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Pharmaceutical Substances Syntheses, Patents, Applications - Part 7 docx

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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 1

Alibendol 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 2

62 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 3

Alizapride 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 4

64 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 5

Allobarbital 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 6

66 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 7

Allylestrenol 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 8

6 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 9

Aloxiprin 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 10

70 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,

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