FR2479823A2 - Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2479823A2 FR2479823A2 FR8007659A FR8007659A FR2479823A2 FR 2479823 A2 FR2479823 A2 FR 2479823A2 FR 8007659 A FR8007659 A FR 8007659A FR 8007659 A FR8007659 A FR 8007659A FR 2479823 A2 FR2479823 A2 FR 2479823A2
- Authority
- FR
- France
- Prior art keywords
- sep
- formula
- compound
- chloro
- fluoro
- 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.)
- Granted
Links
- 239000000935 antidepressant agent Substances 0.000 title abstract description 3
- 229940005513 antidepressants Drugs 0.000 title abstract description 3
- GXVIPLSBEKJPCW-UHFFFAOYSA-N 5-(hydroxymethyl)-3-phenyl-3H-furan-2-one Chemical compound C1(=CC=CC=C1)C1C(OC(=C1)CO)=O GXVIPLSBEKJPCW-UHFFFAOYSA-N 0.000 title 1
- 239000002243 precursor Substances 0.000 title 1
- -1 3-methylbutoxy, cyclohexylmethoxy, metanitrobenzyloxy Chemical group 0.000 claims abstract description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000000243 solution Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- KRQHBUXUXOPOON-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(Cl)=C1 KRQHBUXUXOPOON-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 238000007360 debenzoylation reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102000010909 Monoamine Oxidase Human genes 0.000 abstract description 3
- 108010062431 Monoamine oxidase Proteins 0.000 abstract description 3
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 230000002441 reversible effect Effects 0.000 abstract description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N 3-methoxypyridine Chemical compound COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 241000699670 Mus sp. Species 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 230000001154 acute effect Effects 0.000 abstract 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 abstract 1
- 230000002490 cerebral effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229960003057 nialamide Drugs 0.000 description 2
- 229960001779 pargyline Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- IGLYMJRIWWIQQE-QUOODJBBSA-N (1S,2R)-2-phenylcyclopropan-1-amine (1R,2S)-2-phenylcyclopropan-1-amine Chemical compound N[C@H]1C[C@@H]1C1=CC=CC=C1.N[C@@H]1C[C@H]1C1=CC=CC=C1 IGLYMJRIWWIQQE-QUOODJBBSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- JCVDWIAVFOPBGX-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)propanal Chemical compound ClC1=CC=C(CCC=O)C(Cl)=C1 JCVDWIAVFOPBGX-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 102100021935 C-C motif chemokine 26 Human genes 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- FTZGFEKLDHOITO-UHFFFAOYSA-N FC=1C=C(C(Cl)Cl)C=CC1F Chemical compound FC=1C=C(C(Cl)Cl)C=CC1F FTZGFEKLDHOITO-UHFFFAOYSA-N 0.000 description 1
- 101000897493 Homo sapiens C-C motif chemokine 26 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940077481 dl- 5-hydroxytryptophan Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PDZGAEAUKGKKDE-UHFFFAOYSA-N lithium;naphthalene Chemical compound [Li].C1=CC=CC2=CC=CC=C21 PDZGAEAUKGKKDE-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229960003741 tranylcypromine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007659A FR2479823A2 (fr) | 1980-04-04 | 1980-04-04 | Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique |
| CH2975/80A CH647772A5 (fr) | 1979-05-07 | 1980-04-17 | Derives de la 5h-furanone-2 et de la 3h-dihydro-furanone-2, leurs procedes de preparation, et medicament les contenant. |
| GB8014057A GB2053196B (en) | 1979-05-07 | 1980-04-29 | Derivatives of 5h-furanone-2 and of 3h-dihydrofuranone-2,the process for preparing the same and their application in therapeutics |
| SE8003228A SE448384B (sv) | 1979-05-07 | 1980-04-29 | Derivat av 5h-furanon-2 och 3h-dihydrofuranon-2, forfarande for deras framstellning samt farmaceutisk komposition vilken som aktiv komponent innehaller nemnda derivat |
| GR61821A GR67293B (enExample) | 1979-05-07 | 1980-04-30 | |
| CA000351037A CA1136628A (en) | 1979-05-07 | 1980-05-01 | Derivatives of 5h-furanone-2 and of 3h-dihydro- furanone-2, the process for preparing the same and their application in therapeutics |
| ES491154A ES491154A0 (es) | 1979-05-07 | 1980-05-03 | Procedimiento para la preparacion de derivados furanonicos |
| LU82420A LU82420A1 (fr) | 1979-05-07 | 1980-05-05 | Nouveaux derives de la 5 h-furanone-2 et de la 3 h-dihydrofuranone-2,leur procede de preparation et leur application en therapeutique |
| IT21795/80A IT1151009B (it) | 1979-05-07 | 1980-05-05 | Derivati del 5h-furanone-2 e del 3h-diidrofuranone-2,loro procedimento di preparazione e loro applicazione terapeutica |
| BE2/477A BE883124A (fr) | 1979-05-07 | 1980-05-06 | Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydro-furanone-2, leur procede de preparation et leur application en therapeutique |
| MX10143880U MX6734E (es) | 1979-05-07 | 1980-05-06 | Procedimiento para preparar derivados de la 3h-dihidrofuranona-2 |
| AU58131/80A AU535880B2 (en) | 1979-05-07 | 1980-05-06 | 5h-furanone-2 and 3h-dihydrofuranone-2 derivatives |
| DE19803017499 DE3017499A1 (de) | 1979-05-07 | 1980-05-07 | Neue derivate des 5h-furan-2-ons und 3h-dihydrofuran-2-ons, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel |
| NL8002618A NL8002618A (nl) | 1979-05-07 | 1980-05-07 | Nieuwe 5hfuranon-2 en 3h-dihydrofuranon-2 derivaten, werkwijze voor hun bereiding en hun toepassing als geneesmiddel. |
| US06/352,911 US4372967A (en) | 1979-05-07 | 1982-02-26 | 3H-Dihydrofuranone-2 derivatives and pharmaceutical use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007659A FR2479823A2 (fr) | 1980-04-04 | 1980-04-04 | Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2479823A2 true FR2479823A2 (fr) | 1981-10-09 |
| FR2479823B2 FR2479823B2 (enExample) | 1983-04-15 |
Family
ID=9240553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8007659A Granted FR2479823A2 (fr) | 1979-05-07 | 1980-04-04 | Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2479823A2 (enExample) |
-
1980
- 1980-04-04 FR FR8007659A patent/FR2479823A2/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2479823B2 (enExample) | 1983-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH653999A5 (fr) | Derives aminomethyl-5 oxazolidiniques, procede de preparation et composition pharmaceutique. | |
| FR2476088A2 (fr) | Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique | |
| CH640837A5 (fr) | Derives de l'imidazole. | |
| CH650780A5 (fr) | N-aryl oxazolidinones-2, leur procede de preparation et composition pharmaceutique les contenant. | |
| FR2548666A1 (fr) | Nouveaux derives du nor-tropane et du granatane, leur procede de preparation et leur application en therapeutique | |
| EP0343050B1 (fr) | Dérivés de phényl-6 pipérazinyl-alkyl-3 1H,3H-pyrimidinedione-2,4, leur préparation et leur application en thérapeutique | |
| EP0041410B1 (fr) | Nouveaux éthers tricycliques, leurs procédés de préparation et leur utilisation comme médicament | |
| CH647772A5 (fr) | Derives de la 5h-furanone-2 et de la 3h-dihydro-furanone-2, leurs procedes de preparation, et medicament les contenant. | |
| FR2526434A1 (fr) | Nouveaux azepino-indoles, leur preparation et leur utilisation comme medicaments | |
| US4346102A (en) | 3H-Dihydrofuranone-2 derivatives and pharmaceutical use thereof | |
| MC1845A1 (fr) | Derives de pyrimidine | |
| EP0275742B1 (fr) | Dérivés 5-hydroxyéthylés de l'oxazolidinone-2, leurs procédés de préparation et leurs applications en thérapeutique | |
| BE854655A (fr) | 9-hydroxyhexahydrobenzo (c) quinoleines et intermediaires de synthese | |
| FR2479823A2 (fr) | Nouveaux derives de la 5h-furanone-2 et de la 3h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique | |
| US4200638A (en) | Indole derivatives and therapeutically acting drugs | |
| EP0294258A1 (fr) | Dérivés d'hydrazine, procédé d'obtention et compositions pharmaceutiques les contenant | |
| CH632999A5 (fr) | (2-thio)urees 1,3-disubstituees. | |
| FR2518992A1 (fr) | Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique | |
| FR2506769A2 (fr) | Para-((cyano-5 n pentyl-1) phenyl)-3 methoxymethyl-5 oxazolidinone-2, son procede de preparation et ses applications en therapeutique | |
| EP0061406B1 (fr) | Dérivés d'acide benzamido-alkyl-hydroxamique, procédé de préparation et composition thérapeutique | |
| EP0043811B1 (fr) | Nouvelles indolonaphtyridines et leur utilisation en tant que médicaments | |
| EP0347305B1 (fr) | [(Aryl-4-pipérazinyl-1)-2 éthoxy]-3 p-cymène, les dérivés ortho, méta, para monosubstitués ou disubstitués sur le noyau phényle dudit produit, le procédé de préparation desdits dérivés, et les médicaments contenant lesdits composés comme principe actif | |
| EP0100257B1 (fr) | Nouveaux dérivés aminoalkyl naphtaléniques, leurs sels d'addition d'acide et le procédé de préparation ainsi que l'application en thérapeutique de ces dérivés et sels | |
| EP0259228B1 (fr) | Dérivés 5-aminoéthylés de l'oxazolidinone-2, leur procédé de préparation et leur application en thérapeutique | |
| EP0017523B1 (fr) | Nouveaux dérivés du dithiépinno (1,4)(2,3-c)pyrrole, leur préparation et les médicaments qui les contiennent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property |