Pharmaceutical Substances Syntheses, Patents, Applications - Part 78 potx

Erythromycin ethylsuccinate E 77 1 CH3 erythromycin propionyl chloride CH3 erythromycin monopropionate (I) I CH, loury1 sulfate Erythromycin estolate Reference(s): US 3 000 874 (Eli Lilly; 19.9.1961; prior. 8.4.1959). DE 1 114 499 (Eli Lilly; 27.6.1959). Formulation(s): - cleavable tabl. 125 mg, 250 mg; cps. 250 mg; susp. 125 mg15 rnl, 250 mg15 ml; syrup 250 mg (base equivalent) Trade Name(s): D: Infectomycin Togiren (Schwarzhaupt); I: Ilosone (Lilly) (Infectopharrn) wfrn Marocid (Lifepharrna) Neo-Eryclnurn (Schering); F: Propiocine (Roussel); wfm Stellamicina (Pierrel) wfm Rubitracine (Takeda). J: Ilosone (Shionogi) Sanasepton (Pharbita) comb.; wfrn USA: Ilosone (Dista) GB: Ilosone (Lilly) Erythromycin ethylsuccinate ATC: D 10AF02; D10AF52; JO1 FA01 ; SOlAA17 Use: antibiotic RN: 1264-62-6 MF: C,,H7SN0,, MW: 862.06 EINECS: 2 15-033-8 LD,,,: >10 gkg (M, p.0.) CN: erythromycin 2'-(ethyl butanedioate) 772 E Erythromycin gluceptate No2C0, ocetone ___, erythromycin ethyl succinyl chloride Reference(s): DE 1 121 056 (Abbott; appl. 1957; USA-prior. 1956). chewing tablets: DOS 2 758 942 (Abbott; appl. 30.12.1977). Erythromycin ethylsuccinote Formulation(s): f. c. tabl. 400 mg; powder 1 gl4.5 g; susp. 125 mg15 ml; syrup 100 mg15 ml, 200 mg/5 ml, 400 mg15 ml, 600 mg15 ml (base equivalent) Trade Narne(s): D: Dura Erythromycin 1000 Granulat (durachemie) Durapaediat (durachemie) GB: Erythrocin Granulat/- Ampullen (Abbott) Erythromycin-ratiopharm (ratiopharm) I: Monomycin (Griinenthal) Paediathrocin (Abbott) combination preparations F: Abboticine (Abbott) Ery 125 e 250 (Bouchara) Erycocci (Pharmafarm) Erythrocine (Abbott) Erythrogram (Pharma 2000) Arpimycin (Rozemont) Erymin (Elan) Erythrocin I. M. (Abbott) Erythroped A (Abbott) Eritrocina (Abbott) Eritroger bustine (Isnardi); wfm Neobalsamocetina sosp. (Alfa Farm.)-comb.; wfm Proterytrin (Proter); wfm Proterytrin cps e i.m. (Proter); wfm Rossomicina sosp. (Pierrel); wfm Eryromycen (Kissei) Ery throcin (Abbott- Dainippon) Erythro ES (Sankyo) Erythromycin ES (Taito Pfizer) Esinol (Toyama) Evesin (Torii) USA: E.E.S. (Abbott) Eryped (Abbott) Eryzole (Alra) Pediazole (Ross) Erythromycin gluceptate (Erythromycin glucoheptonate) ATC: JOIFAOI; SOlAA17 Use: antibiotic RN: 23067- 13-2 MF: C,,H,,NO,, . C7H,,08 MW: 960.12 EINECS: 245-407-6 LD,,,: 453 mglkg (M, i.v.); 288 mglkg (R, i.v.) CN: D-glycero-D-gulo-heptonic acid compd. with erythromycin (1:l) Erythromycin lactobionate E 773 erythromycin COOH CH3 Erythromycin gluceptote Reference(s): US 2 852 429 (Lilly; 1958; appl. 1953). DE 941 640 (Lilly ; appl. 1954; USA-prior. 1953). Formulation(s): vial 1 g (base equivalent) Trade Name(s): D: Erycinum Trockensubstanz USA: Ilotycin gluceptate (Dista) (Schering); wfm Erythromycin lactobionate ATC: JOlFAO1; SOlAA17 Use: antibiotic RN: 3847-29-8 MF: C37H67N013 . C,2H22012 MW: 1092.23 EINECS: 223-348-7 LD,,: 735 mglkg (M, i.p.1 CN: 4-O-P-D-galactopyranosyl-D-gluconic acid compd. with erythromycin (1:l) COOH erythromycin lactobionic acid 774 E Erythromycin monopropionate mercaptosuccinate COOH Erythromycin loctobionote Rej'ers~lce(s): US 2 761 859 (Abbott; 1956; appl. 1953). Fonnulntion(s): vial 500 mg, 1000 mg (base equivalent) Trade Narne(s): D: Erythrocin I.V. (Abbott) I: Eritro (Forrnulario Naz.) GB: Erythrocin I.V. J: Erythromycin (Santen) Lactobionate (Abbott); USA: Erythrocin Lactobionate- w fm I.V. (Abbott); wfrn Erythromycin monopropionate ATC: JO~FA mercaptosuccinate Use: macrolide antibiotic (RV- I I ) RN: 84252-06-2 MF: C,oH,INO,, . C,H,O,S MW: 940.16 LD,,,: >3000 mglkg (M, p.0.) CN: erythromycin-2'-propanoate ~nercaptobutanedioate (I :I) erythromycin Erythromycin monopropionate mercaptosuccinate EP 57 489 (Pierrel; appl. 2.1.1982; F-prior. 2.2. I98 I). EP 174 395 (Pierrel; appl. 2.1.1982; F-prior. 2.2.1982). US 4 476 120 (Refarmed; 10.9.1984; appl. 2.2.1982; I-prior: 2.2.1 98 1). Fonnulation(s): gran. 200 mg; tabl. 500 rng F Erythromycin stearate E 775 Trade Name(s): I: Zalig (Pierrel; 1989) Erythromycin stearate ATC. ~07CC02 Use: antib~otic RN: 97327-17-8 MF: C,,H,,,NO,, MW. 1000.41 LD5,: 31 12 mg/kg (M, pa) CN: erythromycin 2'-octadecanoate CH3 erythromycin 0 0 stearoyl chloride CH3 Erythromycin stearate Reference(s): US 2 862 921 (Upjohn; 1958; appl. 1953). Formulation(s): f. c. tabl. 250 mg, 500 mg Trade Name(s): Erythromycin steorote I D: Dura Erythromycin Emestid 500 (Abbott); wfm J: Erythrocin (Abbott- (durachemie) GB: Erythrocin (Abbott) Dainippon) Erythrocin Filmtabletten I: Eritrocina Cpr (Abbott) USA: Erythrocin Stearate (Abbott) Lauromicina (Lafare) (Abbott) F: Abboticine (Abbott); wfm generic 776 E Escin Escin (Aescin) ATC: COSCX; C05CX01 Use: anti-inflammatory (inhibition of edema formation and decrease of vesscl fragility), vein therapeutic RN: 6805-41-0 MF: C,,H,,O,, MW: 1101.24 EINECS: 229-880-6 LD,,,: 6.7 mglkg (M, i.p.); 2 mgkg (M, i.v.); 165 mglkg (M, p.0.); 38.59 mglkg (M, s.c.); 10.15 mglkg (R,i.p.); 16OOglkg (R,i.v.); 833 mglkg (R, p.0.): 150mg/kg(R, s.c.) CN: 3,s-epoxypicene escin deriv. sodium salt RN: 20977-05-3 MF: unspecified MW: unspecified EINECS: 244-133-4 LD,,,: 8299 pglkg (M, i.p.); 4730 mgkg (M, i.v.); 134 mgkg (M, p.0.); 92.53 mglkg (M, s.c.); 91 80 pglkg (R, i.p.); 8131 pglkg (R, i.v.); 400 mglkg (R, p.0.); 131 mglkg (R, s.c.); 91 30 ~glkg (g. p., i.v.); 5 mglkg (rabbit, i.v.) 0 CH, K 0 Escin Extraction of Aesculus hippocustunurn L. (horse-chestnut) and purification on cation-exchanger (H+-form), resp. precipitation with cholesterol. Reference(s): extraction and puri,fication: DE 916 664 (Riedel-de Haen; appl. 1952). DE 950 027 (Klinge; appl. 195 1). DAS 1 034 816 (VEB Arzneimittelwerk Dresden; appl. 1955). DAS 1 045 597 (Dr. W. Schwabe; appl. 1953). GB 820 787 (Klinge; appl. 1956). GB 820 788 (Klinge; appl. 1956). DE 1 058 208 (Klinge; appl. 1953). DAS 1 095 989 (Madaus; appl. 11.3.1959). US 3 163 636 (Klinge; 29.12.1964; D-prior. 14.6.1960). DAS 1 182 385 (Chem. Fabrik Tempelhof; appl. 29.1.1962). US 3 238 190 (Madaus; 1.3.1966; prior. 31.1.1961, 23.10.1963). DOS 1617 570 (J. Klosa; appl. 13.4.1967). DOS 1 617 581 (Knoll; appl. 11.8.1967). DAS 1617 413 (Klinge; appl. 31.8.1967). DE 1 667 884 (Knoll; appl. 20.1.1968). DOS 1 902 608 (Nattermann; appl. 20.1.1969; A-prior. 31.5.1968). DOS 2 339 760 (Klinge; appl. 6.8.1973). DAS 2 733 204 (LEK; appl. 22.7.1977; YU-prior. 12.8.1976). 7 Esmolol E 777 "water soluble" (X-ray amorphous) escin: DE 1 282 852 (Madaus; appl. 14.12.1962). DOS 1 902 609 (Nattermann; appl. 20.1.1969). DOS 2 257 755 (LEK; appl. 24.11.1972; YU-prior. 6.12.1971). GB 1 550 845 (Madaus; appl. 7.7.1976; D-prior. 11.7.1975). separation of a- and p-escin: DAS 1 125 117 (Klinge; appl. 14.6.1960). US 3 110 71 1 (Klinge; 12.1 1.1963; D-prior. 14.6.1960). conversion of p- into a-escin: US 3 450 691 (Klinge; 17.6.1969; appl. 7.6.1967). Formulation(s): amp. 5 mg (as sodium salt); cps. 2 mg; drg. 10 mg, 15 mg, 20 mg; gel 1 gI100 g-comb.; s. r. drg. 40 mg Trade Narne(s): D: Essaven (Nattermann) comb. Galleb forte (Hoyer)-comb. Heweven (Hevert)-comb. Opino, Gel (Troponwerke)- comb. Opino retard (Troponwerke)-comb. Opino spezial (Troponwerke)-comb. Pe-Ce Ven (Terra-Bio- Chemie)-comb. Proveno (Madam)-comb. Reparil (Madaus) Revicain (Wiedemann)- comb. Veno Kattwiga (Kattwiga)- comb. Venoplant (Schwabe)- comb. Venostasin (K1inge)-comb. F: Flogencyl (Parke Davis) Reparil (Madaus) numerous combination preparations I: Bres (Farmacologico J: Milanese)-comb. Dermocinetic (1rbi)-comb. Essaven (Nattermann)- comb. Etascin (Rorer)-comb. Opino (Bayropharm)- comb. Premium (SIT)-comb. Rectoreparil (IB1)-comb. Reparil (1BI)-comb. Somatoline (Manetti Roberts)-comb. Tioscina (Inverni della Beffa)-comb. Tochief (Ohta) Tochikinon (Toho) Yochimin (Choseido- Seiyaku) Esmolol ATC: C07AB09 Use: anti-arrhythmic, P-adrenoceptor antagonist, perioperative prophylactic use in supraventricular tachycardia RN: 81147-92-4 MF: C,,H,,NO, MW: 295.38 CN: (f)-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]benzenepropanoic acid methyl ester hydrochIoride RN: 81 161-17-3 MF: C,,H,sNO,. HCl MW: 331.84 LD,,: 93 mgkg (M, i.v.); 71 mgkg (R, i.v.); 32 mgkg (dog, i.v.) methyl 3-(4-hydroxy- epichloro- pheny1)propionote hydrin methyl 3-[4-(2.3-epoxy- propoxy)phenyl]propionate (I) 778 E Estazolam Reference(s): EP 41 491 (Hassle; appl. 27.5.1981 ; S-prior. 2.6.1980). EP 53 435 (American Hospital Supply; appl. 29.10.1981; USA-prior. 28.1 1.1980). Erhardt, P.W. et al.: J. Med. Chem. (JMCMAR) 25, 1408 (1982). US 4 387 103 (American Hospital Supply; 7.6.1983; prior. 28.1 1.1980). H C NH2 1 + 3'7' + CH3 isopropylornine injectable,formulation: US 4 857 552 (Du Pont; 15.8.1989; prior. 8.6.1988). US 4 593 119 (American Hospital Supply; 3.6.1986; prior. 28.1 1.1980). OH H~C~#,.)-,,O CH3 Esrnolol alternative synthesis: ES 549 138 (Sune Coma; appl. 21.1 1.1985). Formulation(s): amp. 2.5 g110 ml; vial 100 mg/lO ml (as hydrochloride) Trade Name(s): D: Brevibloc (Baxter) F: Brevibloc (Isotec; 1989) USA: .Brevibloc (Ohmeda; 1987) Estazolam ATC: N05CD04 Use: hypnotic, sedative, tranquilizer RN: 29975-16-4 MF: C,,Hl1ClN4 MW: 294.75 EINECS: 249-982-4 LD,,,: 600 mglkg (M, p.0.); 2500 mglkg (R, p.0.) CN: 8-chloro-6-phenyl-4H-[1,2,4]tnazolo[4,3-a][l,4]benzodiazepine 2-omino-5-chloro- ominooceto- benzophenone (I) nitrile formic I Estazo~am I acid (Ill) Estradiol E 779 pyridine I + H,N+O'-'~~~ OHCI , 0 glycine ethyl ester hydrochloride d phosphorus(V) sulfide hydro-lH-l.4- benzodiozepine Estozolam 1 US 3 701 782 (Upjohn; 3 1.10.1972; prior. 10.2.1972). Hester, J.B. eta].: J. Med. Chern. (JMCMAR) 14, 1078 (1971). US 4 116 956 (Takeda; 26.9.1978; J-prior. 5.1 1.1968, 17.12.1968,25.12.1968, 13.2.1968). DOS 1 955 349 (Takeda; appl. 4.1 1.1969; J-prior. 5.1 1.1968). DOS 1 965 894 (Takeda; appl. 4.1 1.1969; J-prior. 5.1 1.1968, 17.12.1968, 25.12.1968, 13.2.1969). DOS 2 012 190 (Upjohn; appl. 14.3.1970; USA-prior. 17.3.1969). US 3 987 052 (Upjohn; 19.10.1976; prior. 17.3.1969, 29.10.1969). DOS 2 114 441 (Takeda; appl. 25.3.1971; J-prior. 27.3.1970, 23.4.1970,28.5.1970). US 4 102 881 (Takeda; 25.7.1978; J-prior. 27.3.1970, 23.4.1970,28.5.1970). DOS 2 302 525 (Upjohn; appl. 19.1.1973; USA-prior. 31.1.1972). review: Schulte, E.: Dtsch. Apoth. Ztg. (DAZEA2) 115, 1253, 1828 (1975). Formulation(s): tabl. 1 rng, 2 mg Trade Narnefs): F: Nuctalon (Cassenne; 1978) I: Esilgan (Cyanamid; 1983); J: Eurodin (Takeda; 1975) wfm USA: ProSom (Ahbott) Estradiol (Oestradiol) ATC: G03CA03 Usc: estrogen RN: 50-28-2 MF: CL8H2,02 MW: 272.39 EINECS: 200-023-8 CN: (17P)-estra-1,3,5(10)-triene-3.17-dial estrons Estradiol 780 E Estradiol w 1. H,, Pt 1. H,. Raney-Ni 2. benroyl chloride 2. KOH. CH,OH 3. Cr0,. CH,COOH 4. KOH I * Br2 ___, bromine collidine d 11 Reference(s): a Ehrhart, Ruschig, 111, 317. US 2 096 744 (Schermg Corp.; 1937; D-prior. 1932). DRP 698 796 (Schering AG; appl. 1932). b lnhoffen, H.H.; Zuhlbdorff, G Ber. Dtsch. Chcm. Ges. (BDCGAS) 74, 1911 (1941). US 2 361 847 (Schering Corp. 1944; D-prior. 1937). Ullmanns Encykl. Tech. Chem., 3. Aufl., Vol. 8,657. starring material: The Merck Index, 12th Ed., 630 (1996). alternative syntheses: GB 485 388 (Lab. Franq. de Chimiothtrapie; appl. 1936). US 2 225 419 (Schering Corp.; 1940; D-prior. 1937). US 3 128 238 (Lilly; 7.4.1974; appl. 14.9.1962). total synthesis: Eder, U. et al.: Chem. Ber. (CHBEAM) 109, 2948 (1976). Formulation(s): gel 0.5 mglg, 1 mglg; tabl. 2 mg, 4 mg; transdermal plaster 0.75 mg, 1.5 mg, 2 mg, 3 mg, 4 mg, 8 mg; vaginal tabl. 0.025 mg Trade Name(s): D: Aknefug Emulsion (Wo1ff)- comb. Cerella (Asche) Crinohermal fem. (Herma1)-comb. Cutanum (Jenapharm) DERMESTRIL (Opfermann) Estracomb 7TS (Novartis Pharma)-comb. Estraderm (Novartis Pharma) Estramon (Hexal) Estrifam I-forte (Novo Nordisk; RhGne-Poulenc Rorer) ESTRING (Pharmacia & Upjohn) Evorel (Janssen-Cilag) Fem7 (Merck) Kliogest (Novo Nordisk; Rh6ne-Poulenc Rorer)- comb. Linoladiol (Wo1ff)-comb Linoladiol-H (Wo1ff)- comb. Menorest (Novo Nordisk; RhBne-Poulenc Rorer) Osmil (Novartis Pharma)- comb. Sandrena (Organon) Sisare Gel (Nourypharma) Tradelia (Sanofi Winthrop) Trisequens (Novo Nordisk; Rh6ne-Poulenc Rarer)- comb. . 2997 5-1 6-4 MF: C,,Hl1ClN4 MW: 294.75 EINECS: 24 9-9 8 2-4 LD,,,: 600 mglkg (M, p.0.); 2500 mglkg (R, p.0.) CN: 8-chloro-6-phenyl-4H-[1,2,4]tnazolo[4,3-a][l,4]benzodiazepine 2-omino-5-chloro-. methyl 3-( 4-hydroxy- epichloro- pheny1)propionote hydrin methyl 3-[ 4-( 2.3-epoxy- propoxy)phenyl]propionate (I) 778 E Estazolam Reference(s): EP 41 491 (Hassle; appl. 27.5.1981 ; S-prior SOlAA17 Use: antibiotic RN: 384 7-2 9-8 MF: C37H67N013 . C,2H22012 MW: 1092.23 EINECS: 22 3-3 4 8-7 LD,,: 735 mglkg (M, i.p.1 CN: 4-O-P-D-galactopyranosyl-D-gluconic acid compd. with erythromycin