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Isobolographic studies were performed to analyze the effects of combinations of chlorpromazine, acetylpromazine, and cyanopromazine with bromural (I) and triallylacetylurea (II).In the conditioned flight reflex of the rat a potentiation of the effect was found; the toxicity on subcutaneous application was additive.I had a higher potentiating effect than II.

Justus Liebigs Annalen der Chemie

Constitution of sinistrin

Author: Gorlich, Bruno

Glucosinistrin (I), a nonreducing polysaccharide, was isolated from alc. extracts of white squill (II) (Scilla maritima).Acid hydrolysis of I gave D-fructose (III) and D-glucose (IV) in the ratio approx. 4:1.Shredded II was dried in an air stream at 60-70%, ground, and sieved; 1 kg. was successively stirred with 8.7 and 5 l. 96% EtOH.The united extracts contained about 60 g. solids; hydrolysis with 2% H₂SO₄ (50 min. at 90°) showed about 30 g. reducing compounds (calculated as III).The extracts evaporated in vacuo to about 1 l. gave 15-20 g. pale yellow hygroscopic precipitate of crude I, which washed with absoluteEtOH and Et₂O, dissolved in 150 cc. H₂O, C added, the mixture filtered, the filtrate evaporated in vacuo with addition of EtOH to remove H₂O, the residue kept in an ice box several days, filtered, the white flocculent powder stirred with dry Et₂O, decanted, and dried over P₂O₅ gave about 12 g. purer I, [α]²⁰_D -9.6° (c 5, H₂O), still faintly reducing to Fehling solutionIt was precipitated 4 to 5 times from concentrated aqueous solution with 5:95 dry Et₂O-absolute EtOH and washed with dry Et₂O to give 8-9 g. I, deliquescent, microcrystalline powder, nonreducing to Fehling solution no color with iodine, decomposed at 145-166° (foaming), [α]²⁰_D -18.6° (c 3, H₂O).I (500 mg.) in 25 cc. 1% H₂SO₄ kept at 80° 30 min., the solution cooled, made to 100 cc. with H₂O, and stirred 2 hrs. with 20 g.Duolite A; ascending chromatography on S. and S. 2043b with 40:50:10 butanol-H₂O-HOAc with a developing spray of 0.5 g. benzidine in 20 cc. EtOH plus 80 cc. absolute EtOH, showed III and IV.A similar hydrolyzate (40 min.) was neutralized with dilute NaOH solution, made to 50 cc., and aliquots analyzed to give III-IV 3.82:1 (or 3.77:1) [α]²⁰_D -63.0 to -63.5° (c 4).A 1:4 mixture of aqueous solutions of IV ([α]²⁰_D 52.5°, 24 hrs.) and III ([α]²⁰_D -92.0°) had [α]²⁰_D -62.2° (c 4, 24 hrs.).Control experiments showed that in N H₂SO₄ (48-72 hrs. at 20-25°) and in 0.4N H₂SO₄ (50 min. at 90°), no appreciable epimerization of III to aldoses occurred.I (100 mg.) in 20 cc. N H₂SO₄ kept 48 hrs. at 20°, brought to pH 6.5 with N KOH and to 170 cc. with distilled H₂O, and analyzed showed 72.0 mg. III and 18.0 mg. IV (4:1 ratio).IV was also determined with glucose oxidase: 17.68 mg. IV/100 mg. I. I (4 g.) in 100 cc. 1% H₂SO₄ kept 50 min. at 80°, the mixture neutralized with BaCO₃, C added, the mixture filtered, evaporated in vacuo to a thin sirup, MeOH and HOAc added, the solution nucleated with III, and kept in an ice box several days gave 650 mg. crystalline III, m. 90-5°, [α]²⁰_D -89.0°, intense blue in diphenylamine test; p-nitrophenylhydrazone, yellow needles, m. 167-71°.I (11 g.) in 300 cc. 1% H₂SO₄ kept 50 min. at 80°, the mixture neutralized with BaCO₃, evaporated in vacuo to 100 cc., cooled to 0°, 8 g. Ca(OH)₂ added, the mixture shaken, kept 30 min., the Ca fructosate centrifuged, the solution freed from Ca with CO₂, evaporated in vacuo at 30° to a thin sirup, 2 cc. HOAc added, the solution nucleated with IV, kept 10 days in an ice box, stirred with absolute EtOH, filtered, and the crystals washed with Me₂CO and Et₂O gave 1.2 g. mixture of IV (950 mg.) plus III (105 mg.), which dissolved in water, the solution evaporated to a sirup, this nucleated with IV, and kept several days gave 600 mg. mixture of IV (580 mg.) plus III (20 mg.), m. 140-2°, [α]²⁰_D 48.0° (c 2.5, H₂O, 24 hrs.), diphenylamine reaction weakly pos.; diphenylformazan derivative, red needles from butanol, m. 175-6.5°.I (5.0 g.) in 200 cc. 1% H₂SO₄ kept 50 min. at 80°, the solution neutralized with BaCO₃, evaporated to a sirup, this cooled to 0°, 2 cc. concentrated HCl and 2 cc. EtSH added, the mixture shaken 15 min., 5 cc. H₂O added, the solution cooled to 0°, filtered, and recrystallized from H₂O to give 0.5-0.7 g. needles of IV di-Et dithioacetal, m. 126-7°, [α]²⁰_D -8.8° (c 1, MeOH).I ([α]²⁰_D -18.6°, 5 g.) was precipitated 5 times from concentrated aqueous solution with absolute EtOH, washed with absolute Et₂O, and dried in vacuo, [α]²⁰_D -22.6° (c 2.5, H₂O); hydrolysis and sugar analysis gave the III-IV ratio as 4.89:1.

Arzneimittel-Forschung

Irritating and inflammatory compounds

Author: Haas, H.

The local and systemic action of irritants are reviewed.100 references.

100 Deals associated with Knoll AG

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100 Translational Medicine associated with Knoll AG

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Pipeline

Pipeline Snapshot as of 23 Dec 2024

The statistics for drugs in the Pipeline is the current organization and its subsidiaries are counted as organizations,Early Phase 1 is incorporated into Phase 1, Phase 1/2 is incorporated into phase 2, and phase 2/3 is incorporated into phase 3

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