Pharmaceutical Substances Syntheses, Patents, Applications - Part 38 pdf

Cefaloglycin
C
371
Pivacef (Firma)
Zetacef (Menarini)
J:
Cephalomax (Daisan)
Cephazal (Hokuriku)
Cepol (Torii)
CEX (Glaxo)
Ciponium (Nippon
Kay aku)
Derantel (Nippon
Chemiphar)
Garasin (Wakamoto)
Iwalexin (Iwaki)
Keflex (Shionogi)
Larixin (Toyama)
Madlexin
(Meiji)
Mamalexin (Showa)
Mepilacin-DS (Kanto
Ishi)
Ohlexin (Ohta)
Oracocin (Tobishi)
Oroxin (Otsuka) USA:
Rinesal (Kissei)
Salitex (Banyu)
Segoramin (Takata)
Sencephalin (Takeda)
Suciralin (Mohan)

Sync1 (Toyo Jozo)
Taicelexin (Taiyo)
Tokiolexin (Isei)
Xakl (SS Seiyaku)
Keflex (Dista; 1971)
Cefaloglycin
(Cephaloglycin)
ATC: JOlDA
Use: antibiotic
RN: 3577-01-3 MF:
C,,HI,N306S MW: 405.43 EINECS: 222-696-7
LD,,:
>10 gikg (M, p.0.);
>10 gikg (R, p.0.)
CN:
[6R-(6a,7~(R*))]-3-[(acetyloxy)methyl]-7-[(amin~phenylacetyl)amino]-8-oxo-5-thia-l-
azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
dihydrate
RN: 22202-75-1 MF: C,,H,,N306S
.
2H20 MW: 441.46
&COOH
HGbo
N-Cbo-D-phenyl-
glycine
Hp.
Pd-C
I
Reference (s):

b
1.
isobutyl chloroformate
2.
7-aminocephalosporanic
acid
COOH
0
N-Cbo-cefaloglycin
(I)
COOH
0
NH,
Cefologlycin
0
Cbo:
-'?o
b
GB 985 747 (Eli Lilly; appl. 22.8.1962; USA-prior. 11.9.1961).
US 3 497 505 (Eli Lilly; 24.2.1970; appl. 24.10.1966).
GB 1 017 624 (Merck
&
Co.; appl. 10.1.1963; USA-prior. 16.1.1962).
acylation via silyl-derivatives:
DOS 1 942 454 (Lilly; appl. 20.8.1969; USA-prior. 23.8.1968).
microbiological acylation:
US 4 073 687 (Shionogi; 14.2.1978; J-prior. 14.5.1975).
Formulation(s):
cps. 250 mg, 500 mg
372

C
Cefaloridine
Trade Name(s):
J: Kefglycin (Shionogi) USA: Kafocin (Lilly); wfm
Cefaloridine
(Cephaloridine)
ATC: JOlDA02
Use: antibiotic
RN: 50-59-9 MF: Cl,H,,N3O4S2 MW: 415.49 EINECS: 200-052-6
LD,,,: 2200 mgkg
(M,
i.v.); >20 glkg
(M,
p.0.);
1065 mgkg (R, i.v.); 2500 mgkg (R, p.0.)
CN:
(6R-trans)-l-[[2-carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-l-azabicyclo[4.2.0]oct-2-en-3-
yl]methyl]pyridinium hydroxide inner salt
COOH
o
COO-
pH
6.5
H
cefolotin pyridine Cefoloridine
Reference(s):
GB 1 030 630 (Glaxo; appl. 14.12.1962).
DE 1 445 828 (Glaxo; appl. 14.12.1963; GB-prior. 14.12.1962, 2.12.1963).
FR
1 384 197 (Glaxo; appl. 13.12.1963; GB-prior. 14.12.1962, 2.12.1963).

.
DAS 1 670 599 (Lilly; appl. 17.1.1966; USA-prior. 5.3.1965).
DAS
1
795 581 (Glaxo; appl. 4.1 1.1964; GB-prior. 13.7.1964, 29.9.1964).
DE 1 795 61 0 (Glaxo; appl. 4.11.1964; GB-prior. 4.1 1.1963, 13.7.1964. 29.9.1964).
Formulation(s):
amp. 250 mgl2 ml, 500 mgl3 ml, 1 g14 ml
Trade Name(s):
D: Cepaloridin-Glaxo (Glaxo); KCflodin (Lilly); wfm Keflodin (Shionogi)
wfm I: Ceporin (Glaxo) USA: Loridine (Lilly); wfm
generics
J: Ceporan (Torii)
F: CCporine (Glaxo); wfm CER (Glaxo)
Cefalotin
(Cephalotin)
ATC: JOlDA03
Use: antibiotic
RN: 153-61-7 MF: C,6H,,N20,S2 MW: 396.44 EINECS: 205-815-7
LD,,,: 4990 mgkg (M, i.v.);
>5 glkg (R, i.v.)
CN:
(6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-l-azabicyclo[4.2.O]oct-2-ene-
2-carboxylic acid
monosodium salt
RN: 58-71-9 MF: C16H,,N2Na06S, MW: 418.43 EINECS: 200-394-6
LD,,,: 4800 mglkg (M, i.v.);
5600 mgkg (R, i.v.); >10 glkg (R, p.0.)
Cefamandole
C

373
2-(2-thieny1)- 7-aminocepholo-
ocetyl chloride sporanic acid
Cefalotin
Reference(s):
DE 1 445 684 (Eli Lilly; appl. 4.6.1962; USA-prior. 8.6.1961).
BE618 663 (Eli Lilly; appl. 7.6.1962; USA-prior. 8.6.1961).
DAS
1
670 641 (Lilly; appl. 23.1 1.1967; USA-prior. 23.1 1.1966).
DOS 2 730 579 (Pierre1 S.p.A.; appl. 6.7.1977; GB-prior. 10.7.1976).
acylation via silyl-derivatives of
7-aminocephalosporanic acid:
DOS 1 942 454 (Lilly; appl. 20.8.1969; USA-prior. 23.8.1968).
acylation via
1,3,2-dioxaboranyl-derivatives:
DOS 2 755 902 (Dobfar; appl. 15.12.1977; I-prior. 16.12.1976).
total synthesis:
Ratcliffe, R.W.; Christensen, G.B.: Tetrahedron
Lett.
(TELEAY)
1973,
4649.
"easily soluble form" for parenteral application by freeze-drying:
US 4029 655 (Lilly; 14.6.1977; appl. 11.4.1975).
US 4 132 848 (Lilly; 2.1.1979; prior. 3.1 1.1977).
DOS 2752 442 (Lilly; appl. 24.1 1.1977).
crystalline sterile preparation for parenteral application:
US 4 029 655 (Lilly; 14.6.1977; appl. 11.4.1975).
Formulation(s):

amp. 500 mg, 1 g, 2
g,
4 g (as sodium salt)
Trade Name(s):
D: Cepovenin (Hoechst;
J:
Cephation (Meiji) Sucira N (Mohan)
1973); wfm CET (Glaxo) Synclotin (Toyo Jozo)
F:
CCfalotine (Panpharma) Coaxin (Tobishi) Toricelocin (Torii)
KCflin (Lilly; 1966)
Keflin (Shionogi
Lilly) USA: Keflin (Lilly; 1975); wfm
generics Resting (Ono)
Seffin Neutral (Glaxo;
I: Cefalo (Formulario Naz.) Sodium Cephalotin (Green 1984); wfm
Keflin (Lilly) Cross)
Cefamandole
ATC: JOlDA07
Use: antibiotic
RN: 34444-01-4 MF: C,,Hl,N,05S, MW: 462.51 EINECS: 252-030-0
CN:
[6R-[6a,7~(R*)]]-7-[(hydroxyphenylacetyl)amino]-3-[[(l-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-
thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
formate
monosodium salt (nafate)
RN:
42540-40-9 MF: C,,H17N,Na0,S, MW: 512.50 EINECS: 255-877-4
LDSo:

3915 mglkg (M, i.v.);
2562 mgkg (R, i.v.)
374
C
Cefamandole
fol.mic 7-orninocepholosporonic 7-formomidocepholo-
ocid ocid
sporonic ocid
(I)
1. pH
6.9
HA,
HA
2.
conc.
HCI
COOH
N-'?.
+
+
NOS
1
-methyl-
1H-tetrozole-
5-thiol
sodium solt
7-amino-3-(1 -methyl-
tetrazol-5-ylthiomethyl)
3-cephem-4-corboxylic
ocid

(I!)
D-onhydro-0-
carboxymondelic
acid (from
D(-)-
rnondelic ocid
ond phosgene)
Cefamondole
I
Referencefs):
US 3 641 021 (Lilly; 8.2.1972; appl. 18.4.1969).
DE
2 01
8
600 (Lilly; appl. 17.4.1970; USA-prior. 18.4.1969).
DAS 2 065 621 (Lilly; appl. 17.4.1970; USA-prior. 18.4.1969).
US 3 840 531 (Lilly; 8.10.1974; appl. 21.3.1972).
US 3 903 278 (Smith Kline Corp.;
2.9.1975; prior. 4.1 1.1971).
DOS 2 730 579 (Pierrel S.p.A.; appl. 6.7.1977; GB-prior. 10.7.1976).
preparation andor purification
via the
trimethylsilyl-derivatives:
DOS 2 71 1 095 (Lilly; appl. 14.3.1977; USA-prior. 17.3.1976).
pur$cation:
US
4 11 5 644 (Lilly; 19.9.1978; appl. 19.9.1978).
DOS 2 839 670 (Lilly; appl. 12.9.1978; USA-prior. 19.9.1977).
crystalline sodium salt:
US

4
054 738 (Lilly; 18.10.1977; appl. 22.12.1975).
US 4 168 376 (Lilly; 18.9.1979; appl. 5.6.1978).
lithium salt:
GB
1
546 757 (Lilly; appl. 10.4.1975; valid from 7.4.1976).
0,formyl-derivative:
US 3 928 592 (Lilly; 23.12.1975; appl. 21.2.1974).
GB
1
493 676 (Lilly; appl. 20.2.1975; USA-prior. 22.2.1974).
GB 1 546 898 (Lilly; appl. 7.4:1976; USA-prior. 11.4.1975).
DOS 2 506 622 (Lilly; appl. 17.2.1975; USA-prior. 22.2.1974).
crystalline
sodium .salt
of
0-formylcefamandole:
US 4 006 138 (Lilly; 1.2.1977; appl. 11.4.1975).
Cefapirin
C
375
complex
of
cefamandole sodium
with
1,4-dioxane
and
water:
US 3 947 414 (Lilly; 30.3.1976; appl. 23.12.1974).

complex
of
cefamandole sodium
with
ethyl L-(-)-lactate:
US 3 947 415 (Lilly; 30.3.1976; appl. 23.12.1974).
Formulation(s):
vial 0.5 g,
I
g, 2 g (as nafate)
Trade Name(s):
D: Mandokef (Lilly
;
1977) Cefaseptolo (Miba) Mandolsan (San Carlo)
F:
Kefandol (Lilly) Cefiran (Pierrel) Neocefal (Metapharma)
GB:
Kefadol (Dista; 1978) Cemado (Francia Farm.) Septomandolo (IPA)
1: Bergacef (Bergamon) Fado (Caber)
J:
Kefadole (Shionogi)
Cedol (Eurofarmaco) Lampomandol (AGIPS) USA: Mandol (Lilly; 1978)
Cefarn (Magis) Mancef (Lafare)
Cefarnen (Menarini) Mandokef (Lilly)
Cefapirin
ATC:
JOIDA~O
(Cephapirin; Cefaprin) Use: P-lactam antibiotic
RN: 21593-23-7 MF: C17H,7N,0,S, MW: 423.47 EINECS: 244-466-5
LD,,: >760 mglkg (M, i.v.); 26.1 g/kg (M, p.0.);

6048 mglkg (R, i.v.); 16.356 g/kg (R, p.0.)
'
CN:
(6R-trans)-3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-5-thia-l-azabicyclo[4.2.0]oct-
2-ene-2-carboxylic acid
monosodium salt
RN:
LD,,:
@
24356-60-3 MF: C,,H,,N,NaO,S, MW: 445.45 EINECS: 246-194-2
4600 mglkg (M, i.v.); 26.1 glkg (M, p.0.);
4580 mglkg (R, i.v.); 16.4 glkg (R, p.0.);
2500 mglkg (dog, i.v.)
4-chloro- thioglycolic 4-pyridylthio-
(1)
pyridine acid acetic acid
brornoocetyl
bromide
7-arninocepholo-
Cefopirin
sporonic acid
(11)
-
7
376
C
Cefatrizine
Reference(s):
Crast, L.B. et al.:
J.

Med. Chem. (JMCMAR)
16,
1413 (1973).
US 3 422 I00 (Bristol-Myers; 14.1.1969; appl. 2.5.1967; prior. 5.1.1 967)
US 3 503 967 (Bristol-Myers; 31.3.1970; appl. 26.8.1968).
US 3 578 661 (Bristol-Myers; 11.5.1971; appl. 2.6.1969).
DE
1
670 301 (Bristol-Myers; appl. 5.1.1968; USA-prior. 5.1.1967).
ac)ilation via
1,3,2-dioxaboranyl-derivatives:
DOS 2 755 902 (Dobfar; appl. 15.12.1977; I-prior. 16.12.1976).
salts with amino acids:
FR-appl. 2 479 228 (Dobfar; appl. 25.3.1981; I-prior. 1.4.1980).
Formulation(s):
vial 0.5
g,
1
g,
2
g,
4
g
(as sodium salt)
Trade Name(s):
D: Bristocef (Bristol; 1974); Brisporin (Bristol It. Sud); Cefatrexyl (Nihon Bristol)
wfm wfm Cepotril (Tobishi-Kaken)
F: Cefalojcct (Bristol-Myers Piricef (CT); wfm
Ceropirin (Nichiiko)
Squibb; 1974)

J:
Antibalin (Nippon
Taicelepirin (Taiyo)
I:
Ambrocef (Lusofarmaco); Chemiphar)
Vacian (Kantoishi)
wfm Cefarin (Fuji) USA: Cefadyl (Bristol; 1974)
Cefatrizine
ATC: JDlDA21
Use: p-lactam antibiotic
RN: 5 1627- 14-6 MF: C,uH,uN60,S2 MW: 462.5 1 EINECS: 257-324-2
CN:
[6R-[6a,7~(R*)]]-7-[[amino(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(1H-1,2,3-triazol-4-
ylthio)methyl]-5-thia-l-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
7-orninocepholo- 4-mercopto-
sporonic acid 1,Z.J-triozole
7(R)-omino-3-[(I ,2,3-
triozol-4-ylthio)methyl]-
3-cephern-4-corboxylic
ocid
(I)
triethylomine.
N.N-dimethyloniline.
hexomethyldisilozone
NHz
0(-)-2-(4-hydroxypheny1)-
glycyl chloride
hydrochloride
I

Cefotrizine
Reference(s):
US 3 899 394 (Bristol-Myers; 12.8.1975; prior. 26.12.1972).
US 3 867 380 (SmithKline Corp.; 18.2.1975; prior. 17.12.1970, 18.2.1971, 14.6.1972).
DOS 2 364 192 (Bristol-Myers; appl. 21.12.1973; USA-prior. 26.12.1972).
DAS 2 622 985 (Bristol-Myers; appl. 21
S.1976; USA-prior. 23.5.1975).
US
3
970 65
1
(Bristol-Myers: 20.7.1976; prior. 7.1.1974, 18.12.1974).
US 3 985 747 (Bristol-Myers; 12.10.1976; appl. 24.5.1974).
Cefazedone
C
377
acylation via 1,3,2-dioxabomnyl derivatives:
DOS
2
755 902 (Dobfar; appl. 15.12.1977; I-prior. 16.12.1976).
Formulation(s):
cps. 125 mg, 250 mg, 500 mg; susp. 5
%;
syrup 125 mg, 250 mg
Trade Name(s):
F:
CCfaperos (Bristol-Myers
Squibb; 1987)
1:
Cefatrix (tekfarma bko

Cefotrizin (Firma)
Cetrazil (Herdel)
Faretrizin (Lafare)
Ipatrizina (IPA)
Kefoxina (CT)
Ketrizin (Esseti)
Lampotrix (Leben's) Trixilan (Pulitzer)
Latocef (Delsaz
&
Trizina (Francia Farm.)
Filippini) Zanitrin (Bristol It. Sud)
Miracef (Tosi-Novara) Zinaf (Crosara)
Novacef (Locatelli) Zitrix (Metapharma)
Orotrix (San
Carlo) J: Bricef (Bristol)
Tamyl (Fisons Italchimici)
Cepticol (Banyu; 1980)
Tricef (Eurofarmaco)
Trixidine (ASTA
Medica)
Cefazedone
ATC: JOlDA15
Use: antibiotic
RN:
56187-47-4 MF: C18H,5CI,N505S, MW: 548.45
CN:
(6R-trans)-7-[[(3,5-dichloro-4-oxo-l(4H)-pyridinyl)acetyI]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-
yl)thio]methyl]-8-oxo-5-thia-l-azabicyclo[42.O]oct-2-ene-2-carboxylic
acid
3.5-dichloro- ethyl bromo-

4-pyridone acetate
3.5-dichloro-4-
oxopyridin-1 -yl-
acetic acid
(I)
1.
DMF,
SOCIZ,
-
40
oc
2.
,
N(C,H5),.
CH,CI,.
-20
OC
COOH
0
I
2.
7-aminocepholosporonic acid
CI
"fi
\
'ANp
()"?pH3
H
lhiodiazole
Z-mercapto-

Cefazedone
5-methyl-1,3.4-
378
C
Cefazolin
Reference(s):
Gericke, R.; Rogalski, W.: Arzneh-Forsch. (ARZNAD)
29
(I),
362 (1979).
DOS 2 427 224
(E.
Merck; appl. 6.6.1974).
DOS 2 345 402 (E. Merck; appl. 8.9.1973).
DOS 2 621
01 1 (E. Merck; appl. 12.5.1976).
GB 1 436 989 (E. Merck; appl. 5.9.1974; D-prior. 8.9.1973,6.6.1974).
US 4 153 693 (E. Merck; 8.5.1979; D-prior. 8.9.1973,6.6.1974).
GB 1 539 158 (E. Merck; appl. 11.5.1977; D-prior. 12.5.1976).
Formulution(s):
vial 1 g, 2 g
Trade Narne(s):
D: Refosporin (E. Merck);
wfrn
Cefazolin
(Cephazolin)
ATC: JOlDA04
Use: antibiotic
RN: 25953-19-9 MF: Cj4HI4NRO4S3 MW: 454.52 EINECS: 247-362-8
LDS,,: 3 gkg (M, i.v.)

CN:
(6R-trans)-3-[[(5-rnethyl-l,3,4-thiadiazol-2-yl)thio]rnethyl]-8-ox0-7-[(lH-tetrazol-l-yla~etyl)amino]-5-
thia-
1
-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
monosodium saIt
RN: 271 64-46-1 MF: CI4HI,N,NaO,S3 MW: 476.50 EINECS: 248-278-4
LDSI; 3900 rnglkg (M, i.v.);
>l
1
glkg (M, p.0.);
2760 rnglkg
(R,
i.v.); >ll glkg
(R,
p.0.);
2200 rnglkg (dog, i.v.)
2-mercopto-
5-methyl-
1
J.4-
thiodiozole
Cefozolin
US
3 5 16 997 (Fujisawa; 23.6.1970; appl. 12.4.1968; J-prior. 15.4.1967, 24.lO.l967,28.10.1967).
DE 1 170 168 (Fujisawa; appl. 10.4.1968; J-prior. 14.4.1967).
Cefbuperazone
C
379

corresponding:
GB
1 206 305 (Fujisawa; appl.
1
1.4.1968; J-prior. 15.4.1967).
NL
6
805 179 (Fujisawa; appl. 1 1.4.1968; J-prior.
1
5.4.1967).
DOS 1953 861 (Fujisawa; appl. 25.10.1969).
alternative syntheses:
DOS 2 055 796 (Fujisawa; appl. 13.1 1.1970; J-prior. 17.
I
1.1969).
DOS
2
540 374 (Lilly; appl. 10.9.1975; USA-prior. 12.9.1974).
acylation via
1,3,2-dioxaboranyl-derivatives:
DOS
2
755 902 (Dobfar; appl. 15.12.1977; I-prior. 16.12.1976).
pur#cation:
US
4
115 645 (Lilly; 19.9.1978; appl. 10.5.1977).
sodium salt:
DOS 2752 443 (Lilly; appl. 24.1 1.1977; USA-prior. 24.11.1976).
sodium salt monohydrate:

US
4 104 470 (Lilly; 1.8.1978; appl. 3.6.1977).
mpidly soluble spray dried
sociimn
salt:
US4 146 971 (Lilly; 3.4.1979; prior. 24.1 1.1976, 14.12.1977).
suspension for parenteral application:
GB 1 546 479 (Lilly; appl. 23.4.1976; USA-prior. 28.4.1975).
Fonulation(s):
vial 250 mg, 500 mg, 1
g,
2
g
(as sodium salt)
Trade Namefs):
D: Elzogram (Lilly; 1974)
Gramaxin (Roche; 1974)
F:
Cefacidal (Bristol-Myers
Squibb; 1976)
Kefzol (Lilly; 1976)
GB: Kefzol (Lilly; 1974)
I:
Acef (Eurofarmaco)
Biazolina (1st. Italiano
Ferm.)
Cefabiozim (IPA) Zolisint (Locatelli)
Cefamezin (Carlo Erba)
J:
Cefamezin (Fujisawa;

Cefazil (Delsaz
&
1971)
Filippini) USA: Anccf (SmithKline
Cromezin (Crosara) Bcccham; 1973)
Firmacef (Firma) Kefzol (Lilly; 1973)
Recef (Farma Uno)
Totacef (Bristol It. Sud)
Zolin (San
Carlo)
Cefbuperazone
ATC: JOlDA
Use: p-lactam antibiotic
RN:
76610-84-9 MF: C,,H,,N,O,S,
MW:
627.66
CN:
[6R-[6a,7a,7(2R*,3S*)l]-7-[[2-[[(4-ethyl-2,3-dioxo-
1-piperazinyl)carbonyl]amino]-3-hydroxy-
1
-
oxobutyl]amino]-7-methnxy-3-[[(I-methyl-
IN-tetrazol-5-yl)thio]methyl]-8-0x0-5-thia-1-
azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid
A
H3C
OH
1.

trimethylchlorosilane
A
OH$
OH
2.
2,3-dioxo-4-ethyl-
1
-piperazine-
D-threonine
corbonyl chloride
7(R)-(2.3-dioxo-4-ethyl-
(cf, piperocillin synthesis)
1
-piperozinecorboxornido)-
3(S)-hydroxybutyric
380
C
Cefbupcrazone
1.
TosOH, dioxane
t
2.
diphenyldiozo-
methane
7-ominocepholo- diphenylmethyl
sporonic acid 7-aminocephalo-
sparonate
(11)
1-methyl-1
H-

diphenylrnethyl
tetrozole-5- 7(R)-amino-3-(1 -methyl-
thiol
1
H-tetrazol-5-ylthiomethy1)-
3-cephem-4-carboxylote (Ul)
n
1.
H3C-FC/O
.
CH2C12, CI-COOC2H5. -15 "C
2.
I11
I
1.
4-methylmorpholine,
0
ethyl chloroformote
1.
CH2C12, THF, -70 OC
2.
H3C-4-
Lit.
CH30H
3
(CH3)3C-OCI
4.
AcOH
5. NoHCOJ. pH 6.5
IV

3. tert-butyl hypochlorit/
onisole. CF3COOH
v
b
trifluoroacetic
acid
Cefbuperozone
Referenceis):
DOS
2 939 747
(Toyama;
appl.
1.10.1979;
J-prior.
23.4.1979,7.8.1979).
FR
2
455 051
(Toyama;
appl. 4.10.1979;
J-prior.
23.4.1979,7.8.1979).
US
4 263 292
(Toyama;
21.4.1981;
J-prior.
13.6.1978, 23.4.1979,7.8.1979).
GB
2 048 241

(Toyama;
appl.
26.9.1979;
J-prior.
23.4.1979, 7.8.1979).