Framycetin F 941 H3cL0 CH3 0 \p,l.NJ,N-~~ NONO,. HCOOH + C'mNco * ofi\ ki H sodium nitrite 07 CH3 formlc ocid Reference(s): EP 117 959 (ADIR; appl. 16.11.1983; F-prior. 17.11.1982). US 4 567 169 (ADIR; 28.1 .l986; F-prior. 17.1 1.1982). synthesis of a-aminoethylphosphonic acid diethyl cster: Berlin, K.D. et al.: J. Org. Chem. (JOCEAH) 33,3090 (1968). Kowalik, J.; Mastalerz, P.: Synthesis (SYNTBF) 1981, 57. Oleksyszyn, J.; Tyka, R.: Tetrahedron LeU. (TELEAY) 22, 2823 (1977) Formulation(s): amp. 208 mg Trade Namels): F: Muphoran (Servier; 1990) Fotemustine I Framycetin (Neomycin B) ATC: ROlAXO8 Use: antibiotic RN: 119-04-0 MF: C23H46N6013 MW: 614.65 EINECS: 204-292-2 CN: 0-2,6-diamino-2,6-dideoxy-a-~-glucopyranosyl(1+4)-0-[0-2,6-diamino-2,6-dideoxy-~-~- idopyranosyl-(1+3)-~-~-ribofuranosyl-(l+5)]-2-deoxy-~-streptamine sulfate (1:3) RN: 4146-30-9 MF: C2,H,N60,3 . 3H2S04 MW: 908.88 EINECS: 223-969-3 I Fromycetin From fermentation solutions of Streptomycesfradiae. 942 F Fumagillin Reference(s): lJS 2 799 620 (Rutgers Res. Found.; 16.7.1957; prior. 29.6.1956). purification: US 2 848 365 (Upjohn; 1958; appl. 1950). US 3 005 815 (Merck & Co.; 24.10.1961; prior. 1955, 1957). US 3 022 228 (S. B. Penick; 20.2.1962; appl. 19.1.1960). US 3 108 996 (Upjohn; 29.10.1963; appl. 30.7.1962). Formulatiort(s): cream 0.5 %; drops 1.25 %; eye drops 0.5 %; ointment 20 mglg; powder 20 mglg; spray 500 mg1203.5 g; tabl. 250 mg (as sulfate) Trude Name(s): D: Leukase (SmithKline Beecham) Sofra Tiill (Albert-Roussel, Hoechst) F: NComycine Diamant (Diaman1)-comb. and more than 50 combination preparations GB: Sofradex (F1orizel)-comb. Soframycin (Hoechst). comb. Sofra-Tulle (Hocchst; as sulfate) 1: Cheliboldo (Terapeutic0)- comb. Crisolax (Lifepharma)- comb. Sofra-tulle (Roussel) J: Dexmy (Takeda) Fradio (Nippon Kayaku) USA: Coly-Mycin (Parke Davis)- comb. Cortisporin (Monarch; as sulfate) Lazersporin-C (Pedinol; as sulfate) NeoDecadron (Merck; as sulfate) Neomycin Sulfate (Roxane) Neomycin Sulfate (Teva) Neosporin (Glaxo Wellcome; as sulfate) Neosporin (Warner- Lambert) Fumagillin ATC: D06A Use: antibiotic RN: 231 10-15-8 MF: C,,H,,O, MW: 458.55 EINECS: 245-433-8 LD,,: 2 glkg (M, p.0.) CN: [3R-[3a,4a(2R*,3R*),5P,6P(all-E)]]-2,4,6,8-decatetraenedioic acid mono[5-methoxy-4-[2-methyl-3-(3- methyl-2-butenyl)oxiranyl~-1-oxaspiro[2.5]oct-6-yl] ester dicyclohexylammonium salt (1: 1) RN: 41567-78-6 MF: C,6H,40, . C,,H,,N MW: 639.87 Furnogillin I From fermentation solutions of Aspergillusfurnigutus. Reference(s): US 2 803 586 (Abbott; 1957; prior. 1953). pur@cation: Tarbell, D.S. et al.: J. Am. Chem. Soc. (JACSAT) 77,5613 (1955). 7 Furazabol F 943 structure and stereochemistry: Chapman, D.D. et al.: J. Am. Chem. Soc. (JACSAT) 82, 1009 (1960). Chapman, D.D. et al.: J. Am. Chem. Soc. (JACSAT) 83,3096 (1961). Tarbell, D.S. et al.: J. Am. Chem. Soc. (JACSAT) 77, 5610 (1955). McCorkindale, N.J.; Sime, J.G.: Proc. Chem. Soc., London (PCSLAW) 1961, 331. 'her; Tarbell, D.S.: Proc. Natl. Acad. Sci. USA (PNASA6) 48,733 (1962). total synthesis: Corey, E.J.; Snider, B.B.: J. Am. Chem. Soc. (JACSAT) 94, 2549 (1972). Trade Name(s): USA: Fugillin (Upjohn); wfm Fumidil (Abbott); wfm Furazabol ATC: A14A Use: anabolic RN: 1239-29-8 MF: C,,,H,,N,O, MW: 330.47 EINECS: 214-983-0 LD,,,: 1731 mglkg (M, p.0.); >4 gh (R, p.0.) CN: (5a,17~)-17-methylandrostano[2,3-c][1,2,5]oxadiazol-l7-01 HO-NH2 . HCI, pyridine . hydroxylornine hydrochloride Reference(s): US 3 415 818 (Sterling; 10.12.1968; appl. 8.7.1965). 1 .H3CkN/Br . pyridine H 2. PCIS I b 1. N-brornoocetornide 2, phosphorus pentachloride further method: H US 3 245 988 (Daiichi; 12.4.1966; J-prior. 10.4.1963, 15.7.1963, 5.12.1963, 12.2.1964). Formulation(s): tabl. 1 mg Trade Name(s): J: Miotolon (Daiichi Seiyaku) 944 F Furazolidone Furazolidone ATC: GOlAX06 Use: topical anti-infective, topical antiprotozoal, chemotherapeutic (trichomonas) RN: 67-45-8 MF: C,H,N,O, MW: 225.16 EINECS: 200-653-3 LD,,,: 1782 mglkg (M, p.0.); 2336 mgkg (R, p.0.) CN: 3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone NH2 2-hydrozino- ethonol NH2 diethyl 3-ornino-2- corbonote oxozolidone Nb / NO, 5-nitrofurfurol 1 Furozolidone Reference(s): US 2 759 931 (Norwich Pharm. Co.; 1956; prior. 1953). US 2 927 110 (Norwich Pharm. Co.; 1.3.19h0; prior. 23.1.1958). Formulation(s): liquid 50 mg/15 ml; tabl. 100 mg Trade Name(s): F: Furoxane (Oberval); wfm Furoxone (Formenti) J: Ginvel (Fujita) Tricofuron (Oberval); wfm . Ginecofuran (Crosara)- Medaron (Yamanouchi) GB: Furoxone (Eaton); wfm comb. Purazolin T (Hokuriku) I: Furadone (Vebi) Tricofur (Formenti)-comb. USA: Furoxone (Roberts) Furosemide (Frusemide) ATC: C03CAO1 Use: diuretic RN: 54-31-9 MF: CI2H,,ClN2O5S MW: 330.75 EINECS: 200-203-6 LD,,,: 308 mg/kg (M, i.v.); 2 g/kg (M, p.0.); 800 mglkg (R, i.v.); 2600 mglkg (R, p.0.); >400 mglkg (dog, i.v.); 2 glkg (dog, p.0.) CN: 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid Fursultiamine F 945 1. CIS03H 2. NH, 1. chlorosulfonic acid 2,4-dichloro- 5-sulfomoyl-4.5. bcnzoic acid dichlorobenzoic ocid H,N,,fJ . A, diglyme . furfurylamine Reference(s): US 3 058 882 (Hoechst; 16.10.1962; D-prior. 28.12.1959). DE 1 122 541 (Hoechst; appl. 28.12.1959). akernative syntheses: DE 1213 846 (Hoechst; appl 13.4.1963). DE 1 220 436 (Hoechst; appl. 21.10.1 964). DE 1 277 860 (Hoechst; appl. 4.5.1966) DE 1 295 566 (Hoechst; appl. 23.3.1968). DAS 1 806 581 (Hoechst; appl. 2.1 1.1968). review: Sturm, K. et al.: Chem. Ber. (CHBEAM) 99, 328 (1966). Furosemide Formulation(s): amp. 80 mg, 500 mg; s. r. cps. 30 mg, 60 mg, 120 mg; sol. 20 mg, 40 mg, 50 mg, 250 mg (as sodium salt); tabl. 20 mg, 25 mg, 40 mg Trade Narne(s): D: Diurapid (Jenapharm) durafurid (durachemie) Furanthril (medphano) F: Furesis (Bristol-Myers Squibb)-comb. furo (ct-Arzneimittel) Furo-Puren (Klinge- Nattermann Puren) GB: Furorese (Hexal) Furosemid (ratiopharm; Riker; Stadapharm) 1: Fusid (GRY) Hydro-Rapid-Tablinen (Sanorania) Lasix (Hoechst) Odemase (Azupharma) Osyrol (Hoechst)-comb. Sigasalur (Siegfried) J: generic and combination preparations Aldalix (Momanto)-comb. Furos6mide (Biogal6nique) Lasilix (Hoechbt) Logirkne (Pharmacia & Upjohn)-comb. Lasix (Hoechst) numerous combination preparations Fluss (Rousse1)-comb. Lasitone (Hoechst Italia Sud)-comb. Lasix (Hoechst) Lasix Reserpin (Hoechst)- comb. Spirofur (Lepetit)-comb. generics Accent (Toyama) Arasemide (Arakawa) Diusemide (Nakataki) Diuzol (Wakamoto) Franyl (Seiko Eiyo) Fuluvamide (Kanto) Furfan (Nippon Roussel- Chugai) Kutrix (Kyowa) Lasix (Hoechst) Lowpston (Maruko) Polysquall A (Tokyo Hosei) Profemin (Toa Eiyo- Yamanouchi) Protargen (Ohta) Radonna (Nippon Kayaku) Rasisemid (Kodamaj Urex (Mochida) USA: Lasix (Hoechst Marion Roussel) Fursultiamine ATC: All Use: neurotropic analgesic RN: 804-30-8 MF: C,,H,,N,O& MW: 398.55 EINECS: 212-357-1 LDS,,: 430 mgkg (M, i.v.); 2200 mglkg (M, p.0.); 2200 mgkg (R, p.0.) CN: N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-l-methyl-2-[[(tetrahydro-2- furanyl)methyl]dithio]-1-butenyllformamide 946 F Fursultiamine N CH, NaOH Ho4N4x cl- d CH, NH2 CH, NH2 thiamine sodium S-tetrahydro- furfuryl thiosulfate Fursultiarnine US 3 016 380 (Takeda; 9.1.1962; J-prior. 16.8.1957). Forrnulation(s): amp. 5 mglml; drg. 50 mg; tabl. 5 mg, 25 mg, 50 mg Trade Narne(s): D: Dolo-judolor (Woe1m)- judolor-Dragees (ICN); . judolor Dragees (Woelm); comb.; wfm wfm wfm J: Alinamin F (Takeda) Gabapentin G 947 Gabapentin ATC: ~03~x12 (GOE 2450; Go 3450; CI 945) Use: anticonvulsant RN: 60142-96-3 MF: CyH17N02 MW: 171.24 EINECS: 262-076-3 CN: I-(Aminomethyl)cyclohexaneacetic acid hydrochloride RN: 60142-95-2 MF: CyH17N02 . HC1 MW: 207.70 EINECS: 262-075-8 cyclo- ethyl cyanoacetate hexonone (I) 1.1 -cyclohexane- diacetic acid NH,-OH - HCL 0 b benzenesulfonyl NaOH, H20, 100aC (Lossen rearrangement) IV - I Gabapentin 1 ,l -cyclahexane- diacetic anhydride (1U) V dimethyl malonate dimethyl cycla- hexylidenemalonate 948 G Gabapentin ethyl diethyl- phosphinylacetate KOH, THF doncH3 ethyl cyclo- hexylidene- acetate (VI) KZC03, DMSO, 0JCH3 Hz. Pd-C, 9SaC ethanol VI + H3C-NO, d VII ethyl 1 -(nitro- methyl)cyclo- hexaneacetate 1. H3C-CN 2. KCN, HCN I + 1. acetanitrile 1. oq. HCI 2. ion exchange _____, Gabopentin El CN HCI, ethanol, toluene 1 -cyanacycla- hexoneacetonitrile 1. NaOH. CHjOH Hz, Rh-Pd-C. 2. HCI VIlI - Gabapentine 1 -cyanocyclo- hexoneacetic acid -Y" ' Gabexate G 949 LiCI. H20, 1.r" , KCN, toluene DMSO. 150°C 0JCH3 2. HP, ~h-c Gabapentine 1. benzyl alcohol ethyl (I-cyano- Reference(s): a DE 2 61 1 690 (Goedecke; D-prior. 19.3.1976). US 4 152 326 (Warner-Lambert; 1.5.1979; D-prior. 19.3.1976). b EP 358 092 (Lonza; appl. 29.8.1989; CH-prior. 1.9.1988). c EP 414 274 (Goedecke AG; appl. 24.8.1990; D-prior. 25.8.1989). d US 5 319 135 (Warner-Lambert; 7.6.1994; USA-prior. 25.8.1989). EP 414 262 (Warner-lambert; appl. 24.8.1990; USA-prior. 25.8.1989). e CA 2 030 107 (I7.5.199l; appl. 15.1 1.1990; CH-prior. 16.1 1.1989). preparation of alternale crystal forms: WO 9 828 255 (Teva Pharm.; appl. 24.12.1997; IL-prior. 24.12.1996). high-purity monohydrate: EP 340 677 (Warner-Lambert; appl. 28.4.1989; USA-prior. 2.5.1988). Formulation(s): cps. 100 mg, 300 mg, 400 mg Trade Name(s): D: Neurontin (Parke Davis) GB: Neurontin (Parke Davis) USA: Neurontin (Parke Davis) F: Neurontin (Parke Davis) I: Neurontin (Parke Davis) Gabexate ATC: B02AB49 Use: protease inhibitor RN: 39492-01-8 MF: C,,H,,N,O, MW: 321.38 CN: 4-[[6-[(aminoiminomethyl)amino]-1-oxohexyl]oxy]benzoic acid ethyl ester monomesylate RN: 56974-61-9 MF: C,,H,,N,O, . CH,O,S MW: 417.48 LD,,: 218mg/kg(M, i.v.); 8 glkg (M, p.0.); 4020 mgkg (R, I.v.); 6480 mg/kg (R, p.0.) Y HOOC-# NH, o-guonidinocaproic acid " chloride wguanidina- coproyl chloride (I) ethyl 4-hydraxy- benzoate I Gabexote I pyridine. THF ____* 0 950 C; Gallamine triethiodide Reference(s): DOS 2 050 484 (Ono; appl. 14.10.1970; J-prior. 14.10.1969). US 3 751 447 (Ono; 7.8.1973; J-prior. 14.10.1969). Formi~lation(s): amp. 100 mgI5 rnl (as mesylate) Trade Name(s): J: Foy (Ono; 1978) Gallamine triethiodide ATC: M03 Use: muscle relaxant, ganglionic blocker RN: 65-29-2 MF: C,,,H,,I,N,O, MW: 89 1.54 EINECS: 200-605-1 LD,,,: 1800 ~glkg (M, i.v.); 425 mglkg (M, p.0.); 5100 pg/kg (R, i.v.); >I glkg (R, p.0.); 800 ~glkg (dog, i.v.) CN: 2,2',2"-[1,2,3-benzenetriyltris(oxy)]tris[N, N,N-triethyethanaminium] triiodide 1. NoNH2 ki060H 2. tCH3 o 1. sodium omide pyrogollol 2. 2-diethylomino- 1,2,3-tris(2-diethylomino- ethyl chloride ethoxy)benzene (1) ethyl iodide Gollomine triethiodide Formulation(s): amp. 20 mglml, 40 mgl2 ml, 40 mglml, 100 mg Trade Name(s): D: Flaxedil (Abbott); wfm J: Gallamine Inj. "Teisan" F: Flaxtdil (Specia); wfrn (Teikoku Kagaku-Nagase) GB: Flaxedil (Concord) USA: Flaxedil (Lederle); wfm . 11 9-0 4-0 MF: C23H46N6013 MW: 614.65 EINECS: 20 4-2 9 2-2 CN: 0-2 ,6-diamino-2,6-dideoxy-a-~-glucopyranosyl(1+4 )-0 -[ 0-2 ,6-diamino-2,6-dideoxy- ~-~ - idopyranosyl-(1+3 )-~ -~ -ribofuranosyl-(l+5) ]-2 -deoxy-~-streptamine. 1 0-1 5-8 MF: C,,H,,O, MW: 458.55 EINECS: 24 5-4 3 3-8 LD,,: 2 glkg (M, p.0.) CN: [3R-[3a,4a(2R*,3R*),5P,6P(all-E)] ]-2 ,4,6,8-decatetraenedioic acid mono[5-methoxy- 4-[ 2-methyl- 3-( 3- methyl-2-butenyl)oxiranyl ~-1 -oxaspiro[2.5]oct-6-yl]. 80 4-3 0-8 MF: C,,H,,N,O& MW: 398.55 EINECS: 21 2-3 5 7-1 LDS,,: 430 mgkg (M, i.v.); 2200 mglkg (M, p.0.); 2200 mgkg (R, p.0.) CN: N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-N-[4-hydroxy-l-methyl- 2-[ [(tetrahydro-2-