BG60760B2 - Нови трифенилалканови и трифенилалкенови производни, метод за тяхното получаване и използването им - Google Patents
Нови трифенилалканови и трифенилалкенови производни, метод за тяхното получаване и използването им Download PDFInfo
- Publication number
- BG60760B2 BG60760B2 BG098379A BG9837994A BG60760B2 BG 60760 B2 BG60760 B2 BG 60760B2 BG 098379 A BG098379 A BG 098379A BG 9837994 A BG9837994 A BG 9837994A BG 60760 B2 BG60760 B2 BG 60760B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- diphenyl
- formula
- pharmaceutically acceptable
- compound
- esters
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 150000002148 esters Chemical class 0.000 claims abstract description 36
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 25
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 122
- 239000000203 mixture Substances 0.000 claims description 89
- -1 benzyloxy, methoxymethoxy, 2,3-dihydroxypropoxy Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- FEXCPMJYLYUGGR-UHFFFAOYSA-N 2-[4-(2,3-diphenyloxolan-2-yl)phenoxy]-n,n-dimethylethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C1(C=2C=CC=CC=2)C(C=2C=CC=CC=2)CCO1 FEXCPMJYLYUGGR-UHFFFAOYSA-N 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- KJYBEHXAXJZIIF-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)-2-phenyloxolan-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1C(C=2C=CC(O)=CC=2)(C=2C=CC=CC=2)OCC1 KJYBEHXAXJZIIF-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- VDEALWYBHYSLSS-UHFFFAOYSA-N 1,2-bis(4-hydroxyphenyl)-1-phenylbutane-1,4-diol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC(O)=CC=1)C(CCO)C1=CC=C(O)C=C1 VDEALWYBHYSLSS-UHFFFAOYSA-N 0.000 claims description 3
- HZPJJMOFPSHKFE-UHFFFAOYSA-N 4-(4-chloro-1,2-diphenylbut-1-enyl)phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)=C(CCCl)C1=CC=CC=C1 HZPJJMOFPSHKFE-UHFFFAOYSA-N 0.000 claims description 3
- FXFXZVNVLVWXKZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3,4-diphenylbut-3-en-1-ol Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)=C(CCO)C1=CC=CC=C1 FXFXZVNVLVWXKZ-UHFFFAOYSA-N 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229940088597 hormone Drugs 0.000 claims description 3
- 239000005556 hormone Substances 0.000 claims description 3
- FNDFQVSARMSYGF-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-1,2-diphenylbutane-1,4-diol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC(O)=CC=1)C(CCO)C1=CC=CC=C1 FNDFQVSARMSYGF-UHFFFAOYSA-N 0.000 claims description 2
- XFCLJVABOIYOMF-UHFFFAOYSA-N 2-[4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC=CC=1)=C(CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-UHFFFAOYSA-N 0.000 claims description 2
- NXFNODKYDRLSQI-UHFFFAOYSA-N 4-(2,3-diphenyloxan-2-yl)phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC=CC=2)C(C=2C=CC=CC=2)CCCO1 NXFNODKYDRLSQI-UHFFFAOYSA-N 0.000 claims description 2
- LJOBGVGUZNXOMF-UHFFFAOYSA-N 4-(4-chloro-1,2-diphenylbutyl)phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)C(CCCl)C1=CC=CC=C1 LJOBGVGUZNXOMF-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 3
- CILUUGLLYLAHMG-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylbutane-1,4-diol Chemical compound C1=CC(OCCN(C)C)=CC=C1C(O)(C=1C=CC=CC=1)C(CCO)C1=CC=CC=C1 CILUUGLLYLAHMG-UHFFFAOYSA-N 0.000 claims 1
- NGCCIJKMKNEEJB-UHFFFAOYSA-N 2-[4-(4-bromo-1,2-diphenylbut-1-enyl)phenoxy]-n,n-dimethylethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC=CC=1)=C(CCBr)C1=CC=CC=C1 NGCCIJKMKNEEJB-UHFFFAOYSA-N 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 230000003054 hormonal effect Effects 0.000 abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- 239000000047 product Substances 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 47
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 40
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 12
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Classifications
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
- C07C29/1285—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis of esters of organic acids
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/28—Alcohols containing only six-membered aromatic rings as cyclic part with unsaturation outside the aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
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- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
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- C07C39/24—Halogenated derivatives
- C07C39/373—Halogenated derivatives with all hydroxy groups on non-condensed rings and with unsaturation outside the aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C43/02—Ethers
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- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
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- C07C43/02—Ethers
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- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
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- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI821879A FI67538C (fi) | 1982-05-27 | 1982-05-27 | Foerfarande foer framstaellning av (z)-1,2-difenyl-1-(4-(2-(n n-dimetylamino)etoxi)fenyl)-1-buten |
GB08218414A GB2126576B (en) | 1982-06-25 | 1982-06-25 | Alkane and alkene derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
BG60760B2 true BG60760B2 (bg) | 1996-02-29 |
Family
ID=26157340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG098379A BG60760B2 (bg) | 1982-05-27 | 1994-01-18 | Нови трифенилалканови и трифенилалкенови производни, метод за тяхното получаване и използването им |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0095875B1 (xx) |
JP (3) | JPH037239A (xx) |
AU (1) | AU556608B2 (xx) |
BG (1) | BG60760B2 (xx) |
CA (1) | CA1185977A (xx) |
DD (1) | DD230864A1 (xx) |
DE (1) | DE3366021D1 (xx) |
DK (1) | DK170927B1 (xx) |
FI (1) | FI77839C (xx) |
IE (1) | IE55023B1 (xx) |
IL (1) | IL68784A (xx) |
LU (1) | LU88803I2 (xx) |
NL (1) | NL960021I2 (xx) |
NO (1) | NO156164C (xx) |
NZ (1) | NZ204349A (xx) |
SG (1) | SG65488G (xx) |
SU (1) | SU1508955A3 (xx) |
UA (1) | UA5558A1 (xx) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
DE3722807A1 (de) * | 1987-07-10 | 1989-01-19 | Hoechst Ag | Neue 3,5-dihydroxycarbonsaeuren und deren derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
CA2092996A1 (en) * | 1990-10-01 | 1992-04-02 | David Yang | High affinity tamoxifen derivatives and uses thereof |
US5811447A (en) | 1993-01-28 | 1998-09-22 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
US6515009B1 (en) | 1991-09-27 | 2003-02-04 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
GB9207437D0 (en) * | 1992-04-03 | 1992-05-20 | Orion Yhtymae Oy | Topical administration of toremifene and its metabolites |
DE4212628A1 (de) * | 1992-04-15 | 1993-10-21 | Manfred Dr Metzler | Neue Bis-phenyl-hexene |
US6251920B1 (en) | 1993-05-13 | 2001-06-26 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies |
US5770609A (en) | 1993-01-28 | 1998-06-23 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies |
US6491938B2 (en) | 1993-05-13 | 2002-12-10 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
DE69435137D1 (de) | 1993-05-13 | 2008-10-16 | Poniard Pharmaceuticals Inc | Prävention und behandlung von pathologien, die mit einer abnormalen proliferationglatter muskelzellen verbunden sind |
US6197789B1 (en) | 1995-06-07 | 2001-03-06 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies with tamoxifen analogues |
US5681835A (en) * | 1994-04-25 | 1997-10-28 | Glaxo Wellcome Inc. | Non-steroidal ligands for the estrogen receptor |
WO1998046588A2 (en) | 1997-04-11 | 1998-10-22 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
CA2301032C (en) | 1997-08-15 | 2009-01-13 | Duke University | A method of preventing or treating estrogen-dependent diseases and disorders |
DE1003496T1 (de) * | 1998-05-07 | 2000-11-02 | Univ Tennessee Res Corp | Methode zur Vorbeugung von Prostatakrebs |
US6413533B1 (en) | 1998-05-07 | 2002-07-02 | The University Of Tennessee Research Corporation | Method for chemoprevention of prostate cancer |
US6632447B1 (en) | 1998-05-07 | 2003-10-14 | The University Of Tennessee Research Corporation | Method for chemoprevention of prostate cancer |
AU2003203589B2 (en) * | 1998-05-07 | 2005-10-27 | The University Of Tennessee Research Corporation | A method for chemoprevention of prostate cancer |
US6413535B1 (en) | 1998-05-07 | 2002-07-02 | The University Of Tennessee Research Corporation | Method for chemoprevention of prostate cancer |
US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
SI1235776T1 (sl) * | 1999-11-16 | 2006-06-30 | Hormos Medical Corp | Trifenilalkenski derivati in njihova uporaba kot selektivni estrogenski receptorski modulatorji |
TW593256B (en) * | 1999-11-16 | 2004-06-21 | Hormos Medical Oy Ltd | Triphenylalkene derivatives and their use as selective estrogen receptor modulators |
FI111710B (fi) | 2001-05-04 | 2003-09-15 | Hormos Medical Oy Ltd | Menetelmä terapeuttisesti aktiivisen yhdisteen valmistamiseksi |
FI20030747A0 (fi) | 2003-05-19 | 2003-05-19 | Orion Corp | Toremifeenin kiteytysmenetelmä |
US20040248989A1 (en) | 2003-06-05 | 2004-12-09 | Risto Santti | Method for the treatment or prevention of lower urinary tract symptoms |
CN101448490A (zh) | 2006-05-22 | 2009-06-03 | 霍尔莫斯医疗有限公司 | 治疗慢性非细菌性前列腺炎的选择性雌激素受体调节剂或者芳香酶抑制剂 |
US7504530B2 (en) | 2007-02-14 | 2009-03-17 | Hormos Medical Ltd. | Methods for the preparation of fispemifene from ospemifene |
EP2121553B1 (en) | 2007-02-14 | 2012-06-27 | Hormos Medical Ltd. | Method for the preparation of therapeutically valuable triphenylbutene derivatives |
FI121626B (fi) * | 2009-01-29 | 2011-02-15 | Stora Enso Oyj | Menetelmä olefiinisten monomeerien tuottamiseksi |
JP6174156B2 (ja) | 2012-10-19 | 2017-08-02 | フェルミオン オサケ ユキチュア | オスペミフェンの製造方法 |
KR101819639B1 (ko) * | 2016-06-27 | 2018-01-17 | 주식회사 케미메디 | 신규한 아릴에텐 유도체 및 이를 유효성분으로 함유하는 약제학적 조성물 |
-
1983
- 1983-05-09 FI FI831584A patent/FI77839C/fi not_active IP Right Cessation
- 1983-05-20 LU LU88803C patent/LU88803I2/fr unknown
- 1983-05-20 DE DE8383302912T patent/DE3366021D1/de not_active Expired
- 1983-05-20 CA CA000428668A patent/CA1185977A/en not_active Expired
- 1983-05-20 EP EP83302912A patent/EP0095875B1/en not_active Expired
- 1983-05-24 DD DD83251216A patent/DD230864A1/de not_active IP Right Cessation
- 1983-05-25 IL IL68784A patent/IL68784A/xx not_active IP Right Cessation
- 1983-05-25 AU AU14946/83A patent/AU556608B2/en not_active Expired
- 1983-05-25 NZ NZ204349A patent/NZ204349A/en unknown
- 1983-05-26 DK DK236583A patent/DK170927B1/da not_active IP Right Cessation
- 1983-05-26 SU SU833597902A patent/SU1508955A3/ru active
- 1983-05-26 IE IE1247/83A patent/IE55023B1/en not_active IP Right Cessation
- 1983-05-26 UA UA3597902A patent/UA5558A1/uk unknown
- 1983-05-26 NO NO831873A patent/NO156164C/no not_active IP Right Cessation
-
1988
- 1988-09-30 SG SG654/88A patent/SG65488G/en unknown
-
1990
- 1990-04-26 JP JP2114935A patent/JPH037239A/ja active Granted
-
1992
- 1992-10-27 JP JP4289137A patent/JPH0678257B2/ja not_active Expired - Lifetime
- 1992-10-27 JP JP4289136A patent/JPH0742241B2/ja not_active Expired - Lifetime
-
1994
- 1994-01-18 BG BG098379A patent/BG60760B2/bg unknown
-
1996
- 1996-08-14 NL NL960021C patent/NL960021I2/nl unknown
Also Published As
Publication number | Publication date |
---|---|
JPH037239A (ja) | 1991-01-14 |
AU556608B2 (en) | 1986-11-13 |
NL960021I1 (nl) | 1996-11-01 |
IL68784A0 (en) | 1983-09-30 |
CA1185977A (en) | 1985-04-23 |
DK170927B1 (da) | 1996-03-18 |
JPH0656724A (ja) | 1994-03-01 |
NO156164C (no) | 1987-08-05 |
FI831584A0 (fi) | 1983-05-09 |
JPH06100485A (ja) | 1994-04-12 |
FI77839C (fi) | 1989-05-10 |
IE55023B1 (en) | 1990-04-25 |
SG65488G (en) | 1989-06-16 |
JPH0579654B2 (xx) | 1993-11-04 |
SU1508955A3 (ru) | 1989-09-15 |
NL960021I2 (nl) | 1997-07-01 |
NZ204349A (en) | 1985-03-20 |
FI831584L (fi) | 1983-11-28 |
DE3366021D1 (en) | 1986-10-16 |
NO156164B (no) | 1987-04-27 |
DK236583A (da) | 1983-11-28 |
DD230864A1 (de) | 1985-12-11 |
UA5558A1 (uk) | 1994-12-28 |
DK236583D0 (da) | 1983-05-26 |
IL68784A (en) | 1986-11-30 |
NO831873L (no) | 1983-11-28 |
JPH0742241B2 (ja) | 1995-05-10 |
EP0095875A3 (en) | 1984-07-25 |
IE831247L (en) | 1983-11-27 |
FI77839B (fi) | 1989-01-31 |
LU88803I2 (fr) | 1996-11-05 |
EP0095875A2 (en) | 1983-12-07 |
JPH0678257B2 (ja) | 1994-10-05 |
AU1494683A (en) | 1984-01-19 |
EP0095875B1 (en) | 1986-09-10 |
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