Pharmaceutical Substances Syntheses, Patents, Applications - Part 9 pot

Amcinonide
A
8
1
Amcinonide
(Triamcinolone acetate cyclopentanoide)
ATC: D07AC11; H02AB
Use: topical glucocorticoid
RN: 51022-69-6 MF:
C,,H,,FO, MW: 502.58 EINECS: 256-915-2
LDs,: >5 @g (M, p.0.);
>2 glkg (R, p.0.)
CN: (1 1
P,
16a)-21-(acety1oxy)-
16,17-[cyclopentylidenebis(oxy)]-9-fluoro-ll-hydroxypregna-1,4-diene-3,20-
dione
triarncinolone cyclopentanone triarncinolone cyclopentanonide
(I)
Reference(s):
GB 1 442 925 (American Cyanamid; USA-prior. 17.8.1973).
ocetonhydride
DOS 2 437 847 (American Cyanamid; applT 6.8.1974; USA-prior. 17.8.1973).
BE
818 929 (American Cyanamid; appl. 16.8.1974; USA-prior. 17.8.1973).
US 4 158 055 (American Cyanamid; 12.6.1979; USA-prior. 6.6.1975).
Arncinonide
Formulation(s):
cream 0.1
%;
lotion 0.1

%;
ointment 0.1
%
Trade Narne(s):
D: Amciderm (HermaVMerck; Penticort Neomycine USA: Cyclocort (Fujisawa; 1979)
1985) (Wyeth-Leder1e)-comb.
F:
Penticort (Wyeth-Lederle;
I:
Amcinil (Crosara)
1980)
J:
Visderm (Lederle; 1982)
Amezinium metilsulfate
ATC: COlCAOO
Use: selective noradrenergic
antihypotensive
RN: 30578-37-1 MF:
C,,H,,N,O
.
CH,O,S MW: 313.33 EINECS: 250-248-0
LD,,: 28 mgkg (M, i.v.); 1330 mglkg (M, p.0.);
24 mgkg (R, i.v.); 1410 mgkg (R, p.0.);
60 mgkg (dog, i.v.); 100 mglkg (dog, p.0.)
CN:
4-amino-6-methoxy-1-phenylpyridazinium
methyl sulfate
82
A
Amfebutamone

chloride
RN: 51410-15-2 MF: CllH,,CIN,O MW: 237.69
2-butyne-
rnucachloric
1.4-dial acid
hydrazine
C
I
I
NH2
sulfate
pyridozinone
(I)
Reference(s):
Reicheneder, F. et al.: Arsneim Forsch. (ARZNAD)
31
(11), 1.529 (1981).
DE 1 912 941 (BASF; appl. 14.3.1969).
DOS 2 139 687 (BASF; appl. 7.8.1971).
DOS 2 21 1 662 (BASF; appl. 10.3.1972).
DOS 3 1 14 496 (BASF; appl.
10.4.1981).
EP 63 267 (BASF; appl. 31.3.1982; D-prior. 10.4.1981).
4-amino-5- 4-om~no-1-
precursors:
DE 2 100 685 (BASF; appl. 8.1.1971).
Arneziniurn rnetilsulfote
Formulation(s):
amp. 5 mg; tabl. 10 mg
chlaro-1- phenyl-6(1

H)-
phenyl-6(1H)- pyridazinone
pyridozinone
Trade Nanze(s):
D: Regulton (Knoll)
Supratonin (Griinenthal)
Amfebutamone
(Bupropion)
ATC: N06AE
Use: antidepressant
RN: 34911-55-2 MF: C,,H,,ClNO MW: 239.75
LD,,: 544 mg/kg (M, p.0.)
CN:
(+)-
1-(3-chloropheny1)-2-[(I
,1 -dimethylethyl)amino]-1 -propanone
hydrochloride
RN: 31677-93-7 MF: C,,H,,ClNO
.
HCl MW: 276.21 EINECS: 250-759-9
LD,,,: 230 mgkg (M, i.p.); 575 mgkg (M, p.0.);
210 mg/kg (R, i.p.); 600 mglkg (R, p.0.)
I
Amfenac sodium
A
83
3-chloro-
ethylmagnesium
5'-chloro-
benzonitrile

bromide
propiophenone
tert-butyl-
amine
I
Amfebutamone
Rejerence(s):
DOS 2 059 61
8
(Wellcome; appl. 3.12.1970; GB-prior. 4.12.1969).
DOS 2 064 934 (Wellcome; appl. 3.12.1970; GB-prior. 4.12.1 969).
CA 977 778 (Wellcome; appl. 15.1 1.1970).
I
Formulation(s):
s. r. tabl. 100 mg, 150 mg (as hydrochloride); tabl. 75 mg, 100 mg
Trade Name(s):
USA: Wellbutrin (Glaxo
Wellcome)
Zyban (Glaxo Wellcome)
Amfenac
sodium
RN: 61941-56-8 MF: C,,H,,NNaO, MW: 277.26
LD,,: 550 mgkg (M, i.v.); 615 mgkg (M, p.0.);
277 mgkg (R, i.v.1; 31 1 mglkg (R, p.0.)
CN:
2-amino-3-benzoylbenzeneacetic
acid monosodium salt
monohydrate
RN: 61618-27-7 MF:
C,,H,,NNaO,

.
H20 MW: 295.27
amfenac
RN: 51579-82-9 MF: C15H,,N0, MW: 255.27
LD,,: 615 mgkg (M, p.0.);
31 1 mglkg (R, p.0.)
1.
HZ.
Pd-C.
NoOH
2.
NoN02.
HCI
ATC: MOlAB
Use: non-steroidal anti-inflammatory,
analgesic
3.
SKI2
W
2.
sodium
nitrite
phenyl-
3.
tin(ll)
chloride
NH2
ocetone
N
-2

84
A
Amfepramone
Amfenoc sodium
u
Reference(s):
DOS
2
324 768 (Robins; appl. 16.5.1973; USA-prior. 17.5.1972).
US 4 045 576 (Robins; USA-prior. 17.5.1972)
Welstead, W.J. et a].:
J.
Med.
hem.
(JMCMAR)
22,
1074 (1979).
1 -aminoindolin-2-one:
Lora Tamayo,
M.
et al.: Org. Prep. Proced. Int. (OPPIAK) 8,45 (1976)
Trade
Name(s):
J: Fenazox (Meiji Seika)
Amfepramone
(Diethy lpropion)
ATC: A08AA03
Use: appetite depressant
RN: 90-84-6 MF: C13H19N0 MW: 205.30 EINECS: 202-019-1
LD,,: 160 mglkg (M, p.0.);

>400 mgkg (R, p.0.)
CN: 2-(diethylamino)- l -phenyl- 1-propanone
hydrochloride
RN: 134-80-5
MF:
C,3H19N0
.
HC1 MW: 241.76 EINECS: 205-156-5
LD,,,: 50 mglkg (M, i.v.); 385 mglkg
(M,
p.0.);
400 mglkg (R, p.0.)
propiophenone a-bromo-
propiophenone
I
Amfepromone
(
Reference(s):
US
3
001 910 (Temmler-Werke; 26.9.1961; D-prior. 16.4.1958).
Amidephrine mesilate
A
85
Formulafion(s):
cps. 25 mg, 75 mg; s. r. cps. 375 mg; s. r. tabl. 75 mg; tabl. 25 rng, 75 mg
Trade
Name(s):
D: Regenon retard (Tcmmler)
GB:

Tenuate (Synomed)
F:
Moderatan (ThCranol-
Deglaude)
PrCfamone (Dexo)
Tenuate-Dospan (Marion
I:
Merrell)
Amidephrine
mesilate
(Amidefrine mesilate)
Apisate (Wyeth)-comb.; USA: Tenuate (Merrcll-National);
wfm wfm
Tenuate (Merrell); wfm
Tepanil (Riker); wfm
Tcnuate
Dospan (Merrell);
wfrn
Linea
Valeas (Valeas)
Tenuate Dospan (Lepctit)
ATC: R03A
Use: rhinological therapcutic,
vasoconstrictor, sympathomimetic
RN: 1421-68-7 MF:
CloH,6N203S. CH403S MW: 340.42
LD,,,: 190 mgkg
(M, i.v.);
2284 mglkg (M, p.0.);
13 mgkg

(R,
p.0);
1400 gkg (dog, Lv.)
CN:
'
(+)-N-[3-[l
-hydroxy-2-(methylamino)ethyl]phenyl]mcthanesulfonamide
monomethanesulfonate
amidephrine
RN: 37571-84-9 MF: C,,Hl,N,03S MW: 244.32
methonesulfonyl 3-orninooceto-
chloride phenone
3-methylsulfonylornino-
acetophenone
(I)
a-brorno-3-methyl-
a-bcnzylrnethylomino-3-
sulfanylominoocetophenone
rnethylsulfonylorninoacetophenone
(II)
I
Amidephrine mesilote
J
FR-M
3
027 (Mead Johnson; appl. 23.1.1963; USA-prior. 24.1.1962, 14.12.1962).
For-mulation(s):
sol. 0.1
%
Trade Name(s):

GB:
Dricol (Brislol); wfm
86
A
Amidotrizoic acid
Amidgtrizoic acid
(Diatrizoic acid)
ATC: V08AAO1
Use: X-ray contrast medium
RN: 117-96-4 MF: CllHyI,N204 MW: 613.92 EINECS: 204-223-6
LD,,,: 8900 mglkg (M, i.v.);
>12.3 glkg (R, i.v.)
CN:
3,5-bis(acety1amino)-2,4,6-triiodobenzoic
acid
monosodium salt
RN: 737-3 1-5 MF: CllH,I,N2Na04 MW: 635.90 EINECS: 212-004-1
LD,,,: 14 glkg (M, i.v.); >7 gkg (M,R, p.0.);
11.4 glkg (R, i.v.);
13.2 g/kg (dog, i.v.)
meglumine salt
RN: 8064-12-8 MF: C,,H,13N,Na04
.
CllHyI,N,O,~ C,H,,NO, MW: 1445.03
LD,,: 11.5 gkg (M, i.v.);
29.2 mglkg
(R,
i.v.)
Hz.
Pd-C

.6:",
KICIZ
-
potossiumb
02N
H2N dichloro-
reH2
H2N
I
iodate
3.5-dinitrobenzoic acid 3,5-diaminobenzoic acid 3,5-diamino-2.4,6-
triiadobenzaic acid
(I)
ocetic onhydride
I
Amidolrizaic acid
I
0 0
H2S04
I
+
H3CKoKCH3
d
Reference (s):
Larsen, A.A. et al.: J. Am. Chem. Soc. (JACSAT)
78,
3210 (1956).
GB 748 319 (Schering AG; appl. 1954; D-prior. 1953).
GB 782 3 13 (Mallinckrodt; appl. 1955; USA-prior. 1954).
US 3 076 024 (Sterling Drug; 29.1 .l963; appl. 19.2.1954).

DE 1 260 477 (Schering AG; appl. 1954; USA-prior. 1953).
COOH
H3C
1
N
H
IH
salts with amino acids:
DAS 2 261 584 (Dr. F. Kohler Chemie; appl. 15.12.1972).
Formulation(s):
amp. 0.65 glml; inj. sol. 31 %-73
%
Tradv Name(s):
D: Angiografin (Schering)
Gastrografin (Schering)
Peritrast (Kohler; as lysine
salt)
Urografin (Schering)
Urovison (Schering)
F: Angiografine (Schering)
Gastrografine (Schering)
RadiosClectan (Schering)
GB: Gastrografin (Schering
Chemicals); wfrn
Hypaque (Winthrop); wfrn
Urografin (Schering
Chemicals); wfrn
I:
Gastrografin (Schering)-
comb.

Selectografin
(Schering)-
comb.
J:
Urografin (Schering-
Nichidoku Yakuhin)
USA: Cardiografin (Squibb); wfrn
Cystografin (Squibb); wfrn
Gastrografin (Squibb); wfrn
Hypaque-Cysto
(Winthrop); wfrn
Hypaque-Diu (Winthrop);
wfrn
Amifostine
A
87
Hypaque Sodium Reno-M-30 (Squibb); wfm Renovist (Squibb); wfm
(Winthrop); wfm Reno-M-60 (Squibb); wfm Sinografin
(Squibb)-comb.
Meglumine Diatrizoate Reno-M-DIP (Squibb); with adipiodon; wfm
(Squibb); wfm wfm
Amifos
tine
ATC: ~03~~05
(Eth~ophos; Gammaphos; NSC-296961;
WR
272
1)
Use: mucolytic agent, radioprotector,
reduction of cisplatin induced renal

toxicity
RN: 20537-88-6 MF:
CsHlsN203PS MW: 214.23
LD,,,: 557 mg/kg (M, i.v.); 842 mg/kg (M, p.0.);
826 mglkg (R, p.0.)
CN:
2-[(3-aminopropyl)amino]ethanethiol
dihydrogen phosphate (ester)
bromide dihydrobromide
I
I
H
H2"
HzN-N-Br
"
2HBr
tr~sod~um th~ophosphote
dodecohydrate
2-(3-ominopropylamino)ethyl
Reference(s):
DD 289 448 (Amt fiir Atomsicherheit; appl. 29.7.1982; DDR-prior. 29.7.1982).
DD 289 449 (Amt fiir Atomsicherheit; appl. 29.7.1983; DDR-prior. 29.7.1983).
H
Amifastine
composition having improved stability:
WO 9 403 179 (US Bioscience; appl. 30.7.1993; USA-prior. 31.7.1992).
preparation of monohydrate:
JP54 046 722 (Yamanouchi; appl. 12.4.1979; J-prior. 21.9.1977).
preparation via
2-(3-aminopropy1amino)ethyI

bromide:
SU 751 030 (Kortun; 30.6.1981; SU-prior. 4.1.1979).
use forprotection during radio- and chemotherapy:
US 5 298 499 (Res. Triangle Inst.; appl. 5.7.1991; USA-prior. 5.7.1991).
WO 8 907 942 (US Bioscience; appl. 21.2.1989; USA-prior. 23.2.1988).
US 5 167 947 (Southwest Res.
Inst.; appl. 26.10:1989; USA-prior. 26.10.1989).
US 3 892 824 (Southern Res. Inst.; appl. 16.12.1988; USA-prior. 16.12.1988).
use for reducing side effects with
azidothymidine:
WO 9 014 007 (US Bioscience; appl. 9.5.1990; USA-prior. 24.5.1989)
use for prevention of cytostatic alopecia:
DE
3 509 071 (ASTA-Werke; appl. 14.3.1985; D-prior. 29.3.1984).
Formulation(s):
amp. 500 mg; vial 500 mg dry substance for inj.
Trade Name(s):
D: Ethyol (Essex Pharma; GB: Ethyol (Schering-Plough)
1995)
8
8
A
Amikacin
Amikacin
ATC: D06AX12; JOIGB06; SOIAA21
Use: aminoglycoside antibiotic
RN: 37517-28-5 MF: C22H43NJ013 MW: 585.61 EINECS: 253-538-5
LD5,:
280 mgkg (M, i.v.); >6 glkg (M, p.0.)
CN:

(S)-O-3-amino-3-deoxy-~-~-glucopyranosyl-(1+6)-0-[6-amino-6-deoxy-a-u-glucopyranosyl-(l~4)]-
N1-(4-amino-2-hydroxy- l
-0xobuty1)-2-deoxy-D-streptamine
sulfate
(12)
RN: 39831-55-5 MF: C,H,3NS0,3. 2H2S0,
MW:
781.76 EINECS: 254-648-6
LD,,:
18 1 mg/kg (M, i.v.); >I0679 gkg (M, p.0.);
234 mglkg (R, i.v.); >4 glkg (R, p.0.);
383 rnglkg (dog,
i.v.)
kanarnycin
A
(4.
v.)
NH~
~~-(benz~lax~carbon~I)kanarn~cin
A
(I)
I
Arnikacin
LC-)-
y-benzylaxycarbonylornino-
a-hydroxybutyric acid
succinirnido ester
GB
1 401 221 (Bristol Myers; appl. 13.7.1972; USA-prior. 13.7.1971).
DE 2 234

3
15 (Bristol-Myers; appl. 12.7.1972; USA-prior. 27.1.1972. 13.7.1971).
US
3 781 268 (Bristol-Myers; 25.12.1973; prior. 27.1.1972, 13.7.1971).
Kawaguchi,
H.
et al.: J. Antibiot. (JANTAJ) 25, 695 (1972).
Amiloride
A
89
alternative syntheses:
NL
7 401 517 (Bristol-Myers; appl. 4.2.1974; USA-prior. 7.2.1973).
NL
7 414 668 (Bristol-Myers; appl. 11.11.1974; USA-prior. 14.11.1973, 23.5.1974).
US
3 974 137 (Bristol-Myers; 10.8.1976; prior. 23.5.1974).
DOS 2 432 644 (Takeda; appl. 8.7.1974; J-prior. 12.7.1973).
DOS 2 716 533 (Pfizer; appl. 14.4.1977; GB-prior. 14.4.1976).
DOS 2 818 822 (Bristol-Myers; appl. 28.4.1978; USA-prior. 28.4.1977, 20.3.1978).
DOS 2 818 992 (Bristol-Myers; appl. 28.4.1978; USA-prior. 28.4.1977; 20.3.1978).
disulfate pentahydrate:
FR
2 308 373 (Bristol-Myers; appl. 22.3.1976; USA-prior. 23.4.1975).
review:
Kawaguchi, H.; Hiroshi: Drug Action Drug Resist. Bact. (DADRBY) 2,45 (1975).
Formulation(s):
cream 2.5
%,
5

%;
eye drops 0.3
%,
0.5
%;
gel 5.5; vial 100 mg/2 ml, 250 mgl2
ml,
500 mg/2 ml
Trade Name(s):
D: Biklin (Bristol-Myers
Squibb; 1976)
F:
Amiklin (Bristol-Myers
Squibb)
GB: Amikin (Bristol-Myers
Squibb; 1976)
I: Amicasil (Biotekfarma)
Bb-k8 (Bristol; 1978)
Chemacin (CT)
Pierami (Pierrel; 1980)
Likacin (Lisapharma; Sifamic (SIFI)
1981) J: Amikacin Sulfate (Banyu)
Lukadin (San Carlo) Biklin (Banyu-Bristol-
Migracin (SmithKline Myers Squibb)
Beecham) USA:. Amilun (BMS; 1976)
Mikavir (Salus Research;
1986)
Amiloride
ATC: C03DBOl
Use: diuretic, antihypertonic

RN: 2609-46-3 MF:
C,HuClN70 MW: 229.63 EINECS: 220-024-7
CN:
3,5-diamino-N-(aminoiminomethyl)-6-chloropyrazinecarboxamide
monohydrochloride
RN: 2016-88-8 MF: C6HuC1N70
.
HC1 MW: 266.09 EINECS: 217-958-2
YHO
+
CHO
glyoxal 5.6-diaminouracil lumazine 3-aminopyrazine-
2-carboxylic acid
(1)
methanol methyl 3-omino-
methyl 6-chloro-
pyrazine-2-carboxylote 3.5-diaminopyrazine-
2-carboxylate
(U)
90
A
Amineptine
guonidine
I
Arniloride
I
Reference(s):
DE 1 470 053 (Mercle
&
Co.; appl. 28.10.1963; USA-prior. 30.10.1962).

US 3 313 813 (Merck
&
Co.; 11.4.1967; prior. 30.10.1962,7.10.1963).
GB 1 066 855 (Merck
&
Co.; appl. 24.10.1963; USA-prior. 30.10.1962,7.10.1963).
Bicking, J.B. et al.: J. Med. Chem. (JMCMAR) 8,638 (1965).
Cragoe, E.J. et al.:
J. Med. Chem. (JMCMAR)
10,
66 (1967).
improved method for 5,6-diaminouracil:
DOS 2 831 037 (Lonza; appl. 14.7.1978; CH-prior. 20.7.1977).
combination with etacrynic acid:
US 3 781 430 (Merck
&
Co.; 25.12.1973; prior.
30.10.1962,7.10.1963,7.2.1966,
18.2.1969, 21.12.1971).
Fomulation(s):
tabl. 2.5 mg, 5 mg, 10 mg in comb. with hydrochlorothiazide (as hydrochloride)
Trade Name(s):
D: Amiduret (Trommsdorff;
1985)-comb.
Diaphal (Pierre Fabre
Pharma)-comb.
Diursan (TAD)-comb.
Esmalorid (Merck)-comb.
Moducrin (MSD; 1978)-
comb.

Moduretik, -mite (Du Pont
Pharma; 1973)-comb.
Rhefluin, -mite (Kytta-
Siegfried)-comb.
F:
LogirCne (Pharmacia
&
Upjohn SA)-comb.
Modamide (Merck Sharp
&
Dohme; 1973)
Moducren (Merck Sharp
&
Dohme-Chibret; 1979)-
comb.
Modurktic (Merck Sharp
&
Dohme; 1973)-comb.
GB: Amilco (Baker Norton;
1983)-comb. with
hydrochlorothiazole
Burinex
A
(Leo)-comb.
I:
FruCo (Baker Norton)-
comb. USA:
Frumil (RhGne-Poulenc
Rorer; 1983)-comb.
Kalten (Zeneca; 1985)-

comb.
Lasoride (Hoechst; 1987)-
comb.
Moducren (Morson; 198 1)-
comb.
Moduret-25 (Du Pont;
1984)-comb.
Moduretic (Du Pont; 1970)
Navispare
(Novartis)-comb.
Moduretic (Merck Sharp
&
Dohme; 1975)-comb.
Midamor (Merck Sharp
&
Dohme; 1981)
Moduretic (Merck Sharp
&
Dohme; 1981)-comb.
Amineptine
ATC: N06AA19
Use: psychoanaleptic, CNS stimulant
RN: 57574-09-1 MF: C22H27N02 MW: 337.46 EINECS: 260-818-0
LD,,,: 1 15 mglkg (M, i.p.)
CN: 7-[(10,1
l-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)amino]heptoic
acid
hydrochloride
RN: 30272-08-3 MF: C2,HZ7NO,
.

HCI MW: 373.92 EINECS: 250-107-3
LD,,: 405 mglkg (M, p.0.)