Pharmaceutical Substances Syntheses, Patents, Applications - Part 21 doc

Bentiarnine
B
201
2J.4-trihydroxy-
benzoldehyde
H2,Pd-C
I
DL-serine N-(DL-seryl)-2,3,4-
hydrozide
trihydroxybenzaldehyde
hydrazone
(I)
Reference(s):
DE 1 165 607 (Roche; appl. 8.5.1962; CH-prior. 16.6.1961).
US
3
178 476 (Rochc; 13.4.1965; CH-prior. 16.6.1961).
L-form:
US
3
557 292 (Roche; 19.1.1971; appl. 16.8.1968).
DE 1 941 284 (Roche; appl. 13.8.1969; CH-prior. 16.8.1968).
DAS
1
966 821 (Roche; appl. 13.8.1969; CH-prior. 16.8.1968).
Fomularion(s):
cps. 12.5 mg, 14.25 mg, 25
mg,
28.5 mg, 50 mg; dispersible tabl. 12.5 mg 25 mg; s. r. cps.
28.5 mg; tabl. 28.5 mg, 57 mg
Trade Namefs):

D: Madopar (Roche)-comb.
I:
with levodopa
F:
Modopar (Roche)-comb.
with levodopa
GB:
Madopar (Roche)-comb.
J:
with levodopa
Bentiamine
(Dibenthiamine; Dibenzoylthiamine)
Madopar (Roche)-comb.; Madopair (Roche)-comb.
wfm with levodopa
Madopar (Roche)-comb. Neodopasol (Daiichi)-
with levodopa; wfm
comb. with levodopa
EC-doparl (Kyowa Hakko)-
comb. with levodopa
ATC: All
Use: vitamin B,-derivative, neurotropic
analgesic
RN: 299-88-7 MF: CZH2,N4O4S MW: 490.58 EINECS: 206-084-7
LD,:
7480 rnglkg
(M,
p.0.)
CN: benzenecarbothioic acid
S-[2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-
1-[2-

(benzoyloxy)ethyl]-1-propenyl]
ester
thiamine
N-(4-amino-2-methylpyrimidin-
(q
v.)
5-ylrnethy1)-N-(4-hydroxy-1-
methyl-2-mercaptobutl-enyl)-
forrnarnide
(1)
202
B
Bentiromide
Reference(s):
US 2 752 348 (Takeda; 1956; J-prior. 1952).
Matsukawa, T.; Kawasaki, H.: Yakugaku Zasshi (YKKZAJ)
23,
705 (1953).
benzoyl
Trade Name(s):
D: only combination
preparations; wfm
Bentiamine
Bentiromide
ATC: V04c~03
Use: pancreas function diagnostic
RN: 37106-97-1 MF: C23H20N20, MW: 404.42 EINECS: 253-349-8
LD,,: 1020 mgkg (M, i.v.); >6 g/kg (M,
p.0.);
485 mg/kg (R, i.v.); >6 glkg (R, p.0.)

CN:
(S)-4-[[2-(benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl]amino]benzoic
acid
chloride
L-tyrosine benzoyl
chloride
N-benzoyl-L-
tyroeine
(I)
2.
ethyl chloroformate
3.
4-ominobenzoic acid
I
Bentiromide
Benneville, P.L. de et al.: J. Med. Chem. (JMCMAR)
15,
1098 (1 972).
US 3 745 212 (Rohrn
&
Haas; 10.7.1973; appl. 19.1 1.1970).
DE 2 156 835 (Rohm
&
Haas; appl. 16.1 1.1971; USA-prior. 19.1 1.1970).
Formulation(s):
sol. 500 mg/lO ml; tabl. 333 rng
Trade Name(s):
D:
PFT
Roche (Roche); wfm J: PFD (Eisai); wfm USA: Chymex (Adria); wfm

Benzalkonium chloride
B
203
Benzalkonium chloride
RN:
8001-54-5 MF: unspecified MW: unspecified
CN:
benzalkonium chloride
R-OH
mixture of
fatty olcohols
(by hydrogenation of
the mixture of coconut
fatv acids)
ATC: DO8AJO1; D09AA11; R02AA I6
Use: antiseptic, cation active tenside
pH3
1.
CISOJH
0
m,
,
175
"C
2.
NoOH
I1
FH3
-b
R-0-S-ONa

'H3
I
I
R-N,
dimethylornine
0
CH3
benzyl
chloride
Benzalkoniurn chloride
L
Ehrhart, Ruschig
IV,
50.
Guyer et al.: Helv. Chim. Acta (HCACAV)
20,
1462 (1937).
~alston, A.W. et al.:
J.
Am. Chem. Soc. (JACSAT) 69,2095 (1947)
Formulation(s):
nail lacquer
I
oz.; sol. 1 oz.
Trade Name(s):
D:
Baktonium (Bode)
Laudamonium (Henkel)
Ly soform-Killovon
(Ly

soform)
Sagrotan Med (Schiilke
&
Mayr)
and 100 more combination
preparations
F:
Biseptine (Nicholas)-comb.
Chlomre de benzalkonium
ThCramex (ThCramex)
Kenalcol (Bristol-Myers
Squibb)
Pharmatex (InnothCra)
Rhinoflumicin (Zambon)-
comb.
Sparaplaie Na
(MCdicine
VCgetale)
GB: Bradosol (Novartis)
Conotrane
(Yamanowhi)-
.
comb.
Dermol (Dermal)-comb.
Drapolene (Warner-
Lambert)-comb.
Emulsiderm (Dermal)-
comb.
Ionil T
(A1con)-comb.

Oilatum Plus (Stiefe1)-
comb.
Timodine (Reckitt
&
Co1man)-comb.
I:
Alfac (Bracco)
Alfafluorone
(Biotekfarma)-comb.
Atisteril (Ati)
Benzal (Tariff. Nazionale)
Citralkon (Schiapparelli
Salute)
mixture of
N,N-dimethyl-
olkylomines
(I)
Citrosil (Glaxo)
Dil Mill (SIT)
Herbagola propoli (Grica
Chemical)
Lacribase Saluzine
(Allergan)
Quatersal (Ascor)
Sapocitrosil (Glaxo)
Steramina "G" (Formenti)
Streptosil (Boehringer lng.)
Video bagno (Farmila)
Video gocce (Farmila)
Vittoria Lazione

(Ottolenghi)
J: Osvan (Daigo-Takeda)
USA: Amino-Cerv (Milex)-comb.
Ony-Clear (Pedinol)
Zephiran (Winthrop-Breon)
204
B
Benzarone
Benzarone
ATC: CO5CX
Use: antihemorrhagic, antispasmodic, vein
therapeutic
RN: 1477-19-6 MF:
CI,H140, MW: 266.30 EINECS: 216-026-2
LD,,: >12 gkg (M, p.0.);
>12 gkg
(R,
p.0.)
CN:
(2-ethyl-3-benzofuranyl)(4-hydroxyphenyl)methanone
cl CH3
-
acH3 H2N-NH,.
H,O.
Roney-Ni
CHO
0 0
hydrozine
hydrate
solicyl- chloroocetone 2-ocetyl-

aldehyde benzofuron
2-ethylbenzofuran
(I)
I
+
-
FH3 pyridine
hydrochloride
4-methoxy- 2-ethyl-3-(4-rnethoxy-
benzoyl chloride benzoyl)benzofuron
Reference(s):
DE 1 076 702 (Labaz; appl. 20.12.1957; B-prior. 21.12.1956).
US 3 012 042 (Labaz; 5.12.1961; B-prior. 21.12.1956).
Benzorone
alternative synthesis of 2-acetylbenzofuran (ffom benzofuran and acetic anhydridelH,P04):
Buu-HOP, N.P.: J. Chem. Soc. (JCSOA9)
1964,
173.
Formulation(s): tabl. 100 mg
Trade
Name(s):
D: Fragivix (Sanol); wfm F: Derol (Lab@-comb. with I: Fragivix (Sigma-Tau); wfm
Vasoc (Lindopharm); wfm lidocaine; wfm Venagil (Logifarm); wfm
Fragivix (Labaz); wfm Venagil (Scalari); wfm
Benzathine benzylpenicillin
ATC: JolC~08
(Benethamine Penicilline; Benzilpenicillin; Penicillin
G
depot
antibiotic

Benzathine)
RN: 1538-09-6 MF: C,6H,,N204S
.
1/2Cl6HzON, MW: 909.14 EINECS: 216-260-5
LD,,: 2 gfkg
(M,
p.0.)
CN:
[2S-(2a,5a,6~)J-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-l-azabicyclo[3.2.0]heptane-2-
carboxylic acid compd. with
N,N-bis(phenylmethy1)-1,2-ethanediamine
(2: 1)
ethylene- benzoldehyde
1
-2-bis(benzy1iden-
diornine omino)ethane
Benzatropine
B
205
N,N'-dibenzyl- benzylpenicillin Benzothine benzylpenicillin
ethylenediomine
(I)
Reference(s):
US
2 627 491 (Wyeth; 1953; prior. 1950).
Formulation(s):
gel
0.1
gI100 g
Trade Name(s):

D: Depotpen (Daue1sberg)- F: Extencillinc (Spccia) Wycillina A.
P.
(Carlo
comb.
GB: Penidural (Wyeth); wfm Erba)
Sulfa-Tardocillin
(Bayer)-
I:
Benzil
B
(Formulario Naz.)
J:
Bicillin (Banyu)
comb.
Tri-Wycillina
A.
P. (Carlo USA: Bicillin (Wyeth); wfm
Tardocillin (Bayer)
Erba)-comb.
Permapen (Pfizer); wfm
Benzatropine
(Benztropine)
ATC: N04ACOl
Use: parasympatholytic, antiparkinsonian
RN: 86-13-5 MF: C2,H2,N0 MW: 307.44
LD,,: 25 mgkg (M, i.v.)
CN:
endo-3-(diphenylmethoxy)-8-methyl-8-azabicyclo[32.l]octane
mesylate
RN:

132-17-2 MF: CZIHz5NO. CH4O3S MW: 403.54 EINECS: 205-048-8
LD,,:
24
mgkg (M, i.v.); 9 1 mgkg (M, p.0.);
940 mglkg
(R,
p.0.)
diphenyl- tropine
diozomethone
US
2 595 405 (Merck
&
Co.; 1952; prior. 1949).
Formulation(s):
amp.
2
mg; tabl. 0.5 mg, lmg,
2
mg
Trade Namefs
J:
,
.
D: Cogentinol (Astra)
GB: Cogentin (Merck Sharp
&
USA: Cogentin (Merck Sharp
&
F:
Cogentine (Merck Sharp

&
Dohme; as mesylate) Dohme; as mesylate)
Dohme);
wfrn
206
B
Benzbromarone
Benzbromarone
ATC: MO~AB;
NO~ACOI
Use: uricosuric agent
RN: 3562-84-3 MF: C,,H,,Br,O, MW: 424.09 EINECS: 222-630-7
LD,,,: 77 mglkg (M, i.v.); 61 8 mgkg (M, p.0.);
248 mglkg (R, p.0.)
CN:
(3,5-dibromo-4-hydroxyphenyl)(2-ethyl-3-benzofuranyl)methanone
\
B
r
Benzbromarone
DE 1 080 144 (Labaz; appl. 20.12.1957; B-prior. 21.12.1956).
US 3 012 042 (Labaz; 5.12.1961; B-prior. 21.12.1956).
combination with
allopurinol:
GB 1 493 237 (Henning Berlin; appl. 11.5.1976; D-prior. 10.12.1975).
Fornzrrlntion(s):
f. c. tabl. 20 mg
Trade Name(s):
D:
Acifugan (Henning Berlin)- Azubromaron (Azupharma)

I:
Desuric (Sigma-Tau); wfm
comb. Harpagin (Merz
&
Co.)
J:
Urinorm (Torii)
Allomaron (Nattermann) Narcaricin (Heumann)
comb.
F:
DCsuric (Sanofi Winthrop)
Benzethonium chloride
ATC: R02AA09
Use: disinfectant, antiseptic
RN: 121 -54-0 MF: C27H42C1N0, MW: 448.09 EINECS: 204-479-9
LD,,,: 30 mgkg (M, i.v.); 338 mglkg (M, p.0.);
19 mgkg (R, i.v.); 368 mglkg (R, p.0.)
CN:
N,N-dimethyl-N-[2-[2-[4-(1,1,3,3-tetramethylbutyl)phenoxy]ethoxy]ethyl]benzenemethanaminium
chloride
4-(1,1,3.3-tetromethyl-
bis(2-chloro-
2-[Z-[4-(1.1.3.3-tetramethyl-
butyl)phenol
ethyl)
ether butyl)phenoxy]ethoxy]ethyl
chloride
(I)
Benzilonium bromide
B

207
Reference(s):
US 2 115 250 (Rohm
&
Haas; 1938; appl. 1936).
US 2 170 11 1 (Rohm
&
Haas; 1939; appl. 1936).
US 2 229 024 (Rohm
&
Haas; 1941; appl. 1939).
N.N-dimethyl-
Formularion(s):
many different formulations
Benzethonium chloride
Trade Name(s):
D: Brand- und Wundgel Ta-Ro-Cap (Soekami)- Ribex Gola (Formenti)
(Medics)-comb.
comb.; wfm Sterilix (Formenti)
F:
Alcolkne (A1con)-comb.; Vasol (Fumouze)-comb.;
J:
Hyamine-T (Sankyo)
wfm
wfm Neostelin-Green (Bayer-
Ineka (Soekami)-comb.; GB: Emko (Syntex)-comb. Nihonshika)
wfm
I: Air Sanitzer (Chifa)
benzylamine
Benzilonium bromide

ATC: A03AB
Use: anticholinergic
RN: 1050-48-2 MF:
C,,H,,BrNO, MW: 434.37 EINECS: 213-885-5
LD,,,: 11.2
mgkg (M, i.v.); 363 mglkg (M, p.0.);
760 mglkg
(K,
p.0.)
CN: 1,l
-diethyl-3-[(hydroxydiphenylacetyl)oxy]pyrrolidinium
bromide
ethyl benzilote
1
-ethyl-3-
1
-ethyl-3-pyrrolidinyl
I
Benzilonium bromide
hydroxy- benzilate
pyrrolidine
Reference(s):
GB 821 436 (Parke Davis; appl. 22.2.1956).
DE 1 136 338 (Parke Davis; appl. 12.2.1957; GB-prior. 22.2.1956,29.1 .l957).
Formulation(s):
cps. 10 mg; tabl. 10 mg
Trade Natne(s):
D: Minelcin (Parke Davis);
F:
Portyn (Parke Davis); wfm

J:
Portyn (Parke Davis-
wfm GB: Portyn (Parke Davis); wfm Sankyo)
208
B
Benziodarone
Benziodarone
ATC: COIDA; COlDX04
Use: coronary vasodilator, uricosuric agent
RN: 68-90-6 MF:
C,,HI2I2O3 MW: 518.09 EINECS: 200-695-2
LDso: 450 mglkg (M, p.0.)
CN:
(2-ethyl-3-benzofuranyl)(4-hydroxy-3,5-diiodophenyl)methanone
benzarone
(4.
v.)
1
Benziodarone
1
Reference(s):
GB 836 272 (Labaz; appl. 17.12.1957; R-prior. 21.12.1956).
Formulation(s):
cps. in comb. with allopurinol
Trade Name(s):
F: Ampliuril pH (Labaz); wfm Amplivix (Labaz); wfm I: Uricodue (IF1)-comb.
Benzocaine
(Ethoforme)
ATC: C05AD03; D04AB04; NOlBAOS;
R02ADO 1

Use: local anesthetic
RN: 94-09-7 MF:
C,H,,NO, MW: 165.19 EINECS: 202-303-5
LDso: 216 mglkg
(M,
i.p.)
CN: 4-aminobenzoic acid ethyl ester
ethyl 4-nitro-
benzoate
0
0-CH,
6
NH2
Benzocaine
Reference(s):
Org. Synth. (ORSYAT) 8,66 (1928).
Formulation(s):
cream 100 mg; ointment 5
%,
10
%,
20
%;
pills 4 mg, 8 mg, 20 mg; powder 60 mg; suppos.
100 mg
Trade Name(s):
D: Anaesthesin (Ritsert) I: Anes Par (Tariff. Cetacaine (Cetylite)
Flavamed (Berlin-Chemie) Integrativo) Hurricaine (Beutlich)
Subcutin (Ritsert) Gengivarium (Kemyos) Tympagesic (Savage)
Zahnerol (Janssen) USA: Americaine (Medeva)

GB: generics Auralgan (Wyeth-Ayerst)
Benzoctamine
B
209
Benzoctamine
ATC: NOSBDO1
Use: psychosedative, tranquilizer
RN: 17243-39-9 MF: C,,H,,N MW: 249.36
LD,,:
30 mgkg
(M,
i.v.); 280 mg/kg (M, p.0.);
36 mgkg
(R,
i.v.); 600 mglkg
(R,
p.0.);
>10 mglkg (dog, i.v.); >200 mglkg (dog, p.0.)
CN:
N-methyl-9,1O-ethanoanthracene-9(1OH)-methanamine
hydrochloride
RN: 10085-81-1
MF:
CI8Hl9N
.
HC1 MW; 285.82 EINECS: 233-216-0
LD,:
26 mgkg (R, i.v.); 700 mglkg (R, p.0.)
H~c.~XHO
POCI~

CHO
onthracene
N-methyl-
onthrocene-9-
lormonilide
carboxoidehyde
1.
HJC-NH2
g,,O-dihy,jro-g,lO-
2.
Benzoctomine
ethanoanthrocene-
9-carboxaldehyde
(1)
Reference(s):
Wilhelm, M.; Schmidt,
P.:
Helv. Chim. Acta (HCACAV)
52,
1385 (1969).
BE
610 863 (Ciba; appl. 28.1 1.1961; CH-prior. 29.11.1960, 10.10.1961).
US
3
399 201 (Ciba; 27.8.1968; CH-prior. 29.1 1.1960, 10.10.1961, 1.1 1.1963, 23.12.1964, 24.1 1.1965,
10.12.1965).
DE
1 228 605 (Ciba; appl. 24.1
1
.l96l; CH-prior. 29.11.1960, 10.10.1961).

Fomtulation(s):
syrup 2 mg/2 ml; tabl. 5 mg, 10 mg
Trade Narnefs):
D:
Tacitin (Ciba); wfm
F:
Tacitine (Ciba); wfm GB: Tacitin (Ciba); wfm
Benzonatate
ATC: RO5DBO1
Use: antitussive
RN: 104-31-4 MF: C,,HS,NO,, MW: 603.75 EINECS: 203-194-7
LD,,:
9
mgkg (M, i.v.); 400 mglkg
(M,
p.0.)
CN: 4-(butv1arnino)benzoic acid 3.6.9.12.1 5.1
8.21,24,27-nonaoxaoctacos-l
-yl
ester
210
B
Benzoyl peroxide
ominobenzoote monomethyl ether
1
J
0 0-CH3
6
NoOCH3
+

HO-CH2-(CH,-0-CH,),-H
+
HN-CH,
ethyl 4-butyl- nonoethylene glycol
Reference(s):
US 2 714 608 (Ciba; 1955; CH-prior. 1950).
US 2 714 609 (Ciba; 1955; CH-prior. 1950).
0 0-CH2-(CH2-O-CH2)9-H
6
HN,,A,CH~
Benzonatote
Formulation(sj:
cps. 100 mg; perk I00 mg
Trade Name(s):
USA: Tessalon (Forest)
Benzoyl peroxide
(Peroxide de benzoy le)
ATC: DlOAEOl
Use: keratolytic, antiseptic
RN: 94-36-0 MF: C14H1004 MW: 242.23 EINECS: 202-327-6
LD,,,: 5700 mglkg
(M,
p.0.);
7710
mgkg
(R, p.0.)
CN: dibenzoyl peroxide
benzoyl
chloride
1

Benzoyl peroxide
1
Reference(s):
Ullmanns Encykl. Tech. Chem., 4. Aufl., Vol. 17,671.
stabilization of aqueous formulations with
sodium dioctylsulfosuccinate:
US
4 387 107 (Dermik Labs.; 7.6.1983; prior. 25.7.1979, 16.12.1980).
alternative formulntions:
US 3 535 422 (Stiefel Labs.; 20.10.1970: prior. 30.3.1966. 11.3.1968).
US 4 056 61 1 (Stiefel Labs.; 1.1 1 .1977; appl. 16.4.1973).
US
4
545 990 (L'Oreal; 8.10.1985; appl. 21.1 1.1983; LU-prior. 22.1 1.1982).
combination with
salicylic acid:
US 4 318 907 (Westwood; 9.3.1982; appl. 4.4.1978).
US
4
355 028 (Westwood; l9.lO.1982; appl. 30.4.1981)
Formulation(s):
cps. 100 mg; gel 5
%,
10
%
Trade Name(s):
D:
Abmederm (gepephann) Benzaknen (Galderma)
Akne-Aid-Lotion (Stiefel) Benzoxyl20 Lotion
Aknefug-oxid (Wolff)

(Stiefel)
Akneroxid (Hermal) Pan Oxyl (Stiefel)
Sanoxit (Galderma)
Scherogel (Asche)
Ultra Clearasil (Wick
Pharma)