Pharmaceutical Substances Syntheses, Patents, Applications - Part 87 potx

Flecainide
F
861
hydrochloride
RN: 3717-88-2 MF: C24H25N04. HCI MW: 427.93 EINECS: 223-066-4
LD,,:
28 mgkg (M, i.v.); 740 mgkg (M, p.0.);
25 mglkg (R, i.v.); 1040 mglkg (R, p.0.)
salicylic propiony! P-propionyloxy-
acid chloride benzoic acid
3-propionyl-
salicylic acid
(1)
,
180-190
OC
SOC12
I
+
b
b
n
0
0
sodium
/
CH3
benzoote
benzoic anhydride
0
8-carboxy-3-

methylflavone
Reference(s):
US
2 921 070 (Recordati; 12.1.1960; CH-prior. 5.1 1.1957).
8-chloroformyl- 1-(2-hydraxy-
alternative synthesis:
US
3 350 41 1 (Seceph; 31.10.1967; I-prior. 10.10.1963).
Flavaxate
Formulation(s):
f.
c. tabl. 200 mg; tabl. 100 mg (as hydrochloride)
3-methylflovone
(11)
ethy1)piperidine
Tmde Name(s):
D:
Spasuret (Sanofi Winthrop) 1: Cistalgan (Recordat$
J:
Bladderon (Nippon
F:
Urispas (Negma) comb. Shinyaku)
GB:
Urispas (Shire) Genurin (Recordati) USA: Urispas (SmithKline
Beecham)
Flecainide
ATC: COlBC04
Use: antiarrhythmic
RN: 54143-55-4 MF: C17H,F,N,03 MW: 414.35
CN:

N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
acetate
RN: 54143-56-5 MF: C17H20F,N203
.
C2H402 MW: 474.40
862
F
Fleroxacin
O\\
0
CF3 NOHC03
H2N4
H
0
+
/s\(
-
F~C
o
~~c-0
-I
pyridine
2.5-dihydroxy-
2.2.2-trifluoro- 2.2,2-trifluoroethyl
benzoic acid ethyl trifluoro-
2.5-bis(2.2.2-trifluoro-
methonesulfonote eth0xy)benzoote
(1)
I
Flecoinide

Reference(s):
DE
2 5 13 916 (Riker; prior. 27.3.1975).
US 3 900 481 (Riker; 19.8.1975; prior. 1.4.1974).
US 3 655 728 (Riker; 1
1.4.1972; prior. 22.7.1970).
US 4 005 209 (Riker; 25.1.1975; prior. 27.5.1975).
Bannit, E.H. eta].:
J.
Med. Chem. (JMCMAR)
18,
1130 (1975);
20,
821 (1977).
Fomiulation(s):
amp. 50 rng; tabl. 50 rng, 100 rng (as acetate)
Trade Name(s):
D: Tarnbocor (3M Medica;
GB:
Tarnbocor (3M Health J: Tarnbocor (Eisai)
1982) Care; 1983) USA: Tambocor (3M; 1985)
F:
FlCcai'ne (3M SantC; 1984)
I:
Almarytrn (Synthelabo;
1986)
Fleroxacin
(AM 833; Ro 23-6240; Megalocin)
ATC: JOlMAO8
Use: antibacterial

RN: 79660-72-3 MF: C,,H,,F,N,O, MW: 369.34
LD,,,:
20.4 mglkg (R, i. v.]; >4 glkg (R, p. 0.);
21.7 rnglkg (M, i. v.); >4 glkg (M, p. 0.);
>I
glkg (dog, p. 0.)
CN:
6,8-Difluoro-l-(2-fluoroethyl)-l,4-dihydro-7-(4-rnethyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylicacid
monohydrochloride
RN: 79660-53-0 MF: C,,H,,F,N,O,
.
HCl MW: 405.80
6,7,8-trifluoro-4-
1
-bromo-2-
hydroxy-3-quinoline- fluoroethone
corboxylic acid
(cf. lomefloxocin)
6.7.8-trifluoro-l-
(2-fluoroethy1)-1.4-
dihydro-4-oxoquinoline
3-corboxylic ocid
(I)
Floctafenine
F
863
Reference(s):
'
a
BE

887 574 (Kyorin Pharm.; appl. 19.2.198 1; BE-prior. 19.8.1980).
1
ZA
8 502 065 (Kyorin Pharm.; appl. 20.3 1985; ZA-prior. 20.3.1985).
b
ES
2
010 862 (Inke
S
A.; appl. 13.2.1989).
purification
and
recovery using porous absorbents:
PO8 259 541 (Kyorin Seiyaku; appl. 23.3.1995).
synthesis offluorine-labeled
fleroxacin:
Livni,
E.
et
al.:
Nucl. Med. Biol. (NMBIEO)
20
(I),
883-897 (1993)
N-rnethyl-
Formulation(s):
amp. for inj. 400
mg;
f.
c.

tabl. 200 mg, 400 mg; tab!. 200 mg, 400 mg; v1al400 mg1100
ml
Fleroxocin
Trade Name(s):
D:
Quinodis (Rochel
Griinenthal)
piperozine
Floctafenine
ATC:
N02BG04
Use: analgesic
RN:
23779-99-9 MF: CmHl,F3N204
MW:
406.36 EINECS: 245-881-4
LD,,:
180 mglkg (M, i.v.); 1960 mglkg (M. p.0.):
160 mglkg
(R,
i.v.);
535 mglkg (R, p.0.);
>1 glkg (dog, p.0.)
CN:
2-[[8-(trifluoromethyl)-4-quinolinyl]amino]benzoic
acid 2,3-dihydroxypropyl ester
2-trifluoro-
diethyl ethoxy-
methyl-
methylenemalonote

oniline
864
F
Flomoxef
3-ethoxycarbonyl-4-
hydroxy-8-trifluoro-
methylquinoline
(I)
4-hydroxy-8-
trifluoromethyl-
auinoline
HOTo
O<CH,
H3C
NaH, toluene
-,
111
4-chloro-8- methyl
trifuoromethyl- anthronilate
quinoline
(11)
'33
Floctatenine
DE
1
815 467 (Roussel-Uclal;
appl.
18.12.1968; F-prior. 29.12.1967,29.3.1968, 23.8.1968).
US 3 644 368 (Roussel-Uclaf; 22.2.1972; F-prior. 29.12.1967,23.8.1968).
US 3 818 090 (Roussel-Uclaf; 22.2.1972; prior. 7.7.1971).

Formulation(s):
tabl.
200 mg
Trade Name(s):
D:
Idarac
(Roussel; 1978); F:
ldarac
(Roussel Diamant;
I:
Idarac
(Roussel;
1977)
wfm 1976)
Flomoxef
(6315-S)
ATC: J0lC
Use:
antibacterial
(p-lactam antibiotic)
RN: 99665-00-6 MF: C,,HlRF2N,O7S,
MW:
496.47
CN:
(6R-ci.~)-7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[l-(2-hydroxyethyl)-lH-tetrazol-5-yl]thio]methyl]-
7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
Flomoxef
F
865

@
side choin
I:
NaOC2H5
I.
KOH
Fyc!
0
C2H50H
0
2.
HCI
F
F~s,,~~~~~~
-
F
S-COOH
F
Y
F
chloro-
difluoro-
methane
ethyl (difluoro-
rnethylthio)ocetate
(difluorornethyl-
thio)acetic acid
(I)
ethanalomine carbon
disufide

methyl N-(2-hydroxy-
ethyl)dithiocorbornate (11)
1-(2-hydroxyethy1)-
1H-tetrozole-5-thiol (IV)
8
final product:
NoOCH,, DMF
N-
diphenylrnethyl
7a-banzarnido-3-
chlorornethyl-1 -oxo-
3-cepkm-4-corboxylote
(cf. latomoxef synthesis)
p-rnethyl-
benzyl
chloroforrnote
866
F
Flopropione
hypochlorite
PI"?!;
1.
PC15, pyridine
1.
I,
pyridine
2.
NaHCO,
VII
CH3

~suji, T. et a].: J. Antibiot. (JANTAJ)
38,
466 (1984).
US 4 532 233 (Shionogi; 30.7.1985; J-prior. 23.12.1982).
DOS 3 345 989 (Shionogi; appl. 20.12.1983; J-prior.
23.12.1982).
EP 128 536 (Shionogi; appl. 7.6.1984; J-prior. 14.6.1983).
purification:
DOS 3 503 303 (Shionogi; appl. 31.1.1985; J-prior. 2.2.1984).
Formulation(s):
vial (dry substance for
inj.)
500 mg, lg
Trade Name(s):
J: Flumarin (Shionogi)
Flopropione
ATC: A03A
Use: antispasmodic
RN: 2295-58-1 MF:
C,H,,O, MW: 182.18 EINECS: 218-942-8
LD,,,: 300 mglkg (M, i.v.); 2780 mglkg (M, p.0.);
246 mg/kg (R, i.v.); 2380 mglkg
(R,
p.0.)
CN: 1
-(2,4,6-trihydroxypheny1)-
1-propanone
Florantyrone
F
867

phloroglucinol propionitrile Flopropione
Reference(s):
Canter et al.:
J.
Chem. Soc. (JCSOA9) 1931, 1245.
Shinoda,
K.:
Yakugaku Zasshi (YKKZAJ) 35,235 (1927).
Howells et a].: J. Am. Chem. Soc. (JACSAT) 54, 2451 (1932).
pharmacology:
Cahen,
R.;
Boucherie, A,: C. R. Seances Soc. Biol. Ses Fil. (CRSBAW) 157, 112 (1963).
Formukztion(s):
cps. 40 mg; gran. 80 mg/g, 160 mg/g
Trade Name(s):
J:
Chlonarin (Kanebo) Cospanon (Eisai)
Colenfupan (Nichiiko) Pasmus (Daiichi)
generic
Florantyrone
ATC: A03A
Use: choleretic
RN: 519-95-9 MF: C2,H1,O3 MW: 302.33 EINECS: 208-279-2
CN:
y-0x0-8-fluoranthenebutanoic
acid
succinic fluoronthene
onhydride
I

Florantyrone
Reference(s):
US
2
560 425 (Miles Labs.; 195 1; prior. 1948).
Trade Name(s):
I:
Bilyn (Janus); wfm Idroepar (Beolet); wfm USA: Zanchol (Searle); wfm
Cistoplex (Borromeo); wfm
J:
Zanchol (G.D Dainippon)
Floredil
ATC: COlDB
Use: coronary vasodilator
RN: 53731-36-5 MF: Cl,H2,N0, MW: 295.38
CN:
4-[2-(3,5-diethoxyphenoxy)ethyl]morpholine
868
F
Flosequinan
2-morpholino- 3,5-diethoxy-
I
Floredil
ethyl chloride phenol
Reference
(s):
DOS
2 020 464 (Orsymonde; appl. 27.4.1970; GB-prior. 29.4.1969).
Fnrmulation(s):
cps.

200
mg
Trude
Name(s):
F:
Carfonal (Lafon);
wfm
Flosequinan
(BTS
49037;
BTS
49465)
ATC: COlDBOl
Use:
vasodilator, antihypertensive
RN:
76568-02-0
MF:
CllH,oFN02S
MW:
239.27
CN:
7-Fluoro- 1
-methyl-3-(methylsulfiny1)-4(1H)-quinolinone
cu, cuc12.
H20
F
H
COCI~
FaC'

+
H2N-CH1
b
+
I
COOH
2-chloro-4-fluoro
benzoic ocid
4-fluoro-N-
methylonthranilic
ocid
7-fluoro-1 -methyl- trirnethyl-
3.1
-benzoxozine- sulfoxonium
2.4-dione
(I)
iodide
trimethyl
orthoformate
(111)
dirnethyloxosulfonium
4-fluoro-2-(methylomino)-
benzaylmethylide
(11)
I
Flosequinan
I
Fluanisone
F
869

111
I
+
II
Flosequinan
0
-
Fq3,cH3
-
0 0
dirnsyl sodium
1
-[4-fluoro-2-
(methylomina)phenyl]-
2-(methylsulfinyl)-
ethanone
"Q""
+
3-fluoro-
aniline
phxO-ph
IV
d
diphenyl
ether
Reference
(s):
methyl (methylthi0)-
acetate
methyl 3-(3-fluoro-

aniline)-2-(methylthb-
acrylate (IV)
?\
1.
H3C,
,S/O'CH~
0
\b
2.
MCPBA.
CHZCIZ
-
Flosequinan
1.
dimethyl sulfate
0
2.
3-chloroperbenzoic
acid
a
DE
3
011 994 (Boots; appl. 27.3.1980; GB-prior. 27.3.1979).
b,cBirch, A.M. et al.: J. Chem. Soc., Perkin Trans. 1 (JCPRB4)
1994,
387.
EP317 149 (Boots; appl. 7.1 1.1988; GB-prior. 18.11.1987).
Formulation(s):
tabl. 50 mg, 100 mg
Trade

Name(s):
GB:
Manoplax (Boots)
Fluanisone
ATC: NOSAD09
Use:
neuroleptic
RN:
1480-19-9 MF: C2,H2,FN202 MW: 356.44 EINECS: 216-038-8
LDg: 25 mgikg (M, i.v.); 550 mglkg (M, p.0.);
20 mgkg (R. i.v.)
CN:
l-(4-fluorophenyl)-4-[4-(2-methoxyphenyl)-l-piperazinyl]-l-butanone
I
-(2-rnethoxy- 4-chloro-4'-fluoro-
Fluonisone
pheny1)piperazine butyrophenone
870
F
Fluazacort
Reference(s):
DAS 1 185 6 15 (Janssen; appl. 25.3.1960; USA-prior. 26.3.1959).
US 2 997 472 (Janssen; 22.8.1961; prior. 26.3.1959).
Formulation(s):
sol. 6.25 rnglrnl
Trade Name(s):
D: Sedalande (Delalande);
F:
Saalande (Delalande);
wfrn wfrn

Fluazacort
(Azacortid)
ATC: D07AB
Use: topical glucocorticoid, anti-
inflammatory
RN:
19888-56-3 MF: C,sH,oFNO, MW: 459.51 EINECS: 243-400-2
LD,,,: 54
mgkg (M, s.c.);
580 rnglkg (R, s.c.)
CN: (1
1~,16~)-21-(acetyloxy)-9-fluoro-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[l7,16-d]oxazole-3,20-
dione
3p-ocetoxy-11.20-
dioxo- 16-pregnene
(from hecogenin.
cf. olfoxolone
synthesis)
pyridine
+
I
1.
NoBH,
2.
HCI, CHJOH
CH3S02CI,
O
CH
DMF,
,

,,
MXN+'HJ
collidine