Pharmaceutical Substances Syntheses, Patents, Applications - Part 192 pdf

Styramate
S
191
1
Formulation(s):
amp. 0.125 mg, 0.25 mg
Trade Name(s):
D:
Alvonal MR (Godecke); Stabilocard (Godecke); Theo-Alvonal (G6deckc);
wfm
wrm wfm
Sty ramate
ATC:
MO~BAO~
Use: muscle relaxant, antispasmodic
RN 94-35-9
MF
C,H,,NO,
MW;
181.19 EINECS: 202-326-0
LD,,,: 1240 mgkg (M, p.0.)
CN: 1-phenyl- l,2-ethancdiol 2-carbamate
1-phenyl-1,2-
ethanediol
Referencers):
GB
841 626 (Armour; appl. 1956; USA-prior. 1955).
Trade Namers):
GB:
Sinaxar (Armour); wfm
J:

Menfula (Taisho)-comb. Sinaxar (Tokyo Tanabe)
Succinylsulfathiazole
ATC: A07AB04
Use: chemotherapeutic, antibacterial
RN: 116-43-8
MF:
C,,H,,N,O,S,
MW:
355.40 EINECS: 204-141-0
LD,: 10 glkg
(M,
i.v.)
CN:
4-oxo-4-[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]butanoic
acid
succinic sulfathiozole
onhydride
(4. v.)
Reference(s):
US
2 324 013 (Sharp
&
Dohme; 1943; appl. 1941).
US
2 324 014 (Sharp
&
Dome; 1943;
appl.
1941).
Formulation(s):

tabl. 500 mg
Succinylsulfathiozole
Trade Name(s):
F:
Thiacyl (Thkraplix); wfm
GB:
Cremomycin (Merck Sharp Cremostrep (Merck Sharp
&
Dohme)-comb.; wfm
B
Dohme)-comb.; wfm
1912
S
Sucralfate
Cremosuxidine (Merck I: Cremosulfa strept.
Sharp
&
Dohme); wfm (Ange1ini)-comb.; wfm
Sulfasuxidine (Merck Streptoguanidin
Sharp
&
Dohme); wfm
(Lisapharma)-comb.; wfm
Sucralfate
ATC: ~02~x02
Use: ulcer therapeutic
RN: 54182-58-0 MF: C,2H54A116075SN MW: 2086.73 EINECS: 259-018-4
LD,,,:
>8
g/kg (M, p.0.);

>12 glkg (R, p.0.)
CN:
hexadeca-~-hydroxytetracosahydroxy[~,-[[1,3,4,6-tetra-O-sulfo-~-~-fructofuranosyl
WD-
glucopyranoside
tetrakis(sulfato-~0')](8-)]]hexadecaaluminum
1.
SO3,
pyridine
2.
AI(OH)~CI
sucrose
Sucralfate
DE 1 568 346 (Chugai; appl. 3 1.10.1966; J-prior. 5.1 1.1965).
US 3 432 489 (Chugai; 11.3.1969; J-prior. 5.11.1965).
FR
1
500 571 (Chugai; appl. 3.11.1966; S-prior. 5.11 .l965).
Nagashima, R.; Yoshida, N.: Arzneim Forsch. (ARZNAD)
29,
1668 (1979).
formulations with amino acids:
EP 107 209 (Chugai; appl. 26.10.1983; J-prior. 27.10.1982).
Fortnularion(s):
chewing tabl. 1 g; gran. 1 g; susp.
1
g/5 ml; tabl. 0.5 g, 1 g
Trade Name(s):
D: Sucrabest (Hexal)
Sucralfat-ratiopharm

(ratiopharm)
Sucraphil (Philopharm)
Ulcogant
(Lipha; Merck)
F: Ktal (EG Labo)
Sucralfate (GNR-pharma)
Ulcar
(Houdt)
GB: Antepsin (Wyeth)
I:
Antepsin (Baldacci)
Crafilm (Francia Farm.)
Gastrogel (Giuliani)
Sucrager (Ripari-Gero)
Sucral (Bioprogress)
Sucralfin (Inverni della
Beffa)
Sucramal (Sanofi
Winthrop)
Sucrate (Lisapharma)
Suril (Ibirn)
J: Adopilon (Kantoishi)
Altsamin (Taiyo-Sanwa)
Bingast (Maruko)
Bisma (Sana)
Ritaalumin (Hotta)
Shualmin (Rorer-Funai)
Sibonarl
(Mohan-
Wakamoto)

Tredol (Kaigai-Nippon
Kayaku)
Ulban-A (Toho)
Ulcerlmin (Chugai)
Yuwan-S (Sawai-Meiji)
USA: Carafate
(Hoechst Marion
Roussel)
generics
Sufentanil
S
1913
Sufentanil
ATC: NOIAH03
Use: narcotic, analgesic
RN: 56030-54-7 MF: C2,H1,N20,S MW: 386.56
CN:
N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-p1peridinyl]-N-phenylpropanamide
citrate
(1:l)
RN: 60561 -1 7-3 MF: C,2H,,N20,S
,
C,H,O, MW: 578.68 EINECS: 262-295-4
LD,,: 18.7 mglkg (M, i.v.);
17.9 mg/kg (R, i.v.);
14.1 mglkg (dog,
I
v.)
2-thiophene- methane
ethanol sulfonyl

chloride
Sulentonil
(cf. alfentanil synthesis)
Reference(s):
DE
2
610 228 (Janssen; prior. 11.3.1976).
US
3 998 834 (Janssen; 21.12.1976; prior. 14.3.1975, 13.1.1976, 13.9.1976).
Daele,
P.G.H.
van et-al.: Arzneim Forsch. (ARZNAD)
26,
1521 (1976).
Formulation(s):
amp. 50 pglml, 100 pg/2 ml, 500 pg15 ml (as citrate)
Trade Name(s):
D:
Sulfenta (Janssen-Cilag)
F:
Sulfenta (Janssen-Cilag; as I: Fentatienil (Angelini)
citrate) USA: Sufenta (Janssen; 1984)
Sulbactam
(CP-45899-2)
ATC: JOlCGOl
Use:
antibacterial in combination with
P-
lactam antibiotics, semisynthetic
O-

lactamase inhibitor
RN: 68373-14-8 MF: C8H,lNOSS MW: 233.24 EINECS: 269-878-2
CN:
(2S-cis)-3,3-dimethyl-7-oxo-4-thia-l-azabicyclo[3.2.0]heptane-2-carboxylic
acid 4,4-dioxide
sodium
salt
RN: 69388-84-7 MF: C,H,,NNaO,S MW: 255.23 EINECS: 273-984-4
19
14
S
Sulbenicillin
COOH
BrZ, CHZCIZ,
COOH
KMn04, H3P04
'I
BrH
perrnongonote
6-arninopeni-
cillanic ocid
6.6-dibroma-
penicillonic acid
66-dibromo-
penicillanic ocid
5.5-dioxide
(I)
Reference(s):
Volkmann, R.A. et a].:
J.

Org. Chem. (JOCEAH) 47, 3344 (1982).
US 4 234 579 (Pfizer; l8.ll.l98O; appl. 5.3.1979; USA-prior. 7.6.1977, 21.2.1978, 29.3.1978).
US 4 420
426
(Pfizer; 13.12.1983; appl. 9.12.1980: USA-prior. 5.3.1979).
DE 2 824 535 (Pfizer; appl. 5.6.1978; USA-prior. 7.6.1977,21.2.1978).
DE 2 9 12 51 1 (Pfizer; appl. 29.3.1979; USA-prior. 29.3.1978, 27.11.1978).
combination
with
cefoperazone:
US
4
276 285 (Pfizer; 30.6.1981; appl. 5.3.1978; USA-prior. 7.6.1977, 21.2.1 978, 29.3.1978,27.11.1978).
Formulation(s).
vial 750
mg,
I
g,
1.5
g,
3 g (as sodium sulfate)
Trade
Nnme(s):
D: Combactam 1,O g (Pfizer) Unacirn (Jouveinal; as Unasyn (Pfizer)-comb, with
Unacid (Pfizer; 1987)- sodium salt)-comb. with ampicillin
comb. with ampicillin ampicillin
J:
Sulperazone (Pfizer Taito;
F:
BCtamaze (Pfizer; as I: Bethacil (Bioindustria). 1986)-comb.

sodium salt) comb. with ampicillin USA: Unasyn (Pfizer; 1987)-
Loricin (Sigma-Tau)-comb. comb. with ampicillin
with ampicillin
Sulbenicillin
ATC: J01CA16
Use: antibiotic
RN: 34779-28-7
MF:
C,,HIRN2O,S2
MW:
414.46 EINECS: 252-209-3
CN:
[2S-(2a,5a,6~)]-3,3-dimethyl-7-oxo-6-[(phenylsulfoacetyl)amino]-4-th1a-l-azabicyclo[3.2.0]hcptane-2-
carboxylic acid
disodium salt
RN:
28002-18-8
MF:
C,,H,,N,Na,O,S, MW: 458.42 EINECS: 248-769-3
LD,,,: 7900 mgtkg (M, i.v.); >15
gkg
(M, p.0.);
6
glkg
(R, i.v.); >15 g/kg (R, p.0.)
SO3, dichloroethone
a00H
-
QOOH
S0CI2

SO,H SO,H
phenylacetic
a-sulfophenyl-
(0
acid acetic ocid
Sulbentine
S
1915
6-aminopeni- Sulbenicillin
cillanic acid
Referenceis):
DE 1 933 629 (Takeda; prior. 2.7.1969).
DOS 1948 943 (Takeda; appl. 27.9.1969; J-prior. 28.9.1968).
DAS 1 966 850 (Takeda; appl. 27.9.1969; J-prior. 28.9.1968).
US
3
660 379 (Takeda; 2.5.1972; appl. 29.9.1969; J-prior. 28.9.1968).
US 3 891 763 (Takeda; 24.6.1975; prior. 18.1.1972).
Formulation(s):
vial 1 g, 2 g, 4 g (as disodium salt)
Trade Name(s):
1:
Kedacillina (Bracco; 1982)
J:
Kedacillin (Takeda)
Lilacillin (Takeda)
Sulbentine
(Dibenzthione)
ATC: DOIAE09
Use: anlifungal

RN: 350-12-9 MF: Cl,H,,N2S2 MW: 314.48 EINECS: 206-497-2
LDs,;
l
I00
mg/kg (M,
i.p.)
CN:
tetrahydro-3,5-bis(phenylmethyl)-2H-1,3,5-thiadiazine-2-thione
benzylomine form- corbon Sulbentine
aldehyde
'
disulfide
Reference(s):
DD 20 634 (appl. 17.8.1958).
Formularion(s):
gel 3 gll 00
g;
ointment 3 gll 00 g; sol. 3 g1100 g
Trade Nameis):
D:
Fungiplex (Hermal); wfm
I:
Fungiplex (Bruschettini); J: Dampa D (Nippon
wfm
Shinyaku)
Sulconazole
ATC: NOlAH03
Use: antifungal
RN: 61318-90-9
MF:

C,,H15CI,N,S MW: 397.76
CN:
(~)-1-[2-[[(4-chlorophenyI)methyl]thio]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
mononitrate
RN: 61318-91-0
MF:
C,,H,SCI,N2S
.
HNO, MW: 460.77
LD,,,: 2475 mgkg (M, p.0.);
1741 mgkg
(R,
p.0.)
1916
S
Sulfabenzamide
+OH
1.
thionyl chloride
2.
4-chlorobenzyl
Q
mercaptan
ethanol
(cf. rniconazole synthesis)
DOS
2 541
833
(Syntex; appl. 19.9.1975; USA-prior. 23.9.1974, 7.7.1975).
US 4 055 652 (Syntex; 25.10.1977; appl. 8.3.1976; prior. 7.7.1975).

Formulation(s):
cream 1
%;
sol. 1
%
(as nitrate)
Trade Name(s):
F:
M
yk (Cassenne) I: Exelderm (Schwarz) USA: Exelderm (Westwood-
GB: Exelderm (Zeneca; 1985)
J:
Exelderm (Tanabe; 1986) Squibb)
Sulfabenzamide
(Benzoylsulfanilamide; Sulphabenzamide)
ATC:
D08;
JOlE
Use: chemotherapeutic (sulfonamide),
antibacterial
RN:
127-71-9 MF: C,,H,,N,O,S
MW:
276.32 EINECS: 204-859-4
LD,,,:
320 mglkg (M, i.v.)
CN:
N-[(4-aminophenyl)suIfonyl]benzamide
sulfanilamide benzoyl
(9-

v.)
chloride
(1)
I
Sulfabenzarnide
Sulfacarbamide
S
19
17
4-acetamido-
bsnzenesulfonomide
(cf.
sulfanilamide
synthesis)
Reference(s):
a
Siebenmann, C.; Schnitzer, R.J.: J. Am. Chem. Soc. (JACSAT)
65,
2126 (1943).
b
US 2 240 496 (Monsanto; 1941; appl. 1939).
GB
541 958 (Schering AG; appl. 1938; D-prior. 1938).
Formulation(s):
pessaries 185 mg; vaginal cream 37 mg/g
Trade Name(s):
D:
Neosultrin (Ci1ag)-comb.;
GB:
Sultrin (Janssen-Ci1ag)- USA: Sultrin (Ortho-McNeil

wfm comb. Pharmaceutical)-comb.
Sulfacarbamide
(Sulphaurea; Sulfanylurea)
ATC: D08;
JOE
Use: chemotherapeutic, antibacterial
RN: 547-44-4 MF: C,H,N,O,S
MW:
215.23 EINECS. 208-922-7
LD,:
405
mg/kg
(M,
i.p.)
CN:
4-amino-N-(aminocarbonyl)benzenesulfonamide
4-acetamidobemene- potassium (4-acetomidobenzene-
sulfonamide cyaiate sulfonyl)ureo
Reference(s):
US
2
41
1
661 (Geigy; 1946; CH-prior. 1939),
Formulation(s):
drg. 0.5 g; syrup 0.1 glml
191
8
S
Sulfacetamide

Trade Nume(s);
D:
Cysto-Myacyne O.W.G. Spasmo-Euvernil GB: IJromide
(Consolidated
(Schur)-comb.; wfm (Heyden)-comb.; wfm Chemicals)-comb.; wfm
Euvernil (Hcyden); wfm
Sulfacetamide
(N'-acctylsulfanilamide;
Sulphacetamide)
ATC: SOIAB04
Use: chemotherapeutic (eye infection),
antibacterial
RN: 144-80-9 MF:
C,HloN2O,S MW: 214.25 EINECS: 205-640-6
LD,,,: 16.5
glkg
(M, p.0.);
6.6 glkg
(R,
i.v.)
CN:
N-[(4-aminophenyl)sulfonyllacetamide
monosodium
salt
RN:
127-56-0 MF: C,H,N,NaO$ MW: 236.23 ETNECS: 204-848-4
LD,,,: 6
glkg
(M, s.c.)
4-orninobenzene- ocetornide

sulfonyl chloride
4-ominobenrene- acetic anhydride
sulfonomide
Reference(s):
US 2 41 1 495 (Schering Corp.; 1946; D-prior. 1938).
Fornlulutiorz(s).
eye drops 100 mglml; ophthalmic ointment 2 mglg, 100 mglg (as sodium salt); pessarics
143.75 mg
Trude Namc(s):
D: Albucid (Chauvin
ankerpharm)
Blefcon (A1con)-comb.
Rlephamide (Pharm-
Allergan)-comb.
Cornhiamid
(Winze+
comb.
F:
Antkbor (Lah. Riol. de
I'Ile-De-France)-comb
GB: Sultrin (Janssen-Wag)- Cosmiciclina (Alfa 1ntes)-
comb. comb.
I: Antisettico Astr. Sed. Prontamid (SIT)
(Bruschettini)-comb. Rinosulfargolo
Aureomix (SIT)-comb.
(Bruschettini)-comb.
Brumeton (Bruschettini). Visublefarite (Pharmec)-
comb. comb.
Chemy
terra1 (SIT)-comb.

Sulfachlorpyridazine
S
19
19
I: Neo-Gerison (Yamanouchi) Sultrin (Ortho-McNeil
USA: Blephamide (Allergan) Pharmaceutical)-comb.
Sulfachlorp yridazine
ATC:
DO^;
JOIED
Use: chemotherapeutic (urogenital tract
infections), antibacterial
RN: 80-32-0 MF: C,,H9C1N4O,S MW: 284.73 EINECS: 201-269-9
CN:
4-amino-N-(6-chloro-3-pyridazinyl)benzenesulfonamide
4-arninobenzene-
sulfonomide
3,6-dichloro-
pyridozine
Reference(s):
US 2 790 798 (American Cyanamid; 1957; prior. 1955).
Formulation(s): tabl. 500 mg
Trade Name(s):
I:
Durasulf (Dessy); wfm USA: Consulid (Ciba-Geigy); Sonilyn (Mallinckrodt);
Sulfaclorazina (Ellem); wfm wfm
wfm
Nefrosul (Riker);
wfm
b

Sulfacitine
ATC:
JO~E
(Sulfacy tine)
Use: chemotherapeut~c (depot
sulfonamide), ant~bacter~al
RN. 17784-12-2 MF: C1,H,,N40,S MW: 294 34
CN: 4-amno-N-(1
-ethyl-1,2-d1hydro-2-oxo-4-pynmidinyl)ben~enesulfonam1de
3-ethylamino- potassium
propionitrile cyonate
BrZ, nitrobenzene pyridine
*HBr
,
.CH,
N
N-CH,
11
K
0
4-ocetornidobenzene-
sulfonyl chloride
1-ethyl-5,6-dihydro-
1
-ethylcykosine
cytosine hydrobromide
(I)
1920
S
Sulfadiazine

I
Sulfacitine
I
Refererzce(s):
LJS 3 375 247 (Parke Davis; 26.3.1968; appl. 2.8.1965).
DE
1
620 140 (Parke Davis; appl. 1.8.1966; USA-prior. 2.8.1965).
Doub,
L.
et al.:
J.
Med. Chem. (JMCMAR)
13>
242 (1970).
Formulation(s):
tabl. 250 mg
Trade Name(s):
USA: Renoquid (Parke Davis);
wfm
Sulfadiazine
(Sulphadiazine)
ATC: JOIEC02
Use: chemotherapeutic
RN: 68-35-9
MF:
CloH,oN40,S MW: 250.28 EINECS: 200-685-8
LD,,,: 180 mglkg (M, i.v.); 1500
mg/kg
(M,

p.0.);
880 mg/kg (R,
i.v.)
CN:
4-amino-N-2-pyrimidtnylbenzenesulfonarnide
silver
salt
RN: 22199-08-2 MF: C,oH,AgN40,S
MW:
357.14
4-acetamidobenzene-
2-amino-
sulfonyl
chlaride
pyrimidine
Sulfadiazine
L
US
2
407 966 (Sharp
&
Dohme; 1946).
US
2 410 793 (American Cyanamid; 1946).
Furmulation(s):
cream 1
%;
tabl. 500
mg
(as

silver salt)
Trade
Name(s):
D:
Brandiazinc (medphano) Flammazine (Solvay
Arzneimittel)