CA2022887A1 - Utilisation therapeutique de benzenes substitues leurs formules et nouveaux benzenes substitues - Google Patents
Utilisation therapeutique de benzenes substitues leurs formules et nouveaux benzenes substituesInfo
- Publication number
- CA2022887A1 CA2022887A1 CA 2022887 CA2022887A CA2022887A1 CA 2022887 A1 CA2022887 A1 CA 2022887A1 CA 2022887 CA2022887 CA 2022887 CA 2022887 A CA2022887 A CA 2022887A CA 2022887 A1 CA2022887 A1 CA 2022887A1
- Authority
- CA
- Canada
- Prior art keywords
- quinuclidine
- hydroxy
- dimethoxyphenyl
- methoxyphenyl
- compound
- 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.)
- Abandoned
Links
- 239000000203 mixture Chemical class 0.000 title claims abstract description 24
- 238000009472 formulation Methods 0.000 title claims abstract description 5
- 150000001555 benzenes Chemical class 0.000 title claims abstract 5
- 230000001225 therapeutic effect Effects 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 239000000651 prodrug Substances 0.000 claims abstract description 13
- 229940002612 prodrug Drugs 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
- -1 3-hydroxy-quinuclidin-3-yl Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- QXFOGBGAJZGKEL-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=CC=CC(Cl)=C1 QXFOGBGAJZGKEL-UHFFFAOYSA-N 0.000 claims description 5
- IPBNTLFZWWCTJO-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-azabicyclo[2.2.1]heptan-3-ol Chemical compound COC1=CC=CC(C2(O)C3CCN(C3)C2)=C1 IPBNTLFZWWCTJO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- IEDWYZPPADZKMF-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=CC=CC=C1Cl IEDWYZPPADZKMF-UHFFFAOYSA-N 0.000 claims description 4
- IYAGWCWGPKWGPV-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC=CC(C2C3CCN(CC3)C2)=C1 IYAGWCWGPKWGPV-UHFFFAOYSA-N 0.000 claims description 4
- HFMCBDPKGXVABF-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=CC=CC(C(F)(F)F)=C1 HFMCBDPKGXVABF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- JYIUTODHUYMBBE-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1=C2OCOC2=CC(C2(C3CCN(CC3)C2)O)=C1 JYIUTODHUYMBBE-UHFFFAOYSA-N 0.000 claims description 3
- LUVXYDHIONLYLO-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound O1CCOC2=CC(C3(C4CCN(CC4)C3)O)=CC=C21 LUVXYDHIONLYLO-UHFFFAOYSA-N 0.000 claims description 3
- BQLUVNRFONFGRS-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound COC1=CC=CC(C2(O)C3CCN(CC3)C2)=C1OC BQLUVNRFONFGRS-UHFFFAOYSA-N 0.000 claims description 3
- XSFNLYNOMCOEMV-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC=CC(C2C3CCN(CC3)C2)=C1OC XSFNLYNOMCOEMV-UHFFFAOYSA-N 0.000 claims description 3
- VTPFJZVDYQCNHJ-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound COC1=CC=C(OC)C(C2(O)C3CCN(CC3)C2)=C1 VTPFJZVDYQCNHJ-UHFFFAOYSA-N 0.000 claims description 3
- WNQOPMUMGXPFKC-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=CC(Cl)=CC(Cl)=C1 WNQOPMUMGXPFKC-UHFFFAOYSA-N 0.000 claims description 3
- SSWVYNSLNQEDLJ-UHFFFAOYSA-N 3-[3,5-bis(trifluoromethyl)phenyl]-1-azabicyclo[2.2.2]octane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2C3CCN(CC3)C2)=C1 SSWVYNSLNQEDLJ-UHFFFAOYSA-N 0.000 claims description 3
- RHLLYWFOOIXSCR-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]-1-azabicyclo[2.2.2]octane Chemical compound FC(F)(F)C1=CC=CC(C2C3CCN(CC3)C2)=C1 RHLLYWFOOIXSCR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- DFIUNWKXXSRGMG-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-azabicyclo[2.2.2]octane Chemical compound C1N(CC2)CCC2C1C1=CC=C(OCCO2)C2=C1 DFIUNWKXXSRGMG-UHFFFAOYSA-N 0.000 claims description 2
- QRQFNMMHUUJTNW-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound COC1=CC(OC)=CC=C1C1(O)C(CC2)CCN2C1 QRQFNMMHUUJTNW-UHFFFAOYSA-N 0.000 claims description 2
- COYJULQODXRIJF-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC(OC)=CC=C1C1C(CC2)CCN2C1 COYJULQODXRIJF-UHFFFAOYSA-N 0.000 claims description 2
- OPPAOLXAAOFBPN-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC=C(OC)C(C2C3CCN(CC3)C2)=C1 OPPAOLXAAOFBPN-UHFFFAOYSA-N 0.000 claims description 2
- JWRUAMGFFGRLCD-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1(O)C(CC2)CCN2C1 JWRUAMGFFGRLCD-UHFFFAOYSA-N 0.000 claims description 2
- JZNDQILBHRZUCG-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound C1=C(OC)C(OC)=CC=C1C1C(CC2)CCN2C1 JZNDQILBHRZUCG-UHFFFAOYSA-N 0.000 claims description 2
- AQDTWWBHZFOLIV-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound COC1=CC(OC)=CC(C2(O)C3CCN(CC3)C2)=C1 AQDTWWBHZFOLIV-UHFFFAOYSA-N 0.000 claims description 2
- PNICCQXBCQQADM-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC(OC)=CC(C2C3CCN(CC3)C2)=C1 PNICCQXBCQQADM-UHFFFAOYSA-N 0.000 claims description 2
- PRVNBHIZQNJTNH-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-azabicyclo[2.2.1]hept-2-ene Chemical compound COC1=CC=CC(C=2C3CCN(C3)C=2)=C1 PRVNBHIZQNJTNH-UHFFFAOYSA-N 0.000 claims description 2
- MARUBENJISFXSZ-UHFFFAOYSA-N 3-[3,5-bis(trifluoromethyl)phenyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MARUBENJISFXSZ-UHFFFAOYSA-N 0.000 claims description 2
- IIFWJQHYOLEMGD-UHFFFAOYSA-N 6-(3-methoxyphenyl)-1-azabicyclo[3.2.1]oct-6-ene Chemical compound COC1=CC=CC(C=2C3CN(CCC3)C=2)=C1 IIFWJQHYOLEMGD-UHFFFAOYSA-N 0.000 claims description 2
- TZLROMATBNRPJQ-UHFFFAOYSA-N 6-(3-methoxyphenyl)-1-azabicyclo[3.2.1]octan-6-ol Chemical compound COC1=CC=CC(C2(O)C3CN(CCC3)C2)=C1 TZLROMATBNRPJQ-UHFFFAOYSA-N 0.000 claims description 2
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 2
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000926 neurological effect Effects 0.000 claims description 2
- 208000020016 psychiatric disease Diseases 0.000 claims description 2
- 150000008584 quinuclidines Chemical class 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- ZHEVEWLUHPDLJZ-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC(Cl)=CC(C2C3CCN(CC3)C2)=C1 ZHEVEWLUHPDLJZ-UHFFFAOYSA-N 0.000 claims 1
- HFLRXMUJMLBTLM-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-azabicyclo[2.2.1]heptane Chemical compound COC1=CC=CC(C2C3CCN(C3)C2)=C1 HFLRXMUJMLBTLM-UHFFFAOYSA-N 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 238000005906 dihydroxylation reaction Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- 239000012458 free base Substances 0.000 description 75
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- 239000000243 solution Substances 0.000 description 28
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 26
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- FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 230000016776 visual perception Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2022887 CA2022887A1 (fr) | 1989-08-08 | 1990-08-08 | Utilisation therapeutique de benzenes substitues leurs formules et nouveaux benzenes substitues |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8918061.6 | 1989-08-08 | ||
| CA 2022887 CA2022887A1 (fr) | 1989-08-08 | 1990-08-08 | Utilisation therapeutique de benzenes substitues leurs formules et nouveaux benzenes substitues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2022887A1 true CA2022887A1 (fr) | 1991-02-09 |
Family
ID=4145674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2022887 Abandoned CA2022887A1 (fr) | 1989-08-08 | 1990-08-08 | Utilisation therapeutique de benzenes substitues leurs formules et nouveaux benzenes substitues |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2022887A1 (fr) |
-
1990
- 1990-08-08 CA CA 2022887 patent/CA2022887A1/fr not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |