WO1998001440B1 - Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds and uses thereof - Google Patents
Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds and uses thereofInfo
- Publication number
- WO1998001440B1 WO1998001440B1 PCT/US1997/010870 US9710870W WO9801440B1 WO 1998001440 B1 WO1998001440 B1 WO 1998001440B1 US 9710870 W US9710870 W US 9710870W WO 9801440 B1 WO9801440 B1 WO 9801440B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- pharmaceutical composition
- saturated
- dithiaheterocyclic
- pharmaceutically acceptable
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 24
- 150000001875 compounds Chemical class 0.000 title claims abstract 15
- 230000000840 anti-viral Effects 0.000 title claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 11
- 208000001756 Virus Disease Diseases 0.000 claims abstract 5
- 241001430294 unidentified retrovirus Species 0.000 claims abstract 5
- 210000001124 Body Fluids Anatomy 0.000 claims abstract 3
- 239000010839 body fluid Substances 0.000 claims abstract 3
- 230000000415 inactivating Effects 0.000 claims abstract 2
- -1 1,2 dithiolane compound Chemical class 0.000 claims 11
- 239000003937 drug carrier Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000011780 sodium chloride Substances 0.000 claims 7
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- CXWGKAYMVASWDQ-UHFFFAOYSA-N Dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 230000003647 oxidation Effects 0.000 claims 4
- 238000007254 oxidation reaction Methods 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004434 sulfur atoms Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910004730 OSO2 Inorganic materials 0.000 claims 2
- 206010047461 Viral infection Diseases 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- QGRBLDWNIGDYOW-UHFFFAOYSA-N dithiane 1,1-dioxide Chemical compound O=S1(=O)CCCCS1 QGRBLDWNIGDYOW-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 2
- 230000017613 viral reproduction Effects 0.000 claims 2
- PAORVUMOXXAMPL-VIFPVBQESA-N (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-VIFPVBQESA-N 0.000 claims 1
- 241001446316 Bohle iridovirus Species 0.000 claims 1
- 241000714266 Bovine leukemia virus Species 0.000 claims 1
- 241000713730 Equine infectious anemia virus Species 0.000 claims 1
- 208000005721 HIV Infections Diseases 0.000 claims 1
- 241000714260 Human T-lymphotropic virus 1 Species 0.000 claims 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims 1
- 241000713821 Mason-Pfizer monkey virus Species 0.000 claims 1
- 241000713333 Mouse mammary tumor virus Species 0.000 claims 1
- 241000724205 Rice stripe tenuivirus Species 0.000 claims 1
- 241000702287 Sugarcane streak virus Species 0.000 claims 1
- 208000010094 Visna Diseases 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 201000009910 diseases by infectious agent Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- 239000000934 spermatocidal agent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Abstract
The present invention is directed to pharmaceutical compositions including a saturated 1,2-dithiaheterocyclic compound having anti-viral activity. The present invention also provides a kit containing the pharmaceutical composition and methods of treating or preventing viral disease using the composition, as well as methods for inactivating retrovirus in a body fluid.
Claims
AMENDED CLAIMS
[received by the International Bureau on 22 April 1998 (22.04.98); original claims 1-21 replaced by amended claims 1-21 (5 pages)]
1 ) A method of inhibiting retro virus replication comprising exposing said retrovirus to an effect amount of a pharmaceutical composition comprising (i) pharmaceutically acceptable carrier, and (ii) saturated 1 ,2-dithiaheterocyclic compound, pharmaceutically acceptable salt thereof, or a mixture thereof; wherein the saturated 1,2-dithiaheterocyclic compound is a 1,2-dithiane or 1,2 dithiolane compound, and the saturated 1,2-dithiaheterocyclic compound comprises a ring sulfur atom present in a -S(O)- or -SO2- oxidation state.
2) The method of claim 1 wherein the saturated 1,2-dithiaheterocyclic compound includes at least one ring carbon atom including a substituent selected from the group consisting of hydroxy, hydroxyalkyl, alkyl, cycloalkyl, acyl, alkoxy, cycloalkoxy, carboxyalkyl, acyloxyalkyl, -C(O)OH, -C(O)O-R5, acyloxy, aryl, - OSO2R6, and -NR7R8, wherein R5 and R6 are independently alkyl, cycloalkyl or aryl, and R7 and R8 are independently hydrogen, alkyl, cycloalkyl or aryl.
3) A method of inactivating retrovirus in a body fluid comprising exposing said body fluid to an effective amount of a pharmaceutical composition to inactivate the retrovirus; wherein the pharmaceutical composition comprises (i) pharmaceutically acceptable carrier, and (ii) saturated 1,2-dithiaheterocyclic compound, pharmaceutically acceptable salt thereof, or a mixture thereof; and the saturated 1,2-dithiaheterocyclic compound is a 1,2-dithiane or 1,2 dithiolane compound, and the saturated 1 ,2-dithiaheterocyclic compound comprises a ring sulfur atom present in a -S(O)- or -SO2- oxidation state.
4) A method of treating viral disease in a patient comprising administering an effective amount of a pharmaceutical composition to the patient; wherein the pharmaceutical composition comprises (i) pharmaceutically acceptable carrier, and (ii) saturated 1,2-dithiaheterocyclic compound, pharmaceutically acceptable salt thereof, or a mixture thereof; and
the saturated 1,2-dithiaheterocyclic compound is a 1,2-dithiane or 1,2 dithiolane compound, and the saturated 1,2-dithiaheterocyclic compound a ring sulfur atom present in a -S(O)- or -SO2- oxidation state.
5) The method of claim 4 wherein the viral disease is caused by infection by fflV-1, HIV-2, SIV, BIV, EIAV, Visna, CaEV, HTLV-1, BLV, MPMV, MMTV, RSV, MuLV, FeLV, BaEV, or SSV.
6) A kit for treating a viral infection comprising:
(i) a vessel containing an effective antiviral amount of a pharmaceutical composition; and
(ii) instructions for using the composition for treating a viral infection; wherein the pharmaceutical composition comprises (i) pharmaceutically acceptable carrier, and (ii) saturated 1 ,2-dithiaheterocyclic compound, pharmaceutically acceptable salt thereof, or a mixture thereof; and the saturated 1,2-dithiaheterocyclic compound is a 1,2-dithiane or 1,2 dithiolane compound, and the saturated 1,2-dithiaheterocyclic compound comprises a ring sulfur atom present in a -S(O)- or -SO2- oxidation state.
7) A pharmaceutical composition comprising (i) pharmaceutically acceptable carrier; and (ii) saturated 1 ,2-dithiolane compound, pharmaceutically acceptable salt thereof, or a mixture thereof, wherein the 1 ,2-dithiolane compound has the formula:
8) The pharmaceutical composition of claim 7 wherein R1 and R2 are independently C(l)-C(3)hydroxyalkyl or C(2)-C(4)acyloxyalkyl.
9) The pharmaceutical composition of claim 8 wherein R1 and R2 are independently -CH2OH or -CH2OAc.
10) The pharmaceutical composition of claim 7 wherein Y is -SO2-.
11) The pharmaceutical composition of claim 7 wherein R1 and R2 are -CH2OH.
12) A pharmaceutical composition comprising (i) pharmaceutically acceptable carrier; and (ii) saturated 1,2-dithiane compound, pharmaceutically acceptable salt thereof, or a mixture thereof, wherein the 1,2-dithiane compound has the formula:
13) The pharmaceutical composition of claim 12 wherein R1 and R2 are independently C(l)-C(3)hydroxyalkyl, or C(2)-C(4)acyloxyalkyl.
14) The pharmaceutical composition of claim 12 wherein R1 and R2 are independently hydroxy or acetoxy.
15) The pharmaceutical composition of claim 12 wherein R1 and R2 are -CH2OH, and Y is -SO2-.
16) The pharmaceutical composition of claim 12 wherein the 1 ,2-dithiane compound has the formula:
17) The pharmaceutical composition of claim 16 wherein Y is -SO2-.
18) The pharmaceutical composition of claim 12, further comprising a nucleoside analog, a protease inhibitor, or a mixture thereof.
19) The pharmaceutical composition of claim 12, further comprising an antiviral agent, a spermicidal agent, a bactericidal agent, or a mixture thereof.
20) A pharmaceutical composition comprising (i) pharmaceutically acceptable carrier; and (ii) saturated 1,2-dithiolane compound, pharmaceutically acceptable salt thereof, or a mixture thereof, wherein the 1,2-dithiolane compound has the formula:
wherein Y is -S-, -S(O)- or -SO2-; and R1 and R2 together are =N-NH-C(O)-NH2; or R1 and R2 together are -NH-C(O)-NH-C(O)-; or R1 is -NH2 and R2 is -CO2H.
40
21) A method of preparing a chiral cw-4,5-dihydroxy- 1,2-dithiane 1,1-dioxide comprising:
(i) reacting a chiral cw-4,5-dihydroxy- 1,2-dithiane 1,1-dioxide with (R)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride to form a Mosher diester of cis 1,2-dithiane 1,1 dioxide;
(ii) separating the diastereomers of the Mosher diester of cis 1,2-dithiane 1,1 dioxide; and
(iii) hydrolzying a diasteromer of the ester to form a chiral s-4,5-dihydroxy- 1 ,2-dithiane 1 , 1 -dioxide.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/214,331 US6046228A (en) | 1996-07-05 | 1997-07-03 | Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds and uses thereof |
| AU44085/97A AU737038B2 (en) | 1996-07-05 | 1997-07-03 | Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds and uses thereof |
| AT97942372T ATE310738T1 (en) | 1996-07-05 | 1997-07-03 | ANTIVIRAL PHARMACEUTICAL PREPARATIONS CONTAINING SATURATED 1,2-DITHIAHETEROCYCLIC COMPOUNDS |
| EP97942372A EP1023284B1 (en) | 1996-07-05 | 1997-07-03 | Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds |
| DE69734734T DE69734734D1 (en) | 1996-07-05 | 1997-07-03 | SATURATED 1,2-DITHIACHETEROCYCLIC COMPOUNDS CONTAINING ANTIVIRAL PHARMACEUTICAL PREPARATIONS |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2166596P | 1996-07-05 | 1996-07-05 | |
| US60/021,665 | 1996-07-05 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| WO1998001440A2 WO1998001440A2 (en) | 1998-01-15 |
| WO1998001440A3 WO1998001440A3 (en) | 1998-05-14 |
| WO1998001440B1 true WO1998001440B1 (en) | 1998-06-11 |
| WO1998001440A9 WO1998001440A9 (en) | 1998-07-16 |
Family
ID=21805475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/010870 WO1998001440A2 (en) | 1996-07-05 | 1997-07-03 | Anti-viral pharmaceutical compositions containing saturated 1,2-dithiaheterocyclic compounds and uses thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6046228A (en) |
| EP (1) | EP1023284B1 (en) |
| AT (1) | ATE310738T1 (en) |
| AU (1) | AU737038B2 (en) |
| CA (1) | CA2260128A1 (en) |
| DE (1) | DE69734734D1 (en) |
| WO (1) | WO1998001440A2 (en) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6417180B1 (en) * | 1998-10-07 | 2002-07-09 | University Of Massachusetts | Zinc finger-reactive antimicrobial compounds |
| DE69920497T2 (en) * | 1998-10-26 | 2006-02-09 | The Research Foundation Of State University Of New York | LIPONSAÜREDERIVATE AND ITS USE IN THE TREATMENT OF DISEASES |
| US6204288B1 (en) | 1999-03-08 | 2001-03-20 | The University Of Mississippi | 1,2-dithiolane derivatives |
| US6288106B1 (en) * | 1999-05-25 | 2001-09-11 | Chronorx, Llc | Processes for the synthesis and use of various α-lipoic acid complexes |
| WO2001025226A1 (en) * | 1999-10-05 | 2001-04-12 | Bethesda Pharmaceuticals, Inc. | Dithiolane derivatives |
| US6664287B2 (en) * | 2000-03-15 | 2003-12-16 | Bethesda Pharmaceuticals, Inc. | Antioxidants |
| US6638915B1 (en) * | 2000-06-30 | 2003-10-28 | Harold Killam | Anti-viral composition |
| EP1172110A3 (en) * | 2000-07-07 | 2003-09-17 | Basf Aktiengesellschaft | Use of lipoic acid as a bioavailaty enhancer of mineral salts |
| US7528274B2 (en) | 2001-08-03 | 2009-05-05 | The United States Of America As Represented By The Department Of Health And Human Services | Acylthiols and component thiol compositions as anti-HIV and anti-retroviral agents |
| TWI281916B (en) * | 2001-10-25 | 2007-06-01 | Lilly Co Eli | Antitumor compounds and methods |
| DE10163836A1 (en) | 2001-12-22 | 2003-07-10 | Friz Biochem Gmbh | Multifunctional reagent for the synthesis of thiol modified oligomers |
| US7101676B2 (en) * | 2002-01-11 | 2006-09-05 | Douglas Buechter | Methods for identifying compounds which inhibit binding of nucleocapsid 7 protein to HIV-1 RNA |
| EP1575549A4 (en) * | 2002-10-08 | 2008-05-07 | Us Gov Health & Human Serv | Identification of anti-hiv compounds inhibiting virus assembly and binding of nucleocapsid protein to nucleic acid |
| JP2010520333A (en) | 2007-03-01 | 2010-06-10 | セダーズ−シナイ メディカル センター | Antioxidant polymer containing [1,2] -dithiolane moiety and use thereof |
| WO2009086547A1 (en) | 2008-01-03 | 2009-07-09 | Cedars-Sinai Medical Center | Antioxidant nanosphere comprising [1,2]-dithiolane moieties |
| WO2009148698A1 (en) | 2008-06-02 | 2009-12-10 | Cedars-Sinai Medical Center | Nanometer-sized prodrugs of nsaids |
| KR101493125B1 (en) | 2008-11-24 | 2015-02-12 | 세다르스-신나이 메디칼 센터 | Antioxidant camptothecin derivatives and antioxidant antineoplastic nanospheres thereof |
| EP2580191A2 (en) | 2010-06-10 | 2013-04-17 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Thioether prodrug compositions as anti-hiv and anti-retroviral agents |
| DK2691530T3 (en) | 2011-06-10 | 2018-05-22 | Univ Oregon Health & Science | CMV GLYCOPROTEIN AND RECOMBINANT VECTORS |
| US9428589B2 (en) | 2012-11-15 | 2016-08-30 | Brandeis University | Tethering cysteine residues using cyclic disulfides |
| WO2014088923A1 (en) * | 2012-12-06 | 2014-06-12 | Merck Sharp & Dohme Corp. | Nucleoside kinase bypass compositions and methods |
| WO2015035003A1 (en) | 2013-09-05 | 2015-03-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thioether prodrug compositions as anti-hiv and anti-retroviral agents |
| WO2017017669A1 (en) * | 2015-07-24 | 2017-02-02 | Aposense Ltd. | Pro-drugs and related methods |
| CA2994298A1 (en) | 2015-08-18 | 2017-02-23 | Brandeis University | Tethering cysteine residues using cyclic disulfides |
| WO2022049219A1 (en) | 2020-09-02 | 2022-03-10 | Université De Genève | Methods for treating viral infection |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158621A (en) * | 1962-06-20 | 1964-11-24 | American Cyanamid Co | Dithiolium compounds and their preparation |
| CH656382A5 (en) * | 1983-10-24 | 1986-06-30 | Sandoz Ag | SULFOXIDES, METHOD FOR THEIR PRODUCTION AND THEIR USE. |
| ATE70974T1 (en) * | 1987-12-04 | 1992-01-15 | Asta Pharma Ag | INJECTABLE SOLUTION OF THIOCT ACID SALT WITH TROMETAMOLE AND/OR BASIC AMINO ACIDS. |
| AT500684B8 (en) * | 1989-11-09 | 2006-11-15 | Meda Pharma Gmbh & Co Kg | USE OF SWEAT CARBOXYLIC ACIDS FOR THE MANUFACTURE OF A MEDICAMENT FOR COMBATING DISEASES OF RETROVIRUSES |
| ES2091948T3 (en) * | 1990-11-13 | 1996-11-16 | Iaf Biochem Int | 1,3-OXATIOLANES SUBSTITUTED WITH ANTIVIRIC PROPERTIES. |
| FR2676057B1 (en) * | 1991-05-02 | 1995-03-03 | Therapeutique Moder Lab | DERIVATIVES OF 1,2-DITHIOLE-3-THIONE, PROCESS FOR THE PREPARATION OF THESE DERIVATIVES, AS WELL AS THE USE OF THESE DERIVATIVES AS SYNTHESIS INTERMEDIATES OR AS MEDICAMENTS. |
| US6001555A (en) * | 1994-09-23 | 1999-12-14 | The United States Of America As Represented By The Department Of Health And Human Services | Method for identifying and using compounds that inactivate HIV-1 and other retroviruses by attacking highly conserved zinc fingers in the viral nucleocapsid protein |
| US5693460A (en) * | 1996-06-24 | 1997-12-02 | Eastman Kodak Company | Silver halide photographic elements containing dioxide compunds a stabilizers |
| EP0855396A1 (en) * | 1997-01-22 | 1998-07-29 | ASTA Medica Aktiengesellschaft | Thioctic acid metabolites and methods of use thereof |
-
1997
- 1997-07-03 WO PCT/US1997/010870 patent/WO1998001440A2/en active IP Right Grant
- 1997-07-03 AT AT97942372T patent/ATE310738T1/en not_active IP Right Cessation
- 1997-07-03 CA CA002260128A patent/CA2260128A1/en not_active Abandoned
- 1997-07-03 AU AU44085/97A patent/AU737038B2/en not_active Ceased
- 1997-07-03 US US09/214,331 patent/US6046228A/en not_active Expired - Lifetime
- 1997-07-03 EP EP97942372A patent/EP1023284B1/en not_active Expired - Lifetime
- 1997-07-03 DE DE69734734T patent/DE69734734D1/en not_active Expired - Lifetime
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