Hoffmann-la Roche Inc.

The United States of America As Represented by the United States

The United States of America

George F Field

William J Zally

Armin Walser

Peter R Hammond

Rodney I Fryer

Eugene J Trybulski

James F Feeman

Leo Henryk Sternbach

John R Vermeulen

Novel water soluble dyes of the formula I are provided ##STR1## wherein R.sup.1 and R.sup.4 are alkyl of 1 to 4 carbon atoms or hydrogen; or R.sup.1 -R.sup.2 or R.sup.2 -R.sup.4 form part of aliphatic heterocyclic rings; R.sup.2 is hydrogen or joined with R.sup.1 or R.sup.4 as described above; R.sup.3 is --(CH.sub.2).sub.m --SO.sub.3.sup.-, where m is 1 to 6;

Water soluble laser dyes

A novel method for the synthesis of 6-hydroxyindolines and new fluorescent dyes produced therefrom, which dyes are ring-constrained indoline-based rhodamine class dyes. These dyes have absorption and emission spectra which make them particularly useful in certain dye laser applications.

Preparation of 6-hydroxyindolines and their use for preparation of novel

New oxazine compounds useful as dye laser media in solution, are superiior to prior art materials. The oxazine dyes useful when pumped by the 578.2 nm copper line to operate in the 700-800 nm range are described by formula I ##STR1##

Oxazine laser dyes

The invention relates to compounds of the formula: ##STR1## wherein R is hydrogen or lower alkyl, R.sub.1, R.sub.2, R.sub.3 and R.sub.4, independently, are hydrogen, lower alkyl, lower alkenyl, cycloalkyl or phenyl unsubstituted or substituted by up to 3 substituents independently selected from lower alkyl, lower alkoxy or halogen, or R.sub.1 and R.sub.2 taken together with the carbon atom are alkylene of 2 to 5 carbon atoms unsubstituted or substituted by lower alkyl, and n is an integer of from 0 to 3,

Cycloalkylthiazoles

Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 and R.sub.2 may be either the same or different and each is hydrogen or lower alkyl;

4-Piperidino-2-phenylquinolines

There are presented compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.6 is halo and R.sub.5 is hydrogen or halo; and compounds of the formulas ##STR2## wherein R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 and is selected from the group consisting of alkoxy, amino or mono-lower alkyl amino; R.sub.35 is hydrogen or lower alkyl; R.sub.5 is hydrogen or halo; and R.sub.7 is methyl or chloromethyl, all of which are useful in the preparation of pyrazolobenzazepines.

4-(2-Benzoylphenyl-1-pyazole and 4-(2-benzoylphenyl)-1-pyrazoline

There are presented compounds of the formulas ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 is alkoxy, amino or mono- lower alkyl amino; R.sub.6 is nitro or halo and R.sub.5 is hydrogen or halo, and the pharmaceutically acceptable salts thereof. The pyrazolobenzazepines are useful as anxiolytic and sedative agents. Also provided are processes and intermediates in the production of the above pyrazolobenzazepines.

Pyrazolobenzazepines

A multistep process is presented for the preparation of imidazobenzodiazepines of the formula ##STR1## wherein X and Y are selected from the group consisting of hydrogen, halogen and trifluoromethyl. Also presented are novel intermediates utilized in the process. The end products are useful as sedatives, anxiolytics, muscle relaxants and anticonvulsants. The end products are especially useful in intravenous compositions for use in preoperative anesthesia.

Imidazolecarboxaldehydes

Novel intermediates of the formula ##STR1## wherein X and Y are hydrogen, halogen or trifluoromethyl and R.sub.1 is hydrogen or lower alkyl are presented. Also disclosed is a process leading to the intermediates and their conversion to imidazobenzodiazepines, compounds of pharmacological activity.

Intermediates for the production of imidazobenzodiazepines

2-[[2-Methyl-1-[2-benzoyl(or

This invention relates to a synthesis of biotin by the reduction of dehydrobiotin. The dehydrobiotin is prepared from 6-hydroxy-7-nitro-heptanoic acid methyl ester. Novel intermediates are also obtained by this synthesis.

Hydroxybiotin

Novel pyrazino-1,4-diazepines are disclosed together with processes for their preparation and novel intermediates used in these processes. These novel diazepines are useful as sedatives, muscle-relaxants and anti-convulsants.

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West Caldwell, NJ, United States of America

George F Field