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Pharmaceutical Substances Syntheses, Patents, Applications - Part 61 pps

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as phenylpropionatc- Ciba; as pivalate; wfm comb.; wfm comb.; wfrn I: Cortiron Schering; wfrn J: Syncorta Takeda F: Syncortyl Rousscl Neodin Lusofarrnaco; USA: Doca Acetate Organon; Perc

Trang 1

Desoxycortone acetate D 601

CH 0 H3 H 3 c G " - c H 3 +

8 0 OC

isopropenyl acetate

3$-hydroxy-20-0x0-5,16- formic

pregnodiene (1) acid

(fmm diosgenin)

K

0 CH,

@ A1[OCH(CH3)zl3 cyclo- aluminum hexonone triisopropylate

Desoxycortone acetate

Oesoxycortone acetate iodine

progesterone

pregnenolone diethyl oxolote

NaOCH3

Trang 2

602 D Detajmium bitartrate

CH,COOH

H,C-CO-CH, Go A1[oCH(CH&

VI + N -+

cyclo- olurninurn hexanone triisopropylate

Reference(s):

a Sondheimer, F et al.: J Am Chern Soc (JACSAT) 79,5034 (1957)

synthesis of I:

Wall, M.E.: J Am Chem Soc (JACSAT) 77,5665 (1955)

b Ringold, H.J.; Stork, G.: J Am Chem Soc (JACSAT) 80, 250 (1958)

c Ruschig, H.: Angew Chem (ANCEAD) 60,247 (1948)

Ruschig, H.: Chem Ber (CHBEAM) 88, 878 (1955)

alternative syntheses:

DE 871 153 (Hoechst; appl 1937)

DE 875 353 (Schering AG; appl 1938)

US 2 3 12 480 (Roche-Organon; 1943, CH-prior 1937)

US 2 409 043 (Schering Corp.; 1946, D-prior 1939)

US 2 470 903 (W C Ross; 1949; GB-prior 1945)

Serini, A et al.: Ber Dtsch Chern Ges (BDCGAS) 72,391 (1939)

Wilds, A.L.; Shunk, C.H.: J Am Chem Soc (JACSAT) 70, 2427 (1948)

review:

Ullrnanns Encykl Tech Chern., 4 Aufl., Vol 13, 52

Formulation(s): amp 10 mglml

Trade Name(s):

D: Docabolin (Nourypharrna; GB: Percorten M Crystals Sinsurrene (Parke Davis)

as phenylpropionatc- (Ciba; as pivalate); wfm comb.; wfm

comb.); wfrn I: Cortiron (Schering); wfrn J: Syncorta (Takeda) F: Syncortyl (Rousscl Neodin (Lusofarrnaco); USA: Doca Acetate (Organon);

Percorten (Ciba); wfrn

Use: antiarrhythmic RN: 53862-8 1-0 MF: C27H,2N30, C,H606 H 2 0 MW: 624.75

LDs,,: 6000 pg/kg (R, i.v.)

dihydroxybutanedioic acid (1:l) rnonohydrate

tartrate (1:l)

RN: 33774-52-6 MF: C27H,,N,0, C,H,O, MW: 606.74

LD,,,: 10 rnglkg (R, i.v.); 290 mglkg (R, p.0.)

epichloro- diethylamine 1 -diethylomino-

Trang 3

Dexamethasone D 603

H

ajmaline

L-tartaric acid

HO,

H

Oetajmiurn bitartrate

DE 2 025 286 (VEB Arzneimittelwerk Dresden; appl 23.5.1970; DDR-prior 28.7.1969)

GB 1 244 597 (VEB Arzneimittelwerk Dresden; appl 5.7.1970; DDR-prior 28.7.1969)

Formulation(s): sugar coated tabl 25 mg

Trade Name(s):

D: Tachmalcor (ASTA Medica

AWD)

Dexamethasone

(Dexametasone)

ATC: AOlAC02; C05AA09; D07AB 19; D07XB05; DlOAA03; H02AB02; ROlAD03; SOIBAOI; SOICBOI; S02BA06; S03BA01

Use: glucocorticoid

RN: 50-02-2 MF: CzzHz,F05 MW: 392.47 EINECS: 200-003-9

LD,,: >3 g/kg (R, p.0.)

CN: (1 1 P,16n)-9-fluoro-11,17,21-trihydroxy- 16-methylpregna-1,4-diene-3,20-dione

H3C-MgI, LiBr

methylmagnesium lithium

Trang 4

604 D Dexamethasone

1 (H3C-CO)20 Tos-OH

0-OH

1 bromine OK , & - - 3 H :

2 sodium iodide HO.%'' H H

CrO,, pyridine

oxide

1 bromine

3 sernicarbozide

3 pyruvic ocid

2 NoBH,

3 H+ CH3 - H3C-SO2-Cl, rnethonesulfonyl pyridine

boranote

NaOBr

IVsodium

hypobrornite

H2F2 CHCly THF

-

rnicrobiologicol dehydration

[Schizornycetes (ATCC-7063)] or Se02

I Dexamethosone I

Trang 5

Reference(s):

a Arth, G.E et a].: J Am Chern Soc (JACSAT) 8 0 , 3 160 (1958)

DE 1 113 690 (Merck & Co.; appl 22.2.1958; USA-prior 27.2.1957)

Applezweig, N.: Steroid Drugs, Vol 1 , 7 2 (New York, Toronto, London 1962)

b Oliveto, E.P et al.: J Am Chern Soc (JACSAT) 80,4431 (1958)

US 2 852 51 1 (Olin Mathieson; 1958; prior 1953)

US 3 007 923 (Lab Franq de ChirniothCrapie, 7.1 1.1961; appl 12.1.1960; F-pr~or 22.1.1959)

Applezweig, N.: Steroid Drugs, Vol 1, 74 (New York, Toronto, London 1962)

' synthesis from tigogenin:

Ohta, T et al.: Org Process Res Dev (OPRDFK) 1 , 4 2 0 (1997)

synthesis of VII:

Oliveto, E.P et al.: J Am Chem Soc (JACSAT) 80, 4431 (1958)

Marker, R.E.; Crooks, H.: J Am Chern Soc (JACSAT) 64, 1280 (1942)

GB 869 511 (Upjohn; appl 24.4.1959; U S A - ~ ~ ~ O ~ : 26.5.1958)

alternative synthesis:

US4041 055 (Upjohn; 9.8.1977; appl 17.1 1.1975)

review:

Ullmanns Encykl Tech Chem., 4 Aufl., Vol 13, 57

Formulation(sJ: aerosol 0.075 mglper pump; amp 5 mglrnl; eye drops 1 rnglrnl; f c tabl 0.5 rng, 0.75 mg,

1.5 mg; ointment 0.1 %; sol 0.03 %; suppos 2.2 rng

Trade Name(s):

D: afpred forte Dexa (Hefa-

Frenon)

Anernul (Medopharm)

Baycuten (Bayropharm; as

acetate)-comb

Chibro-Cadou (Chibret)

Cortidexason Crinale,

Salbe (Dermapharn1)-

comb

Cortisumman (Dr Winzer)

Corto-Tavegil (Novartis

Pharma)-comb

Dexa-Allvoran (TAD)

Dexa Biciron (A1con)-

comb

Dexagel (Mann)

Dexa Loscon (Galderma)

Dexamonozon (Medice)

Dexamytex (Mann)-comb

Dexa-Philogout (Azupharma) Dexa Polyspectral (Alcon) Dexa-Rhinospray (Boehringer Ing.) Dexa-sine (Thilo) Duodexa N Salbe (Kade) Fortecortin (Merck) Isopto-Dex (Alcon)-comb

Lipotalan (Merckle) F:

Localison (Dorsch)-comb

Millicorten (Novartis Pharma)-comb

Nystalocal (Nourypharrna)- comb

Otobacid (Axhe)-comb

Predni (Sanirania) GR:

Predni-F-Tablinen (Sanorania)

Predni-F-Tablinen (Sanorania) Sokaral (Pharma-Allergan) Solutio Cordes (lchthyol) Spersadex (CIBA Vision) Tuttozem (S trathrnann) Tuttozem N (Mayo) various combination preparations and generics DCcadron (Merck Sharp &

Dohrne-Chibret) Dectancyl (Roussel Diarnant; as acetate) Maxidex (Alcon) numerous combination preparations

Decadron (Merck Sharp &

Dohrne) Maxidex (A1con)-comb

Trang 6

606 D Dexamethasone tert-butylacetate

Eurason D (Ciba-Geigy) Metasolon (Shionogi) Mitasone (Toyo Pharmar) Orgadron (Organon- Sankyo)

Rheumadex (Nakataki) comb

Rheumatol (Sankyo)-comb Santeson (Santa) Sawasone (Sawai) Sunia-D Comp (Zeria Shinyaku)

Maxitrol (Aleon)-comb

Otomize (Stafford-Miller)

Sofradex (Florize1)-conlb

1: Antimicotico liquid01

pomata (1FI)-comb

Aurizone (SIF1)-comb

Decadron (Merck Sharp &

Dohme)

Desalark (Farmacologico

Milanese)

Desamix-neomicina

(Savoma)-comb

Deseronil (Sea)

Fluorobioptal (Farmila)-

comb

Lasoproct (Bayer)-comb

Luxazone (Allergan)

Nasicort~n (Bracco)-con&

Neocortofcn (Ripari-Gero)-

comb

Rinedrone (Deca)-comb

Tobradere (Aleon)-comb

Visumetazone (Merck

Sharp & Dohme)

various combination preparations J: Alpermell (Nippon Shinyaku) Amumetazon (Choseido) Aphtasolon (Showa Yakka) Bisno-DS (Ohta)

Carulon (Yamanouchi) Corson (Takeda) Dab M (Zenyaku) Decaderm (Banyu) Decadron (Banyu) Dectan (Nippon Roussel- Chugai)

Dekisachosei (Choseido) Delenar (Schering- Shionogi)-comb

Dersene (Ikeda) Dethamedin (Oh ta) Dexa A (Shinsei Sawai) Dexaltin (Nippon Kayaku) Dexamamalet (Showa) Dexame (Dojin) Dexasone (Hokuriku)

USA: ~ a l a i o n e (Forest; as

acetate) Decadron (Merck) Decadron (Merck; as acetate)

Decaspray (Merck) TobraDex (Alcon) several combmation preparations and generics

Use: glucocorticoid RN: 24668-75-5 MF: C,,H,,FO, MW: 490.61 EINECS: 246-389-2

CN: (1 10,16a)-21-(3,3-dimethyl-1 -oxobutoxy)-9-fluoro-11,17-dihydroxy- 16-methylpregna- 14-diene-3,20- dione

dexornethosone tert-butylacetic

Dexarnethosone tert-butylocetate

R<ference(s):

DOS 2 317 954 (Jelen Zaklady Farm Polfa; appl 10.4.1973; PL-prior 21.4.1972)

uerosol:

US 3 282 78 1 (Merck & Co 1.11.1966; prior 25.11.1960)

Formulution(s): nasal drops 0.2 mg

Trade Nume(s):

D: Dissiden (Al1egopharma)- Nasicortin (Merck)-comb.; USA: Decadron T.B.A (Merck

Trang 7

Dexamethasone 21-isonicotinate D 607

Use: glucocorticoid RN: 2265-64-7 MF: C28H32FN0, MW: 497.56 EINECS: 218-866-5

LD,,: 3470 mgkg (M, p.0.);

3562 mglkg (R, p.0.)

CN: (1 1 P,16a)-9-fluoro- 1 1,17-dihydroxy- 16-methyl-21 -[(4-pyridinylcarbonyl)oxy]pregna-1,4-diene-3,20-

dione

dexamethasane isonicotinoyl Dexarnethasone 21 -isonicotinate

(9 v.1 chloride

Reference(s):

ZA 623 489 (Thomae; appl 1.8.1962; D-prior 19.8.1961)

Formulation(s): aerosol 0.125 mglpuff, 0.02 mg; eye drops 0.25 mglml; sol 0.025 %

Trade Narne(s):

D: Auxiloson (Boehringer Dexa Biciron (A1con)- F: Auxisone (Boehringer Ing.)

Corti Biciron (S & K Dexa Loscon (Galderma) (Boehringcr 1ng.)-comb

(Boehringer Ing.)-comb

Use: glucocorticoid RN: 39026-39-6 MF: C,H,,FO, MW: 654.90 EINECS: 254-254-4

CN: [ l l ~,16a,21-(Z,Z)]-9-fluoro-l1,17-dihydroxy- 16-methyl-2l-[(l-oxo-9,12-octadecadienyl)oxy]-pregna-

1,4-diene-3,20-dione

dexamethasane

(9 v.)

rnethanesulfonyl chloride

Trang 8

608 D Dexarnethasone ohosohate

potossium lhnolote I Dexornethosone 21 -linolo(e I

Reference(s):

GB 1 292 785 (ISF; valid from 19.4.1971; I-prior 17.10.1970)

Formulation(s): cream 0.2 %; lotion 0.15 %

Trade Name(s):

I : Kanaderm 200 (Firma)- Situalin Antibiotic0

comb with kanamycine (Puropharma)-comb with

Situalin (Puropharma) bekanamy cinc

Use: glucocorticoid RN: 3 12-93-6 MF: C,,H,,FO,P MW: 472.45 EINECS: 206-232-0

CN: (1 1 P, l6a)-Y-fluoro-l l , 17-dihydroxy- 16-methy1-21-(phosphonooxy)pregna-1,4-diene-3,20-dione

disodium salt

RN: 2392-39-4 MF: C,,H,,FNa20,P MW: 516.41 EINECS: 219-243-0

LD,,,: 1800 m g k g (M, p.0.)

dexarnethasone dirnorpholino-

(9 v.) phosphinic

chloride

1 ion exchonge

2 NaHCOJ

I

Trang 9

Dexamethasone pivalate D 609

Referencefs):

DE 1 134 075 (Merck AG, appl 26.11.1959)

alternative synthesis:

U S 2 939 873 (Merck & Co.; 7.6.1960; appl 26.1.1959; prior 20.1 1.1957)

Jrmscher, K.: Chem Ind (London) (CHINAG) 1961, 1035

Forrnulation(s): amp 5 mglml, 48 mgl2 ml, 20 mgl5 ml, 8 mgl2 ml, 120 mgl5 ml; eye drops 1.1 mglml;

ointment 0.2 %

Trade Name(s):

D: Dexabene (Merckle)

Dexa-Brachialin

(Steigerwald)

Dexa-Effekton (Brenner-

Efeka)

Spersadexolin (Dispersa)-

comb

Totocortin (Winzer)

various combination

preparations and generics

F: CCbCdex (Chauvin; as

disodium salt)

Ctbtdexacol (Chauvin; as

disodium salt)-comb

Chibro-Cardon (Merck Sharp & Dohme-Chibret;

as monosodium salt)-comb

Corticttine (Chauvin; as monosodium salt)-comb

Dexagrane (Leurquin; as monosodium salt) J:

Frakidex (Chauvin; as monosodium salt)-comb

Soludtcadron (Merck Sharp & Dohme-Chibret;

as monosodium salt) I: Decadron Fosfato (Merck USA:

Sharp & Dohme) Desalark (Farm Mil.)

Eta-Biocortilen (SIF1)- comb with neomycine Eta-Cortilen (SIFI) Kanazone (SIT)-comb

with kanamycine Soldesam (Farm Mil.) Corson (Takeda) Decadron (Banyu) Donray (Kodama) Orgadrone (Sanky o) Solcort (Fuji) Teikason (Teika) Decadron Phosphate (Merck)

Neo-Decadron Phosphate (Merck)-comb

RN: 1926-94-9 MF: C2,H3,FO6 MW: 476.59 EINECS: 217-659-7

CN: (1 1~,16a)-21-(2,2-dimethyl-l-oxopropoxy)-9-fluoro-11,17-dihydroxy-l6-methylpregna-l,4-diene-3,20-

dione

dexarnethosone pivaloyl

1 Dexomethosane pivalate (9, v.) chloride

Reference (s):

US 3 033 881 (Ciba; 8.5.1962; CH-prior 4.7.1958)

CH 398 585 (Ciba; appl 1956)

alternative syntheses:

ES 320 497 (Lab M Cuatrecasas; appl 30.11.1965)

DOS 2 3 17 954 (Jelen Zaklady ~ a r h Polfa; appl 10.4.1973; PL-prior 21.4.1972)

Formulation(s): ointment 0.02 %

Trang 10

6 10 D Dexamethasone valerate

Trade Name(s);

D: Millicorten-Vioform (Ciba)

Use: glucocorticoid RN: 33755-46-3 MF: C,H,,FO, MW: 476.59 EINECS: 25 1-669-2

LD,,: >3 g k g (M, p.0.);

>3 glkg (R, p.0.)

CN: (1 1 P, 16a)-9-fluoro- 11,21-dihydroxy- 16-methyl- 17-[( 1-oxopentyl)oxy]pregna- 1,4-diene-3,20-dione

(cf betornethasone volerate)

17,21-(1 -butyl-1-methoxyrnethylene-

dioxy)-3.20-dioxo-9-fluoro-1 lp-hydroxy-

Reference(s):

DOS 2.1 11 114 (Inst Luso Farmaco; appl 9.3.1971 ; I-prior 14.3.1970)

Dexornethosone volerote

alternative syntheses:

DOS 2 055 221 (Lab Chim Farm Blasina; appl 10.1 1.1970)

16a-methyl-1.4-pregnodiene

Fnrmulation(s): cream 0 l %

Trade Narnefs):

I: Dermadex (SmithKline J: Voalla (Maruho)

Use: antihistaminic RN: 132-21 -8 MF: C1,Hl,BrN2 MW: 3 19.25 EINECS: 205-053-5

CN: (S)-y-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanamine

maleate (1:l)

RN: 2391-03-9 MF: C,,H,,BrN, C,H,O, MW: 435.32 EINECS: 219-236-2

LD,,,: 25 m g k g (M, i.v.); 176 mglkg (M, p.0.);

191 mglkg (R, p.0.)

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