P Gestodene G 961 1. methone- sulfanyl chloride Reference(s): BE 847 090 (Schering AG; appl. 8.10.1976; D-prior. 10.10.1975, 12.8.1976). DOS 2 546 062 (Schering AG; appl. 10.10.1975). DE 2 636 404 (Schering AG; appl. 12.8.1976). DE 2 636 405 (Schering AG; appl. 12.8.1976). DOS 2 636 407 (Schering AG, appl. 12.8.1979). Hofmeister, H. et al.: Arzneirn Forsch. (ARZNAD) 36, 781 (1986). alternative synthesis from 3-alkoxy-l8-methyl-3,5-estradien-l7-one derivatives: EP 201 452 (Schering AG; appl. 7.5.1986; D-prior. 10.5.1985). US4719 054 (Schering AG; 12.1.1988; appl. 9.5.1986; D-prior. 10.5.1985). medical we for oral contraception in combination with ethynyl-estradiol: EP 148 724 (Schering AG; appl. 18.12.1984; D-prior. 22.12.1983). US 4 621 079 (Schcring AG; 4.1 1.1986; appl. 21.12.1984; D-prior. 22.12.1983). medical use for treatment of P-TGF dependent tumors: EP 399 631 (Schering AG; appl. 17.5.1990; D-prior. 17.5.1989). tramdermal delivery system: EP 370 220 (Schering AG; appl. 11.10.1989; D-prior. 27.10.1988). Formulation(s): drg. and tabl. 75 pg in combination with 30 pg ethynylestradiol Trade Name(s): D: Femovan (Schering; 1987)- comb. with ethynylestradiol Minulet (Wyeth)-comb. F: Harrnonet (Wyeth- Lederle)-comb. with ethynylestradiol Meliane (&hering)-comb. with ethynylestradiol Minulet (Wyeth-Leder1e)- comb. with ethynylestradiol Moneva (&hering)-comb. with ethynylestradiol Phaeva (Schering)-comb. I: with ethynylestradiol Tri-minulet (Wyeth)-comb. with ethynylestradiol GB: Fernodene (Schering; 1987)-comb. with ethynylestradiol Minulet (Wyeth; 1997)- comb. with ethynylestradiol Triadene (Schering)-comb. with ethynylestradiol Ginoden (Schering; 1987)- comb. with eth ynylestradiol Milvane (&hering)-comb. wilh ethynylestradiol Minulet (Wyeth; 1988)- comb. with ethynylestradiol Il-iminulet (Wyeth)-comb. with ethynylestradiol 962 G Gestonorone caproate Gestonorone caproate (Gestronol hexanoate) ATC: G04C Use: progestogen (for treatment of prostate hypertrophy RN: 1253-28-7 MF: C2,H3,04 MW: 414.59 EINECS: 215-010-2 LD,,,: >10 glkg (M, p.0.); >10 glkg (R, p.0.) CN: 17-[(I -oxohexyl)oxy]-l9-norpregn-4-ene-3,20-dione 17-hydroxy-19- norprogesterone (from 38-hydroxy-20-0x0-5,16- pregnodiene; cf. pregnenolone synthesis) 0' - p-tolueneaulfonic '"iCH3 mid copraic anhydride Geslonorone coproote DE 1 074 582 (Schering AG; appl. 24.9.1958). Popper, A. et al.: Arzneh-Forsch. (ARZNAD) 19,352 (1969). (also starting material). Formulation(s): amp. 200 mg Trade Namefs): D: Depostat (Schering); wfm GB: Depostat (Schering); wfm I: Depostat (Schering) F: Depostat (SEPPS); wfm generic J: Depostat (Nihon Schering) Gestrinone ATC: G03D; G03XA02 Use: orally active progestogen (for treatment of endometriosis), antigonadotropin RN: 16320-04-0 MF: C2,H2402 MW: 308.42 CN: (l7a)- 13-ethyl-17-hydro~y-18,19-dinorpregna-4,9,1 I-trien-20-yn-3-one 3. N-bromo- succinirnide CH3 CH3 3.5.17-trioxo-1 1 - brorno- 13-ethyl- 4.5-secogon-9-ene Gestrinone G 963 C H & 1. 2. CH3-MgBr, HCeCH &H . (COOH), / b 0 ' 1. ethylene glycol. oxalic acid 2. methylrnognesiurn (0 / 13-ethyigona- 3.3-ethylenediouy- 4.9,l 1-triene- bromide, ocetylene (11) 13-ethyl-17@-hydroxy- 3.17-dione (I) Gestrinone CH CH '1' 1 P(OC,H5), &OH 2 ~0; acetone .SO. & HCOOW HCIO, 1 triethyl phosph~te . 0 ' 0 ' 13-ethyl-? 7- ethynyl-11@,17@- dihydroxygano- 4.9-diene-3-one Reference(s): a DE 1 593 307 (Roussel-Uclaf; appl. 1966; F-prior. 1965). b DE 1 618 810 (Roussel-Uclaf; appl. 1967; F-prior. 1966). alternative synthesis: DOS 2 212 589 (Roussel-Uclaf; appl. 15.3.1972; F-prior. 19.3.1971). GB 1 069 709 (Roussel-Uclaf; appl. 1966; F-prior. 1964). synthesis of 13P-ethyl-4,9,1l -gonatriene-3,17-dione: FR 1 526 962 (Roussel-Uclaf; appl. 6.1.1967). alternative synthesis: NL 6 517 141 (Roussel-Uclaf; appl. 1965; F-prior. 1964). 964 G Gitaloxin synthesis of 3,5-dioxo-13-ethyl-17~-hydroxy-4,5-secogon-9-ene: NL 6 414 702 (Roussel-Uclaf; appl. 1965; F-prior. 1963, 1964). GB 1 096 761 (Roussel-Uclaf; appl. 1964; F-prior. 1963). synthesis of 13-ethyl-17-ethynyl-1 lP,17P-dihydroxygona-4,9-diene-3-one: FR-M 5 435 (Roussel-Uclaf; appl. 1966). Formulation(s): cps. 2.5 mg Trade Name(s): GB: Dimetriose (Florizel) I: Dimetrose (Poli) Gi taloxin (1 6-Fonnylgitoxin) ATC: COl AA Use: cardiac glycoside RN: 3261-53-8 MF: C4,HMOIS MW: 808.96 EINECS: 221-864-7 LDso: 28.7 g/kg (M, p.0.); 29.960 mglkg (R, p.0.) CN: (3P,5P, 1 6P)-3-[(O-2,6-dideoxy-P-D-ribo-hexopyranosyL(1 +4)-0-2,6-dideoxy-P-D-ribo-hexopyranosyl- (1 +4)-2.6-dideoxy-P-D-ribo-hexopyranosy1)oxyl- 16-(fonny1oxy)- 14-hydroxycard-2q22)-enolide + HCOOH OH Reference(s): DE 1 026 3 12 (Boehringer Mannh.; appl. 1955). extraction from Digitalis purpurea: DOS 1 042 838 (Boehringer Mannh.; appl. 1958). mixed crystals with digitoxin: DE 1 140 315 (Boehringer Mannh.; appl. 1961). injection solution: BE 618 160 (Christians; appl. 25.5.1962). review: Georges, A. et al.: Therapie (THERAP) 18, 209 (1963). Formulation(s): tabl. 0.1 mg Trade Name(s): F: Cristaloxine (Sedaph); wfm r Gitoformate G 965 Gitoformate (Pentaforrnylgitoxin) ATC: COlAA09 Use: cardiac glycoside RN: 10176-39-3 MF: C4,HMOI9 MW. 921.00 EINECS: 233-450-3 LD,: 23.9 mdkg (M, p.0.); 39.01 mglkg (R, p.0.) CN: (3~,5~,16~)-3-[(0-2,6-dideoxy-3,4-di-O-formyl-~-~-ribo-hexopyranosyl-(1+4)-0-2,6-dideoxy-3-0- formyl-P-D-ribo-hexopyranosyl-(1 +4)-2,6-dideoxy-3-0-formyl-~-~-ribo-hexopyranosyl)oxy]-l6- (formy1oxy)- 14-hydroxycard-20(22)-enolide HCOOH formic acid Rtference(s): BE 625 447 (Manufacture de Produits Pharmaceutique; appl. 28.1 1.1962). Formulation(s): tabl. 0.04 mg, 0.06 mg Trade Name(s): D: Dynocard (Madaus); wfm I. Formiloxine (Menarini); wfm Glafenine ATC: N02RG03 Use: analgesic, anti-inflammatory RN: 3820-67-5 MF: Cl,H,,ClN2O, MW: 372.81 EINECS: 223-315-7 LD,,: 1486 mgkg (M, p.0.); 2300 mgkg (R, p.o.1 CN: 2-[(7-chloro-4-qu1nolinyl)amino]benzoic acid 2,3-dihydroxypropyl ester ? chloride 4-hydroxymethyl- 966 G Glaziovine (1) 4,7-dichlaro- Glafenine quinoline Rr;ference(s): US 3 232 944 (Roussel-Uclaf; 1.2.1966; F-prior. 20.8.1962). FR-M 2 41 3 (Roussel-Uclaf; appl. 20.1 1.1962; prior. 20.8.1962). anthranilic acid monoglyceride,from isatoic anhydride: E-appl. 678 (Pierre Fabre; appl. 18.7.1978; F-prior. 26.7.1977). F;irmulatiort(s): suppos. 500 mg; tabl. 200 mg Trude Name(s): D: Gliianan (Albert-Roussel); Glifanan (Roussel); wfm I: Glifan (Roussel- w fm Privadol (Roland-Marie); - Maestretti); wfm F: Adalgur (Rousse1)-comb.; wfm J: Glifanan (Nippon Roussel) wfm Glaziovine ATC: N05B Use: tranquilizer RN: 17127-48-9 MF: C,,H,,NO, MW: 297.35 CN: (i)-2',3',8',8'a-tetrahydro-6'-hydroxy-5'-metloxy-1'-methylspiro[2,5-cyclol~exadiene-l,7'(1'H)- cyclopent[ij]isoquinolin]-4-me H3C-0 polyphosphoric acid H$/O~, H3C-0 q\ CH3 + HO CH3 COOH 0 , I rneihoxyrneihylene- triphenylphosphorane 6.7-dirnethoxy-2-methyl- 1.2.3.4-tetrahydroisoquino- line- 1 -acetic acid 0 0 ~~~"v cH3 ,c-so, H.0 '3. 9- H,C,~~~, . Koc(cH,), - HO rnethanesulfonic CH3 methyl vinyl potassium ' I' /" acid OHC ketone tert-butylate H3C Glibenclamide G 967 1. pyridine 2. Br2. tier. CH3CooH . H3cKy$\ CH3 B r 0 Reference(s): DOS 2 363 53 1 (Siphar; appl. 20.12.1973; CH-prior. 22.12.1972). GB 1 459 210 (Siphar; valid from 18.12.1973; CH-prior. 22.12.1972). alternative syntheses: US 3 886 166 (Siphar; 27.5.1975; CH-prior. 22.12.1972, 26.2.1973). DOS 2 363 529 (Siphar; appl. 20.12.1973; CH-prior. 22.12.1972,26.2.1973). Kametani, T. et al.: Tetrahedron Lett. (TELEAY) 1973, 4219. DOS 2 363 530 (Siphar; appl. 20.12.1973; CH-prior. 22.12.1972). isolation from the leaves of Ocorea glaziovii: Gilbert. B. et al.: J. Am. Chem. Soc. (JACSAT) 86, 694 (1964). Formulation(s): tabl. 200 mg Trade Name(s): I: Suavedol (Simes); wfm Glibenclamide (Gly buride) ATC: AlOBBOl Use: antidiabetic RN: 10238-21-8 MF: C2,H2,CIN,0sS MW: 494.01 EINECS: 233-570-6 LDs,: 3250 mgkg (M, p.0.); >20 gkg (R, p.0.); >10 gkg (dog, p.0.) CN: 5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide 2-phenyl- chloride ethylornine 5-chloro-2-meth- oxybenzoic ocid 968 G Glibornuride 1. CIS03H U 2. NH, OCN~ I * 1 chlorc- "'eH cyclohexyl sulfonic 0-CH, acid isocyanote I Glibenclarnide Aumiiller, W. et al.: Arzneim Forsch. (ARZNAD) 16, 1640 (1966). DE 1 283 837 (Hoechst; appl. 13.7.1967; CDN-prior. 21.7.1966) DE 1 301 812 (Hoechst; appl. 27.7.1965). BE 684 652 (Hoechst; appl. 27.7.1966; D-prior. 27.7.1965). US 3 454 635 (Hoechst; 8.7.1969; appl. 13.7.1966; D-prior. 2.12.1965). Fortnulation(s): tabl. 1.75 mg, 2.5 mg, 3.5 mg, 5 mg Trade Name(s): D: Azuglucon (Azuchemie) Bastiverit (Bastian-Werk) duraglucon (durachemie) Euglucon N (RocheIHMR; 1969) Glimidstada (Stada) F: Gluconorm (Wolff) Glucoreduct (Sanofi Winthrop) Glucoromed (Lichtenstein) Gluco Tablinen (Sanorania) Glucovital (Wolff) GB: Glycolande (Synthelabo) Humedia (APS) Maninil (Berlin-Chemie) I: Praeciglucon (Pfleger) Semi-Euglucon N (Rochel HMR) Semi-Gliben-Puren N (Isis Puren) Daonil (Hoechst) Euglucan (Boehringer Mannh.) Hemi-Daonil (Hoechst) Miglucan (Boehringer Mannh.) Daonil (Hoechst) Euglucon (Hoechst) Semi-Daonil (Hoechst) Daonil (Hoechst) Euglucon (Boehringer Mannh.) Gliben (Gentill) Glibomet (Guidotti)-comb Gliboral (Guidotti) Glucomide (Lipha)-comb. combination preparat~ons J: Daonil (Hoechst) Euglucon (Yamanouchi) USA: Diabeta (Hoechst Marion Roussel) Glynase (Pharmacia & Upjohn) Micronase (Pharmacia & Upjohn) Glibornuride ATC: AIOBB04 Use: antidiabetic RN: 26944-48-9 MF: C,,H,,N,O,S MW: 366.48 EINECS: 248-124-6 LDso: >20 glkg (M, p.0.); 18 glkg (R, p.o.1 CN: [1S-(endo,endo)]-N-[[(3-hydroxy-4,7,7-trimethylbicyclo[2.2.l]hept-2-yl)amino]carbonyl]-4- methylbenzenesulfonamide Gliclazide G 969 ,,,\J H 2 4 ,,,,,,, + HO pyridine ___* OH CH3 CH3 Reference (s): DE 1 695 201 (Hoffmann-La Roche; appl. 21.9.1967; CH-prior. 28.10.1966,24.4.1967, 17.7 US 3 654 357 (Roche; 4.4.1 972; CH-prior. 26.4.1968). US 3 787 491 (Hoffmann-La Roche; 22.1.1974; prior. 29.9.197 1). US 3 860 724 (Hoffmann-La Roche; 14.1.1975; prior. 29.9.197 1). H H CH3 CH3 3endo-amino- ethyl 4-toluenesulfonyl- Formulation(s): tabl. 25 mg Glibornuride Trade Naine(s): D: Gluborid (Griinenthal) F: Glutril (Roche; 1972) Glutril (ICN; 1972) GB: Glutril (Roche; 1975); wfm 0-borneol corbarnote Gliclazide ATC: AIOBB09 Use: antidiabetic RN: 21 187-98-4 MF: Cl,H,,N303S MW: 323.42 EINECS: 244-260-5 LD,: 295 mglkg (M, i.v.); 3 g/kg (M, p.0.); 382 mgkg (R, i.v.); 3 glkg (R, p.0.) CN: N-[[(hexahydrocyclopenta[c]pyrrol-2(1H)-namide NoN02, HCI LiAIH, 3-amino-3- ozabicyclo- [3.3.0]octone (I) ethyl 4-toluene- sulfonylcorbarnate I Gliclozide I Referencefs): US 3 501 495 (Science Union; 17.3.1970; GB-prior. 10.2.1966). FR 1 510714 (Science Union; appl. 9.2.1967; GB-prior. 10.2.1966). Formulation(s): tabl. 40 mg, 80 mg Trade Name(s): D: Diamicron (Servier F: Diamicron (Servier) I: Diabrezide (Molteni) Deutschland) GB: Diamicron (Servier) Diamicron (Servier) 970 G Glimepiride - J: Glimicron (Dainippon) Glimepiride (Hoe 490) ATC: AlOBBl2 Use: insulin-sparing sulfonylurea, antidiabetic RN: 93479-97- 1 MF: C,,H3,N,0,S MW: 490.63 CN: 1ratzs-3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(4- methylcyclohexyl)amino]carbonyl]amino]sulfonyl]pheny1]ethyl]-2-oxo- 1 H-pyrrole-1-carboxamide H H 1. CIS03H ,I 1. chlorosu- H3C fonic acid 3-ethyl-4- 2-phenylethyl methyl-A'- isocyanate pyrrolin-2-one H OCN (1) trans-4-methyl- cyclohexyl isacyonate Glimepiride DE 2 951 135 (Hoechst AG; appl. 25.6.1981; D-prior. 19.12.1979). preparation oj'3-ethyl-4-methyl-A3-pyrrolin-2-one Siedel: Justus Liebigs Ann. Chem. (JLACBF) 554, 144, 155 (1943). Plleninger; Decker: Justus Liebigs Ann. Chem. (JLACBF) 598, 198,205 (1956). Bishop, J.E.; Nagy, J.O.; O'Connell, J.F.; Rapoport, H.: J. Am. Chem. Soc. (JACSAT) 113 (21), 8024 (1991). Schoenleber, R.W.; Kim, Y.; Rapoport, H.: J. Am. Chem. Soc. (JACSAT) 106 (9), 2645 (1984). Tipton, A,; Ligthner, D.A.: Monatsh. Chem. (MOCMB7) 130 (3), 425 (1999). for treatment of'arteriosclerosis: EP 604 853 (Hoechst Japan; appl. 6.7.1994; J-prior. 28.12.1992). jbrmulation: EP 649 660 (Hoechst AG; appl. 26.4.1995; D-prior. 26.1.1993). controlled release: DE 4 336 159 (Hoechst AG; appl. 27.4.1994; D-prior. 22.1.1993). Jbr trmtnlent of'obesiiy: WO 9 303 724 (Upjohn Co.; appl. 4.3.1993; USA-prior. 26.8.1991). Formulation(s): tabl. 1 mg, 2 mg, 3 mg, 4 mg Trade Name(s): D: Amarel (Hoechst) USA: Amaryl (~oechst Marion F: Amarel (Hoechst HoudC) Roussel) . 1 6P )-3 -[ (O-2,6-dideoxy-P-D-ribo-hexopyranosyL(1 +4 )-0 -2 ,6-dideoxy-P-D-ribo-hexopyranosyl- (1 +4 )-2 .6-dideoxy-P-D-ribo-hexopyranosy1)oxyl- 1 6-( fonny1oxy )- 14-hydroxycard-2q22)-enolide +. 1632 0-0 4-0 MF: C2,H2402 MW: 308.42 CN: (l7a )- 13-ethyl-17-hydro~y-18,19-dinorpregna-4,9,1 I-trien-20-yn-3-one 3. N-bromo- succinirnide CH3 CH3 3.5.17-trioxo-1 1 - brorno- 13-ethyl- 4.5-secogon-9-ene. (3~,5~,16~ )-3 -[ ( 0-2 ,6-dideoxy-3,4-di-O-formyl- ~-~ -ribo-hexopyranosyl-(1+4 )-0 -2 ,6-dideoxy- 3-0 - formyl-P-D-ribo-hexopyranosyl-(1 +4 )-2 ,6-dideoxy- 3-0 -formyl- ~-~ -ribo-hexopyranosyl)oxy]-l 6- (formy1oxy )- 14-hydroxycard-20(22)-enolide HCOOH formic acid