DE1643711A1 - Cyclic ketones and a process for their preparation - Google Patents

Cyclic ketones and a process for their preparation

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Publication number
DE1643711A1
DE1643711A1 DE19671643711 DE1643711A DE1643711A1 DE 1643711 A1 DE1643711 A1 DE 1643711A1 DE 19671643711 DE19671643711 DE 19671643711 DE 1643711 A DE1643711 A DE 1643711A DE 1643711 A1 DE1643711 A1 DE 1643711A1
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DE
Germany
Prior art keywords
salts
methyl
lower alkyl
radical
ring
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.)
Pending
Application number
DE19671643711
Other languages
German (de)
Inventor
Juergen Dr Curtze
Dietrich Prof Jerchel
Klaus Dr Thomas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CH Boehringer Sohn AG and Co KG
Original Assignee
CH Boehringer Sohn AG and Co KG
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.)
Filing date
Publication date
Application filed by CH Boehringer Sohn AG and Co KG filed Critical CH Boehringer Sohn AG and Co KG
Priority to DE19671643711 priority Critical patent/DE1643711A1/en
Priority to ES361276A priority patent/ES361276A1/en
Priority to NL6817786A priority patent/NL6817786A/xx
Priority to BE725369D priority patent/BE725369A/xx
Priority to AT1212768A priority patent/AT281819B/en
Priority to FR1599916D priority patent/FR1599916A/fr
Priority to IL31261A priority patent/IL31261A0/en
Priority to GB59194/68A priority patent/GB1218778A/en
Priority to FR183278A priority patent/FR8449M/fr
Priority to FR183317A priority patent/FR8450M/fr
Publication of DE1643711A1 publication Critical patent/DE1643711A1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
    • C07D337/02—Seven-membered rings
    • C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Description

ease. /3M
Dr. Ho/neease. / 3M
Dr. Ho / ne

Dr. F. Zumsteirt - Dr. E. AssmannDr. F. Zumsteirt - Dr. E. Assmann

Dr. R. i£osnigibergsrDr. R. i £ osnigibergsr

DIpIi Phyis. R» H&iicbauerDIpIi Phyis. R »H & iicbauer

PoienlairiwSll&PoienlairiwSll &

/Auneften % Bräuhaussfta^ 4/B / Auneften % Bräuhaussfta ^ 4 / B

G*B. BOEHRINÖEE SoHF^ lMElffiBIK ML G * B. BOEHRINÖEE SoHF ^ lMElffiBIK ML

Cyclische Ketone und einYiYerfährenzm ihrer HerstellungCyclic ketones and einYiYerfähren zm their production

Die Erfindung betrifft cyclische Ketone der allgemeinen Formel „ The invention relates to cyclic ketones of the general formula "

und gegeTjenenfalls ihre Salze mit atnorganisiGhen organischen Säuren bzw. Basent sowie ein Verfahren ihrer Herstellung·and t gegeTjenenfalls their salts with acids or bases atnorganisiGhen organic as well as a method of its manufacture ·

Die Symbole B> E^, %» %r ^ 1^ Γ haiien fblgeniie Bedeutuügen: The symbols B> E ^, % »% r ^ 1 ^ Γ have fblgeniie meanings:

2O98T8/T2422O98T8 / T242

1643?111643? 11

B steht für einen mit dem Hing des Ketone kondensierten Benzolring oder ein mit dem Ring des Ketone kondensiertes Uaphthalinringsystem;B stands for one condensed with the hang of the ketone Benzene ring or a uaphthalene ring system condensed with the ring of the ketone;

X bedeutet eine der Gruppen -(CH2)J5--* -0-XCH2) oder -S'(0)n-(OH2J1n-, die gegebenenfalls über das Heteroatom an das aromatische System gebunden sind und die niederalkyl- oder phenylsubstituiert sein können und in denen k 1, 2 oder 3, m 1 oder 2 und η 0, 1 oder 2 ist}X denotes one of the groups - (CH 2 ) J 5 - * -0-XCH 2 ) or -S '(0) n - (OH 2 J 1n -, which are optionally bonded to the aromatic system via the hetero atom and which lower alkyl or phenyl and in which k is 1, 2 or 3, m is 1 or 2 and η is 0, 1 or 2}

Y bedeutet eine der Gruppen -S-, -SO2-, -NH- oderY means one of the groups -S-, -SO 2 -, -NH- or

0
It 0
It

B Γ ^CH-CH2- NC^ (II)B Γ ^ CH-CH 2 - NC ^ (II)

und R2 stellen Wasserstoff- oder Halogenatome, Hydroxy-, Acyloxy-, niedere Alkyl-, niedere Alkoxy- oder niedere Alkylmercaptogruppen dar und sind gleich oder verschieden;and R 2 represent hydrogen or halogen atoms, hydroxy, acyloxy, lower alkyl, lower alkoxy or lower alkyl mercapto groups and are identical or different;

steht für Phenyl- oder Naphthylreste, die ein- oder mehrfach durch Halogenatome, Hydroxy-, Acyloxy-, niedere Alkyl-, niedere Alkoxy-, niedere Alkylmercapto-, niedere Dialkylamino-, Carboxy-, Carbalkoxy-, Carbamyl-, SuIf amyl-, löfcro- und Trifluormethylgruppenstands for phenyl or naphthyl radicals, the one or several times by halogen atoms, hydroxy, acyloxy, lower alkyl, lower alkoxy, lower alkyl mercapto, lower dialkylamino, carboxy, carbalkoxy, carbamyl, sulfamyl, löfcro and trifluoromethyl groups

209818/1242209818/1242

substituiert sein können, für einen gegebenenfalls ein- oder mehrfach durch niedere Alkylreste substituierten pyridyl- oder Pyrimidylrest oder (falls Y den Rest der allgemeinen formel II bedeutet) für die Gruppe - NH-COR, worin R ein Wasserstoffatom, einen Alkylrest, einen gegebenenfalls substituierten Phenylrest oder einen heterocyclischen 5- oder 6-Ring mit einem Heteroatom bezeichnet.may be substituted for one, optionally one or more times, by lower alkyl radicals substituted pyridyl or pyrimidyl radical or (if Y is the remainder of the general formula II) for the group - NH-COR, in which R is a hydrogen atom, an alkyl radical, an optionally substituted phenyl radical or a heterocyclic 5- or 6-membered ring denoted by a heteroatom.

Es wurde gefunden, daß man Verbindungen der formel I erhält, indem man eine Mannichbase der FormelIt has been found that compounds of the formula I are obtained by using a Mannich base of the formula

0
Il 0
Il

R1 σR 1 σ

B J>CH - OH2 - Q (III),B J> CH - OH 2 - Q (III),

in der Q eine (vorzugsweise aliphatisch) mono- oder disubstituierte Aminogruppe bedeutet, in Form ihrer Salze, vorzugsweise der Hydrohalogenide, mit einer NH- oder SH-aciden Verbindung der Formelin which Q is a (preferably aliphatic) mono- or disubstituted amino group, in the form of their Salts, preferably of the hydrohalides, with an NH- or SH-acidic compound of the formula

H-T-R3 (IV)HTR 3 (IV)

umsetzt, in der R^ das gleiche wie R5 bedeutet, jedochconverts, in which R ^ means the same as R 5 , however

209818/1242 φ 209818/1242 φ

zusätzlich auch dann für -NH-COR stehen kann, wenn Y gleich der Gruppe -NH- ist. Palis es sich bei der eingesetzten Verbindung der Formel IV um ein Hydraziii mit einer freien NH2-Gruppe handelt, d.h. H-Y-R3 eine Verbindung der Formel H2N-NH-COR darstellt,,erfolgt die Umsetzung zwischen 2 Mol der Mannichbase bzw. eines ihrer Salze und einem Mol des Hydrazide.can also stand for -NH-COR if Y is the same as the group -NH-. If the compound of the formula IV used is a hydrazine with a free NH 2 group, ie HYR 3 is a compound of the formula H 2 N-NH-COR, the reaction takes place between 2 moles of the Mannich base or one their salts and one mole of the hydrazide.

Bas Reaktionsprodukt ist dann eine solche Verbindung der Formel I, in der Y den Rest der Formel II bedeutet.f _yi)ie erfindungsgemäße Umsetzung erfolgt in einem polaren LösungsiBittel, z.B. Dimethylformamid, Dimethylaulfoxid oder einem aliphatischen Alkohol, in der Wärme. Sind die zunächst erhaltenen Verfahrensprodukte der Formel I saure oder basische Substanzen, so werden sie gewünschtenfalls nach üblichen Methoden in die physiologisch unbedenklichen Salze geeigneter anorganischer oder organischer Basen bzw. Säuren übergeführt.Bas reaction product is then such a compound of formula I, et.f Matters the radical of the formula II in which Y _yi) ie reaction of the invention takes place in a polar LösungsiBittel, for example dimethylformamide, Dimethylaulfoxid or an aliphatic alcohol, in the heat. If the process products of the formula I initially obtained are acidic or basic substances, they are, if desired, converted into the physiologically acceptable salts of suitable inorganic or organic bases or acids by customary methods.

Die als Ausgangsstoffe verwendeten Salze von Keton-Mannichbasen sind teilweise bekannt; die bisher nicht beschriebenen Verbindungen werden nach üblichen Methoden hergestellt, z.B. durch Erwärmen des entsprechenden Ketone mit Formaldehyd und primären oder sekundärenThe salts of ketone Mannich bases used as starting materials are partly known; the compounds not previously described are made by customary methods produced, e.g. by heating the corresponding ketone with formaldehyde and primary or secondary

209818/1242209818/1242

18437111843711

Aminhydrohalogeniden in einem Lösungsmittel, wie Äthanol vgl. H. Hellmann U. G. Opitz: a-Aminoalkylierung (Verlag Chemie 1960)? 0. Dann u. W.-D. Arndt, Annalen 587«38 (1954)ί G. De Stevens, CA· 61, 9480,Amine hydrohalides in a solvent, such as ethanol, see H. Hellmann UG Opitz: a-Aminoalkylierung (Verlag Chemie 1960)? 0. Then u. W.-D. Arndt, Annals 587 "38 (1954) ί G. De Stevens, CA · 61, 9480,

Die neuen Verbindungen sind pharmazeutisch interessant; sie zeigen insbesondere eine starke antimikrobielle Wirksamkeit. Pur die Anwendung werden die erfindungsgemäßen Substanzen mit Hilfs- und Trägeretoffen zu den üblichen galenisehen Zubereitungen verarbeitet, z.B. zu Tabletten, Dragees, Kapseln, Salben, Tinkturen.The new compounds are pharmaceutically interesting; in particular, they show a strong antimicrobial Effectiveness. The inventive Substances with auxiliary and carrier substances processed in the usual galenic preparations, e.g. for tablets, coated tablets, capsules, ointments, tinctures.

' 209818/1242'209818/1242

Die folgenden Beispiele sollen die Erfindung näher erläutern:The following examples are intended to further illustrate the invention explain:

Beispielexample

g~(chroBian-»4-on~5-yl-methyl)->thiosalicylsäure 2f4 g 3-(Dimethylaminoniethyl)-chroman-4-on-hydrochlorid werden mit 1,54 g Thiosalicylsäure in 20 ml Äthanol drei Stunden unter Rückfluß erhitzt. Beim Abkühlen scheiden sich farblose Kristalle ab, die nach Umkristallisieren aus Äthanol einen Schmelzpunkt von 169-1710O haben. g ~ (chroBian- »4-on ~ 5-yl-methyl) -> thiosalicylic acid 2f4 g of 3- (dimethylaminoniethyl) -chroman-4-one hydrochloride are refluxed with 1.54 g of thiosalicylic acid in 20 ml of ethanol for three hours . On cooling, colorless crystals separate out, which have a melting point of 169-171 0 O after recrystallization from ethanol.

Analog werden(in den nachstehenden Tabellen(dielaufge· führten Verbindungen hergestellt:The connections listed in the following tables are established in the same way:

Tabelle 1Table 1

(Indanonderivate)(Indanone derivatives)

Nr.No. Rl R l YY R3 R 3 SchmelzpunktMelting point 11 H .H . SS. 2-Oarboxyphenyl2-arboxyphenyl 162162 22 HH SS. 4-Pyridyl4-pyridyl 100100 33 HH NHNH 2-Carboxyphenyl2-carboxyphenyl 158158 44th HH NHNH 4-SuIfamylpheny14-sulfamylpheny1 188188 55 HH SS. 2-iyridyl2-iyridyl 172
(fiydrobromid)172
(hydrobromide)

209818/124 2209818/124 2

Fortsetzung !TabelleContinuation! Table

R3 R 3 SchmelzpunktMelting point 4-Tolyl4-tolyl 180180 2,6-Dimethyl-4-pyrldyl2,6-dimethyl-4-pyrldyl 115115 4-Carboxyphenyl4-carboxyphenyl 196196 2-Methyl-5-ch.lorpb.enyl2-methyl-5-ch.lorpb.enyl 118118 2-Methyl-5-chlorphenyl2-methyl-5-chlorophenyl 100100 2-Carboxyphenyl2-carboxyphenyl 152152 2-Pyrimidyl2-pyrimidyl 6666 4-Nitrophenyl4-nitrophenyl 156156

H SO2 H S H KH 4-Cl NH 7-OH NH 7-OH S H S H NHH SO 2 HSH KH 4-Cl NH 7-OH NH 7-OH SHSH NH

TabelleTabel

Nr. R1 No. R 1

- Y - R» (Tetraionderivate)- Y - R »(tetraion derivatives)

SchmelzpunktMelting point

IHS 2-Carboxyphenyl 2 H S 4-PyridylIHS 2-carboxyphenyl 2 H S 4-pyridyl

180180

190 (Hydrochlorid)190 (hydrochloride)

209818/124?209818/124?

Tabelle 3Table 3

-Y-R, (Ohromanonderivate)-Y-R, (Ohromanonderivate)

Nr.No. Rl R l YY SS. -NH-OO-Jp^-NH-OO-Jp ^ SchmelzpunktMelting point 11 HH fiVCH2< fiV CH2 < SS. -NH-OHO-NH-OHO 146-147146-147 O OH2-NCO OH 2 -NC SS. 188188 22 HH SS. 2-Carboxyphenyl2-carboxyphenyl 33 HH S .S. 4-Pyridyl4-pyridyl 169-171169-171 44th HH SS. 1-Me thyl-4-pyridyl1-methyl-4-pyridyl 84 -8684 -86 55 HH NHNH 4-Tolyl4-tolyl 216-218
(Bydrcgodid)216-218
(Bydrcgodid) 66th HH NHNH 2-Carboxyph.enyl2-carboxyphene enyl 6060 77th 6-016-01 NHNH 4-Pyridyl4-pyridyl 197-198 ·197-198 88th 6-016-01 NHNH 4-Carb oxyphenyl4-carb oxyphenyl 8080 99 HH NHNH 4-Me thoxyphenyl4-methoxyphenyl 196-198196-198 IOIO HH NHNH 4-Sülfamylphenyl4-sulphamylphenyl 78-7978-79 1111 HH NHNH 2-Carbamylphenyl2-carbamylphenyl 184-186184-186 1212th HH 3-Hydroxy-4-carb-
oxyphenyl3-hydroxy-4-carb-
oxyphenyl 258-259258-259 1313th HH 3-Carboxyphenyl3-carboxyphenyl 151-152151-152 1414th HH 4-Dinethylamino-
phenyl4-dinethylamino
phenyl 131-132131-132 1515th HH 106-108106-108

209818/1242209818/1242

Portsetzung Tabelle 3Port setting Table 3

Nr.No. Rl R l TT R3 R 3 SchmelzpunktMelting point 1616 HH NHNH 4-Äthoxyphenyl4-ethoxyphenyl 79-8179-81 1717th 6-Br6-Br SS. 4-Pyridyl4-pyridyl 90-9290-92 1818th 6-Br6-Br SS. 2-Carboxyphenyl2-carboxyphenyl 198-200198-200 1919th 6-Br6-Br NHNH 4-Methoxyphenyl4-methoxyphenyl 90-9290-92 2020th 6-Br6-Br NHNH 4-Carboxyphenyl4-carboxyphenyl 195-187195-187

Tabelle 4Table 4

-Y-Rx (Thiachromanonderi- 7 vate)-Y-Rx (Thiachromanonderi- 7 derivatives)

Nr.No. 6-Cl6-Cl YY R3 R 3 -NH-CO -T^i-NH-CO -T ^ i SchmelzpunktMelting point 11 6-Cl6-Cl SS. 2-Garboxyphenyl2-Garboxyphenyl 199-200199-200 22 6-Cl6-Cl NHNH 4-Carb oxyphenyl4-carb oxyphenyl 176176 33 6-016-01 NHNH 4-Tolyl4-tolyl 85-8685-86 44th 6-Cl6-Cl SO2 SO 2 PhenylPhenyl 133-134133-134 55 6-Cl6-Cl NHNH 4-Su.lf amylphenyl4-Su.lf amylphenyl 197-198197-198 66th 6-Cl6-Cl SS. 2,6-Dimethyl-4-
pyridyl2,6-dimethyl-4-
pyridyl 151-152151-152 77th -CH2^-CH 2 ^ 191-193191-193

209818/1242209818/1242

Tabelle 5Table 5

(2,3,4,5-Tetrahydrol-benzoxepin-5-on— (2,3,4,5-tetrahydrol-benzoxepin-5-one—

derivate)derivatives)

NrNo Rl R l R2 R 2 TT R3 R 3 SchmelzpunktMelting point 11 8-CHj8-CHj HH SS. 4-Pyridyl4-pyridyl 180
(Hydrobromid)180
(Hydrobromide) CVJCVJ 7-CHj7-CHj HH SS. 4-Pyridyl4-pyridyl 200
(Hydrobromid)200
(Hydrobromide) 33 7-CHj7-CHj HH NHNH PhenylPhenyl 9494 44th HH HH SS. 4-Pyridyl4-pyridyl 130
(Hydrobromid)130
(Hydrobromide) 55 8-CHj8-CHj 9-CHj9-CHj SS. 4-Pyridyl4-pyridyl 162
(Hydrobromid)162
(Hydrobromide) 66th 7-CHj7-CHj 8-CH3 8-CH 3 SS. 4-Pyridyl4-pyridyl 168
(Hydrobromid)168
(Hydrobromide)

Tabelle 6Table 6

- Y-R,- Y-R,

(2,3,4,5-Tetrahydro-1-benzothiepin-5-on-derivate) (2,3,4,5-tetrahydro-1-benzothiepin-5-one derivatives)

Nr.No. Rl R l YY R3 R 3 Schmelzpunkt
in 0CMelting point
in 0 C 1
21
2 7-CHj
7-CHj7-CHj
7-CHj S
SO2 S.
SO 2 2-Carboxyphenyl
p-Tolyl2-carboxyphenyl
p-tolyl 158
128158
128

209818/1242209818/1242

- ια-- ια-

Analog dem obigen Beispiel wurden ferner hergestellt:Analogously to the example above, the following were also produced:

S-E 7,8-Dimethylbenz suberon( 1) -yl ( 2 ) -methyl ]-4-mercaptopyridin-hydrobromid, F. 168 G;S-E 7,8-Dimethylbenz suberon (1) -yl (2) -methyl] -4-mercaptopyridine-hydrobromide, M.p. 168 G;

. HBr. HBr

(S-Dioxo-6-chlor thlachr omanon(4)-yl(3)-m ethyl)-phenyl- eulfon, P. 1930O(S-Dioxo-6-chlorothlachr omanon (4) -yl (3) -m ethyl) -phenyl- eulfon, P. 193 0 O

CH2 - SO2 CH 2 - SO 2

S-(2,3-Dihydronaphtho [2,1-b]pyranon(4)-yl(3)-methyl)-S- (2,3-dihydronaphtho [2,1-b] pyranon (4) -yl (3) -methyl) -

thiosalicylsäure, P. 1830Othiosalicylic acid, P. 183 0 O

00OH00OH

OH2 - SOH 2 - S

209818/1242209818/1242

Claims (1)

iifld'chl; geändert werdeniifld'chl; be changed PatentansprücheClaims 1. Verbindungen der allgemeinen Formel1. Compounds of the general formula Il O. Il O. 3H - CH2 - Y - R5 (I), R2 ^V-A- X- 3H - CH 2 - Y - R 5 (I), R 2 ^ VA- X- In derIn the B einen mit dem Ring des Ketone kondensierten Benzolring oder ein mit dem Ring des Ketons kondensiertes Naphthalinringsystem bedeutet,B a benzene ring condensed with the ring of the ketone or denotes a naphthalene ring system condensed with the ring of the ketone, X eine der Gruppen -(GH2)^-, -O-iCH,,^- oder -S(O)n-(OH2)J1J- darstellt, die gegebenenfalls über das Heteroatom an das aromatische System gebunden sind und die niederalkyl- oder phenylsubstituiert sein können und in denen k 1, 2 oder 3, ml oder 2 und η 0, 1 oder 2 ist,X represents one of the groups - (GH 2 ) ^ -, -O-iCH ,, ^ - or -S (O) n - (OH 2 ) J 1 J-, which are optionally bonded to the aromatic system via the hetero atom and which can be lower alkyl or phenyl and in which k is 1, 2 or 3, ml or 2 and η is 0, 1 or 2, Y eine der Gruppen - S -, -SO2-, -HH- oderY is one of the groups - S -, -SO 2 -, -HH- or - CH2 - ϊζ (II)- CH 2 - ϊζ (II) 2098 18/124?2098 18/124? bezeichnet,designated, und R2* die gleich oder verschieden sind, Wasserstoff- oder Halogenatome, Hydroxy-, Acyloxy-, niedere Alkyl-, niedere Alkoxy- oder niedere Alky!mercaptogruppen bedeuten undand R 2 *, which are identical or different, denote hydrogen or halogen atoms, hydroxy, acyloxy, lower alkyl, lower alkoxy or lower alkyl mercapto groups and R* für Phenyl- oder Naphthylreste, die ein oder mehrfach durch Halogenatome, Hydroxy-, Acyloxy-, niedere Alkyl-, niedere Alkoxy-, niedere Alkylmercapto-, niedere Dialkylamino-, Carboxy-, Carbalkoxy-, Carbamyl-, SuIfamyl-, Nitro- und Trifluormethyl substituiert sein können, für einen gegebenenfalls ein- oder mehrfach durch niedere Alkylreste substituierten Pyridyl- oder Pyrimidylrest oder (falls Y den Rest der allgemeinen Formel II darstellt) für die Gruppe -NH-COR, worin R ein Wasserstoffatom, einen Alkylrest, einen gegebenenfalls substituierten Phenylrest oder einen heterocyclischen 5- oder 6-Ring mit einem Heteroatom bezeichnet, R * for phenyl or naphthyl radicals, one or more times by halogen atoms, hydroxy, acyloxy, lower alkyl, lower alkoxy, lower alkyl mercapto, lower Dialkylamino, carboxy, carbalkoxy, carbamyl, sulfamyl, nitro and trifluoromethyl may be substituted can, for a pyridyl or pyridyl group which is optionally substituted one or more times by lower alkyl radicals Pyrimidyl radical or (if Y represents the radical of the general formula II) for the group -NH-COR, in which R a hydrogen atom, an alkyl radical, an optionally substituted phenyl radical or a heterocyclic 5- or 6-ring with a heteroatom, und gegebenenfalls ihre Salze mit anorganischen oder organischen Säuren bzw. Basen · :and optionally their salts with inorganic or organic acids or bases: 2« S-(lndan-l-on-2-ylmethyl)-4-mercaptopyridin und seine Säureadditionssalze· ...2 «S- (indan-l-on-2-ylmethyl) -4-mercaptopyridine and its Acid addition salts ... 209818/ 124?209818/124? 3. IT-(Indan-l-on-2-y!methyl)-anthranilsäure und ihre Salze.3. IT- (indan-l-on-2-y! Methyl) anthranilic acid and its Salts. · N- (Indan-l-on-2-y !methyl) -4-amino-benz olsulf onamid und seine Salze.· N- (indan-1-one-2-y! Methyl) -4-aminobenzenesulfonamide and its salts. 5. S-(Tetralon (l)-yl(2)-methyl)-4-mercaptopyridin und seine Säureadditionssalze·5. S- (tetralone (1) -yl (2) -methyl) -4-mercaptopyridine and its acid addition salts · S- (6-Chlorchromanon( 4)-yl ( 3 )-methyl)-thiosalicylsäure und ihre Salze.S- (6-chlorochromanon (4) -yl (3) -methyl) -thiosalicylic acid and their salts. 7. S- ( 6-OhjLorchromanon(4) -yl (3) -methyl) -4-mercaptopyridin und seine Säureadditionssalze7. S- (6-OhjLorchromanon (4) -yl (3) -methyl) -4-mercaptopyridine and its acid addition salts 8. S-(6-0hlorthiachromanon(4)-yl(3)-methyl)-thiosalicylsäure und ihre Salze.8. S- (6-0hlorthiachromanon (4) -yl (3) -methyl) -thiosalicylic acid and its salts. 9. (6-0hlorthiachromanon(4)-yl(3)-methyl-phenylsulfon.9. (6-0hlorthiachromanon (4) -yl (3) -methyl-phenylsulfone. 10.Pharmazeutische Zubereitungen, gekennzeichnet durch einen Gehalt an einer oder mehreren Verbindungen der Formel I und/oder gegebenenfalls ihrer Salze.10. Pharmaceutical preparations, characterized by a Content of one or more compounds of the formula I and / or, if appropriate, their salts. 11.Verfahren zur Herstellung von Verbindungen der allgemeinen Formel I, dadurch gekennzeichnet, daß man11. Process for the preparation of compounds of the general Formula I, characterized in that one 209818/1242209818/1242 18437111843711 eine Mannich-Base der Formela Mannich base of the formula 0 Il0 Il :oh - Ch2 - Q (in): oh - Ch 2 - Q (in) In der Q eine (vorzugsweise aliphatisch) mono- oder disubstituierte -Aminogruppe bedeutet, in Form ihrer Salze, vorzugsweise der Hydrohalogenlde, mit einer NH- oder SH-aciden Verbindung der allgemeinen FormelIn the Q a (preferably aliphatic) mono- or disubstituted -amino group means in the form of their Salts, preferably the Hydrohalogenlde, with a NH- or SH-acidic compound of the general formula H-T-R,H-T-R, (IV)(IV) umsetzt, In der IU das gleiche wie R* bedeutet, jedoch zusätzlich auch dann für -NH-OOR stehen kann, wenn T gleich der Gruppe - NH - iat.implements, In the IU means the same as R *, however can also stand for -NH-OOR if T is equal to the group - NH - iat. 209818/1242209818/1242
DE19671643711 1967-12-12 1967-12-12 Cyclic ketones and a process for their preparation Pending DE1643711A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE19671643711 DE1643711A1 (en) 1967-12-12 1967-12-12 Cyclic ketones and a process for their preparation
ES361276A ES361276A1 (en) 1967-12-12 1968-12-10 Procedure for the preparation of cycles ketones. (Machine-translation by Google Translate, not legally binding)
NL6817786A NL6817786A (en) 1967-12-12 1968-12-11
BE725369D BE725369A (en) 1967-12-12 1968-12-12
AT1212768A AT281819B (en) 1967-12-12 1968-12-12 Process for the production of new cyclic ketones and their salts
FR1599916D FR1599916A (en) 1967-12-12 1968-12-12
IL31261A IL31261A0 (en) 1967-12-12 1968-12-12 Novel cyclic ketones,their preparation and pharmaceutical preparations containing them
GB59194/68A GB1218778A (en) 1967-12-12 1968-12-12 Cyclic ketones and a process for their preparation
FR183278A FR8449M (en) 1967-12-12 1969-03-12
FR183317A FR8450M (en) 1967-12-12 1970-06-11

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DE19671643711 DE1643711A1 (en) 1967-12-12 1967-12-12 Cyclic ketones and a process for their preparation
DEB0095799 1967-12-12

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DE1643711A1 true DE1643711A1 (en) 1972-04-27

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FR (3) FR1599916A (en)
GB (1) GB1218778A (en)
NL (1) NL6817786A (en)

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FR2081596A1 (en) * 1970-03-31 1971-12-10 Serdex 3-phenethylamino methyl chromones - as antidepressant psychoanaleptic agents
DE102005023944A1 (en) * 2005-05-20 2006-11-23 Grünenthal GmbH Substituted benzo-fused cycloheptanone derivatives and their use for the preparation of medicaments
DE102005039145A1 (en) 2005-05-20 2006-11-23 Grünenthal GmbH Substituted benzo-fused cyclohexanone derivatives and their use for the preparation of medicaments

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BE725369A (en) 1969-06-12
FR1599916A (en) 1970-07-20
FR8450M (en) 1971-07-23
GB1218778A (en) 1971-01-13
FR8449M (en) 1971-07-23

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