RU2011114776A - Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro [4.4] nona-3,6,8-trien-9-carboxylates and a process for the preparation thereof - Google Patents
Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro [4.4] nona-3,6,8-trien-9-carboxylates and a process for the preparation thereof Download PDFInfo
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- RU2011114776A RU2011114776A RU2011114776/04A RU2011114776A RU2011114776A RU 2011114776 A RU2011114776 A RU 2011114776A RU 2011114776/04 A RU2011114776/04 A RU 2011114776/04A RU 2011114776 A RU2011114776 A RU 2011114776A RU 2011114776 A RU2011114776 A RU 2011114776A
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- Russia
- Prior art keywords
- ethyl
- diazaspiro
- nona
- aroyl
- diaryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 9
- VNIDZLOWFDROIW-UHFFFAOYSA-N deca-2,4,7-trienoic acid Chemical class CCC=CCC=CC=CC(O)=O VNIDZLOWFDROIW-UHFFFAOYSA-N 0.000 title claims abstract 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 12
- HPYHPCCSYQLWEX-UHFFFAOYSA-N 2-[amino(phenyl)methylidene]butanoic acid Chemical compound CCC(C(O)=O)=C(N)C1=CC=CC=C1 HPYHPCCSYQLWEX-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000000202 analgesic effect Effects 0.000 claims abstract 2
- 238000009835 boiling Methods 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. Этил 1,6-диарил-4-ароил-3-гидрокси-2-оксо-8-фенил-1,7-диазаспиро[4.4]нона-3,6,8-триен-9-карбоксилаты формулы ! ! где Ar=Ph, C6H4Me-4; R=C6H4Me-4, C6H4OMe-4 ! 2. Этил 1,6-диарил-4-ароил-3-гидрокси-2-оксо-8-фенил-1,7-диазаспиро[4.4]нона-3,6,8-триен-9-карбоксилаты формулы ! ! где Ar=C6H4Me-4; R=C6H4Me-4, C6H4OMe-4, ! обладающие анальгетической активностью. ! 3. Способ получения этил 1,6-диарил-4-ароил-3-гидрокси-2-оксо-8-фенил-1,7-диазаспиро[4.4]нона-3,6,8-триен-9-карбоксилаты общей формулы ! ! где Ar=Ph, C6H4Me-4; R=C6H4Me-4, C6H4OMe-4, ! отличающийся тем, что 1-арил-4,5-диароли-1H-пиррол-2,3-дионы подвергают взаимодействию с этиловым эфиром 3-амино-3-фенилпропеновой кислоты в соотношении 1:1 в среде кипящего абсолютного бензола с последующим выделением целевых продуктов. ! 4. Способ по п.3, отличающийся тем, что процесс ведут при температуре 79-80°С. ! 5. Способ по п.3 или 4, отличающийся тем, что в качестве растворителя используют абсолютный бензол. 1. Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro [4.4] nona-3,6,8-triene-9-carboxylates of the formula! ! where Ar = Ph, C6H4Me-4; R = C6H4Me-4, C6H4OMe-4! 2. Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro [4.4] nona-3,6,8-triene-9-carboxylates of the formula! ! where Ar = C6H4Me-4; R = C6H4Me-4, C6H4OMe-4,! possessing analgesic activity. ! 3. A method of producing ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro [4.4] nona-3,6,8-triene-9-carboxylates of the general formula ! ! where Ar = Ph, C6H4Me-4; R = C6H4Me-4, C6H4OMe-4,! characterized in that 1-aryl-4,5-diaroli-1H-pyrrole-2,3-dions are reacted with ethyl 3-amino-3-phenylpropenoic acid in a ratio of 1: 1 in a medium of boiling absolute benzene, followed by isolation of the target products. ! 4. The method according to claim 3, characterized in that the process is conducted at a temperature of 79-80 ° C. ! 5. The method according to claim 3 or 4, characterized in that absolute benzene is used as the solvent.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2011114776/04A RU2467010C1 (en) | 2011-04-14 | 2011-04-14 | Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro[4,4]nona-3,6,8-trien-9-carboxilates and method of their obtaining |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2011114776/04A RU2467010C1 (en) | 2011-04-14 | 2011-04-14 | Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro[4,4]nona-3,6,8-trien-9-carboxilates and method of their obtaining |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2011114776A true RU2011114776A (en) | 2012-10-20 |
| RU2467010C1 RU2467010C1 (en) | 2012-11-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011114776/04A RU2467010C1 (en) | 2011-04-14 | 2011-04-14 | Ethyl 1,6-diaryl-4-aroyl-3-hydroxy-2-oxo-8-phenyl-1,7-diazaspiro[4,4]nona-3,6,8-trien-9-carboxilates and method of their obtaining |
Country Status (1)
| Country | Link |
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| RU (1) | RU2467010C1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2537999C1 (en) * | 2013-07-15 | 2015-01-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | Method of producing methyl 1,7-diaryl-9-aroyl-4-benzoyl-3-hydroxy-2,6-dioxo-1,7-diazaspiro[4,4]none-3,8-diene-8-carboxylates, exhibiting analgesic activity |
| RU2627276C1 (en) * | 2016-05-25 | 2017-08-04 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | Process for the preparation of 4-aroyl-3-hydroxy-1- (2-hydroxyphenyl) -8-thioxo-1,7-diazaspiro [4,4] non-3-ene-2,6-diones |
| RU2707197C1 (en) * | 2019-06-24 | 2019-11-25 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | 9-aroyl-8-hydroxy-6-(2-hydroxyethyl)-1,3,6-triazaspiro[4,4]non-8-ene-2,4,7-trions, having analgesic activity, and a method for production thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1334099C (en) * | 1988-03-23 | 1995-01-24 | Pen Chung Wang | 1,6-diazaspiro(4,4)nonane-2,7-dione derivatives |
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2011
- 2011-04-14 RU RU2011114776/04A patent/RU2467010C1/en not_active IP Right Cessation
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| Publication number | Publication date |
|---|---|
| RU2467010C1 (en) | 2012-11-20 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130415 |