Pharmaceutical Substances Syntheses, Patents, Applications - Part 171 ppsx

Prednylidene
P
1701
Reference(s):
Gardi,
R.
et
al.:
Gazz. Chim. Ital. (GCITA9) 93,431 (1963).
prednisolone 17-valerote
(I)
prednisolone 17-valerate:
DE
1
214 677 (Francesco Vismara; appl. 1.6.1962; I-prior. 24.6.1961).
US
3 147 249 (Francesco Vismara; 1.9.1964; I-prior. 13.6.1961).
cf. hydrocortisone butyrate, betametasone valerate
Prednivol acetate
Trade Narne(s):
I: Acepreval (Parke Davis-
Vister); wfm
Prednylidene
ATC: H02AB11
Use: glucocorticoid
RN: 599-33-7 MF:
C,,H,,O, MW: 372.46 EINECS: 209-964-9
LD,:
7450
mgkg
(M, p.0.)

CN: (I
1~)-11,17,21-trihydroxy-l6-methylenepregna-l,4-diene-3,20-dione
H202.
OH-
Curvulorio lunoto
OH
(Wokker) Boodijn
1702
P
Prednylidene diethylaminoacetate
Bocilllus sphoericus
or
Corynebocterium simplex
16-methylenehydrocortisone
(ID)
Prednylidene
Reference (s):
DE
1
134 074
(E.
Merck
AG;
appl. 3 1.1 .l959).
Mannhardt, H.J. et a].: Tetrahedron Lett. (TELEAY)
1960,
21.
Taub, D. et al.: J. Org. Chem. (JOCEAH) 25,2258 (1960).
alternative synthesis:
US

3 068 226 (Merck
&
Co.; 1962; prior. 1961, 1959).
Formulation(s): tabl. 6 mg, 24 mg, 60 mg
Trade Name(s):
D: Decortilen (Merck)
I:
Dacortilen Merck (Bracco);
F:
DCcortilbne (Farmex);
wfm
wfm
Prednylidene diethylaminoacetate
ATC: ~02~~11
LJse: glucocorticoid
RN: 6890-42-2 MF: C,,H,,NO, MW: 485.62
CN: N,N-diethylglycine (1 1
P)-
1 l,l7-dihydroxy-
16-methylene-3,20-dioxopregna-
1,4-dien-21-yl ester
hydrochloride
RN: 22887-42-9 MF: C,,H,,NO,. HCI MW: 522.08 EINECS: 245-299-0
prednylidene
(4.
v.)
diethylominoacetic Prednylidene diethylom~noocetote
onhydride
Reference(s):
DE 1 134 074

(E.
Merck AG; appl.
3
1.1.1959).
combination with quinoline derivatives:
BE 829 197 (Grosjean; appl. 16.5.1975).
Formulation(s): amp. 30 mglml, 60 mg/ml
Trade Name(s):
D: Decortilen sol. (Merck)
Pregnenolone
P
1703
Pregnenolone
ATC: L02BA
Use: glucocorticoid
RN:
145-13-1 MF: C2,H32O2 MW: 316.49 EINECS: 205-647-4
CN:
(3P)-3-hydroxypregn-5-en-20-one
succinate
RN: 4598-67-8 MF: C2,H,,05 MW: 416.56 EINECS: 225-001-5
acetate
RN: 1778-02-5 MF: C2,H,,0, MW: 358.52 EINECS: 217-212-6
diosgenin acetic anhydride
(1)
chrorniurn(V1)
oxide
)rCH3
0
CH3

1.
Hz.
Pd
2.
hydrolysis
dehydropregnenolone
ocetate
(11)
Pregnenolone
Reference(s):
Ehrhart-Ruschig, 111,341.
Ullmanns Encykl. Tech. Chern., 3. Aufl., Vol. 8,664, and there cited literature.
alternative syntheses:
Ullmanns Encykl. Tech. Chern.,
3.
Aufl., Vol. 8,660.
Formulation(s):
cream 0.5
%
(as acetate)
Trade Name(s):
F:
Fadiarnone Crkrne (Sauba; USA: Formula 405 (Doak; as Panzalone (Doak; as
as acetate)-comb.; wfrn succinate); wfrn succinate); wfrn
Prenolon (Schering); wfrn
Prenalterol
ATC: COlCA13
Use: cardiotonic
RN: 57526-81-5 MF:
C,,H,,NO, MW: 225.29 EINECS: 260-791-5

CN:
(S)-4-[2-hydroxy-3-[(1-rnethylethyl)arnino]propoxy]phenol
1704
P
Prenalterol
hydrochloride
RN:
61
260-05-7
MF:
C,,HI9NO3
.
HCI
MW:
261.75
O
NaOH
isopropylomine
(n)
OH
0
H
hydroquinone epichloro-
CH3
(W
monobenzyl hydrin
ether
(1)
OH
rocernate resolution with

(+)-di-toluoyltartoric acid
C"3
Prenalterol
p-toluenesulfonyl
chloride
(V)
C"3
5.6-onhydro-1.2-0-
isopropylidene-a-D-
glucofuranose
(VI)
pyridine CH3COOH
vt
+
1
+
+
VII
Prenvlamine
P
1705
1.
NolO,.
CHSOH,
CH,COOH
2.
NOW+,
CHSOH
1.
sodium

periodate
"$
2.
sodium
borohydride
'
OH
(W
OH
I
-(4-benzyloxypheny1)-
2(S),3-dihydroxypropone
(VIE)
1.
V,
pyridine
2.
11,
$H50H
3.
Hz,
Pd-C
Vm
Reference(s):
DOS 2 503 75 1 (Ciba-Geigy; appl. 30.1.1975; CH-prior. 8.2.1974)
racemate:
NL-appl. 7 501 785 (Hassle; appl. 14.2.1974).
US 4 080 471 (Hassle; 21.3.1978; prior. 25.6.1976).
synthesis of
5,6-anhydro- 1

,2-0-isopropylidene-a-D-glucofuranose:
Ohle, H.; Dickhbser, E.: Chem. Ber. (CHBEAM)
58,
2593 (1925).
Ohle, H.; Vargha, L. v.: Chem. Ber. (CHBEAM)
61,
1203 (1 928);
62,
2435 (1 929)
Schmidt, D. Th.: Methods Carbohydr. Chem. (MCACAI)
2,
326 (1963).
Horton, D.; Tsai,
J.:
Methods Carbohydr. Chem. (MCACAI)
8,
177 (1980).
Formulation(s):
amp. 5 mg (as hydrochloride)
Trade Name(s):
GB:
Hyprenan (Astra); wfm Varbian (Ciba Labs); wfrn I: Varbian (Ciba-Geigy); wfrn
Prenylamine
ATC: COIDX02
Use: coronary vasodilator
RN: 390-64-7 MF:
CZ4Hz7N MW: 329.49 EINECS: 206-869-4
LD,,: 250 mglkg (M, i.v.);
11 mglkg (R, i.v.); 250 mglkg (R, p.0.)
CN:

N-(l-rnethyl-2-phenylethyl)-y-phenylbenzenepropanamine
lactate
(1:l)
RN: 69-43-2 MF: C2,HZ7N
.
C,H,O, MW: 419.57 EINECS: 200-705-5
LD,,,: 250 mglkg (M, p.0.);
1 glkg (R, p.o.1;
680 mglkg (dog, p.0.)
giuconate
(1:
1)
RN: 21 156-48-9 MF: C2,HZ7N
.
C,HI2O7 MW: 525.64
LD,,: 14 mgkg (M, i.v.);
I
l
mglkg (R, i.v.)
1706
l'
Pridinol
phenylocetone 3.3-diphenyl-
propylamine
ReJerencr(s):
DB
1
111 642 (Hoechst; appl. 7.5.1958).
DE
1

100
031 (Hoechst; appl. 7.5.1958).
Formulution(s):
drg.
15 mg,
30
mg,
60
mg; tabl.
4
mg, 15 mg, 30 mg,
60
mg (as lactate)
Trade
Nume(s):
D:
Daxauten (Kcttclhack- I: Angiovigor (Violani-
J:
Crepasin (Hoei)
Riker); wfm
Farmavigor); wfm
Epocol (Teisan-Nagase)
Daxauten (Woelm); wfm
Angorsan (Isola-Ibi); wfm Herzcon
(Sana)
Segontin (Albert-Roussel);
Carditin-Same (Savoma); Lactarnine (Daisan)
wfm
wfm
NP 30 (Sanken)

Segontin (Hoechst); wfm
Eucardion (Vita); wfm
.
Onlemin (Ono)
Segontin-Digoxin (Albert-
Incoran (ITA); wfm Prectolact (Showa
Rousse1)-comb.; wfm
Irrorin (Alfa Farm.) Yakuhin)
Segontin-Digoxin
Reocorin (Parmochimica Prenylamine Lactate
(Hoechst)-comb.; wfm Ital.); wfm
(Towa)
F:
Cltmodril (Hoechst)- Segontin (Hoechst); wfm Roinin (Mohan)
comb.; wfm
Wasangor (IR); wfm Segontin (Hoechst)
Segontine (Hoechst); wfm Wasangor (Wassermann);
GB:
Synadrin (Hoechst); wfm wfm
Pridinol
ATC: M03BX03
Use: anticholinergic, antiparkinsonian
RN: 51 1-45-5 MF: C2,HZ5NO
-
MW: 295.43 EINECS: 208-128-0
LD,,:
100 mglkg (M, i.p.); 193 mglkg
(M,
s.c.)
CN: a,a-diphenyl- 1 -pipcridinepropanol

hydrochloride
RN: 968-58-1 MF: C,H,,NO. HCI MW: 331.89 EINECS: 213-529-9
LD,,,:
25 mglkg
(M,
i.v.1;
33 mgkg (R, i.v.)
mesylate
RN:
6856-31-1
MF:
C,,,H,,NO
.
CH,03S MW: 391.53 EINECS: 229-953-2
phenylmogncsium ethyl 3-plperldino-
bromide
(1)
propionate
acetophenone poroform- piperidine 3-piperidino-
oldehyde propiophenone
Reference(s):
DE 875 660 (Hoechst; appl. 1941).
Formulation(s):
amp. 2 mglml; drg. 5 mg (as hydrochloride); tabl. 4 mg (as mesylate)
Trade Name(s):
D: Lyseen-Hommel (Hommel) Ly seen (Novartis) Mitanoline (Toyo Pharmar)
Parks 12 (Hommel)
J:
Hikicenon (Tatsumi) Trilax (Toyo Seiyaku
F:

Parks-12 (Laroze); wfm Konlax (Nippon Shinyaku) Kasei)
I: Algolisina (Celsius)-comb. Loxeen (Maruko-Tobishi)
Prilocaine
ATC: NOlBB04
Use: local anesthetic
RN: 721-50-6 MF: C,,H2,N20 MW: 220.32 EINECS: 21 1-957-0
LD,,: 59.9 mglkg
(M,
i.v.)
CN:
N-(2-methylpheny1)-2-(propy1amino)propanamide
monohydrochloride
RN: 1786-81-8 MF: C,3H20N20. HCI MW: 256.78 EINECS: 217-244-0
LD,,: 55 mgkg
(M,
i.v.);
56.6 mglkg
(R,
i.v.)
Reference(s):
GB
839 943 (Astra; appl. 6.6.1958; S-prior. 26.6.1957).
Lofgren, N.; Tegner, C.: Acta Chem. Scand. (ACHSE7) 14,486,490 (1960).
o-toluidine 2-bromopropionyl
Formulation(s):
cream 25 mglg in comb. with lidocaine; plaster 25 mg; vial 5 mglml, 10 mg/ml, 20 mglml,
30 mglml
Prilocoine
Trade Name(s):
D:

EMLA Creme (Astra)- Emlapatch (Astra) Emla (Astra Farmaceutici).
comb. with lidocaine GB: Citanest (Astra) comb.
Xylonest (Astra)
EMLA (Astra)-comb.
J:
Citanest (Astra-Fujisawa)
Xylonest (Astra)-comb. I: Citanest 3
%
Octapressin USA: Emla (Astra)
F:
Emla (Astra)-comb. (Astra Farmaceutici)-comb.
bromide
1708
P
Primaperone
Primaperone
ATC: COlD
Use: vasodilator, antihypotensive
RN: 1219-35-8 MF: CIsH2,FNO MW: 249.33 EINECS: 214-941-1
CN: 1
-(4-fluoropheny1)-4-(]-piperidyl)-
1 -butanone
hydrochloride
RN: 15847-48-0 MF: C,,H2,FN0. HC1 MW: 285.79
4-chloro-4'-fluora- piperidine
butyrophenone
Primoperone
Refprence(s):
FR
1 301 863 (Science Union; appl. 29.6.1961).

FR
1
459 M (Science Union; appl. 18.8.1961; prior. 29.6.1961).
Trade
Name(s):
F: Diviator (Servier)-comb.;
wfm
Primaquine
(Primachin)
ATC: POlBAO3
Use:
antimalarial
RN: 90-34-6 MF: CISHllN30 MW: 259.35 EINECS: 201-987-2
LD,,,: 15.9
mg/kg
(M, i.v.1; 100
mglkg
(M,
p.0.)
CN:
1V-(6-methox~-8-~uinolin~l)-1,4-pen~anediamine
phosphate
(1:2)
RN: 63-45-6 MF: CIH2,N30 . 2H304P
MW:
455.34 EINECS: 200-560-8
LD,,,: 68
mgkg
(M,
p.0.);

177
mglkg
(R,
p.0.)
H2SO4
Fa,
HCI
H
C
'-0
oH
(Skra~~
synthesis)
4-rnethoxy-2- glycerol 6-rnethoxy- 8-amino-
nitroaniline
8-nitra- 6-rnethoxy-
quinoline quinaline
(I)
'a
0
H2N-NHZ
1

4-brorno-1 -phthol-
irnidapentone
H
C
'0
'0
I

Primaquine
I
Primidone
P
1709
Reference(s):
Elderfield, R.C. et al.: J. Am. Chem. Soc. (JACSAT)
68,
1524 (1946).
Elderfield, R.C. et al.:
J.
Am. Chem. Soc. (JACSAT) 77,4816 (1955).
Fomtulation(s):
tabl. 15 mg
Trade Name(s):
D: Primaquine Bayer (Bayer); GB: Primaquine Phosphate USA: Primaquine Phosphate
wfm (ICI); wfm (Sanofi); wfm
I: Primachina fosfato
(IN)
Prirnidone
(Primaclone)
ATC: N03AA03
Use: antiepileptic, anticonvulsant
RN: 125-33-7 MF:
C,,H,,N,O, MW: 218.26 EINECS: 204-737-0
LDSo: 280 mdkg (M, p.0.);
I500 mglkg (R, p.0.)
CN:
5-ethyldihydro-5-phenyl-4,6(1H,5fl-pyrimidinedione
ethylphenyl- forrnarnide

rnalandiamide
Prirnidone
Reference(s):
US
2 578 847 (ICI; 195 I; GB-prior. 1949).
DE 843 413 (ICI; appl. 1950; GB-prior. 1949).
Formulation(sJ:
susp. 250 mg/5 ml; syrup 125 mg/5 ml; tabl. 250 mg
Trade Name(s):
D: Liskatin (Desitin)
F:
Mysoline (Zeneca)
J:
My soline (Dainippon;
Mylepsinum (Zeneca) GB: Mysoline (Zeneca) Marupi)
ResimatiI (Sanofi I: Mysoline (SIT) Primron (Fujinaga)
Winthrop) USA: Mysoline (Wyeth-Ayerst)
Probenecid
ATC: M04ABOI
Use: uricosuric agent
RN: 57-66-9 MF:
C, 3HI,N0,S MW: 285.36 EINECS: 200-344-3
LD,,: 1666 mglkg (M, p.0.);
1600 mgkg (R, p.0.)
CN:
4-[(dipropylamino)suIfonyl]benzoic
acid
1710
P
Probucol

H
H~c++~-'YH~
o=s=o
o=s=o
CI
dipropylamine 4-corboxybenzene- Probenecid
sulfonyl chloride
Reference(s):
US 2 608 507 (Sharp
&
Dohme; 1952; prior. 1949).
Formularion(s):
tabl. 500 mg
Trade Name(s):
D:
Probenecid (Weimer) Colbenemid (Merck Sharp USA: Benemid (Merck Sharp
&
F:
BCnCmide (ThCraplix);
&
Dohme)-comb.; wfm Dohme)
wfm
I:
Probcnecid (IFI) Col BENEMID (Merck
Prototapen (Bristo1)-comb.;
J:
Benecid (Kaken) Sharp
&
Dohme)-comb.
w fm Probenemid (Merck-

with colchidine
GB:
Benemid (Merck Sharp
&
Banyu)
Dohme)
Probucol
ATC: CIOAXO2
Use: antiarteriosclerotic (cholesterol
depressant and
antihyperlipidemic)
RN: 23288-49-5
MF:
C,,H,,O,S, M
W:
5 16.86 EINECS: 245-560-9
LDSo:
>5
glkg
(M, p.0.);
25 glkg (R, p.0.)
CN: 4.4'-[(I
-methylethylidene)bis(thio)]bis[2,6-bis(1
,I
-dimethylethyl)phenol]
Referc.nce(s):
US
3
576 883 (Consol. Coal; 27.4.1971; prior. 3.6.1969).
US

3
862 332 (Dow; 21.1.1975; prior. 11.5.1967, 19.1 1.1969).
DE 1 767
443
(Dow; appl. 10.5.1968; USA-prior. 11.5.1967).
DE
1 768 334 (Consol. Coal; prior. 2.5.1968).
2.6-di-tert-butyl-
starting material:
1JS
3
129 262 (Consolidation Coal Comp.; 14.4.1964; appl. 8.10.1962).
Probucol
Furmulation(s):
tabl. 250 mg, 500 mg
4-mercaptophenol