DE3740383A1 - Brenzkatechin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe - Google Patents
Brenzkatechin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffeInfo
- Publication number
- DE3740383A1 DE3740383A1 DE19873740383 DE3740383A DE3740383A1 DE 3740383 A1 DE3740383 A1 DE 3740383A1 DE 19873740383 DE19873740383 DE 19873740383 DE 3740383 A DE3740383 A DE 3740383A DE 3740383 A1 DE3740383 A1 DE 3740383A1
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- Germany
- Prior art keywords
- group
- general formula
- compound
- radical
- dihydroxy
- Prior art date
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
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- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
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- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Description
- a) Verbindungen der allgemeinen Formel I, in denen die Reste R₁ und R₂ unabhängig voneinander Wasserstoffatome, C1-4-Alkylreste, gegebenenfalls mit 1-3 C1-4-Alkylresten substituierte Phenylgruppen, Benzylgruppen, gegebenenfalls durch eine C1-4-Alkoxycarbonylgruppe substituierte C1-4-Acylreste oder gegebenenfalls durch ein oder zwei C1-4-Alkylreste substituierte Benzoylgruppen bedeuten;
- b) Verbindungen der allgemeinen Formel I, in denen R₂ ein Wasserstoffatom bedeutet und R₁ einen C1-4-Alkylrest, einen C1-18-Acylrest, eine Benzoylgruppe, eine durch ein oder zwei C1-4-Alkylreste, C1-4-Alkoxyreste oder eine gegebenenfalls durch einen C1-4-Alkylrest substituierte Cyclohexylgruppe substituierte Benzoylgruppe, eine Pivaloylgruppe oder eine Äthoxycarbonylmethylcarbamoyloxygruppe darstellt;
- c) Verbindungen der allgemeinen Formel I, in denen R₁ und R₂ zusammengenommen einen C1-4-Alkylenrest, insbesondere die Methylengruppe, oder eine Cyclohexylidengruppe bedeutet;
- d) Stärker bevorzugt sind die Verbindungen der allgemeinen Formel I, in denen R₁ und R₂ beide Wasserstoffatome, Methyl-, Acetyl-, Propionyl-, Butyryl-, Benzoyl- oder 2,6-Dimethylbenzoylgruppen bedeuten.
- e) Besonders bevorzugt sind die Verbindungen der allgemeinen Formel I, in denen R₁ und R₂ beide Wasserstoffatome sind.
- f) Bevorzugt sind Verbindungen der allgemeinen Formel I, in denen X eine Nitro-, Chlor-, Cyano-, Trifluormethyl-, Methylsulfonyl- oder Sulfonamidogruppe in 5- oder 6-Stellung (gezählt von R₃ in 1-Stellung) bedeutet. Besonders bevorzugt ist X eine 5-Nitrogruppe.
- g) Bevorzugt sind ferner diejenigen Verbindungen der allgemeinen Formel I in denen R₃ eine Nitro-, Chlor-, Cyano-, -CHO, -COOH, Methylsulfonyl, Sulfonamido, C1-4-Alkyl- oder C1-4- Dialkylsulfonamidogruppe oder eine C1-4-Hydroxyalkylgruppe bedeutet;
- h) bevorzugt sind ferner diejenigen Verbindungen der allgemeinen Formel I, in denen R₃ den Rest bedeutet, wobei R₄ ein Wasserstoffatom, einen C1-4-Alkyl-, Cyano- oder C1-4- Acylrest darstellt und R₅ einen Cyano-, Carboxyl-, C1-4- Acyl-, einen gegebenenfalls durch 1-3 Hydroxyl-, Nitro- oder Carboxygruppen, C1-4-Alkyl- oder C1-4-Alkoxyreste oder C1-4-Alkylamino- oder C1-4-Dialkylaminoreste substituierte Benzoylgruppe, einen C1-4-Hydroxyalkylrest, eine Pyridyl- oder Chinolylgruppe, einen C1-8-Carboxyalkylrest, einen C1-4- Alkoxycarbonyl, einen Aminocarbonyl, einen C1-4-Alkyl- oder C1-4-Dialkylaminocarbonylrest darstellt;
- i) bevorzugt sind ferner die Verbindungen der allgemeinen Formel I, in denen R₃ den Rest -(CH₂) m -COR bedeutet, wobei m einen Wert von 1-7, bevorzugt 3-5, insbesondere 4 hat und R eine Hydroxyl- oder Aminogruppe oder eine C1-4-Alkyl- oder C1-4-Dialkylamino- oder eine Adamantylaminogruppe oder einen Rest der Formel -OC1-18-Alkyl bedeutet;
- j) bevorzugt sind schließlich auch die Verbindungen der allgemeinen Formel I, in denen R₃ einen Rest der Formel bedeutet, wobei R₈ ein Wasserstoffatom darstellt und R₉ einen C1-4-Alkyl-, einen Adamantyl-, Benzyl- oder Morpholino- C1-4-Akylrest bedeutet oder R₈ und R₉ zusammengenommen eine Piperidino- oder eine 4-Cyclohexylcarbonylpiperidino oder 1-Piperidylpiperidinogruppe bedeuten.
- k) Besonders bevorzugt sind diejenigen Verbindungen der allgemeinen Formel I, in denen R₃ eine der Gruppen NO₂, CN, CHO, COOH und Cl bedeutet. Insbesondere sind auch die Verbindungen der allgemeinen Formel I bevorzugt, in denen R₃ eine Gruppe der Formel darstellt, wobei R₄ ein Wasserstoffatom, eine Methyl-, Cyano- oder Acetylgruppe bedeutet und R₅ eine Cyano-, Acetyl-, Benzoyl-, Carboxyl-, Hydroxyethyl- oder Trimethoxybenzoylgruppe bedeutet. Schließlich sind besonders bevorzugt die Verbindungen der allgemeinen Formel I, in denen R₃ den Rest -(CH₂)₄-COR darstellt, wobei R eine Amino-, C1-4-Alkylamino-, C1-4-Dialkylamino- oder Adamantylaminogruppe bedeutet.
Claims (46)
(a) eine säure- oder basenkatalysierte Kondensationsreaktion einer Verbindung der allgemeinen Formel II in der R₁, R₂ und X die in Anspruch 1 angegebenen Bedeutungen haben, mit einer Verbindung der Formel III durchführt, die eine aktive Methyl- oder Methylgruppe aufweist und in der R₄ und R₅ die in Anspruch 1 angegebenen Bedeutungen haben, wobei eine Verbindung der allgemeinen Formel Ia erhalten wird, in der die Substituenten wie vorstehend definiert sind, und deren Doppelbindung gegebenenfalls zu einer Einfachbindung reduziert werden kann; oder
(b) ein Keton der allgemeinen Formel IV in der R₁, R₂ und X die im Anspruch 1 angegebenen Bedeutungen haben und R₆ ein Wasserstoffatom oder einen Alkylrest darstellt, mit einem Aldehyd der allgemeinen Formel V in der R₇ ein Wasserstoffatom, einen Alkyl-, Alkoxy- oder Dialkylaminorest bedeutet, zu einer Verbindung der allgemeinen Formel Ib kondensiert, in der R₁, R₂, X, R₆ und R₇ wie vorstehend definiert sind; oder
(c) eine Verbindung der allgemeinen Formel VI in der R₁ und R₂ die im Anspruch 1 angegebenen Bedeutungen haben, mit einem cyclischen Säureanhydrid der allgemeinen Formel VII in der m einen Wert von 1 bis 7 hat, oder mit einem Dicarbonsäureesterchlorid der allgemeinen Formel VIIIHal-(CO) n -(CH₂) m COR (VIII)in der m einen Wert von 0 bis 7 und n den Wert 0 oder 1 hat, R die in Anspruch 1 angegebene Bedeutung hat und Hal ein Halogenatom darstellt, zu einer Verbindung der allgemeinen Formel IX umsetzt, deren aromatischer Ring mit dem Rest X substituiert wird, wobei man eine Verbindung der allgemeinen Formel Ic erhält, die gegebenenfalls zu einer Verbindung der Formel Id reduziert werden kann oder
(d) eine Verbindung der allgemeinen Formel X in der R₁, R₂ und X die im Anspruch 1 angegebenen Bedeutungen haben und Y ein Halogenatom oder einen anderen aktivierten Rest bedeutet, mit einem Amin der allgemeinen Formel XI in der R₈ und R₉ die im Anspruch 1 angegebenen Bedeutungen haben, zu einer Verbindung der Formel Ie umsetzt, in der R₁, R₂, X, R₈ und R₉ die vorstehend angegebenen Bedeutungen haben; oder
(e) ein Anilinderivat der allgemeinen Formel XII in der R₁, R₂ und X die im Anspruch 1 angegebenen Bedeutungen haben, mit einem aktivierten Carbonsäurederivat der allgemeinen Formel XIIIY-CO-R₁₀ (XIII)in der Y und R₁₀ die vorstehend angegebenen Bedeutungen haben, zu einer Verbindung der allgemeinen Formel If umsetzt, in der die Substituenten die vorstehend angegebenen Bedeutungen haben; oder
(f) eine Verbindung der allgemeinen Formel II in der R₁ und R₂ die vorstehend angegebenen Bedeutungen haben und X ein Halogenatom darstellt, mit einem Kupfer- (I)-cyanid in einem polaren aprotischen Lösungsmittel bei erhöhter Temperatur umsetzt, oder gegebenenfalls 2,3- Dihydroxybenzonitril mit Hexamethylentetramin formyliert, wobei eine Verbindung der Formel II erhalten wird, in der X eine Cyanogruppe darstellt; oder
(g) eine Verbindung der Formel XIV nacheinander mit Butyllithium, Trimethylborat und Peroxyameisensäure zu der Verbindung der Formel XV umsetzt, die mit Hexamethylentetramin in Fluoressigsäure zur Verbindung der Formel XVI formyliert werden kann, welche zur Verbindung der Formel XVII entmethyliert werden kann oder
(h) die Verbindung der Formel XVIII mit Peroxyessigsäure behandelt, wobei die Sulfonverbindung der Formel XIX erhalten wird, welche zur Verbindung der Formel XX formyliert wird, die zu der entsprechenden Hydroxyverbindung der Formel XXI entmethyliert werden kann oder
(i) eine Verbindung der allgemeinen Formel XXII in der R₁₁ ein Wasserstoffatom oder einen Alkylrest bedeutet, zu einer Verbindung der allgemeinen Formel XXIII formyliert.
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FI864875A FI864875A0 (fi) | 1986-11-28 | 1986-11-28 | Nya farmakologiskt aktiva foereningar, dessa innehaollande kompositioner samt foerfarande och mellanprodukter foer anvaendning vid framstaellning av dessa. |
GB878712437A GB8712437D0 (en) | 1986-11-28 | 1987-05-27 | Pharmacologically active compounds |
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DE3740383A1 true DE3740383A1 (de) | 1988-06-01 |
DE3740383C2 DE3740383C2 (de) | 1997-09-25 |
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DE1999175025 Active DE19975025I2 (de) | 1986-11-28 | 1987-11-27 | Brenzkatechin-Derivate Verfahren zu ihrer Herstellung und deren Verwending als Arzneimittel |
DE3740383A Expired - Lifetime DE3740383C2 (de) | 1986-11-28 | 1987-11-27 | Brenzkatechin-Derivate, Verfahren zu ihrer Herstellung und deren Verwendung als Arzneimittel |
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US5232923A (en) * | 1988-03-18 | 1993-08-03 | Mitsui Toatsu Chemicals, Incorporated | Catechol derivatives and pharmaceutical preparations containing same |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5236952A (en) * | 1986-03-11 | 1993-08-17 | Hoffmann-La Roche Inc. | Catechol derivatives |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2116579A1 (de) * | 1970-12-07 | 1972-07-13 | Reckitt & Colmann Prod Ltd |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB902586A (en) * | 1960-01-01 | 1962-08-01 | Shell Res Ltd | Herbicidal compositions and novel compounds for use therein |
GB1188364A (en) * | 1967-05-02 | 1970-04-15 | May & Baker Ltd | Quinoline Derivatives |
BE759266A (fr) * | 1969-11-24 | 1971-05-24 | Hoffmann La Roche | Procede pour la preparation de derives de l'indole |
CA1190223A (en) * | 1977-11-01 | 1985-07-09 | Anthony C. Richardson | Substrates for enzymes |
JPS5890534A (ja) * | 1981-11-25 | 1983-05-30 | Ono Pharmaceut Co Ltd | 2−アミノフエノ−ル誘導体、その製造方法およびその誘導体を有効成分として含有する治療剤 |
ES8405409A1 (es) * | 1982-04-03 | 1984-06-01 | Beecham Group Plc | Un procedimiento para la preparacion de derivados de b-lactama. |
US4618627A (en) * | 1983-05-13 | 1986-10-21 | Yamanouchi Pharmaceutical Co., Ltd. | Catechol derivatives and pharmaceutical compositions thereof for inhibiting anaphylaxis (SRS-A) |
FR2557097B1 (fr) * | 1983-12-22 | 1986-06-13 | Rhone Poulenc Spec Chim | Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues |
FR2557098B1 (fr) * | 1983-12-22 | 1986-06-13 | Rhone Poulenc Spec Chim | Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues |
EP0155335A1 (de) * | 1984-03-21 | 1985-09-25 | LUDWIG HEUMANN & CO GMBH | Verfahren zur Herstellung von 3,5-Dimethoxy-4-alkoxybenzaldehyden |
DK175069B1 (da) * | 1986-03-11 | 2004-05-24 | Hoffmann La Roche | Pyrocatecholderivater |
CH676845A5 (de) * | 1986-11-07 | 1991-03-15 | Oreal |
-
1987
- 1987-11-25 YU YU02135/87A patent/YU213587A/xx unknown
- 1987-11-26 EG EG689/87A patent/EG18338A/xx active
- 1987-11-26 MT MT1012A patent/MTP1012B/xx unknown
- 1987-11-26 CN CN87108011A patent/CN1040062C/zh not_active Expired - Lifetime
- 1987-11-27 JP JP62301387A patent/JP2735834B2/ja not_active Expired - Lifetime
- 1987-11-27 DE DE1999175025 patent/DE19975025I2/de active Active
- 1987-11-27 PH PH36138A patent/PH26145A/en unknown
- 1987-11-27 US US07/126,911 patent/US4963590A/en not_active Expired - Lifetime
- 1987-11-27 LU LU87050A patent/LU87050A1/fr unknown
- 1987-11-27 GB GB8727854A patent/GB2200109B/en not_active Expired - Lifetime
- 1987-11-27 RU SU4203731/04A patent/RU2014319C1/ru active
- 1987-11-27 IT IT8722790A patent/IT1225762B/it active Protection Beyond IP Right Term
- 1987-11-27 JP JP62301388A patent/JPH085781B2/ja not_active Expired - Lifetime
- 1987-11-27 AT AT0312987A patent/AT401053B/de not_active IP Right Cessation
- 1987-11-27 MA MA21361A patent/MA21120A1/fr unknown
- 1987-11-27 DE DE3740383A patent/DE3740383C2/de not_active Expired - Lifetime
- 1987-11-27 CS CS888440A patent/CS277018B6/cs not_active IP Right Cessation
- 1987-11-27 HU HU875352A patent/HU206073B/hu active Protection Beyond IP Right Term
- 1987-11-27 CA CA000552987A patent/CA1334967C/en not_active Expired - Lifetime
- 1987-11-27 AR AR87309418A patent/AR243491A1/es active
- 1987-11-27 PL PL1987269091A patent/PL152642B1/pl unknown
- 1987-11-27 CS CS888439A patent/CS276263B6/cs not_active IP Right Cessation
- 1987-11-27 ES ES8703401A patent/ES2008359A6/es not_active Expired
- 1987-11-27 BE BE8701356A patent/BE1003279A5/fr not_active IP Right Cessation
- 1987-11-27 NZ NZ222729A patent/NZ222729A/en unknown
- 1987-11-27 FR FR878716457A patent/FR2607493B1/fr not_active Expired - Lifetime
- 1987-11-27 AU AU81879/87A patent/AU621036B2/en not_active Expired
- 1987-11-27 PT PT86236A patent/PT86236B/pt unknown
- 1987-11-27 NL NL8702857A patent/NL194821C/nl not_active IP Right Cessation
- 1987-11-27 SE SE8704751A patent/SE503434C2/sv not_active IP Right Cessation
- 1987-11-27 CH CH4633/87A patent/CH685436A5/de not_active IP Right Cessation
- 1987-11-27 GR GR871817A patent/GR871817B/el unknown
- 1987-11-27 DK DK198706230A patent/DK175394B1/da not_active IP Right Cessation
- 1987-11-27 NO NO874966A patent/NO171450C/no not_active IP Right Cessation
- 1987-11-27 CA CA000552986A patent/CA1289078C/en not_active Expired - Lifetime
- 1987-11-27 IS IS3290A patent/IS1753B/is unknown
- 1987-11-30 IE IE324287A patent/IE60320B1/en not_active IP Right Cessation
-
1988
- 1988-12-19 CS CS888439A patent/CS843988A3/cs unknown
- 1988-12-19 CS CS888440A patent/CS844088A3/cs unknown
-
1989
- 1989-01-06 YU YU2189A patent/YU48020B/sh unknown
- 1989-01-06 YU YU2289A patent/YU47790B/sh unknown
-
1993
- 1993-06-30 LV LVP-93-805A patent/LV10236B/en unknown
-
1994
- 1994-01-18 BG BG098383A patent/BG60407B2/bg unknown
- 1994-08-04 HK HK75594A patent/HK75594A/xx not_active IP Right Cessation
-
2003
- 2003-09-26 NL NL300136C patent/NL300136I2/nl unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2116579A1 (de) * | 1970-12-07 | 1972-07-13 | Reckitt & Colmann Prod Ltd |
Non-Patent Citations (1)
Title |
---|
BORCHARD, R.T.: J. Red. Chem. 25(1982)258-63 * |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
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US5283352A (en) * | 1986-11-28 | 1994-02-01 | Orion-Yhtyma Oy | Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same |
EP0322738A3 (de) * | 1987-12-24 | 1991-05-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Benzyliden-Malononitril-Derivate zur Hemmung von proliferativen Prozessen in Säugetierzellen |
EP0322738A2 (de) * | 1987-12-24 | 1989-07-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Benzyliden-Malononitril-Derivate zur Hemmung von proliferativen Prozessen in Säugetierzellen |
US5232923A (en) * | 1988-03-18 | 1993-08-03 | Mitsui Toatsu Chemicals, Incorporated | Catechol derivatives and pharmaceutical preparations containing same |
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US6201027B1 (en) | 1998-07-01 | 2001-03-13 | Orion Corporation | Substituted β diketones and their use |
EP2301934A1 (de) | 2005-07-26 | 2011-03-30 | BIAL - Portela & Ca., S.A. | Nitrocatecholderivate als COMT-Inhibitoren |
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