFFAOYSA-N 2-morpholin-4-yl-5-(1-oxidopyridin-1-ium-4-yl)pyridine-3-carbonitrile Chemical compound C1=C[N+]([O-])=CC=C1C(C=C1C#N)=CN=C1N1CCOCC1 BLNLFSSXWDYPFM-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000496 cardiotonic agent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
244000309715 mini pig Species 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
230000036581 peripheral resistance Effects 0.000 description 2
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
ZWFBXDBTHLCSDZ-UHFFFAOYSA-N 2-(2-methoxyethoxy)-6-methyl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OCCOC)=NC(C)=C1C1=CC=NC=C1 ZWFBXDBTHLCSDZ-UHFFFAOYSA-N 0.000 description 1
WGODGFXCRIJNLS-UHFFFAOYSA-N 2-amino-6-methyl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound CC1=NC(N)=C(C#N)C=C1C1=CC=NC=C1 WGODGFXCRIJNLS-UHFFFAOYSA-N 0.000 description 1
YYWUUBRRAZTHJK-UHFFFAOYSA-N 2-chloro-5-pyridin-4-ylpyridine-3-carbonitrile Chemical class C1=C(C#N)C(Cl)=NC=C1C1=CC=NC=C1 YYWUUBRRAZTHJK-UHFFFAOYSA-N 0.000 description 1
PIEIWWPKRZUYEM-UHFFFAOYSA-N 2-chloro-6-ethyl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound CCC1=NC(Cl)=C(C#N)C=C1C1=CC=NC=C1 PIEIWWPKRZUYEM-UHFFFAOYSA-N 0.000 description 1
GIBXLQVADBWCND-UHFFFAOYSA-N 2-chloro-6-methyl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound CC1=NC(Cl)=C(C#N)C=C1C1=CC=NC=C1 GIBXLQVADBWCND-UHFFFAOYSA-N 0.000 description 1
MMZSNTSSFJXCHR-UHFFFAOYSA-N 2-methoxy-6-methyl-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC(C)=C1C1=CC=NC=C1 MMZSNTSSFJXCHR-UHFFFAOYSA-N 0.000 description 1
RMHQDKYZXJVCME-UHFFFAOYSA-N 2-pyridin-4-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=NC=C1 RMHQDKYZXJVCME-UHFFFAOYSA-N 0.000 description 1
YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical compound C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000035487 diastolic blood pressure Effects 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
JFJZZMVDLULRGK-URLMMPGGSA-O tubocurarine Chemical compound C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CCN3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 JFJZZMVDLULRGK-URLMMPGGSA-O 0.000 description 1
229960001844 tubocurarine Drugs 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- 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
- A61P9/08—Vasodilators for multiple indications

Landscapes

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

DD90338543A 1990-03-09 1990-03-09 Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden DD298781A5 (de)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
DD90338543A DD298781A5 (de)	1990-03-09	1990-03-09	Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden
EP91101972A EP0445552A1 (fr)	1990-03-09	1991-02-13	Cyano-3 bipyridine-5,4' oxydes-1', procédés pour leur préparation et leur application pharmaceutique
US07/665,682 US5162533A (en)	1990-03-09	1991-03-07	3-cyano-5,4'-bipyridine-1'-oxide compounds and pharmaceutical compositions and methods containing the same
UA4894774A UA18260A1 (uk)	1990-03-09	1991-03-07	3-ціаh-5,4'-біпіридіh-1'-оксиди та їх фізіологічhо сумісhі солі приєдhаhhя кислот, які мають кардіотоhічhу та судиhорозширювальhу активhість
SU914894774A RU2015968C1 (ru)	1990-03-09	1991-03-07	3-циан-5,4`-бипиридин-1`-оксиды и их физиологически совместимые соли присоединения кислот, обладающие кардиотонической и сосудорасширяющей активностью
PL28933491A PL289334A1 (en)	1990-03-09	1991-03-07	Method of obtaining novel 3-cyano-5,4'-bipyridine 1'-oxides
HU91764A HUT58055A (en)	1990-03-09	1991-03-08	Process for producing 3-cyano-5,4'-bipyridine-1'-oxide derivatives and pharmaceutical compositions compirising same
JP3069280A JPH06287178A (ja)	1990-03-09	1991-03-08	３‐シアン‐５，４´‐ビピリジン‐１´‐オキシド、その製造方法および製薬としての使用

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD90338543A DD298781A5 (de)	1990-03-09	1990-03-09	Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden

Publications (1)

Publication Number	Publication Date
DD298781A5 true DD298781A5 (de)	1992-03-12

Family

ID=5616952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90338543A DD298781A5 (de)	1990-03-09	1990-03-09	Verfahren zur herstellung von 5,4'-bipyridin-1'-oxiden

Country Status (8)

Country	Link
US (1)	US5162533A (fr)
EP (1)	EP0445552A1 (fr)
JP (1)	JPH06287178A (fr)
DD (1)	DD298781A5 (fr)
HU (1)	HUT58055A (fr)
PL (1)	PL289334A1 (fr)
RU (1)	RU2015968C1 (fr)
UA (1)	UA18260A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2323928C1 (ru) *	2006-09-12	2008-05-10	Некоммерческая организация Учреждение Институт проблем химической физики Российской академии наук (статус государственного учреждения) (ИПХФ РАН)	Производные бис-(4-алкиламинопиридиний-1)алканов, способ их получения (варианты) и применение их в качестве веществ, проявляющих антибактериальную и антивирусную активность
RU2332402C1 (ru) *	2006-12-12	2008-08-27	Некоммерческая организация Учреждение Институт проблем химической физики Российской академии наук (статус государственного учреждения) (ИПХФ РАН)	Способ получения бис(4-алкиламинопиридиний-1)алканов

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1542605A (en) *	1977-02-22	1979-03-21	Bristol Myers Co	4-tertiary-amino-2,6-diaminopyridine-1-oxides
IL61537A0 (en) *	1979-12-03	1980-12-31	Sterling Drug Inc	Bipyridyl derivatives,their preparation and pharmaceutical compositions containing them
US4264603A (en) *	1980-03-17	1981-04-28	Sterling Drug Inc.	5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridine-3-amines, their use as cardiotonics and their preparation
US4362734A (en) *	1981-08-26	1982-12-07	Sterling Drug Inc.	2-(Substituted-amino)-5-(pyridinyl-nicotinonitriles, and their cardiotonic use
US4463008A (en) *	1982-11-10	1984-07-31	Sterling Drug Inc.	2-Alkoxy-5-(pyridinyl)pyridines and cardiotonic use thereof
DD263758A1 (de) *	1986-04-01	1989-01-11	Akad Wissenschaften Ddr	Verfahren zur herstellung von 2-amino-5-(pyrid-4-yl)-nicotinsaeure-derivate und ihre n-oxide

1990
- 1990-03-09 DD DD90338543A patent/DD298781A5/de not_active IP Right Cessation
1991
- 1991-02-13 EP EP91101972A patent/EP0445552A1/fr not_active Withdrawn
- 1991-03-07 RU SU914894774A patent/RU2015968C1/ru active
- 1991-03-07 PL PL28933491A patent/PL289334A1/xx unknown
- 1991-03-07 US US07/665,682 patent/US5162533A/en not_active Expired - Fee Related
- 1991-03-07 UA UA4894774A patent/UA18260A1/uk unknown
- 1991-03-08 HU HU91764A patent/HUT58055A/hu unknown
- 1991-03-08 JP JP3069280A patent/JPH06287178A/ja active Pending

Also Published As

Publication number	Publication date
PL289334A1 (en)	1992-05-04
RU2015968C1 (ru)	1994-07-15
JPH06287178A (ja)	1994-10-11
EP0445552A1 (fr)	1991-09-11
HU910764D0 (en)	1991-09-30
US5162533A (en)	1992-11-10
HUT58055A (en)	1992-01-28
UA18260A1 (uk)	1997-12-25

Legal Events

Date	Code	Title
1994-03-31	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
1994-04-14	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
2000-08-17	ENJ	Ceased due to non-payment of renewal fee

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