GB1026401A - Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them - Google Patents
Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing themInfo
- Publication number
- GB1026401A GB1026401A GB666461A GB666461A GB1026401A GB 1026401 A GB1026401 A GB 1026401A GB 666461 A GB666461 A GB 666461A GB 666461 A GB666461 A GB 666461A GB 1026401 A GB1026401 A GB 1026401A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- preparation
- alkyl
- compounds
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title abstract 4
- -1 Isatin thiosemicarbazones Chemical class 0.000 title abstract 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Pseudoisatin Natural products C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 title 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:1026401/C2/1> (wherein R1 is a hydrogen atom or an alkyl, hydroxyalkyl or alkenyl group containing up to 5 carbon atoms and the hydroxy group may itself be esterified by a C1- 5 aliphatic carboxylic acid radical, R2 is an optional substituent and if present is a halogen atom or a C1- 5 alkyl or alkoxy group, and R5 and R6 are the same or different and are straight or branched alkyl or alkenyl groups containing up to 5 carbon atoms each or -NR5R6 is a saturated or unsaturated heterocyclic group containing no further hetero atom, a morpholino group or a piperazino group wherein the second nitrogen atom may be substituted by a C1- 5 alkyl group) and acid addition salts of those compounds which are basic, pharmaceutical preparations containing them, and their preparation by reacting a compound of the formula <FORM:1026401/C2/2> with a compound of the formula H2N.NH.CS.NR5R6 optionally followed by acid addition salt formation when the product is basic. The preparation of a number of starting materials of the third general formula above and salts thereof, in most cases from the corresponding thiocarbamoylthioglycollic acids (preparation described), and of acetophenone 4,4 - (3 - methyl - 3 - azapentamethylene)thiosemicarbazone is described. The compounds of the invention have anti-viral activity and may be administered in the form of pharmaceutical preparations (e.g. tablets, capsules, cachets, ampoules, suppositories, powders, granules, solutions, suspensions and ointments) containing them together with a carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB666461A GB1026401A (en) | 1961-02-23 | 1961-02-23 | Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB666461A GB1026401A (en) | 1961-02-23 | 1961-02-23 | Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1026401A true GB1026401A (en) | 1966-04-20 |
Family
ID=9818567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB666461A Expired GB1026401A (en) | 1961-02-23 | 1961-02-23 | Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1026401A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2184944A (en) * | 1986-01-01 | 1987-07-08 | Univ Ramot | Antiviral agents |
| WO1998030660A1 (en) * | 1997-01-10 | 1998-07-16 | Uniroyal Chemical Company, Inc. | Dithiocarbamyl carboxylic acids and their use as multifunctional additives for lubricating oils |
| WO2008083491A1 (en) * | 2007-01-11 | 2008-07-17 | Critical Outcome Technologies Inc. | Compounds and method for treatment of cancer |
| WO2010006438A1 (en) * | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| US8466151B2 (en) | 2007-12-26 | 2013-06-18 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| US8987272B2 (en) | 2010-04-01 | 2015-03-24 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
-
1961
- 1961-02-23 GB GB666461A patent/GB1026401A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2184944A (en) * | 1986-01-01 | 1987-07-08 | Univ Ramot | Antiviral agents |
| GB2184944B (en) * | 1986-01-01 | 1989-12-28 | Univ Ramot | Antiviral agents |
| WO1998030660A1 (en) * | 1997-01-10 | 1998-07-16 | Uniroyal Chemical Company, Inc. | Dithiocarbamyl carboxylic acids and their use as multifunctional additives for lubricating oils |
| US8822475B2 (en) | 2007-01-11 | 2014-09-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| WO2008083491A1 (en) * | 2007-01-11 | 2008-07-17 | Critical Outcome Technologies Inc. | Compounds and method for treatment of cancer |
| JP2010515693A (en) * | 2007-01-11 | 2010-05-13 | クリティカル・アウトカム・テクノロジーズ・インコーポレイテッド | Compounds and methods for the treatment of cancer |
| US8034815B2 (en) | 2007-01-11 | 2011-10-11 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| US8138191B2 (en) | 2007-01-11 | 2012-03-20 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| US8367675B2 (en) | 2007-01-11 | 2013-02-05 | Critical Outcome Technologies Inc. | Compounds and method for treatment of cancer |
| US8420643B2 (en) | 2007-01-11 | 2013-04-16 | Critical Outcome Technologies Inc. | Compounds and method for treatment of cancer |
| US9284275B2 (en) | 2007-01-11 | 2016-03-15 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| US8580792B2 (en) | 2007-01-11 | 2013-11-12 | Critical Outcome Technologies Inc. | Inhibitor compounds and cancer treatment methods |
| US8466151B2 (en) | 2007-12-26 | 2013-06-18 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| US8895556B2 (en) | 2007-12-26 | 2014-11-25 | Critical Outcome Technologies Inc. | Compounds and method for treatment of cancer |
| WO2010006438A1 (en) * | 2008-07-17 | 2010-01-21 | Critical Outcome Technologies Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| EP3023426A1 (en) | 2008-07-17 | 2016-05-25 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| US8987272B2 (en) | 2010-04-01 | 2015-03-24 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
| US9422282B2 (en) | 2010-04-01 | 2016-08-23 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
| US9624220B2 (en) | 2010-04-01 | 2017-04-18 | Critical Outcome Technologies Inc. | Compounds and method for treatment of HIV |
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