FR2097737A5 - Virustatic 4-substd 1-acylthiosemicarbazides -from carboxylic acid - hydrazide and isothiocyanates or from carboxylic acid chloride and 4- - Google Patents
Virustatic 4-substd 1-acylthiosemicarbazides -from carboxylic acid - hydrazide and isothiocyanates or from carboxylic acid chloride and 4-Info
- Publication number
- FR2097737A5 FR2097737A5 FR7111317A FR7111317A FR2097737A5 FR 2097737 A5 FR2097737 A5 FR 2097737A5 FR 7111317 A FR7111317 A FR 7111317A FR 7111317 A FR7111317 A FR 7111317A FR 2097737 A5 FR2097737 A5 FR 2097737A5
- Authority
- FR
- France
- Prior art keywords
- carboxylic acid
- substd
- isothiocyanates
- virustatic
- hydrazide
- 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract 3
- 150000002540 isothiocyanates Chemical class 0.000 title abstract 2
- 230000001790 virustatic effect Effects 0.000 title abstract 2
- 239000002544 virustatic Substances 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- -1 adamantyl-(1)- Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 abstract 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid Chemical compound CCOC(=O)C(O)=O JRMAQQQTXDJDNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 abstract 1
- YRWGRSSUOWFVBX-UHFFFAOYSA-N ethyl 2-oxo-2-[2-(phenylcarbamothioyl)hydrazinyl]acetate Chemical compound C(=O)(OCC)C(=O)NNC(=S)NC1=CC=CC=C1 YRWGRSSUOWFVBX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 229940117953 phenylisothiocyanate Drugs 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
- 150000003583 thiosemicarbazides Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Cpds. of general formula (I): (where R1 = 4-nitrophenyl, styryl, adamantyl-(1)-, 4-chlorophenoxymethyl, phenyl or carbethoxy; R2 = phenyl, 4-chlorophenyl, cyclohexyl, benzyl, naphthyl-(1)-, naphthyl-(2) or n-butyl); are prepd. by reacting carboxylic acid hydrazide with isothiocyanates or by reacting carboxylic acid chlorides with 4-substd. thiosemicarbazides. In an example, phenylisothiocyanate in ethanol is added dropwise to oxalic acid ethyl ester monohydrazide in ethanol and refluxed to give 88% of 1-carbethoxycarbonyl-4-phenylthiosemicarbazide with virustatic activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD14880370 | 1970-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2097737A5 true FR2097737A5 (en) | 1972-03-03 |
Family
ID=5482717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7111317A Expired FR2097737A5 (en) | 1970-07-14 | 1971-03-31 | Virustatic 4-substd 1-acylthiosemicarbazides -from carboxylic acid - hydrazide and isothiocyanates or from carboxylic acid chloride and 4- |
Country Status (5)
| Country | Link |
|---|---|
| CH (2) | CH547787A (en) |
| DE (1) | DE2126304C3 (en) |
| FR (1) | FR2097737A5 (en) |
| HU (2) | HU164570B (en) |
| SU (2) | SU687069A1 (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2436139A1 (en) * | 1978-09-14 | 1980-04-11 | Gulf Oil Corp | SUBSTITUTED 1-BENZOYL-3-THIOSEMICARBAZIDES, THEIR OBTAINMENT AND THEIR APPLICATION AS PLANT GROWTH REGULATORS |
| EP0030789A3 (en) * | 1979-12-10 | 1981-11-11 | Gulf Oil Corporation | Arylthioureido pyridinecarbamino compounds, a process for their preparation and their use as plant growth regulants |
| US6924312B2 (en) | 2001-07-10 | 2005-08-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7001923B2 (en) | 2001-07-10 | 2006-02-21 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7037940B2 (en) | 2001-07-10 | 2006-05-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7385084B2 (en) | 2004-06-23 | 2008-06-10 | Synta Pharmaceutical Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| US7645904B2 (en) | 2006-09-15 | 2010-01-12 | Synta Pharmaceuticals Corp. | Purification of bis(thiohydrazide amides) |
| US7652168B2 (en) | 2001-07-10 | 2010-01-26 | Synta Pharmaceuticals Corp. | Synthesis of taxol enhancers |
| US7678832B2 (en) | 2005-08-16 | 2010-03-16 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| US7709683B2 (en) | 2005-05-16 | 2010-05-04 | Synta Pharmaceuticals Corp. | Synthesis of bis(thio-hydrazide amide) salts |
| US7763658B2 (en) | 2003-01-15 | 2010-07-27 | Synta Pharmaceuticals Corp. | Treatment for cancers |
| US7939564B2 (en) | 2006-08-31 | 2011-05-10 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| US8017654B2 (en) | 2005-04-15 | 2011-09-13 | Synta Pharmaceuticals Corp. | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| US8148426B2 (en) | 2004-11-19 | 2012-04-03 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing Hsp70 expression |
| US9156783B2 (en) | 2006-08-21 | 2015-10-13 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4134914A (en) * | 1975-08-25 | 1979-01-16 | Eli Lilly And Company | 1-Acyl-4-substituted phenyl thiosemicarbazides |
| JPH03501731A (en) * | 1987-12-31 | 1991-04-18 | スミスクライン・ベックマン・コーポレイション | 4-aralkyl-5-substituted-1,2,4-triazole-5-thiols |
-
1971
- 1971-03-31 FR FR7111317A patent/FR2097737A5/en not_active Expired
- 1971-05-18 SU SU711658626A patent/SU687069A1/en active
- 1971-05-18 SU SU1841244A patent/SU461095A1/en active
- 1971-05-27 DE DE19712126304 patent/DE2126304C3/en not_active Expired
- 1971-07-13 HU HUBE001112 patent/HU164570B/hu unknown
- 1971-07-13 HU HUBE001090 patent/HU164569B/hu unknown
- 1971-07-14 CH CH1037071A patent/CH547787A/en not_active IP Right Cessation
- 1971-07-14 CH CH1036971A patent/CH548990A/en not_active IP Right Cessation
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2436139A1 (en) * | 1978-09-14 | 1980-04-11 | Gulf Oil Corp | SUBSTITUTED 1-BENZOYL-3-THIOSEMICARBAZIDES, THEIR OBTAINMENT AND THEIR APPLICATION AS PLANT GROWTH REGULATORS |
| EP0030789A3 (en) * | 1979-12-10 | 1981-11-11 | Gulf Oil Corporation | Arylthioureido pyridinecarbamino compounds, a process for their preparation and their use as plant growth regulants |
| US7750042B2 (en) | 2001-07-10 | 2010-07-06 | Synta Pharmaceuticals Corp. | Paclitaxel enhancer compound |
| US6924312B2 (en) | 2001-07-10 | 2005-08-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7001923B2 (en) | 2001-07-10 | 2006-02-21 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7037940B2 (en) | 2001-07-10 | 2006-05-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| US7345094B2 (en) | 2001-07-10 | 2008-03-18 | Synta Pharmaceuticals Corp. | Paclitaxel enhancer compounds |
| US7368473B2 (en) | 2001-07-10 | 2008-05-06 | Synta Pharmaceuticals Corp. | Paclitaxel enhancer compounds |
| US9107955B2 (en) | 2001-07-10 | 2015-08-18 | Synta Pharmaceuticals Corp. | Paclitaxel enhancer compounds |
| US7652168B2 (en) | 2001-07-10 | 2010-01-26 | Synta Pharmaceuticals Corp. | Synthesis of taxol enhancers |
| US7671092B2 (en) | 2001-07-10 | 2010-03-02 | Synta Pharmaceuticals Corp. | Paclitaxel enhancer compounds |
| US7763658B2 (en) | 2003-01-15 | 2010-07-27 | Synta Pharmaceuticals Corp. | Treatment for cancers |
| US7579503B2 (en) | 2004-06-23 | 2009-08-25 | Synta Pharmaceuticals Corp. | BIS (thio-hydrazide amide) salts for treatment of cancers |
| US8461208B2 (en) | 2004-06-23 | 2013-06-11 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| US7385084B2 (en) | 2004-06-23 | 2008-06-10 | Synta Pharmaceutical Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| US7795313B2 (en) | 2004-06-23 | 2010-09-14 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| US8048925B2 (en) | 2004-06-23 | 2011-11-01 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| US8148426B2 (en) | 2004-11-19 | 2012-04-03 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing Hsp70 expression |
| US8017654B2 (en) | 2005-04-15 | 2011-09-13 | Synta Pharmaceuticals Corp. | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| US7709683B2 (en) | 2005-05-16 | 2010-05-04 | Synta Pharmaceuticals Corp. | Synthesis of bis(thio-hydrazide amide) salts |
| US7678832B2 (en) | 2005-08-16 | 2010-03-16 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| US8623921B2 (en) | 2005-08-16 | 2014-01-07 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| US9156783B2 (en) | 2006-08-21 | 2015-10-13 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| US7939564B2 (en) | 2006-08-31 | 2011-05-10 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| US7645904B2 (en) | 2006-09-15 | 2010-01-12 | Synta Pharmaceuticals Corp. | Purification of bis(thiohydrazide amides) |
Also Published As
| Publication number | Publication date |
|---|---|
| HU164569B (en) | 1974-03-28 |
| SU687069A1 (en) | 1979-09-25 |
| DE2126304C3 (en) | 1979-11-15 |
| HU164570B (en) | 1974-03-28 |
| DE2126304B2 (en) | 1979-03-29 |
| CH548990A (en) | 1974-05-15 |
| DE2126304A1 (en) | 1972-01-20 |
| SU461095A1 (en) | 1975-02-25 |
| CH547787A (en) | 1974-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |