DE2560633C2 - - Google Patents
Info
- Publication number
- DE2560633C2 DE2560633C2 DE2560633A DE2560633A DE2560633C2 DE 2560633 C2 DE2560633 C2 DE 2560633C2 DE 2560633 A DE2560633 A DE 2560633A DE 2560633 A DE2560633 A DE 2560633A DE 2560633 C2 DE2560633 C2 DE 2560633C2
- Authority
- DE
- Germany
- Prior art keywords
- pyridylcarbodiimide
- substituted
- pyridyl
- group
- room temperature
- Prior art date
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- 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
-
- 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
- C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
-
- 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
- C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Description
Die Erfindung betrifft N-substituierte N′-Pyridyl-carbodiimid-
Verbindungen der allgemeinen Formel:
bei der die R¹-substituierte Carbodiimidgruppe in 3- oder 4-
Stellung des Pyridinringes angeordnet ist und R¹ für eine verzweigte,
gesättigte aliphatische Kohlenwasserstoffgruppe mit
1 bis 8 C-Atomen, eine Phenyl-, Benzyl- oder Phenyläthylgruppe
steht, sowie deren Salze mit nicht-toxischen, pharmazeutisch
annehmbaren Säuren.
Insbesondere kann R¹ eine Isopropyl-, Isobutyl-, sek.Butyl-
oder tert.Butylgruppe oder eine der isomeren Pentylgruppen,
z. B. tert.Pentyl und Neopentyl, eine der isomeren Hexylgruppen,
wie 1-Methyl-1-äthylpropyl, oder der isomeren Heptylgruppen,
z. B. eine 1,1-Diäthylpropylgruppe, eine Phenyl-, Benzyl-
oder Phenyläthylgruppe bedeuten.
Wenn die erfindungsgemäßen Verbindungen ein oder mehrere
asymmetrische C-Atome enthalten, können sie Stereoisomere bilden.
Die vorliegende Erfindung umfaßt auch solche Stereoisomere
und racemische Mischungen derselben.
Ferner bezieht sich die Erfindung auch auf nicht-toxische,
pharmazeutisch annehmbare Salze der Verbindungen der allgemeinen
Formel I mit Säuren.
Die erfindungsgemäßen Verbindungen können durch Umsetzung
mit Cyanamid übergeführt werden in Verbindungen der allgemeinen
Formel
von der auch die tautomeren Formen umfaßt sein sollen und in
der die R¹-substituierte Cyanoguanidylgruppe in 3- oder
4-Stellung des Pyridinringes angeordnet ist und R¹
die oben angegebene Bedeutung hat.
Die aus den erfindungsgemäßen Verbindungen erhältlichen Cyanoguanidine
besitzen eine hypotensive Wirksamkeit, die
eine ausgeprägte Erniedrigung des Blutdruckes bewirkt. Sie
haben eine niedrige Toxizität und infolge dessen einen hohen
therapeutischen Index.
Die Erfindung wird an Hand des folgenden Beispiels näher erläutert.
12,6 g N-tert.Butyl-N′-3-pyridylthioharnstoff wurden bei 0°C
in 125 ml trockenem Tetrahydrofuran suspendiert. Unter kräftigem
Rühren wurden 69 ml einer 1,2 M Lösung von Phosgen in Toluol
zugesetzt. Die Mischung wurde 5 h auf einer Temperatur von 0°C
gehalten und dann im Vakuum eingedampft. Nach Zusatz einer kleinen
Menge Tetrahydrofuran wurde das Eindampfen wiederholt.
Der Rückstand wurde bei 0°C in 100 ml Tetrahydrofuran suspendiert
und mit 20,4 ml N,N-Diisopropyläthylamin versetzt. Die Aufschlämmung
wurde im Vakuum eingedampft und der Rückstand mit
200 ml Petroläther extrahiert, mit Holzkohle versetzt und filtriert.
Beim Eindampfen im Vakuum ergab das Filtrat das gewünschte
Carbodiimid in quantitativer Ausbeute. Das IR-Spektrum
(CHCl₃) zeigte eine charakteristische starke Absorptionsbande
bei 2120-2140 cm-1 (-N=C=N-).
NMR (10% CDCl₃; TMS: δ=0):
1,42, S, 9H; 7,15, M, 1H; 7,27, M 1H; 8,25, DD, 1H; 8,35, DD, 1H.
1,42, S, 9H; 7,15, M, 1H; 7,27, M 1H; 8,25, DD, 1H; 8,35, DD, 1H.
Auf ähnliche Weise wurden hergestellt:
N-(1-Äthyl-1-methylpropyl)-N′-3-pyridylcarbodiimid
N-(1,1-Dimethylbutyl)-N′-3-pyridylcarbodiimid
N-(1,1-Diäthylpropyl)-N′-3-pyridylcarbodiimid
N-tert.Pentyl-N′-3-pyridylcarbodiimid
N-Neopentyl-N′-3-pyridylcarbodiimid
N-Isopropyl-N′-3-pyridylcarbodiimid
N-1-Äthylpropyl-N′-3-pyridylcarbodiimid
N-sek.Butyl-N′-3-pyridylcarbodiimid
N-3-Pyridyl-N′-1,1,2-trimethylpropylcarbodiimid
N-3-Pyridyl-N′-1,2,2-trimethylpropylcarbodiimid
N-3-Pyridyl-N′-1,1,3-trimethylcarbodiimid
N-3-Pyridyl-N′-1,1,3,3-tetramethylbutylcarbodiimid
N-1,3-Dimethylbutyl-N′-3-pyridylcarbodiimid
N-Phenyl-N′-3-pyridylcarbodiimid
N-tert.Butyl-N′-4-pyridylcarbodiimid
N-tert.Pentyl-N′-4-pyridylcarbodiimid
N-1-Äthylpropyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,2,2-trimethylpropylcarbodiimid
N-(1-Äthyl-1-methylpropyl)-N′-3-pyridylcarbodiimid
N-(1,1-Dimethylbutyl)-N′-3-pyridylcarbodiimid
N-(1,1-Diäthylpropyl)-N′-3-pyridylcarbodiimid
N-tert.Pentyl-N′-3-pyridylcarbodiimid
N-Neopentyl-N′-3-pyridylcarbodiimid
N-Isopropyl-N′-3-pyridylcarbodiimid
N-1-Äthylpropyl-N′-3-pyridylcarbodiimid
N-sek.Butyl-N′-3-pyridylcarbodiimid
N-3-Pyridyl-N′-1,1,2-trimethylpropylcarbodiimid
N-3-Pyridyl-N′-1,2,2-trimethylpropylcarbodiimid
N-3-Pyridyl-N′-1,1,3-trimethylcarbodiimid
N-3-Pyridyl-N′-1,1,3,3-tetramethylbutylcarbodiimid
N-1,3-Dimethylbutyl-N′-3-pyridylcarbodiimid
N-Phenyl-N′-3-pyridylcarbodiimid
N-tert.Butyl-N′-4-pyridylcarbodiimid
N-tert.Pentyl-N′-4-pyridylcarbodiimid
N-1-Äthylpropyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,2,2-trimethylpropylcarbodiimid
NMR (10% CDCl₃; TMS: δ=0):
0,98, S, 9H; 1,33, D, J=7Hz, 3H; 3,52, Q, J=7Hz, 1H; 6,33, M, 2H; 8,45, M, 2H
0,98, S, 9H; 1,33, D, J=7Hz, 3H; 3,52, Q, J=7Hz, 1H; 6,33, M, 2H; 8,45, M, 2H
N-4-Pyridyl-N′-1,1,3-trimethylbutylcarbodiimid
N-1,1-Diäthylpropyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,1,3,3-tetramethylbutylcarbodiimid
N-1,5-Dimethylhexyl-N′-4-pyridylcarbodiimid
N-Neopentyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,1,2-trimethylpropylcarbodiimid
N-Benzyl-N′-4-pyridylcarbodiimid
N-1,1-Diäthylpropyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,1,3,3-tetramethylbutylcarbodiimid
N-1,5-Dimethylhexyl-N′-4-pyridylcarbodiimid
N-Neopentyl-N′-4-pyridylcarbodiimid
N-4-Pyridyl-N′-1,1,2-trimethylpropylcarbodiimid
N-Benzyl-N′-4-pyridylcarbodiimid
Claims (2)
1. N-substituierte N′-Pyridyl-carbodiimide der allgemeinen
Formel
in welcher die R¹-substituierte Carbodiimidgruppe in 3- oder
4-Stellung des Pyridinringes angeordnet ist und R¹ für eine
verzweigte, gesättigte, aliphatische Kohlenwasserstoffgruppe
mit bis zu 8 C-Atomen, eine Phenyl-, Benzyl- und Phenyläthylgruppe
steht sowie deren Salze mit nicht-toxischen, pharmazeutisch
annehmbaren Säuren.
2. Verwendung der Verbindungen nach Anspruch 1 zur Herstellung
von N-substituierten N′-Cyano-N′-pyridylguanidinen der
Formel
und deren tautomeren Formen II, in der R¹ wie oben definiert
ist, durch Umsetzung mit Cyanamid bei Raumtemperatur oder etwa
Raumtemperatur, gegebenenfalls unter Verwendung üblicher Lösungsmittel,
und gewünschtenfalls unter Zusatz von basischen
Katalysatoren, wie einem tertiaren Amin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB55209/74A GB1489879A (en) | 1974-12-20 | 1974-12-20 | N'-cyano-n'-3-pyridylguanidines |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2560633C2 true DE2560633C2 (de) | 1988-09-08 |
Family
ID=10473276
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752557438 Granted DE2557438A1 (de) | 1974-12-20 | 1975-12-19 | N-substituierte n"cyano-n'pyridylguanidin-verbindungen |
DE2560633A Expired DE2560633C2 (de) | 1974-12-20 | 1975-12-19 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752557438 Granted DE2557438A1 (de) | 1974-12-20 | 1975-12-19 | N-substituierte n"cyano-n'pyridylguanidin-verbindungen |
Country Status (22)
Country | Link |
---|---|
US (2) | US4057636A (de) |
JP (1) | JPS6028819B2 (de) |
AT (1) | AT346357B (de) |
BE (1) | BE836885A (de) |
CA (1) | CA1067083A (de) |
CH (1) | CH618429A5 (de) |
DD (1) | DD122529A5 (de) |
DE (2) | DE2557438A1 (de) |
DK (1) | DK145341C (de) |
ES (1) | ES443725A1 (de) |
FI (1) | FI60560C (de) |
FR (1) | FR2294703A1 (de) |
GB (1) | GB1489879A (de) |
IE (1) | IE42141B1 (de) |
IT (1) | IT1062213B (de) |
LU (1) | LU74071A1 (de) |
NL (1) | NL184109C (de) |
PH (1) | PH12506A (de) |
SE (1) | SE424637B (de) |
SU (1) | SU683615A3 (de) |
YU (1) | YU39754B (de) |
ZA (1) | ZA757481B (de) |
Families Citing this family (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5562066A (en) * | 1978-11-03 | 1980-05-10 | Toshihiko Okamoto | N-(2-substituted-4-pyridyl)-urea and thio urea, their preparation and plant growth regulator |
US4490533A (en) * | 1980-12-22 | 1984-12-25 | Merck & Co., Inc. | Aminoalkyl pyridine derivatives |
IE52935B1 (en) * | 1981-04-15 | 1988-04-13 | Leo Pharm Prod Ltd | Pharmaceutical preparation |
IE54196B1 (en) * | 1981-09-10 | 1989-07-19 | Leo Pharm Prod Ltd | Chemical compounds |
DK58983D0 (da) * | 1983-02-11 | 1983-02-11 | Leo Pharm Prod Ltd | Farmaceutisk praeparat |
JPS604120A (ja) * | 1983-06-22 | 1985-01-10 | Shionogi & Co Ltd | 作用持続型ピナシジル製剤 |
US4617311A (en) * | 1985-05-17 | 1986-10-14 | Eli Lilly And Company | Antiasthmatic method |
EP0579260A1 (de) * | 1987-07-07 | 1994-01-19 | Beecham Group Plc | Verwendung eines Vasodilators zur Behandlung von pulmonalem Bluthochdruck und/oder Rechtsherzversagen relatierten Krankheiten |
GB8800199D0 (en) * | 1988-01-06 | 1988-02-10 | Beecham Group Plc | Pharmaceutical preparation |
US5244664A (en) * | 1988-01-21 | 1993-09-14 | Leo Pharmaceutical Products Ltd. | Topical preparation for treatment of alopecia |
GB8801318D0 (en) * | 1988-01-21 | 1988-02-17 | Leo Pharm Prod Ltd | Pharmaceutical preparations |
WO1989010757A1 (en) * | 1988-05-10 | 1989-11-16 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemis | New ophthalmic preparation for treating glaucoma |
US5278169A (en) * | 1988-08-09 | 1994-01-11 | E. R. Squibb & Sons, Inc. | Method of treating or prevention of fibrillation of the heart |
NZ229828A (en) * | 1988-08-09 | 1992-03-26 | Squibb & Sons Inc | Aryl cyanoguanidine derivatives and pharmaceutical compositions |
US5011837A (en) * | 1988-08-09 | 1991-04-30 | E. R. Squibb & Sons, Inc. | Aryl cyanoguanidines: potassium channel activators and method of making same |
JP2884412B2 (ja) * | 1988-10-21 | 1999-04-19 | 日本バイエルアグロケム株式会社 | 殺虫性シアノ化合物 |
US5264445A (en) * | 1989-02-03 | 1993-11-23 | Eli Lilly And Company | (-)-N"-cyano-N-3-pyridyl-N'-1,2,2-trimethylpropylguanidine |
KR100220989B1 (ko) * | 1989-02-03 | 1999-09-15 | 피터 지. 스트링거 | 구아니딘 유도체 및 이를 함유하는 약제학적 조성물 |
EP0407346A3 (en) * | 1989-07-07 | 1991-10-02 | Ciba-Geigy Ag | Aminopyridines |
US5006523A (en) * | 1989-10-26 | 1991-04-09 | E. R. Squibb & Sons, Inc. | Antiarrhythmic agents: aryl cyanoguanidine potassium channel blockers |
US5217982A (en) * | 1990-09-25 | 1993-06-08 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive properties |
US5371086A (en) * | 1991-03-15 | 1994-12-06 | The Green Cross Corporation | Aminopyridine compounds |
JPH05294935A (ja) * | 1991-03-15 | 1993-11-09 | Green Cross Corp:The | アミノピリジン系化合物 |
FR2677019B1 (fr) * | 1991-05-27 | 1994-11-25 | Pf Medicament | Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique. |
US5593993A (en) * | 1991-08-02 | 1997-01-14 | Medivir Ab | Method for inhibition of HIV related viruses |
IL102548A (en) * | 1991-08-02 | 1998-08-16 | Medivir Ab | Use of painting derivatives in the preparation of drugs for VIH inhibition and treatment of SDIA and new compounds |
WO1993012788A1 (en) * | 1991-12-23 | 1993-07-08 | The Upjohn Company | Pyridylguanidine compounds for treatment of erectile dysfunction |
US5262419A (en) * | 1992-06-11 | 1993-11-16 | E. R. Squibb & Sons, Inc. | Method for the prophylaxis and/or treatment of ulcerative gastrointestinal conditions using a potassium channel activator |
WO1994004499A1 (en) * | 1992-08-13 | 1994-03-03 | The Upjohn Company | Cyanoguanidines as potassium channel blockers |
GB9219472D0 (en) * | 1992-09-15 | 1992-10-28 | Leo Pharm Prod Ltd | Chemical compounds |
JPH06228100A (ja) * | 1992-12-07 | 1994-08-16 | Green Cross Corp:The | 光学活性アミノピリジン誘導体およびその用途 |
JPH08511264A (ja) * | 1993-06-11 | 1996-11-26 | ジ・アップジョン・カンパニー | K−チャンネル遮断剤としてのピリミジン,シアノグアニジン |
US5547966A (en) * | 1993-10-07 | 1996-08-20 | Bristol-Myers Squibb Company | Aryl urea and related compounds |
US5633374A (en) * | 1993-11-26 | 1997-05-27 | The Upjohn Company | Pyrimidine, cyanoguanidines as K-channel blockers |
AU1556695A (en) * | 1994-01-28 | 1995-08-15 | Pharmacia & Upjohn Company | Cyanoguanidines as k-channel blockers |
US5525742A (en) * | 1994-06-10 | 1996-06-11 | The Upjohn Company | Azidophenylcyanoguanidines as photoaffinity probes |
US5856449A (en) * | 1994-11-17 | 1999-01-05 | Pharmacia & Upjohn Company | Protein affecting KATP channels |
JP2000516621A (ja) * | 1996-08-15 | 2000-12-12 | スミスクライン・ビーチャム・コーポレイション | Il―8レセプターアンタゴニスト |
US5972894A (en) * | 1997-08-07 | 1999-10-26 | Cytran, Inc. | Peptides having potassium channel opener activity |
US6458835B2 (en) | 1997-08-13 | 2002-10-01 | Bristol-Myers Squibb Company | Method of inhibiting or treating chemotherapy-induced hair loss |
US6013668A (en) * | 1997-08-13 | 2000-01-11 | Bristol-Myers Squibb Company | Enantiomers of 4-[[(cyanoimino) [(1,2,2-trimethylpropyl) amino]methyl]amino]benzonitrile |
AU9211098A (en) * | 1997-09-03 | 1999-03-22 | American Home Products Corporation | Thiourea for increasing hdl-cholesterol levels, which are useful as anti-atherosclerotic agents |
AU4080300A (en) | 1999-04-09 | 2000-11-14 | Shionogi Bioresearch Corp. | Cyanoguanidine compounds |
GB9908410D0 (en) | 1999-04-13 | 1999-06-09 | Pfizer Ltd | Pyridines |
AU4841700A (en) * | 1999-05-12 | 2000-11-21 | Nitromed, Inc. | Nitrosated and nitrosylated potassium channel activators, compositions and methods of use |
US6645968B2 (en) | 1999-08-03 | 2003-11-11 | Abbott Laboratories | Potassium channel openers |
CN1705645A (zh) * | 2002-10-24 | 2005-12-07 | 默克专利有限公司 | 作为raf-激酶抑制剂的亚甲基脲衍生物 |
WO2007022964A2 (de) * | 2005-08-24 | 2007-03-01 | Abbott Gmbh & Co. Kg | Hetaryl substituierte guanidinverbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
US20070250567A1 (en) * | 2006-04-20 | 2007-10-25 | Graham Philip R | System and method for controlling a telepresence system |
US20110009446A1 (en) * | 2008-01-11 | 2011-01-13 | Nektar Therapeutics | Oligomer-guanidine class conjugates |
AU2011340037B2 (en) * | 2010-12-09 | 2016-03-17 | Tisbury Pharmaceuticals, Inc. | Multifunctional nitroxide derivatives and uses thereof |
WO2021044413A1 (en) * | 2019-09-03 | 2021-03-11 | Salzman Group Ltd. | Atp-regulated potassium channel openers comprising guanidine and uses thereof |
WO2023176554A1 (ja) * | 2022-03-14 | 2023-09-21 | 国立大学法人東北大学 | 認知機能改善剤 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036083A (en) * | 1959-05-15 | 1962-05-22 | Ciba Geigy Corp | Certain 2-pyridyl lower alkyl guanidines |
GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
-
1974
- 1974-12-20 GB GB55209/74A patent/GB1489879A/en not_active Expired
-
1975
- 1975-11-24 IE IE2554/75A patent/IE42141B1/en unknown
- 1975-11-27 ZA ZA7481A patent/ZA757481B/xx unknown
- 1975-12-01 US US05/636,747 patent/US4057636A/en not_active Expired - Lifetime
- 1975-12-09 CA CA241,325A patent/CA1067083A/en not_active Expired
- 1975-12-10 AT AT936075A patent/AT346357B/de not_active IP Right Cessation
- 1975-12-12 FI FI753520A patent/FI60560C/fi not_active IP Right Cessation
- 1975-12-12 PH PH17861A patent/PH12506A/en unknown
- 1975-12-15 SE SE7514153A patent/SE424637B/xx not_active IP Right Cessation
- 1975-12-15 FR FR7538285A patent/FR2294703A1/fr active Granted
- 1975-12-15 YU YU3162/75A patent/YU39754B/xx unknown
- 1975-12-17 DK DK572975A patent/DK145341C/da not_active IP Right Cessation
- 1975-12-18 DD DD190290A patent/DD122529A5/xx unknown
- 1975-12-18 CH CH1644375A patent/CH618429A5/de not_active IP Right Cessation
- 1975-12-19 DE DE19752557438 patent/DE2557438A1/de active Granted
- 1975-12-19 LU LU74071A patent/LU74071A1/xx unknown
- 1975-12-19 BE BE162952A patent/BE836885A/xx not_active IP Right Cessation
- 1975-12-19 IT IT70152/75A patent/IT1062213B/it active
- 1975-12-19 ES ES443725A patent/ES443725A1/es not_active Expired
- 1975-12-19 NL NLAANVRAGE7514852,A patent/NL184109C/xx not_active IP Right Cessation
- 1975-12-19 JP JP50150732A patent/JPS6028819B2/ja not_active Expired
- 1975-12-19 SU SU752198560A patent/SU683615A3/ru active
- 1975-12-19 DE DE2560633A patent/DE2560633C2/de not_active Expired
-
1981
- 1981-10-22 US US06/314,023 patent/USRE31244E/en not_active Expired - Lifetime
Non-Patent Citations (2)
Title |
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J. Med. Chem. 11, 811, 1968 * |
J.Med.Chem.21, S. 773 (1978), (gutachtlich genannt) * |
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