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Pharmaceutical Substances Syntheses, Patents, Applications - Part 173 pot

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1726 P Propacetamol Trade Name$: D: Atosil Bayer Vital Eusedon Krewel Meuselbach Promethawern Pharma Wernigerode Promethazin-neuraxpharm neuraxpharm Prothazin Rodleben F: Algotropyl pro

Trang 1

Proligestone P 1721

Trade Name(s):

Use: progestogen RN: 23873-85-0 MF: C24H3404 MW: 386.53 EINECS: 245-922-6

CN: 14,17-[propylidenebis(oxy)]pregn-4-ene-3,20-dione

Reference(s):

Sijde, D van der et al.: J Med Chem (JMCMAR) 15,909 (1972)

ZA 681 592 (Koninkl Nederl Gist & Spiritusfabriek; appl 22.2.1968; NL-prior 13.3.1967)

14.17-dihydroxy- propionaldehyde

starting material:

Cooley, G et al.: Tetrahedron Suppl (TETSAE) 7,325 (1966)

Proligestone

Forrnulation(s): vial 100 mg/ml

progesterane

(from Reichstein S)

Trade Name(s):

GB: Delvosteron (Mycpfarm);

wfm

Use: analeptic, central stimulant, depressant

RN: 493-92-5 MF: C,,H,,N MW: 217.36 EINECS: 207-784-5

LDS,,: 157 mglkg (R, p.0.)

CN: 1-[I-(phenylmethyl)butyI]pyrrolidine

hydrochloride

RN: 121 1-28-5 MF: C,5H,,N HCI MW: 253.82 EINECS: 214-917-0

LDS,: 25 mgkg (M, i.v.); 230 mglkg (M, p.0.);

40 mgkg (R, i.v.); 278 mg/kg (R, p.0.)

Trang 2

1722 P Prolonium iodide

Rqference(s):

DE 1 088 962 (Thomae; appl 1956)

DE 1 093 799 (Thomae; appl 1957; addition to DE 1 088 962)

H HZ, PtOZ or Roney-Ni

Formulatinn(s): drg 10 mg

2-0x0-1 -phenylpentane pyrrolidine

Trade Name(s):

1ng.)-comb.; wfrn -

Prolintone

Use: thyroid therapeutic

RN: 123-47-7 MF: C9H2,12N20 MW: 430.1 1 EINECS: 204-630-9

H

N

H,C/ ' C H ~

H3C CH3 iodide tr~methyl- 1.3-diiodo-2-

dirnethyl epichlorohydrin 1.3-bis(dimethylamin0)-

Prolonium iodide

Reference(s):

US 1 526 627 (Baycr; 1925; prior 1924)

Formulation(s): amp 400 mgl2 ml; drg 25 rng, 50 mg, 100 mg; drops 20 mglml; susp 50 mg15 ml; vial 50

mglml

Trade Name(s):

Trang 3

Promazine P 1723

Use: neuroleptic, anti-emetic, antipsychotic

RN: 58-40-2 MF: C,7H2,N2S MW: 284.43 EINECS: 200-382-0

LD,,: 45 mgkg (M, i.v.); 40 1 mglkg (M, p.0.);

14.5 mg/kg (R, i.v.); 350 mglkg (R, p.0.)

CN: N,N-dimethyl-l OH-phenothiazine- 10-propanamine

monohydrochIoride

RN: 53-60-1 MF: C,7H2,N,S HC1 MW: 320.89 EINECS: 200-179-7

LD,,: 38 mgkg (M, i.v.);

29 m a g (R, i.v.); 400 mglkg (R, p.0.)

maleate (2:l)

RN: 4701-69-3 MF: CL7H2,N2S 1/2C4H404 MW: 684.93

phosphate

RN: 1508-27-6 MF: C,,H2,N2S xH,04P MW: unspecified

LD,: 60 mgkg (M , i.v.);

350 m a g (R, p.0.)

omide

propyl chloride

Reference(s):

U S 2 519 886 (RhGne-Poulenc; 1950; F-prior 1945)

DE 824 944 (RhBne-Poulenc; appl 1950; F-prior 1945)

Wirth, W.: Arzneim.-Forsch (ARZNAD) 8, 507 (1958)

Promozine

50 mg/ml (as hydrochloride)

Trade Name(s):

Sinophenin (Rodleben) I: Talofen (Fournier Pierrel) USA: Sparine (Wyeth); wfm

Use: progestogen

RN: 34184-77-5 MF: C2,H3,02 MW: 326.48

CN: (17(3)-17-methyl-17-(1-oxopropyl)estra-4,9-dien-3-one

Trang 4

1724 P Promestriene

methyl ether triphenyl-

phosphorone

LiNH2

& H3 + r-cH3 + lithium

H C , I H I-

" 0 ornide

norpregno-1.3.5(1 O), 16- iodide

tetraene (I)

Li NH, C2H50H

CrO, HZS04

chromium

trioxide

Prornegestone

DOS 2 107 835 (Roussel-Uclaf; appl !8.2.l97 1; F-prior 20.2.1970)

US 3 679 7 14 (Roussel-1 Jclaf; 25.7.1972; F-prior 20.2.1970)

US 3 761 591 (Roussel-Uclaf; 25.9.1973; F-prior 20.2.1970)

synrhcsis of 3-methoxy-20-0x0- 19-norpregna- 1,3,5(10), 16-tetraene:

Krubiner, A.M.; Oliveto, E.P.: J Org Chem (JOCEAH) 31, 24 (1966)

Krubiner, A.M et al.: J Org Chcm (JOCEAH) 34, 3502 (1969)

Formulation(s): tabl 0.125 mg, 0.25 mg 0.5 mg

Trade Name(s):

F: Surgestone (Cassenne)

Use: estrogen RN: 39219-28-8 MF: C22H3202 MW: 328.50 EINECS: 254-361-6

CN: (17~)-17-methoxy-3-propoxyestra-1,3,5(10)-triene

Trang 5

Promethazine P 1725

NaOC2H5 + H3C-Br

sodium

H3C*0

(4 v.)

Reference(s):

DE 2 215 499 (Sogeras; appl 29.3.1972; GB-prior 21.4.1971)

dimethyl sulfonyl

Fomulation(s): cream 1 %; vaginal cps 10 mg

Pramestriene

Trade Name(s):

sodium

Use: antihistaminic, sedative RN: 60-87-7 MF: CI7HmN2S MW: 284.43 EINECS: 200-489-2

LD,,: 40 mglkg (M, i.v.); 326 mglkg (M, p.0.);

45 mgkg (R, i.v.)

CN: N,N,a-trimethyl- 1 OH-phenothiazine- 10-ethanamine

monohydrochloride

RN: 58-33-3 MF: C,7-H20N,S HC1 MW: 320.89 EINECS: 200-375-2

LD,,: 50 mgkg (M, i.v.); 255 mg/kg (M, p.0.);

15 m g k g (R, i v.)

phenothiozine 2-chloro-N.N-

dimethyl-1 -

propanamine

Prornethazine

u

Formulation(s): amp 56 mg12 ml; f c tabl 25 mg; drg 25 mg; drops 20 mglml; suppos 12.5 mg, 25 mg,

50 mg; syrup 1 mglml, 5.65 mg; tabl 12.5 mg, 25 mg, 50 mg (as hydrochloride)

Trang 6

1726 P Propacetamol

Trade Name($):

D: Atosil (Bayer Vital)

Eusedon (Krewel

Meuselbach)

Promethawern (Pharma

Wernigerode)

Promethazin-neuraxpharm

(neuraxpharm)

Prothazin (Rodleben)

F: Algotropyl prornkthazine

(Thera France)-comb

FluisCdal (Elert6)-comb

PaxCladine noctCe

(Beaufour)-comb

Phknergan (Evans Medical)

Rhinathiol promCthazine

(SynthC1abo)-comb

Tussisedal (E1erte)-comb

GB: Avomine (RhGne-Poulenc Rorer)

Parmergan P 100 (Martindale)-comb

Phenergan (Rh6ne-Poulenc Rorer)

Sominex (Seton) I: Allerfen (Sella) Duplamin (Bruschettini)- comb

Fargan (Carlo Erba) Farganesse (Pharmacia &

Upjohn) Fenazil (Sella) Prometazina (Dynacren)

Prometazina Cloridrato (Ecobi)

generics and combination preparations

I: Hiberna (Yoshitorni) Pipolphen (Nakataki) Prothia (Kanto) Pyrethia (Shionogi) USA: Mepergan (Wyeth-Ayerst) Phenergan (Wyeth-Ayerst) gencrics and combination preparations

Use: analgesic (paracetamol prodrug) RN: 66532-85-2 MF: C14H20N203 MW: 264.33 EINECS: 266-390-1

CN: N,N-diethylglycine 4-(acetylamino)phenyI ester

munuhydrochloride

RN: 66532-86-3 MF: C,,H,,N,O, HCI MW: 300.79 EINECS: 266-391-7

Reference(s j:

BE 854 376 (Hexachimie, appl 9.5.1977)

DE 2 721 987 (Hexachimie; appl 14.5.1977)

US 4 127 671 (Hexachimie; 28.1 1.1978; prior 26.5.1977)

dieihyl-

synthesis of p-acetamidophenyl chloroacetate:

Dittert, L.W et al.: J Pharm Sci (JPMSAE) 57, 774 (1968)

Propoceiarnol

Furmulurion(s): amp 1 g (as hydrochloride)

Trude Name(s):

F: Pro-Dafalgan (UPSA)

Trang 7

Propafenone P 1727

Use: antiarrhythmic RN: 54063-53-5 MF: C2iH27N0, MW: 341.45 EINECS: 258-955-6

LD,,: 440 mglkg (M, p.0.)

CN: 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-l-propanone

hydrochloride

RN: 34183-22-7 MF: CzlHZ7NO, HC1 MW: 377.91 EINECS: 251-867-9

LD,,: 25 mgkg (M, i.v.); 341 mglkg (M, p.0.);

18.8 mglkg (R, i.v.); 700 mglkg (R, p.0.);

10 mgkg (dog, i.v.)

1-(2-hydroxyphenyl)-3- epichlorohydrin

phenyl-1 -proponone

Reference(s):

DE 2 001 43 1 (Helopharm; appl 6.1.1970)

GB 1 307 455 (Helopharm; appl 7.7.1971)

US 4 474 986 (BASF; 2.10.1984; appl 18.3.1983; D-prior 19.3.1982)

Formulation(s): amp 70 mg120 ml; drg 10 mg; f c tabl 150 mg, 300 mg; USA: tabl 150 mg, 225 mg,

300 mg (as hydrochloride)

Trade Name(s):

Use: hypnotic RN: 545-93-7 MF: Ci,H,,BrN20, MW: 289.13 EINECS: 208-896-7

LD,,: 90 mgkg (R, s.c.)

CN: 5-(2-bromo-2-propeny1)-5-(1-methylethyl)-2,4,6(1H.3H,5H)-pyrimidinetrione

Trang 8

1728 P Propanidid

C 2

CH30

Rqference(s):

U S 1 622 129 (Riedel AG; 1927; D-prior 1923)

DRP 481 733 (Riedel-deHaen; appl 1923)

DRP 482 841 (Riedel-deHaen; appl 1923)

DRP 485 832 (Riedel-deHaen; appl 1923)

Formulation(s)c tabl 200 mg

Trade Name(s):

Use: anesthetic RN: 1421-14-3 MF: C,,H2,N05 MW: 337.42 EINECS: 215-822;7

LD,,,: 1 13 mglkg (M, i.v.);

81 m g k g (R, i.v.); > I 0 glkg (R, p.0.);

8 0 m g k g (dog, i.v.)

CN: 4-[2-(diethylamino)-2-oxoethoxy]-3-methoxybenzeneacetic acid propyl ester

CH3

N.N-diethylchloro- propyl hornovanillate

H C N

3 - y-0

0 0 ,

CH3

Propanidid

Rcference(s):

DE 1 134 981 (Bayer; appl 6.5.1960)

Formulation(s): amp 1.5 gl30 ml, 500 mg/10 ml

Trade Name(s):

Use: antispasmodic, anticholinergic RN: 50-34-0 MF: C,,H,,BrNO, MW: 448.40 EINECS: 200-030-6

LD,,,: 6400 p g k g (M, i.v.); 445 m g k g (M, p.0.);

4 m g k g (R, i.v.); 370 m g k g (R, p.0.)

CN: N-methyl-N-(l-methylethyl)-N-[2-[(9H-xanthen-9-ylcarbonyl)oxyJethyl]-2-popanaminium bromide

Trang 9

Propatyl nitrate P 1729

& z chloride

xonthene-9-

corboxylic ocid

xonthene-9- carbonyl chloride

bromide

US 2 659 732 (Searle; 1953; appl 1952; prior 1950)

Formularion(s): tabl 7.5 rng, 15 mg

Trade Name(s):

Tensilan (Desitin); wfm I: Lexil (Roche)-comb

Propatyl nitrate

(Ettriol trinitrate)

Use: coronary vasodilator (angina pectoris) RN: 2921-92-8 MF: C,H,,N@!, MW: 269.17 EINECS: 220-866-5

CN: 2-ethyl-2-[(nitrooxy)methyl]-1,3-propanediol dinitrate (ester)

HNO,, H,SO,

HO

trirnethylol-

propane

I P r o p o t l nitrate

Reference(s):

MMard: Meml Poudres (MPOUAT) 35, 1 13 (1 953)

Bou jol: Meml Poudres (MPOUAT) 36.79 (1954)

Fomulation(s): tabl 10 mg

Trade Narne(s1:

F: Atrilon 5 (Winthrop); wfm GB: Gina (Winthrop); wfm J: Etrynit (Yoshitomi); wfm

Trang 10

1730 P Propentofylline

Propentofylline

(HWA-285)

Use: vasodilator, cognition enhancer RN: 55242-55-2 MF: C15H22N,0, MW: 306.37

LD,,,: 168 mglkg (M, i.v.); 780 mglkg (M, p.0.);

180 mglkg (R, i.v.); 940 m g k g (R, p.0.)

CN: 3,7-dihydro-3-methyl- 1-(5-oxohexy1)-7-propyl- 1 H-purine-2,6-dione

1,3-dimethyl-7-

1 -brorno-5-

hexonone

CH3 Propentofylline

Referertce(s):

DE 2 330 742 (Albert; appl 16.6.1973)

DE 2 366 501 (Albert; appl 16.6.1973)

US 4 289 776 (Hoechst; 15.9.1981; D-prior 16.6.1973)

synthesis of 3-methyl-7-propylxanthine:

Ohsaki, T et al.: Chem Pharm Bull (CPBTAL) 36, 877 (1988)

Forrnulafion(s): tabl 100 mg

Trade Narne(s):

J : Hextol (Hoechst; 1988)

Use: antibiotic RN: 551-27-9 MF: C,,HzzN20SS MW: 378.45 EINECS: 208-995-5

CN: [2S-(2c~,5c~,6~)]-3,3-dimethyl-7-oxo-6-[(1-oxo-2-phenoxybutyl)amlno]-4-thia-1- azabicyclo[3.2.0]heptane-2-carboxylic acid

monopotassium salt

KN: 1245-44-9 MF: ClRH2,KN2O,S MW: 416.54 EINECS: 214-993-5

LD,,,: 292 mglkg (M, i.v.);

5 glkg (R, p.0.)

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