RU98100257A - OXAZOLIDINONE DERIVATIVES, THEIR PRODUCTION AND USE thereof IN THERAPY - Google Patents
OXAZOLIDINONE DERIVATIVES, THEIR PRODUCTION AND USE thereof IN THERAPYInfo
- Publication number
- RU98100257A RU98100257A RU98100257/04A RU98100257A RU98100257A RU 98100257 A RU98100257 A RU 98100257A RU 98100257/04 A RU98100257/04 A RU 98100257/04A RU 98100257 A RU98100257 A RU 98100257A RU 98100257 A RU98100257 A RU 98100257A
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- formula
- hydrogen atom
- compound
- atom
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title 1
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 22
- -1 methylenedioxy group Chemical group 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 7
- LSYOFPBORRARMF-UHFFFAOYSA-N 5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical class OCC1CNC(=O)O1 LSYOFPBORRARMF-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000001184 potassium carbonate Substances 0.000 claims 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004434 sulfur atoms Chemical group 0.000 claims 5
- GTIIVHODSNYECK-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical group [CH2]CC(F)(F)F GTIIVHODSNYECK-UHFFFAOYSA-N 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- LYVWJKRCILVKOI-UHFFFAOYSA-N 1,1,1-trifluorobutane Chemical group [CH2]CCC(F)(F)F LYVWJKRCILVKOI-UHFFFAOYSA-N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- ILAHWRKJUDSMFH-UHFFFAOYSA-N Boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N Diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N methyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 2
- PLTALYMSSXETDZ-SNVBAGLBSA-N (4R)-4-(phenylmethoxymethyl)-1,3-dioxolan-2-one Chemical class O1C(=O)OC[C@H]1COCC1=CC=CC=C1 PLTALYMSSXETDZ-SNVBAGLBSA-N 0.000 claims 1
- DNSGQMOSYDHNHO-BYPYZUCNSA-N (4S)-4-(methoxymethyl)-1,3-dioxolan-2-one Chemical class COC[C@H]1COC(=O)O1 DNSGQMOSYDHNHO-BYPYZUCNSA-N 0.000 claims 1
- SQMNCLANJWZZOG-NSHDSACASA-N (5S)-5-(methoxymethyl)-3-[6-(4,4,4-trifluorobutoxy)-1,2-benzoxazol-3-yl]-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](COC)CN1C1=NOC2=CC(OCCCC(F)(F)F)=CC=C12 SQMNCLANJWZZOG-NSHDSACASA-N 0.000 claims 1
- SHPQVJNNBXMZRW-UHFFFAOYSA-N 6-butyldec-5-en-5-yltin Chemical compound CCCCC([Sn])=C(CCCC)CCCC SHPQVJNNBXMZRW-UHFFFAOYSA-N 0.000 claims 1
- 239000004342 Benzoyl peroxide Substances 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- XMAWMRNILPLCMA-UHFFFAOYSA-L N-carboxylatoiminocarbamate;triphenylphosphane Chemical compound [O-]C(=O)N=NC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 XMAWMRNILPLCMA-UHFFFAOYSA-L 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamate Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 claims 1
- 0 OC(CC1)CC2=C1C(C(CC(CC=O)O1)C1=O)=N*2 Chemical compound OC(CC1)CC2=C1C(C(CC(CC=O)O1)C1=O)=N*2 0.000 description 3
Claims (1)
где Х представляет собой атом кислорода, атом серы или группу NR;
R является атомом водорода или C1-C4 алкилом, нормальным или разветвленным;
R1 представляет собой атом водорода или метильную группу;
R2 представляет собой:
(i) группу R3O, в которой R3 является либо атомом водорода либо бензильной группой, возможно замещенной атомом галогена или нитро или метилендиокси группой, либо группой метоксиэтил, бутил, 4,4,4-трифторбутил, 4,4,4-трифтор-3-гидроксибутил или 4,4,4-трифторбут-2-енил, или
(ii) группу -CH= CH-R4 или -CH2-CH2-R4, в которой R4 представляет атом водорода или группу фенил, 3,3,3-трифторпропил или 3,3,3-трифтор-2-гидроксипропил,
в форме энантиомеров или диастереоизомеров, или смесей этих различных форм, включая рацемические смеси.1. Derivatives of 5- (hydroxymethyl) oxazolidin-2-one of general formula I
where X represents an oxygen atom, a sulfur atom or an NR group;
R is a hydrogen atom or C 1 -C 4 alkyl, straight or branched;
R 1 represents a hydrogen atom or a methyl group;
R 2 represents:
(i) an R 3 O group in which R 3 is either a hydrogen atom or a benzyl group optionally substituted with a halogen atom or a nitro or methylenedioxy group or a methoxyethyl, butyl, 4,4,4-trifluorobutyl group, 4,4,4- trifluoro-3-hydroxybutyl or 4,4,4-trifluorobut-2-enyl, or
(ii) a group —CH = CH — R 4 or —CH 2 —CH 2 —R 4 in which R 4 represents a hydrogen atom or a phenyl group, 3,3,3-trifluoropropyl or 3,3,3-trifluoro-2 -hydroxypropyl,
in the form of enantiomers or diastereoisomers, or mixtures of these various forms, including racemic mixtures.
(i) группу R3O, в которой R3 представляет собой либо атом водорода либо бензильную группу, возможно замещенную атомом галогена или нитро- или метилендиокси-группой, либо группу метоксиэтил, бутил, 4,4,4-трифторбутил, 4,4,4-трифтор-3-гидроксибутил или 4,4,4-трифторбут-2-енил, или
(ii) группу -CH=CH-R4 или -СH2-СH2-R4, в которой R4 представляет собой атом водорода или группу фенил, 3,3,3-трифторпропил или 3,3,3-трифтор-2-гидроксипропил,
в форме энантиомеров или диастереоизомеров, или смесей этих разных форм, включая рацемические смеси.4. Derivatives of 5- (hydroxymethyl) oxazolidin-2-one of general formula I according to claim 1, characterized in that X is an oxygen atom, R 1 represents a methyl group or a hydrogen atom, and R 2 represents:
(i) an R 3 O group in which R 3 is either a hydrogen atom or a benzyl group optionally substituted with a halogen atom or a nitro or methylenedioxy group or a methoxyethyl, butyl group, 4,4,4-trifluorobutyl, 4,4 , 4-trifluoro-3-hydroxybutyl or 4,4,4-trifluorobut-2-enyl, or
(ii) a group -CH = CH-R 4 or -CH 2 -CH 2 -R 4 in which R 4 represents a hydrogen atom or a phenyl group, a 3,3,3-trifluoropropyl or 3,3,3-trifluoro 2-hydroxypropyl,
in the form of enantiomers or diastereoisomers, or mixtures of these various forms, including racemic mixtures.
обрабатывают одним из изомеров 4(R) или 4(S) 4-метоксиметил-1,3-диоксолан-2-она формулы IIIa
в присутствии карбоната калия с получением изомера 5(S) или 5(R) соединения формулы Iа
которое дебензилируют каталитическим гидрированием или с помощью кислоты Льюиса с получением изомера 5(S) или 5(R) соединения формулы Ib, R1=CH3
которое обрабатывают либо соединением формулы R3Y, в которой R3 определяют как в формуле I, за исключением значений водорода и незамещенного бензила, а Y представляет собой уходящую группу, такую как атом хлора или брома или тозилокси-группу, в присутствии карбоната калия, либо соединением формулы R3ОН, в котором R3 определено ранее, в присутствии трифенилфосфина и диэтилазодикарбоксилата с получением изомеров 5(S) или 5(R) соединений формулы Iс, R1=CH3
R1=CH3
и, если необходимо, обрабатывают соединения, такие как Х=NСН3, перекисью бензоила с получением соединений формулы Ih, в которых X=NH,
8. Способ получения соединений формулы I, в которой R1 представляет собой атом водорода, причем заместители Х и R2 имеют то же самое значение, что и раньше, характеризующийся тем, что этиловый эфир 6-фенилметокси-1,2-бензизоксазол-3-карбаминовой кислоты формулы II
обрабатывают одним из изомеров 4(S) или 4(R) 4-фенилметоксиметил-1,3-диоксолан-2-она формулы IIIb
в присутствии карбоната калия с получением изомера 5(R) или 5(S) соединения формулы Vl
которое дебензилируют каталитическим гидрированием с получением изомера 5(R) или 5(S) соединения формулы Ib, R1=H
R1=H,
который затем обрабатывают соединением формулы R3Y, в которой R3 определено как в формуле I, за исключением значения водорода, и Y является уходящей группой, такой как атом хлора или брома или тозилокси-группой, в присутствии карбоната калия с получением изомеров 5(R) или 5(S) соединений формулы Ic, R1=H
R1=H
9. Способ получения соединений формулы I, в которой Х представляет собой атом кислорода, атом серы или группу NR, где R является атомом водорода или C1-C4 алкилом, нормальным или разветвленным, R1 представляет собой атом водорода или метильную группу, и R2 представляет собой группу -CH=CH-R4 или -CH2-CH2-R4, где R4 представляет собой атом водорода или группу фенил, 3,3,3-трифторпропил или 3,3,3-трифтор-2-гидроксипропил, характеризующийся тем, что он состоит в обработке соединения формулы Ib, R1=CH3
трифторметансульфоновым ангидридом, взаимодействии полученного таким образом соединения формулы IV
с трибутилвинилоловом в присутствии хлорида лития и тетракис(трифенилфосфин) палладия, обработке соединения формулы Id
озоном, затем диметилсульфидом, взаимодействии соединения формулы V
с трифенилфосфонийиодидом формулы R4СН2РРh3 +I-, в которой R4 определен как в формуле I ранее, за исключением значения водорода, в присутствии карбоната калия, восстановлении соединения формулы Iе
водородом в присутствии катализатора с получением соединения формулы If
в которой R4 определен как ранее, и, наконец, обработке этого соединения трибромидом бора с получением соединения формулы Ig
10. Лекарство, отличающееся тем, что оно образовано соединением формулы I по п.1.7. A method of obtaining compounds of formula I, in which X represents an oxygen atom, or a sulfur atom or an NR group, wherein R is a hydrogen atom or a C 1 -C 4 alkyl, straight or branched chain, R 1 represents a methyl group, R 2 represents represents a group R 3 O, in which R 3 represents either a hydrogen atom or a benzyl group, possibly substituted by a halogen atom or a nitro- or methylenedioxy group, or a methoxyethyl, butyl group, 4,4,4-trifluorobutyl, 4,4,4- trifluoro-3-hydroxybutyl or 4,4,4-trifluorobut-2-enyl, characterized in that the compound of formula II
treated with one of the 4 (R) or 4 (S) 4-methoxymethyl-1,3-dioxolan-2-one isomers of formula IIIa
in the presence of potassium carbonate to obtain the isomer 5 (S) or 5 (R) of the compound of formula Ia
which is debenzylated by catalytic hydrogenation or with a Lewis acid to give the isomer 5 (S) or 5 (R) of a compound of formula Ib, R 1 = CH 3
which is treated either with a compound of formula R 3 Y, in which R 3 is defined as in formula I, with the exception of hydrogen and unsubstituted benzyl, and Y represents a leaving group, such as a chlorine or bromine atom or a tosyloxy group, in the presence of potassium carbonate, or a compound of the formula R 3 OH, in which R 3 is previously determined, in the presence of triphenylphosphine and diethyl azodicarboxylate to give isomers 5 (S) or 5 (R) of compounds of the formula IC, R 1 = CH 3
R 1 = CH 3
and, if necessary, treating compounds, such as X = NCH 3 , with benzoyl peroxide to give compounds of formula Ih in which X = NH,
8. The method of obtaining compounds of formula I, in which R 1 represents a hydrogen atom, and the substituents X and R 2 have the same meaning as before, characterized in that the ethyl ester 6-phenylmethoxy-1,2-benzisoxazole-3 carbamic acid of the formula II
treated with one of 4 (S) or 4 (R) 4-phenylmethoxymethyl-1,3-dioxolan-2-one isomers of formula IIIb
in the presence of potassium carbonate to give the isomer 5 (R) or 5 (S) of a compound of formula Vl
which is debenzylated by catalytic hydrogenation to give the isomer 5 (R) or 5 (S) of a compound of formula Ib, R 1 = H
R 1 = H,
which is then treated with a compound of formula R 3 Y in which R 3 is defined as in formula I, with the exception of the meaning of hydrogen, and Y is a leaving group, such as a chlorine or bromine atom or a tosyloxy group, in the presence of potassium carbonate to give isomers 5 ( R) or 5 (S) compounds of formula Ic, R 1 = H
R 1 = H
9. A method for producing compounds of formula I, in which X represents an oxygen atom, a sulfur atom or an NR group, where R is a hydrogen atom or a C 1 -C 4 alkyl, straight or branched chain, R 1 represents a hydrogen atom or a methyl group, and R 2 represents a group —CH═CH — R 4 or —CH 2 —CH 2 —R 4 , where R 4 represents a hydrogen atom or a phenyl group, 3,3,3-trifluoropropyl or 3,3,3-trifluoro- 2-hydroxypropyl, characterized in that it consists in treating a compound of formula Ib, R 1 = CH 3
trifluoromethanesulfonic anhydride, reacting the compound of formula IV thus obtained
with tributyl vinyltin in the presence of lithium chloride and tetrakis (triphenylphosphine) palladium, treating the compound of formula Id
ozone, then dimethyl sulfide, the interaction of the compounds of formula V
with triphenylphosphonium iodide of the formula R 4 CH 2 PPh 3 + I - , in which R 4 is as previously defined in formula I, except for the meaning of hydrogen, in the presence of potassium carbonate, reduction of the compound of formula Ie
hydrogen in the presence of a catalyst to obtain a compound of formula If
in which R 4 is defined as before, and, finally, processing this compound with boron tribromide to obtain a compound of formula Ig
10. A medicine, characterized in that it is formed by a compound of formula I according to claim 1.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9506563A FR2734820B1 (en) | 1995-06-02 | 1995-06-02 | DERIVATIVES OF 3- (1,2-BENZISOXAZOL-3-YL) OXAZOLIDIN-2-ONE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| FR9506564A FR2734821B1 (en) | 1995-06-02 | 1995-06-02 | 5-METHOXYMETHYL-3- (1,2-BENZISOXAZOL-3-YL) OXAZOLIDIN-2-ONE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| FR95/06564 | 1995-06-02 | ||
| FR95/06563 | 1995-06-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98100257A true RU98100257A (en) | 2000-01-10 |
| RU2164226C2 RU2164226C2 (en) | 2001-03-20 |
Family
ID=26232004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98100257/04A RU2164226C2 (en) | 1995-06-02 | 1996-05-28 | Derivatives of 5-(hydroxymethyl)-oxazolidine-2-one, methods of their synthesis, remedy and pharmaceutical composition |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5843975A (en) |
| EP (1) | EP0835254B1 (en) |
| JP (1) | JP3856829B2 (en) |
| KR (1) | KR100457502B1 (en) |
| CN (1) | CN1075072C (en) |
| AR (1) | AR006301A1 (en) |
| AT (1) | ATE184005T1 (en) |
| AU (1) | AU699367B2 (en) |
| BR (1) | BR9608896A (en) |
| CA (1) | CA2223011C (en) |
| CO (1) | CO4700462A1 (en) |
| CZ (1) | CZ378497A3 (en) |
| DE (1) | DE69604071T2 (en) |
| DK (1) | DK0835254T3 (en) |
| ES (1) | ES2138346T3 (en) |
| GR (1) | GR3031710T3 (en) |
| HK (1) | HK1014938A1 (en) |
| HU (1) | HU224879B1 (en) |
| MX (1) | MX9709410A (en) |
| NO (1) | NO309091B1 (en) |
| NZ (1) | NZ310487A (en) |
| PL (1) | PL183919B1 (en) |
| RU (1) | RU2164226C2 (en) |
| SK (1) | SK281934B6 (en) |
| TW (1) | TW360654B (en) |
| WO (1) | WO1996038444A1 (en) |
| ZA (1) | ZA964563B (en) |
Families Citing this family (11)
| 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 |
| EP2140864A3 (en) * | 2001-01-31 | 2010-01-27 | H.Lundbeck A/S | Use of GAL3 receptor antagonists for the treatment of depression and / or anxiety and compounds useful in such methods |
| JP4542338B2 (en) * | 2001-09-26 | 2010-09-15 | ファイザー イタリア ソシエタ ア レスポンサビリタ リミタータ | Aminoindazole derivatives active as kinase inhibitors, processes for their preparation and pharmaceutical compositions containing them |
| JP2009525318A (en) * | 2006-02-01 | 2009-07-09 | ファイザー・プロダクツ・インク | Benzisoxazole oxazolidinone as an antibacterial agent |
| US7998992B2 (en) * | 2007-03-30 | 2011-08-16 | Institute Of Medicinal Molecular Design, Inc. | Oxazolidinone derivative having inhibitory activity on 11β-hydroxysteroid dehydrogenase type 1 |
| EP2123159A1 (en) * | 2008-05-21 | 2009-11-25 | Bayer CropScience AG | (1,2-Benzisothiazol-3-yl)(thio)carbamates and (1,2-Benzisothiazol-3-yl)(thio)oxamates and their oxidation forms as pesticides |
| EP2513096A1 (en) * | 2009-12-18 | 2012-10-24 | Janssen Pharmaceutica, N.V. | Substituted aminothiazolone indazoles as estrogen related receptor-a modulators |
| AU2011218268A1 (en) * | 2010-02-17 | 2012-09-06 | Janssen Pharmaceutica Nv | Aminothiazolones as estrogen related receptor-alpha modulators |
| WO2016097355A1 (en) * | 2014-12-19 | 2016-06-23 | Ge Healthcare Limited | Labelled oxazolidinone derivatives |
| DE102015012050A1 (en) * | 2015-09-15 | 2017-03-16 | Merck Patent Gmbh | Compounds as ASIC inhibitors and their uses |
| RU2637643C1 (en) * | 2016-09-05 | 2017-12-05 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фундаментальной и клинической иммунологии" (НИИФКИ) | Immunodepressant |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2653017B1 (en) * | 1989-10-17 | 1995-05-05 | Delalande Sa | DERIVATIVES OF ARYL-3 OXAZOLIDINONE-2, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THERAPEUTICS. |
| US5196543A (en) * | 1989-10-17 | 1993-03-23 | Delalande S.A. | 3-aryloxazolidinone derivatives, process for their preparation and their use in therapy |
| US5235063A (en) * | 1989-10-17 | 1993-08-10 | Delalande S.A. | Process of preparing by condensation certain |
| US5182296A (en) * | 1989-10-26 | 1993-01-26 | Tanabe Seiyaky Co., Ltd. | Naphthyloxazolidone derivatives |
| FR2671350A1 (en) * | 1991-01-08 | 1992-07-10 | Adir | NOVEL BENZISOXAZOLE AND BENZISOTHIAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME. |
| WO1992014418A1 (en) * | 1991-02-20 | 1992-09-03 | Yusaku Koda | Articulator |
-
1996
- 1996-05-28 DE DE69604071T patent/DE69604071T2/en not_active Expired - Lifetime
- 1996-05-28 WO PCT/FR1996/000792 patent/WO1996038444A1/en active IP Right Grant
- 1996-05-28 SK SK1614-97A patent/SK281934B6/en not_active IP Right Cessation
- 1996-05-28 CN CN96195713A patent/CN1075072C/en not_active Expired - Lifetime
- 1996-05-28 PL PL96323673A patent/PL183919B1/en unknown
- 1996-05-28 JP JP53624596A patent/JP3856829B2/en not_active Expired - Lifetime
- 1996-05-28 HU HU9901349A patent/HU224879B1/en unknown
- 1996-05-28 ES ES96918719T patent/ES2138346T3/en not_active Expired - Lifetime
- 1996-05-28 CA CA002223011A patent/CA2223011C/en not_active Expired - Lifetime
- 1996-05-28 US US08/973,246 patent/US5843975A/en not_active Expired - Lifetime
- 1996-05-28 DK DK96918719T patent/DK0835254T3/en active
- 1996-05-28 BR BR9608896A patent/BR9608896A/en active IP Right Grant
- 1996-05-28 EP EP96918719A patent/EP0835254B1/en not_active Expired - Lifetime
- 1996-05-28 NZ NZ310487A patent/NZ310487A/en not_active IP Right Cessation
- 1996-05-28 RU RU98100257/04A patent/RU2164226C2/en active
- 1996-05-28 CZ CZ973784A patent/CZ378497A3/en unknown
- 1996-05-28 KR KR1019970708666A patent/KR100457502B1/en not_active IP Right Cessation
- 1996-05-28 AU AU61288/96A patent/AU699367B2/en not_active Expired
- 1996-05-28 AT AT96918719T patent/ATE184005T1/en active
- 1996-05-31 CO CO96028173A patent/CO4700462A1/en unknown
- 1996-06-01 TW TW085106564A patent/TW360654B/en not_active IP Right Cessation
- 1996-06-03 AR ARP960102870A patent/AR006301A1/en active IP Right Grant
- 1996-06-03 ZA ZA964563A patent/ZA964563B/en unknown
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1997
- 1997-12-01 NO NO975530A patent/NO309091B1/en not_active IP Right Cessation
- 1997-12-02 MX MX9709410A patent/MX9709410A/en unknown
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1998
- 1998-12-30 HK HK98119245A patent/HK1014938A1/en not_active IP Right Cessation
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1999
- 1999-11-03 GR GR990402802T patent/GR3031710T3/en unknown
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