DE2126304C3 - In 4-Stellung substituierte 1-Acylthiosemicarbazide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel - Google Patents
In 4-Stellung substituierte 1-Acylthiosemicarbazide, Verfahren zu ihrer Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2126304C3 DE2126304C3 DE19712126304 DE2126304A DE2126304C3 DE 2126304 C3 DE2126304 C3 DE 2126304C3 DE 19712126304 DE19712126304 DE 19712126304 DE 2126304 A DE2126304 A DE 2126304A DE 2126304 C3 DE2126304 C3 DE 2126304C3
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- acylthiosemicarbazides
- general formula
- dissolved
- carboxylic acid
- 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
- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000003814 drug Substances 0.000 title 1
- -1 4-nitrophenyl- Chemical group 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 3
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 238000001816 cooling Methods 0.000 claims 2
- 150000002540 isothiocyanates Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- LVEUHPMMNLURRJ-UHFFFAOYSA-N 1-amino-3-cyclohexylthiourea Chemical compound NNC(=S)NC1CCCCC1 LVEUHPMMNLURRJ-UHFFFAOYSA-N 0.000 claims 1
- XTHYRBHMXJHYCI-UHFFFAOYSA-N 1-cyclohexyl-3-[(4-nitrobenzoyl)amino]thiourea Chemical compound [N+](=O)([O-])C1=CC=C(C(=O)NNC(=S)NC2CCCCC2)C=C1 XTHYRBHMXJHYCI-UHFFFAOYSA-N 0.000 claims 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid Chemical compound CCOC(=O)C(O)=O JRMAQQQTXDJDNC-UHFFFAOYSA-N 0.000 claims 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229940117953 phenylisothiocyanate Drugs 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 230000001790 virustatic effect Effects 0.000 claims 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- SKENFIMMLLMPGH-UHFFFAOYSA-N 1-[[2-(4-chlorophenoxy)acetyl]amino]-3-cyclohexylthiourea Chemical compound C1=CC(Cl)=CC=C1OCC(=O)NNC(=S)NC1CCCCC1 SKENFIMMLLMPGH-UHFFFAOYSA-N 0.000 description 1
- PTFLEBAEIYXJAG-UHFFFAOYSA-N 1-butyl-3-[(2-hydroxybenzoyl)amino]thiourea Chemical compound CCCCNC(=S)NNC(=O)C1=CC=CC=C1O PTFLEBAEIYXJAG-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- TTZUCVNWOZLIGL-UHFFFAOYSA-N chembl362994 Chemical compound C1=CC=C2N(C)C(O)=C(N=NC(S)=N)C2=C1 TTZUCVNWOZLIGL-UHFFFAOYSA-N 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD14880370 | 1970-07-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2126304A1 DE2126304A1 (de) | 1972-01-20 |
| DE2126304B2 DE2126304B2 (de) | 1979-03-29 |
| DE2126304C3 true DE2126304C3 (de) | 1979-11-15 |
Family
ID=5482717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126304 Expired DE2126304C3 (de) | 1970-07-14 | 1971-05-27 | In 4-Stellung substituierte 1-Acylthiosemicarbazide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Country Status (5)
| Country | Link |
|---|---|
| CH (2) | CH547787A (forum.php) |
| DE (1) | DE2126304C3 (forum.php) |
| FR (1) | FR2097737A5 (forum.php) |
| HU (2) | HU164569B (forum.php) |
| SU (2) | SU461095A1 (forum.php) |
Families Citing this family (17)
| 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 |
| GR69827B (forum.php) * | 1978-09-14 | 1982-07-13 | Gulf Oil Corp | |
| US4405791A (en) * | 1979-12-10 | 1983-09-20 | Gulf Oil Corporation | Arylthioureido pyridinecarbamino compounds and use as plant growth regulants |
| AU2948189A (en) * | 1987-12-31 | 1989-08-01 | Smithkline Beckman Corporation | 4-aralkyl-5-substituted-1,2,4-triazole-5-thiols |
| TWI332943B (en) | 2001-07-10 | 2010-11-11 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| US6924312B2 (en) | 2001-07-10 | 2005-08-02 | Synta Pharmaceuticals Corp. | Taxol enhancer compounds |
| TWI297335B (en) | 2001-07-10 | 2008-06-01 | Synta Pharmaceuticals Corp | Taxol enhancer compounds |
| TWI252847B (en) | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| TWI330079B (en) | 2003-01-15 | 2010-09-11 | Synta Pharmaceuticals Corp | Treatment for cancers |
| CA2570698C (en) | 2004-06-23 | 2013-11-19 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) salts for treatment of cancers |
| AU2005306471B2 (en) | 2004-11-19 | 2009-12-17 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amides) for increasing Hsp70 expression |
| JP2008536875A (ja) | 2005-04-15 | 2008-09-11 | シンタ ファーマシューティカルズ コーポレーション | ビス（チオヒドラジド）アミド化合物による併用癌療法 |
| WO2006124736A2 (en) | 2005-05-16 | 2006-11-23 | Synta Pharmaceuticals Corp. | Synthesis of bis(thio-hydrazide amide) salts |
| AU2006279891B2 (en) | 2005-08-16 | 2010-03-11 | Synta Pharmaceuticals Corp. | Bis(thio-hydrazide amide) formulation |
| CA2660524A1 (en) | 2006-08-21 | 2008-02-28 | Synta Pharmaceutical Corp. | Compounds for treating proliferative disorders |
| AU2007290490B2 (en) | 2006-08-31 | 2011-09-08 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| TW200829543A (en) | 2006-09-15 | 2008-07-16 | Synta Pharmaceuticals Corp | Purification of bis(thiohydrazide amides) |
-
1971
- 1971-03-31 FR FR7111317A patent/FR2097737A5/fr not_active Expired
- 1971-05-18 SU SU1841244A patent/SU461095A1/ru active
- 1971-05-18 SU SU711658626A patent/SU687069A1/ru active
- 1971-05-27 DE DE19712126304 patent/DE2126304C3/de not_active Expired
- 1971-07-13 HU HUBE001090 patent/HU164569B/hu unknown
- 1971-07-13 HU HUBE001112 patent/HU164570B/hu unknown
- 1971-07-14 CH CH1037071A patent/CH547787A/xx not_active IP Right Cessation
- 1971-07-14 CH CH1036971A patent/CH548990A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SU687069A1 (ru) | 1979-09-25 |
| HU164569B (forum.php) | 1974-03-28 |
| DE2126304A1 (de) | 1972-01-20 |
| CH548990A (de) | 1974-05-15 |
| CH547787A (de) | 1974-04-11 |
| DE2126304B2 (de) | 1979-03-29 |
| SU461095A1 (ru) | 1975-02-25 |
| FR2097737A5 (en) | 1972-03-03 |
| HU164570B (forum.php) | 1974-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |