2.5 mg, 5 mg as tartrate Alimemozine Trade Names: D: Repeltin Bayer GB: Vallergan RhGne-Poulenc F: Theralhne Evans Medical Rorer; as tartrate ThCralene Pectoral Evans I: in comb.. CN:
Trang 1Alibendol A 6 1
16-dehydroprogesterone 16u, 17a-dihydroxy-
progesterone (I)
acetophenone
1 Algestone acetophenide I
Reference(s):
DE 1 125 423 ( O h Mathieson; appl 1959; USA-prior 1958)
Fried, J et al.: Chem Ind (London) (CHINAG) 1961,465
alternative synthesis;
US 3 008 958 (Olin Mathieson; 1961; prior 1961)
synthesis of intermediates:
US 2 727 909 (Searle; 1955; prior 1954)
US 3 165 541 (Olin Mathieson; 12.1.1965; prior 20.5.1963)
Cooley, G eta].: J Chem Soc (JCSOA9) 1955,4373
Inhoffen, H.H et al.: Chem Ber (CHBEAM) 87,593 (1954)
Hydorn, A.E et al.: Steroids (STEDAM) 3,493 (1964)
injection solution:
US 3 164 520 (Olin Mathieson; 5.1.1965; prior 29.10.1962)
medical me as contraceptive:
GB 1 060 632 ( O h Mathieson; appl 16.8.1963; USA-prior ll.ll.1962)
Formulation(s): cream 2 %
Trade Name(s):
I: Neolutin Depos (Medici)
Use: antispasmodic, choleretic, cholekinetic
RN: 26750-81-2 MF: C,,H,,NO, MW: 251.28 EINECS: 247-960-9
LD,: >3000 mglkg (M, p.0.); >2000 m g k g (M, s.c.)
CN: 2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-(2-propenyl)benzamide
2-hydroxy -3-
methoxy-
benzaldehyde
-
ethyl P-hydroxy- 3-methoxybenzoate
Trang 262 A Alimemazine
0 0-CH,
/,,&h3 + H 2 N m O H *
H,C'
ethyl 5-ollyl-2- ethonolamine Alibendol
hydroxy-3-methoxy-
benzoate (I)
Reference(s):
DE 1 768 615 (Roussel-Uclaf; appl 1968; F-prior 1967)
Clemence, F et al.: Chim Ther (CHTPBA) 5, 188 (1970)
Formulation(s): tabl 100 mg
Trade Name(s):
F: Cebera (Irex)
Alimemazine
(Trimeprazine)
ATC: R06ADO1 Use: antihistaminic, psychosedative RN: 84-96-8 MF: C,,H,,N,S MW: 298.45 EINECS: 201-577-3
LD,,: 33 m g k g (M, i.v.); 300 mglkg (M, p.0.);
35 m g k g (R, i.v.); 210 mglkg (R, p.0.)
CN: N,N,P-trimethyl-lOH-phenothiazine-10-propanamine
tartrate (2:l)
RN: 4330-99-8 MF: C,,H2,N2S 1/2C4H606 MW: 746.99 EINECS: 224-368-9
LD,,: 33 m g k g (M, i.v.); 300 mglkg (M, p.0.);
35 m g k g (R, i.v.); 210 mglkg (R, p.0.)
H
C H CH, + c l A ' C H 3 sodium
omide
Reference(s):
US 2 837 518 (RhGne-Poulenc; 1958; F-prior 1954)
DE 1 034 639 (RhGne-Poulenc; appl 1955; GB-prior 1954 and 1955)
phenothiozine 3-dimethylomino-
Formulation(s): drops 40 mg; tabl 2.5 mg, 5 mg (as tartrate)
Alimemozine
Trade Name(s):
D: Repeltin (Bayer) GB: Vallergan (RhGne-Poulenc
F: Theralhne (Evans Medical) Rorer; as tartrate)
ThCralene Pectoral (Evans I: in comb with prednisolone
Medical)-comb J: Alimezine (Daiichi)
2-methylpropyl chloride
Trang 3Alizapride A 63
Use: antl-emetic, neuroleptic RN: 59338-93-1 MF: C,,H,,N,O, MW: 315.38 EINECS: 261-710-6
LDw: 92.7 mglkg (M, i.v.)
CN: 6-mcthoxy-N-[[I-(2-propenyl)-2-pyrrolidinyl]methyl]-1H-benzotriazole-5-carboxamide
I: F H 3
p-amino- dimethyl methyl 4-amino-
salicylic acid sulfoie 2-methoxybenzoote
(9 v.1
NONO*, HCI
sodium
0
methyl 4.5-diomino- methyl 6 - m t h o x - p~rra1idi.e I Uizopride 1
2-methoxybenzoate (I) benzotriozale-5-
corboxylote
Reference(s):
DE 2 500 919 (Delagrange; appl 11.1.1975)
US 4 039 672 (Delagrange; 2.8.1977; D-priol 1 1.1.1975)
synthesis of methyl 4-amino-2-methoxybenzoate:
DOS 1966 212 (Yamanouchi; appl 29.12.1969; J-prior 2.12.1968, 9.12.1968,4.4.1969)
Formulation(s): amp 50 mg/2 ml; drinking amp 360 mg; suppos 50 mg; tabl 50 mg
Trade Name(s):
D: Vergentan (Synthelabo) I: Limican (Synthelabo)
F: Plitican (S ynthelabo) Nausilen (Baldacci)
Use:
RN: 97-59-6 MF: C4H,N403 MW: 158.12 EINECS: 202-592-8
CN: (2,5-dioxo-4-imidazolidiny1)urea
D03; DO5 wound remedy, antipsoriatic, adstringent, web stimulant, keratolytic, antacid
RN: 13 17-25-5 MF: C4H,A1,CIN40, MW: 3 14.55 EINECS: 215-262-3
LD,,,: 28 g k g ( M A p.o.1
CN: chloro[(2,5-dioxo-4-imidazolidinyl)uretato]tetrahydroxyaluminum
Trang 464 A Aldioxa
Aldioxa
RN: 5579-81 -7 MF: C4H,A1N,0s MW: 218.1 1 EINECS: 226-964-4
LD,,: >8 glkg (M, p.0.)
CN: [(2,.5-dioxo-4-imidazolidinyl)ureato]dihydroxyaluminum
urea glyoxylic
acid
Reference(s):
DOS 1 939 924 (BASF; appl 6.8.1969)
from glyoxal viu "in situr'-glyoxylic acid:
DOS 2 7 14 938 (Akad d Wiss der DDR; appl 2.4.1977; DDR-prior 29 10.1976)
from chloral hydrate via "in situV-glyoxylic acid:
DOS 2 717 698 (Akad d Wiss der DDR; appl 21.4.1977; DDR-prior 29.10.1976)
by oxidation of uric acid with PbO, or H202 or potassium permanganate:
Org Synth (ORSYAT) 1 3 1 (1933)
by oxidation of glycoluril widz H20,:
Biltz, H.; Schiemann, G.: J Prakt Chem (JPCEAO) 113,92 (1926)
US 2 802 01 1 (Carbogen Corp.; 19.57; appl 19.56)
by condensation of glyoxylic acid esters or glyoxylic acid acetul esters with urea:
US 2 1.58 098 (Merck & Co.; 1939; appl 1937)
Formulation(s): cream 0.2 %; ointment 2 %; powder 0.5 %; tabl 100 mg
Trade Name(s):
D: more than 70 combination
preparations
allantoin
Brand- und Wundgel (Eu
Rho Arznei)-comb
Contractubex Gel (Merz &
Co.)-comb
Ellsurex (Ga1derma)-comb
Essaven (Nattermann)-
comb
HAEMO-Exhirud (Sanofi
Winthrop)-comb
Hydro Cordes (Block Drug
Company; Ichthyo1)-comb
Lipo Cordes (Block Drug Company)-comb
Psoralon (Herma1)-comb
Psoriasis-Salbe M (Balneopharm) Ulcurilen (Spitzner)-comb
alcloxa
Ansudor (Basotherm)- comb
aldioxa
Ansudor (Basotherm)- comb
Dexa-Mederma Akne (Merz & Co.)-comb
GB:
Elmedal (Thiemann)-comb Mederima (Merz & Co.)- comb
ZeaSorb Puder (Stiefe1)- comb
alcloxa
Ulfon (Lafon)-comb
aldioxa
Ulfon (Lafon)-comb
allantoin
Actinac (Hoechst)-comb with chloramphenicol and hydrocortisone
Trang 5Allobarbital A 65
Alphosyl (Stafford-Miller)-
comb
Aphosyl HC (Stafford-
Miller)-comb with
hydrocortisone
Dermalex (Sanofi
Winthrop)-comb with
squalene and
hexachlorophane
1: allantoin
Alphosyle (Po1i)-comb
Antiacne Samil (Sami1)- comb
Apsor pomata (ID1 Farrnaceutici)-comb
J: aldioxa
Aldioxa (Isei) Chlokale (Sawai)
USA: allantoin
Alphosyl (Reed &
Camrick)-comb.; wfrn Bahnex (Maxsi1)-comb.;
wfrn
Cervex (Medics)-comb.; wfrn
Cutemol Creme (Summers); wfrn Herpecin-L (Campbell) comb.; wfm
Sufamal (Milex)-comb.; wfm
Vagilia (Lemmon)-comb.; wfrn
Allobarbital
(Allobarbitone)
ATC: N05CA21 Use: hypnotic, sedative RN: 52-43-7 MF: CIOHl,N,O, MW: 208.22 EINECS: 200-140-4
LD,,: 21 8 mglkg (M, i.v.)
CN: 5,5-di-2-propenyl-2,4,6(1H,3H,SH)-pyrimidinetrione
ally1 bramide borbituric 1 Allobarbital 1
acid
Reference(s):
DRP 268 158 (Ciba; appl 1911)
DRP 526 854 (Hoffmann-La Roche; appl 1930)
Formulation(s): tabl 30 mg, 100 mg, 300 mg
Trade Name(s):
D: Toximer (Merck1e)-comb.; F: Spasmo-Cibalgine (Ciba)- I: Allobarb (Tariff
USA: Diadol (Durst); wfrn
Use: uricosuric agent RN: 315-30-0 MF: C,H,N,O MW: 136.1 1 EINECS: 206-250-9
L&: > l glkg (M, p.0.)
CN: 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
Trang 666 A Allopurinol
ethyl cyanoacetate triethy ortho- ethyl ethoxymethylene-
forrnate cyonoacetaie (I)
ethyl 5-amino- pyrazole-4-carboxylate
forrnornide
0
Allopurinol
u
H
0
cyanoaceiarnide forrnamidine
hydrochloride
3-amino-2-cyano- acrylarnide (11)
11
0
Reference(s):
a US 2 868 803 (Ciba; 13.1.1959; CH-prior 10.2.1956)
US 3 624 205 (Burroughs Wellcome; 30.1 1.197 1; USA-prior 25.4.1967)
b DAS 1 720 024 (Wellcome Found; appl: 12.7.1967; GB-prior 14.7.1966)
similar process:
DAS 1 904 894 (Wellcome Found; appl 3 1.1.1969; GB-prior 2.2.1968)
US 4 146 713 (Burroughs Wellcome; 27.3.1979; GB-prior 2.2.1968)
alrernative syntheses:
US 3 474 098 (Burroughs Wellcome; 21.10.1969; prior 29.3.1956)
DAS 2 224 382 (Henning Berlin; appl 18.5.1972)
DE 1 118 221 (Wellcomc Found; appl 4.8.1956; GB-prior 10.8.1955)
DAS 1 814 082 (Wellcome Found; appl 11.12.1968)
DAS 1 950 075 (Henning Berlin; appl 3.10.1969)
DOS 2 018 345 (Delmar Chemicals; appl 16.4.1970; GB-prior 17.4.1969)
cornbirzation with benzbromarone:
GB 1 493 237 (Henning Berlin; appl 11.5.1976; D-prior 10.12.1975)
Formulation(s): tahl 100 mg, 200 mg, 300 mg
Trade Nu~ne(s):
D: ~110-300-Tablinen (ct- Allomaron (Nattermann)
Allo-Puren 1001-300 (Isis Puren)
~ l e m i n o l (gepepharm)
Trang 7Allylestrenol A 67 Cellidrin (Henning)
dura A1 300 (durachemie)
Foligan (Henning Berlin)
Remid 1001-300 (TAD)
Suspend01 (Merckle)
Uribenz 300 (R.A.N.)
Uripurinol 1001300
(Azupharma)
Urosin (Boehringer
Mannh.)
Zyloric (Glaxo Wellcome;
1966) combination preparations F: Zy loric (Glaxo Wellcome;
1968) GB: Zyloric (Glaxo Wellcome; J:
1: Allopuri (Formulario Naz.) Allurit (RBS Pharma)
Allurit (Rh8ne-Poulenc Rorer)
Uricemil ( K T ) Uricodue (IF[)-comb Zyloric (Wellcome; 1969) Zyloric (Tanabe; 1969) Zyloprim (Glaxo Wellcome; 1966)
Allylestrenol
(Allyloestrenol)
ATC: G03DCOI Use: progestogen
RN: 432-60-0 MF: C,,H,,O MW: 300.49 EINECS: 207-082-9
LD,,: >640 mglkg (M, p.0.)
CN: (17P)-17-(2-propenyl)estr-4-en-17-ol
(q.v.) 1,2-dithial
EirtJ9+,CH2
A
allylmagnesium bromide
17P-hydroxy-
4-estrene (I)
17-0x0-4- estrene
/ Allylestrenol
Referencefs):
GB 841 41 1 (Organon; appl 2.4.1958; NL-prior 10.4.1957)
alternative syntheses:
GB 875 549 (Organon; appl 31 l2.1959; NL-prior 13.1.19.59)
US 2 878 267 (Organon; appl 16.4.1958; NL-prior 1 S.1957)
Formulation(s): tabl 5 mg
Trade Name(s):
D: Gestanon (Organon); wfm 1: Gestanon (Organon Italia)
GB: Gestanin (Organon); wfm J: Gestanon (Sankyo)
Use: non-steroidal anti-inflammatory, analgesic
RN: 39718-89-3 MF: C,,Hl,NO, MW: 219.28 EINECS: 254-604-6
LD,,: 2400 mglkg (M, p.0.)
CN: a-methyl-4-[(2-methyl-2-propenyl)amino]benzeneacetic acid
Trang 86 8 A Almitrine
1 HCI YH3 CH3 2.HO-CH3
O 2 N
HN\
C H 3 4-nitrobenzene- form- dimethyl-
acetic ocid oldehyde omine
Hp Pd-C 2 NoOH
f l \ C H 3 - &0\cH3 T= H 3 c v N
0 2 N
/ 0
Referenceis):
Dumaitre, B et al.: Eur J Med Chem (EJMCAS) 14, 207 (1979)
alternative synthesis:
FR 2 289 180 (Lab Bouchara; appl 17.5.1971)
Formulation(s): tabl I50 mg, 300 mg
Trade Name(s):
F: Minalfkne (Bouchara) J: Minalfen (Fujirebio)
Use: analeptic, respiratory stimulant RN: 27469-53-0 MF: C,,H,,F,N, MW: 477.56 EINECS: 248-475-5
CN: 6-[4-[bis(4-fluorophenyl)methyl]-l-piperazinyl]-N,l\r-di-2-propenyl-1,3,5-triazine-2,4-diamine
1 -[bis(4-fluoropheny1)- cyonuric
methyllpiperozine chloride
2-[4-[bis(4-1luorophenyl)-
methyl]-1 -piperozinyl]- 4.6-dichloro-1 3,5-triozine (I)
H2N4~H2 NoOH
ollylomine F
N yN HNd'~~,
Trang 9Aloxiprin A 69
Reference(s):
FR 2 019 646 (Science Union; appl 22.9.1969; GB-prior 2.10.1968)
DOS 1 947 332 (Science Union; appl 18.9.1969; GB-prior 2.10.1968)
US 3 647 794 (Science Union; 7.3.1972; GB-prior 2.10.1968)
GB 1 256 51 3 (Science Union; appl 2.10.1968; valid from 30.9.1969)
Formulation(s): f c tabl 50 mg; vial 15 mg/5 ml; tabl 50 mg
Trade Narne(s):
D: Vectarion (Servier; 1984) F: Duxil (Therval Mtdical; Vectarion (EuthCrapie;
Use: analgesic RN: 9014-67-9 MF: unspecified MW: unspecificd
CN: aloxiprin
polymeric condensotion product of aluminum oxide and ocetylsolicylic acid
aluminum isoprapylate acetylsalicylic ocid Aloxiprin
(q v-1
Reference(s):
Cummings, A.J et al.: J Pharm Pharmacol (JPPMAB) 15, 56 (1963)
Forrnulation(s): tabl 400 mg, 450 mg, 600 mg
Trade Name(s):
GB: Palaprin (Nicholas); wfm Palaprin forte (Nicholas);
wfm
Alphaprodine
(Alfaprodina)
ATC: N02AB Use: analgesic RN: 77-20-3 MF: C,,H,,NO, MW: 261.37 EINECS: 201-011-5
CN: cis-1,3-dimethyl-4-phenyl-4-piperidinol propanoate (ester)
hydrochloride
RN: 561-78-4 MF: C,,H2,NO2 HCI MW: 297.83
LD,,,: 32 m g k g (M, i.v.);
25 m g k g (R, i.v.); 90 mglkg (R, p.0.);
36.2 m g k g (dog, i.v.)
Trang 1070 A Alpidem
bromo- phenyllithium
benzene
H SO
0 0
HSC
propionic anhydride
Alphaprodine
I
Reference(s):
US 2 498 433 (Hoffmann-La Roche; 19.50; prior 1946)
starting material:
I ,3-dimethyl-4-piperidone:
Howton: J Org Chem (JOCEAH) 10,277 (1945)
Formulation(s): amp 4 %, 6 %
Trade Name(s):
USA: Nisentil (Roche); wfm
Use: anxiolytic, o,-agonist RN: 82626-01 -5 MF: C2,Hz3CI2N3O MW: 404.34
CN: 6-chloro-2-(4-chlorophenyl)-N,~propylimidazo[l,2-a]pyridine-3-acetamide
2-omino-5- 4'-chloro-2-brorno- 6-chloro-2-(4-chloro-
chloropyridine acetophenone phenyl)imidazo[l,2-a]-
pyridine
2 NaCN
H,C-N,