250 mg as sulfate Trude Names: D: Leukase SmithKline Beecham Sofra Tiill Albert-Roussel, Hoechst F: NComycine Diamant Diaman1-comb.. and more than 50 combination preparations GB: Sofrad
Trang 1Framycetin F 941
H3cL0 CH3 0
+ C'mNco * o f i \ ki H sodium nitrite
0 7 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
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
Trang 2942 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)
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
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)
Trang 37
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
' h e r ; 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
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 g h (R, p.0.)
CN: (5a,17~)-17-methylandrostano[2,3-c][1,2,5]oxadiazol-l7-01
HO-NH2 HCI, pyridine
hydrochloride
Reference(s):
U S 3 415 818 (Sterling; 10.12.1968; appl 8.7.1965)
1 .H3CkN/Br pyridine
H
2 PCIS
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)
Trang 4944 F Furazolidone
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 m g k g (R, p.0.)
CN: 3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone
N H 2
2-hydrozino-
ethonol
N H 2
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)
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
Trang 5Fursultiamine F 9 4 5
1 CIS03H
2 NH,
1 chlorosulfonic
acid
2,4-dichloro- 5-sulfomoyl-4.5
bcnzoic acid dichlorobenzoic
ocid
H,N,,fJ
A, diglyme
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)
Use: neurotropic analgesic RN: 804-30-8 MF: C,,H,,N,O& MW: 398.55 EINECS: 212-357-1
LDS,,: 430 m g k g (M, i.v.); 2200 mglkg (M, p.0.);
2200 mgkg (R, p.0.)
furanyl)methyl]dithio]-1-butenyllformamide
Trang 6946 F Fursultiamine
N CH,
NaOH
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);
J: Alinamin F (Takeda)
Trang 7Gabapentin G 9 4 7
(GOE 2450; G o 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)
I Gabapentin
1 , l -cyclahexane- diacetic anhydride (1U)
V
dimethyl malonate dimethyl cycla-
Trang 8948 G Gabapentin
ethyl diethyl- phosphinylacetate
ethyl cyclo- hexylidene- acetate (VI)
KZC03, DMSO, 0JCH3 Hz Pd-C,
ethyl 1 -(nitro- methyl)cyclo- hexaneacetate
1 H3C-CN
2 KCN, HCN
1 acetanitrile
1 oq HCI
2 ion exchange
E l
CN HCI, ethanol,
toluene
1 -cyanacycla- hexoneacetonitrile
1 NaOH CHjOH Hz, Rh-Pd-C
2 HCI
1 -cyanocyclo- hexoneacetic
Trang 9Gabexate G 949
LiCI H20, 1 . r " , KCN, toluene
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:
W O 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)
Use: protease inhibitor RN: 39492-01-8 MF: C,,H,,N,O, MW: 321.38
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
o-guonidinocaproic acid
"
chloride
wguanidina- coproyl chloride (I)
ethyl 4-hydraxy- I Gabexote I
pyridine THF
*
0
Trang 10950 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 ~ g l k g (M, i.v.); 425 mglkg (M, p.0.);
5100 pg/kg (R, i.v.); > I glkg (R, p.0.);
800 ~ g l k g (dog, i.v.)
CN: 2,2',2"-[1,2,3-benzenetriyltris(oxy)]tris[N, N,N-triethyethanaminium] triiodide
1 NoNH2
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