RU95114741A - OXAZOLOHINOLINONA DERIVATIVES AND THEIR OBTAINING, MEDICINE AND PHARMACEUTICAL COMPOSITION - Google Patents
OXAZOLOHINOLINONA DERIVATIVES AND THEIR OBTAINING, MEDICINE AND PHARMACEUTICAL COMPOSITIONInfo
- Publication number
- RU95114741A RU95114741A RU95114741/04A RU95114741A RU95114741A RU 95114741 A RU95114741 A RU 95114741A RU 95114741/04 A RU95114741/04 A RU 95114741/04A RU 95114741 A RU95114741 A RU 95114741A RU 95114741 A RU95114741 A RU 95114741A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- enantiomers
- group
- diastereoisomers
- ethyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 14
- 230000000875 corresponding Effects 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 8
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 7
- VNWSQOFZXAQZJV-UHFFFAOYSA-N 1-O-ethyl 2-O-methyl 6-methoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylate Chemical compound COC1=CC=C2N(C(=O)OCC)C(C(=O)OC)CCC2=C1 VNWSQOFZXAQZJV-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 210000004185 Liver Anatomy 0.000 claims 2
- 241000282898 Sus scrofa Species 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims 2
- 125000005679 ethenylmethyl group Chemical group [H]C([H])=C([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- JBBNGYWPUZIKBL-UHFFFAOYSA-N 1-ethoxycarbonyl-6-methoxy-3,4-dihydro-2H-quinoline-2-carboxylic acid Chemical compound COC1=CC=C2N(C(=O)OCC)C(C(O)=O)CCC2=C1 JBBNGYWPUZIKBL-UHFFFAOYSA-N 0.000 claims 1
- CIEMBVRIAAGBIX-UHFFFAOYSA-N 3-(methoxymethyl)-7-(4,4,4-trifluoro-3-hydroxybutoxy)-3,3a,4,5-tetrahydro-[1,3]oxazolo[3,4-a]quinolin-1-one Chemical group FC(F)(F)C(O)CCOC1=CC=C2N3C(=O)OC(COC)C3CCC2=C1 CIEMBVRIAAGBIX-UHFFFAOYSA-N 0.000 claims 1
- JRCKGKSHLTZMIE-UHFFFAOYSA-N 3-(methoxymethyl)-7-(4,4,4-trifluorobutoxy)-3,3a,4,5-tetrahydro-[1,3]oxazolo[3,4-a]quinolin-1-one Chemical group FC(F)(F)CCCOC1=CC=C2N3C(=O)OC(COC)C3CCC2=C1 JRCKGKSHLTZMIE-UHFFFAOYSA-N 0.000 claims 1
- -1 4,4,4-trifluorobutoxy Chemical group 0.000 claims 1
- BYFCXYGRUBUGDN-UHFFFAOYSA-N 7-(4,4,4-trifluoro-3-hydroxybutoxy)-3,3a,4,5-tetrahydro-[1,3]oxazolo[3,4-a]quinolin-1-one Chemical group C1CC2=CC(OCCC(O)C(F)(F)F)=CC=C2N2C(=O)OCC21 BYFCXYGRUBUGDN-UHFFFAOYSA-N 0.000 claims 1
- GUODQZBCVAINET-UHFFFAOYSA-N COCC1OC(N2C1CCC1=CC(=CC=C21)OCCC1(CCCC1)O)=O Chemical group COCC1OC(N2C1CCC1=CC(=CC=C21)OCCC1(CCCC1)O)=O GUODQZBCVAINET-UHFFFAOYSA-N 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- 241000283973 Oryctolagus cuniculus Species 0.000 claims 1
- 241000283898 Ovis Species 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- VKYABZXPNHHDSD-UHFFFAOYSA-N bis(2-methylpropyl)alumanylium;hydride Chemical compound [H-].CC(C)C[Al+]CC(C)C VKYABZXPNHHDSD-UHFFFAOYSA-N 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- NZTNZPDOBQDOSO-UHFFFAOYSA-N lithium;boron(1-) Chemical compound [Li+].[B-] NZTNZPDOBQDOSO-UHFFFAOYSA-N 0.000 claims 1
- 125000005905 mesyloxy group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000002901 organomagnesium compounds Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RWFLWIWTRFASBG-UHFFFAOYSA-N OC1C=CC(C(C(CO2)CC3)C2=O)=C3C1 Chemical compound OC1C=CC(C(C(CO2)CC3)C2=O)=C3C1 RWFLWIWTRFASBG-UHFFFAOYSA-N 0.000 description 1
Claims (12)
в которой n равно 0 или 1; R1 представляет собой атом водорода, либо этенильную, метильную, этильную, фенильную, гидроксиметильную или метоксиметильную группу; а также либо R2 обозначает метильную, трифторметильную или цианогруппу, R3 соответствует атому водорода, либо гидроксильной или бензилоксигруппе, а R4 и R5 являются атомами водорода; либо R2 и R4 вместе образуют группу -(СН2)4-, R3 представляет собой гидроксильную группу, а R5 обозначает атом водорода; либо R2 и R5 вместе образуют группу -О-(СН2)3-, а R3 и R4 являются атомами водорода; либо R2 и R5 вместе образуют группу -(СН2)4-, R3 соответствует гидроксильной группе, а R4 представляет собой атом водорода, в форме изомеров, в том числе в форме энантиомеров и диастереоизомеров, а также смесей указанных различных форм, включая рацемические смеси.1. Derivatives of 3.3a, 4,5-tetrahydro-1H-oxazolo [3,4-a] quinolin-1-one, corresponding to the general formula (I),
in which n is 0 or 1; R 1 represents a hydrogen atom, or an ethenyl, methyl, ethyl, phenyl, hydroxymethyl or methoxymethyl group; and either R 2 is methyl, trifluoromethyl or cyano, R 3 corresponds to a hydrogen atom, or a hydroxyl or benzyloxy group, and R 4 and R 5 are hydrogen atoms; or R 2 and R 4 together form the group - (CH 2 ) 4 -, R 3 represents a hydroxyl group, and R 5 denotes a hydrogen atom; or R 2 and R 5 together form the group -O- (CH 2 ) 3 -, and R 3 and R 4 are hydrogen atoms; or R 2 and R 5 together form a group - (CH 2 ) 4 -, R 3 corresponds to a hydroxyl group, and R 4 represents a hydrogen atom, in the form of isomers, including in the form of enantiomers and diastereoisomers, as well as mixtures of these various forms , including racemic mixtures.
в которой R1 представляет собой атом водорода, либо этенильную, фенильную, гидроксиметильную или метоксиметильную группу, обрабатывают соединением, соответствующим формуле (III),
в которой Х обозначает атом галогена, либо лабильную группу, такую как мезилокси- или тозилоксигруппа, с получением соединения, отвечающего формуле (I), в которой R1 соответствует приведенным выше обозначениям, после чего восстанавливают указанное соединение, описываемое формулой (I), в которой R1 является этенильной группой, с получением соединения, отвечающего формуле (I), в которой R1 представляет собой этильную группу.7. The method of obtaining compounds corresponding to formula (I), characterized in that the compound described by formula (II),
in which R 1 represents a hydrogen atom, or ethenyl, phenyl, hydroxymethyl or methoxymethyl group, is treated with a compound corresponding to formula (III),
in which X represents a halogen atom, or a labile group, such as a mesyloxy or tosyloxy group, to obtain a compound corresponding to formula (I) in which R 1 corresponds to the above notation, after which the indicated compound described by formula (I) is restored, wherein R 1 is an ethenyl group, to obtain a compound of formula (I), wherein R 1 is an ethyl group.
или формулы (V)
где R1 обозначает этенильную, метильную или фенильную группу, для получения которых осуществляют ферментативный гидролиз этил 2-метоксикарбонил-6-метокси-1,2,3,4-тетрагидрохинолин-1-карбоксилата; с помощью экстракции разделяют 3(-) энантиомер этил 2-метоксикарбонил-6-метокси-1,2,3,4-тетрагидрохинолин-1-карбоксилата и R(+) энантиомер этил 2-карбокси-6-метокси-1,2,3,4-тетрагидрохинолин-1-карбоксилата; обрабатывают R(+) энантиомер этил 2-карбокси-6-метокси-1,2,3,4-тетрагидрохинолин-1-карбоксилата тионил хлоридом и метанолом с получением соответствующего 2-метоксикарбонильного производного; - S(-) и R(+) энантиомеры указанного 2-метоксикарбонильного производного приводят во взаимодействие либо с борогидридом лития, в результате чего получают соответственно S(+) и R(-) энантиомеры соединения, описываемого формулой (IV), либо с гидридом диизобутилалюминия, в результате чего получают соответственно S(-) и R(+) энантиомеры соответствующего 2-формильного производного; указанные энантиомеры 2-формильного производного обрабатывают органомагниевым соединением, описываемым формулой R1МgХ, где R1 такое как определено выше, а Х является атомом галогена, а затем - метоксидом натрия, после чего проводят разделение с помощью хроматографии, в результате чего получают указанные диастереоизомеры соединений, отвечающих формуле (V).9. The method according to p. 7, characterized in that the enantiomers and diastereoisomers of the compounds corresponding to formula (II) are obtained from enantiomers or diastereomers of the compounds described by formula (IV)
or formula (V)
where R 1 denotes an ethenyl, methyl or phenyl group, for the preparation of which an enzymatic hydrolysis of ethyl 2-methoxycarbonyl-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate is performed; by extraction, the 3 (-) enantiomer of ethyl 2-methoxycarbonyl-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate and the R (+) enantiomer of ethyl 2-carboxy-6-methoxy-1,2, are separated, 3,4-tetrahydroquinoline-1-carboxylate; process the R (+) enantiomer of ethyl 2-carboxy-6-methoxy-1,2,3,4-tetrahydroquinoline-1-carboxylate with thionyl chloride and methanol to obtain the corresponding 2-methoxycarbonyl derivative; - S (-) and R (+) enantiomers of the specified 2-methoxycarbonyl derivative are reacted with either lithium borohydride, resulting in respectively S (+) and R (-) enantiomers of the compound described by formula (IV), or with hydride diisobutylaluminum, with the result that the S (-) and R (+) enantiomers of the corresponding 2-formyl derivative are obtained, respectively; These enantiomers of the 2-formyl derivative are treated with the organo-magnesium compound described by the formula R 1 MgX, where R 1 is as defined above, X is a halogen atom, and then sodium methoxide, after which the separation is performed using chromatography, resulting in the indicated diastereoisomers compounds corresponding to the formula (V).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9410600 | 1994-09-05 | ||
| FR9410600A FR2724171B1 (en) | 1994-09-05 | 1994-09-05 | DERIVATIVES OF 3.3A, 4,5-TETRAHYDRO-1H-OXAZOLO (3,4-A) QUINOLEIN-1-ONE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU95114741A true RU95114741A (en) | 1997-08-10 |
| RU2141482C1 RU2141482C1 (en) | 1999-11-20 |
Family
ID=9466686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU95114741A RU2141482C1 (en) | 1994-09-05 | 1995-09-04 | Derivatives of oxazoloquinolinone, their synthesis and drug and pharmaceutical composition containing thereof |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5641785A (en) |
| EP (1) | EP0699680B1 (en) |
| JP (1) | JP4225585B2 (en) |
| KR (1) | KR100392523B1 (en) |
| CN (1) | CN1055472C (en) |
| AT (1) | ATE190311T1 (en) |
| AU (1) | AU687591B2 (en) |
| CA (1) | CA2157427C (en) |
| CZ (1) | CZ286128B6 (en) |
| DE (1) | DE69515402T2 (en) |
| DK (1) | DK0699680T3 (en) |
| ES (1) | ES2145886T3 (en) |
| FI (1) | FI110945B (en) |
| FR (1) | FR2724171B1 (en) |
| GR (1) | GR3033554T3 (en) |
| HK (1) | HK1013652A1 (en) |
| HU (1) | HU218587B (en) |
| IL (1) | IL115276A (en) |
| NO (1) | NO306617B1 (en) |
| NZ (1) | NZ272920A (en) |
| PL (1) | PL184412B1 (en) |
| PT (1) | PT699680E (en) |
| RU (1) | RU2141482C1 (en) |
| SI (1) | SI0699680T1 (en) |
| SK (1) | SK281867B6 (en) |
| TW (1) | TW356467B (en) |
| UA (1) | UA41916C2 (en) |
| ZA (1) | ZA957414B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2470937C2 (en) * | 2007-03-09 | 2012-12-27 | Санофи-Авентис | Production and use of substituted dihydro- and tetrahydrooxazolo-pyrimidinones |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1078632A1 (en) * | 1999-08-16 | 2001-02-28 | Sanofi-Synthelabo | Use of monoamine oxydase inhibitors for the manufacture of drugs intended for the treatment of obesity |
| US7553967B2 (en) * | 2004-03-12 | 2009-06-30 | Wyeth | 1,2-Dihydroquinoline derivatives and method for using the same to treat HIV infections |
| RU2366430C2 (en) | 2007-05-23 | 2009-09-10 | Виктор Иванович Рощин | Monoaminooxidase inhibitors, therapeutic agent and pharmaceutical composition |
| AR078171A1 (en) | 2009-09-15 | 2011-10-19 | Sanofi Aventis | DIHYDROBENZOCICLOALQUILOXIMETIL-OXAZOLOPIRIMIDINONES REPLACED, PREPARATION AND USE OF THE SAME |
| CN105949120B (en) * | 2016-05-27 | 2018-07-24 | 广东工业大学 | A kind of application of four teeth chelating type list quinoline and preparation method thereof and metal ion control agent as neurodegenerative disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2624861B1 (en) * | 1987-12-21 | 1990-06-01 | Delalande Sa | TRICYCLIC CARBAMATES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION |
| ES2013391A6 (en) * | 1989-02-08 | 1990-05-01 | Consejo Superior Investigacion | Indole derivates. |
| JPH04295470A (en) * | 1991-03-22 | 1992-10-20 | Wakamoto Pharmaceut Co Ltd | 1,2,4-oxadiazole derivative having monoamine oxidase b enzyme inhibiting activity and its production |
-
1994
- 1994-09-05 FR FR9410600A patent/FR2724171B1/en not_active Expired - Lifetime
-
1995
- 1995-09-01 PT PT95401989T patent/PT699680E/en unknown
- 1995-09-01 SI SI9530413T patent/SI0699680T1/en unknown
- 1995-09-01 ES ES95401989T patent/ES2145886T3/en not_active Expired - Lifetime
- 1995-09-01 DK DK95401989T patent/DK0699680T3/en active
- 1995-09-01 EP EP95401989A patent/EP0699680B1/en not_active Expired - Lifetime
- 1995-09-01 DE DE69515402T patent/DE69515402T2/en not_active Expired - Lifetime
- 1995-09-01 AT AT95401989T patent/ATE190311T1/en active
- 1995-09-01 CA CA2157427A patent/CA2157427C/en not_active Expired - Lifetime
- 1995-09-01 US US08/523,508 patent/US5641785A/en not_active Expired - Lifetime
- 1995-09-02 TW TW084109192A patent/TW356467B/en not_active IP Right Cessation
- 1995-09-04 HU HU9502578A patent/HU218587B/en unknown
- 1995-09-04 AU AU30415/95A patent/AU687591B2/en not_active Expired
- 1995-09-04 JP JP22646295A patent/JP4225585B2/en not_active Expired - Lifetime
- 1995-09-04 KR KR1019950028714A patent/KR100392523B1/en not_active IP Right Cessation
- 1995-09-04 FI FI954141A patent/FI110945B/en not_active IP Right Cessation
- 1995-09-04 RU RU95114741A patent/RU2141482C1/en active
- 1995-09-04 ZA ZA957414A patent/ZA957414B/en unknown
- 1995-09-04 UA UA95094019A patent/UA41916C2/en unknown
- 1995-09-04 NO NO953458A patent/NO306617B1/en not_active IP Right Cessation
- 1995-09-04 NZ NZ272920A patent/NZ272920A/en not_active IP Right Cessation
- 1995-09-04 CN CN95117143A patent/CN1055472C/en not_active Expired - Lifetime
- 1995-09-04 CZ CZ19952262A patent/CZ286128B6/en not_active IP Right Cessation
- 1995-09-04 SK SK1089-95A patent/SK281867B6/en not_active IP Right Cessation
- 1995-09-04 PL PL95310273A patent/PL184412B1/en unknown
- 1995-09-12 IL IL11527695A patent/IL115276A/en not_active IP Right Cessation
-
1998
- 1998-12-23 HK HK98114972A patent/HK1013652A1/en not_active IP Right Cessation
-
2000
- 2000-05-31 GR GR20000401246T patent/GR3033554T3/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2470937C2 (en) * | 2007-03-09 | 2012-12-27 | Санофи-Авентис | Production and use of substituted dihydro- and tetrahydrooxazolo-pyrimidinones |
| US8642603B2 (en) | 2007-03-09 | 2014-02-04 | Sanofi | Substituted dihydro and tetrahydro oxazolopyrimidinones, preparation and use thereof |
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