Patent US4425358A successfully refreshed from Google Patents.
← Back to Patent Explorer
US4425358A Expired / Lapsed US ⏱️ 0.0 years remaining

13-Thia-prostacycline derivatives

Assignee: Chinoin Private Co Ltd
•
Filing: 1982-04-21
•
Granted: 1984-01-10
•
Expires: 2002-04-21
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The invention relates to new optically active or racemic 13-thia-prostacycline derivatives of the Formula I ##STR1## wherein R 1 is hydrogen, a pharmaceutically acceptable cation or a straight or branched chain alkyl group having 1-5 carbon atoms; R 2 is straight or branched chain alkyl having 4-9 carbon atoms or monosubstituted phenoxymethyl; --A--B-- is --CH 2 --CH 2 --, --CH═CH-- of Z-- or E-- configuration or --C.tbd.C--; one of the symbols X and Y is hydrogen, methyl or ethyl and the other is hydroxy, tetrahydropyranyoxy, 1-ethoxy-ethoxy or trialkylsilyloxy; or X and Y together form a --O--CH 2 --CH 2 --O-- group; Z is a sulfur atom or a --SO-- group. The compounds of the Formula I can be prepared by reacting a 13-thia-prostaglandine of the Formula III ##STR2## if desired after oxidation into the corresponding 13-oxide derivative--with a halogenating agent; and treating the 5-halogeno-13-thia-prostacycline of the Formula II ##STR3## thus obtained wherein E is halogen with an organic or inorganic base; and thereafter if desired removing the protecting groups X and/or Y and if desired converting a compound of the Formula I obtained into a salt or setting free the same from a salt. The new compounds of the Formula I possess anti-coagulant and hypotensive properties and can be used in therapy.

Inventors

  • 👤 Csaba Szantay
  • 👤 Lajos Novak
  • 👤 Jozsef Aszodi
  • 👤 Vilmos Simonidesz
  • 👤 Geza Galambos
  • 👤 Gabor Kovacs
  • 👤 Sandor Virag
  • 👤 Istvan Stadler
  • 👤 Peter Kormoczy

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 17:27
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07D307/937; A; A61; A61P; A61P7/00; A61P7/02; A61P9/00; A61P9/12; C07C; C07C405/00; C07C405/0008; C07C405/0033; C07D407/00; C07D407/02; C07D407/12

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 113 words
An optically active or racemic 13-thia-prostacycline of the Formula I ##STR9## wherein R 1 is hydrogen, a pharmaceutically acceptable cation or a straight or branched chain alkyl group having 1-5 carbon atoms; R 2 is straight or branched chain alkyl having 4-9 carbon atoms or is phenoxymethyl substituted by a halo or a trifluoromethyl substituent: --A--B-- is --CH 2 --CH 2 --, --CH═CH-- of Z- or E-configuration or --C.tbd.C; one of the symbols X and Y is hydrogen, methyl or ethyl and the other is hydroxy, tetrahydropyranyloxy, 1-ethoxy-ethoxy or trialkylsilyloxy; or X and Y together form a --O--CH 2 --CH 2 --O-- group; and Z is a sulfur atom or a --SO-- group.
Claim 2
Dependent Claim 113 words
An optically active or racemic 13-thia-prostacycline of the Formula I ##STR9## wherein R 1 is hydrogen, a pharmaceutically acceptable cation or a straight or branched chain alkyl group having 1-5 carbon atoms; R 2 is straight or branched chain alkyl having 4-9 carbon atoms or is phenoxymethyl substituted by a halo or a trifluoromethyl substituent: --A--B-- is --CH 2 --CH 2 --, --CH═CH-- of Z- or E-configuration or --C.tbd.C; one of the symbols X and Y is hydrogen, methyl or ethyl and the other is hydroxy, tetrahydropyranyloxy, 1-ethoxy-ethoxy or trialkylsilyloxy; or X and Y together form a --O--CH 2 --CH 2 --O-- group; and Z is a sulfur atom or a --SO-- group.
Claim 3
Dependent Claim 9 words
13-thia-13,14-dihydro-PGI 2 -methyl ester as defined in claim 1.
Claim 4
Dependent Claim 9 words
15-epi-13-thia-13,14-dihydro-PGI 2 -methyl ester as defined in claim 1.
Claim 5
Dependent Claim 11 words
13-thia-13,14-dihydro-15-dehydro-PGI 2 -methyl ester ethylene ketal as defined in claim 1.
Claim 6
Dependent Claim 10 words
Sodium salt of 13-thia-13,14-dihydro-PGI 2 as defined in claim 1.
Claim 7
Dependent Claim 33 words
A pharmaceutical composition having blood platelet aggregation inhibitory effect comprising as active ingredient a pharmaceutically effective amount of at least one compound in claim 1 in admixture with suitable inert non-toxical pharmaceutical carriers.
Claim 8
Dependent Claim 28 words
A method of treatment for blood platelet aggregation inhibiting effect which comprises administering to a susceptible subject an effective amount of a compound as defined in claim 1.
Claim 9
Dependent Claim 114 words
A compound of the formula II ##STR10## wherein R 1 is hydrogen, a pharmaceutically acceptable cation, or a straight or branched chain alkyl group having 1-5 carbon atoms; R 2 is straight or branched chain alkyl having 4 to 9 carbon atoms or is phenoxymethyl substituted by a halo or a trifluoromethyl substituent; --A--B-- is --CH 2 --CH 2 --, --CH═CH-- of Z- or E-configuration or --C.tbd.C--; one of the symbols X and Y is hydrogen, methyl or ethyl and the other is hydroxy, tetrahydropyranyloxy, 1-ethoxy-ethoxy, or trialkylsilyloxy; or X and Y together form a --O--CH 2 --CH 2 --O-- group; Z is a sulfur atom or a --SO-- group, and E is halogen.
Claim 10
Dependent Claim 114 words
A compound of the formula II ##STR10## wherein R 1 is hydrogen, a pharmaceutically acceptable cation, or a straight or branched chain alkyl group having 1-5 carbon atoms; R 2 is straight or branched chain alkyl having 4 to 9 carbon atoms or is phenoxymethyl substituted by a halo or a trifluoromethyl substituent; --A--B-- is --CH 2 --CH 2 --, --CH═CH-- of Z- or E-configuration or --C.tbd.C--; one of the symbols X and Y is hydrogen, methyl or ethyl and the other is hydroxy, tetrahydropyranyloxy, 1-ethoxy-ethoxy, or trialkylsilyloxy; or X and Y together form a --O--CH 2 --CH 2 --O-- group; Z is a sulfur atom or a --SO-- group, and E is halogen.
Claim 11
Dependent Claim 11 words
5-iodo-13-thio-13, 14-dihydro-PGI 1 , -methyl ester, as defined in claim 8.
Claim 12
Dependent Claim 9 words
15-epi-5-iodo-13-thia-13,14-dihydro-PGI 1 -methyl ester, as defined in claim 8.
Claim 13
Dependent Claim 12 words
5-iodo-13-thia-13, 14-dihydro-15-dehydro-PGI 1 -methyl ester ethylene ketal, as defined in claim 8.

References Cited (Backward Citations)

US4232009A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-01-09 1987-07-11 1988-01-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-01-09 1991-07-11 1992-01-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-01-09 1995-07-11 1996-01-10 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag