HU193268B - Process for preparing novel substituted alkane and alkene derivatives - Google Patents
Process for preparing novel substituted alkane and alkene derivatives Download PDFInfo
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- HU193268B HU193268B HU823395A HU339582A HU193268B HU 193268 B HU193268 B HU 193268B HU 823395 A HU823395 A HU 823395A HU 339582 A HU339582 A HU 339582A HU 193268 B HU193268 B HU 193268B
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- 150000001344 alkene derivatives Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- -1 2,3-epoxypropoxy, 2,3-dihydroxypropoxy Chemical group 0.000 claims abstract description 69
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 238000002360 preparation method Methods 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 2
- 241000238876 Acari Species 0.000 claims description 2
- 241000251468 Actinopterygii Species 0.000 claims description 2
- 150000001559 benzoic acids Chemical class 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 241000208202 Linaceae Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 36
- 239000000203 mixture Substances 0.000 abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 21
- 230000001833 anti-estrogenic effect Effects 0.000 abstract description 7
- 230000000259 anti-tumor effect Effects 0.000 abstract description 7
- 239000000328 estrogen antagonist Substances 0.000 abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 230000001076 estrogenic effect Effects 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 238000005160 1H NMR spectroscopy Methods 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229940011871 estrogen Drugs 0.000 description 13
- 239000000262 estrogen Substances 0.000 description 13
- 230000005764 inhibitory process Effects 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 229960003387 progesterone Drugs 0.000 description 13
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 12
- 239000000186 progesterone Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 206010006187 Breast cancer Diseases 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 7
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 201000008274 breast adenocarcinoma Diseases 0.000 description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 7
- 229960005309 estradiol Drugs 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000003418 antiprogestin Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 5
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 5
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- 230000003623 progesteronic effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000004291 uterus Anatomy 0.000 description 4
- 230000004584 weight gain Effects 0.000 description 4
- 235000019786 weight gain Nutrition 0.000 description 4
- CMTSCGCIUZBCEL-UHFFFAOYSA-N 4-(2-cyclopentyl-1-hydroxy-1-phenylbutyl)phenol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC(O)=CC=1)C(CC)C1CCCC1 CMTSCGCIUZBCEL-UHFFFAOYSA-N 0.000 description 3
- PAODHGOFCCWNRR-UHFFFAOYSA-N 4-cyclopentyl-3-(4-methoxyphenyl)hexan-3-ol Chemical compound C=1C=C(OC)C=CC=1C(O)(CC)C(CC)C1CCCC1 PAODHGOFCCWNRR-UHFFFAOYSA-N 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 0 Cc1ccc(C(*)(C(*)*)O)cc1 Chemical compound Cc1ccc(C(*)(C(*)*)O)cc1 0.000 description 3
- 238000010934 O-alkylation reaction Methods 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 108010038795 estrogen receptors Proteins 0.000 description 3
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- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 2
- PUKBHBOUKVQSSV-UHFFFAOYSA-N 1-(2-cyclopentyl-1-phenylbut-1-enyl)-4-methoxybenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC(OC)=CC=1)=C(CC)C1CCCC1 PUKBHBOUKVQSSV-UHFFFAOYSA-N 0.000 description 2
- MOVOYJFCKMYLHQ-UHFFFAOYSA-N 2-(4-bromophenoxy)-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=C(Br)C=C1 MOVOYJFCKMYLHQ-UHFFFAOYSA-N 0.000 description 2
- ZRDMVLXABUUKLN-UHFFFAOYSA-N 2-[[4-(2-cyclopentyl-1-phenylbut-1-enyl)phenoxy]methyl]oxirane Chemical compound C=1C=CC=CC=1C(C=1C=CC(OCC2OC2)=CC=1)=C(CC)C1CCCC1 ZRDMVLXABUUKLN-UHFFFAOYSA-N 0.000 description 2
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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 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Separation Of Gases By Adsorption (AREA)
- Treating Waste Gases (AREA)
- Inorganic Insulating Materials (AREA)
- Steroid Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08132240A GB2108486B (en) | 1981-10-26 | 1981-10-26 | Alkane and alkene derivatives and their preparation and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU193268B true HU193268B (en) | 1987-09-28 |
Family
ID=10525401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU823395A HU193268B (en) | 1981-10-26 | 1982-10-25 | Process for preparing novel substituted alkane and alkene derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4556677A (esLanguage) |
| EP (1) | EP0078158B1 (esLanguage) |
| JP (1) | JPS5879934A (esLanguage) |
| AT (1) | ATE22065T1 (esLanguage) |
| AU (1) | AU555477B2 (esLanguage) |
| CA (1) | CA1310974C (esLanguage) |
| DD (1) | DD211548A1 (esLanguage) |
| DE (1) | DE3273219D1 (esLanguage) |
| DK (1) | DK472082A (esLanguage) |
| FI (1) | FI77842C (esLanguage) |
| GB (1) | GB2108486B (esLanguage) |
| HU (1) | HU193268B (esLanguage) |
| IE (1) | IE54586B1 (esLanguage) |
| IL (1) | IL67049A (esLanguage) |
| NO (1) | NO159079C (esLanguage) |
| NZ (1) | NZ202269A (esLanguage) |
| SU (1) | SU1329615A3 (esLanguage) |
| ZA (1) | ZA827742B (esLanguage) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2108486B (en) * | 1981-10-26 | 1986-01-29 | Farmos Group Ltd | Alkane and alkene derivatives and their preparation and use |
| US4775660A (en) * | 1984-08-02 | 1988-10-04 | Fernand Labrie | Treatment of breast cancer by combination therapy |
| US4760053A (en) * | 1984-08-02 | 1988-07-26 | Fernand Labrie | Combination therapy for selected sex steroid dependent cancers |
| US4666885A (en) * | 1985-02-08 | 1987-05-19 | Fernand Labrie | Combination therapy for treatment of female breast cancer |
| US4895715A (en) * | 1988-04-14 | 1990-01-23 | Schering Corporation | Method of treating gynecomastia |
| IE62715B1 (en) * | 1989-03-10 | 1995-02-22 | Endorecherche Inc | Combination therapy for treatment of estrogen sensitive diseases |
| NL1018247C2 (nl) | 2001-06-08 | 2002-12-10 | Sara Lee De Nv | Inrichting voor het bereiden van een voor consumptie geschikte drank zoals koffie. |
| JP2004010479A (ja) * | 2002-06-03 | 2004-01-15 | Japan Science & Technology Corp | ブロック共重合体とアンスラサイクリン系抗癌剤を含む新規固型製剤及びその製造法 |
| EP2366026A2 (en) * | 2008-12-12 | 2011-09-21 | Celexion, Llc | Biological synthesis of difunctional alkanes from alpha ketoacids |
| FR3071837B1 (fr) | 2017-09-29 | 2019-11-01 | Institut National De La Recherche Agronomique | Derive de lignine chimiquement stable et procede pour sa preparation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1306604A (fr) * | 1959-03-03 | 1962-10-19 | Ferrosan Ab | Procédé pour préparer des bisphényléthylènes substitués |
| GB1289966A (esLanguage) * | 1968-12-24 | 1972-09-20 | ||
| US3661976A (en) * | 1969-05-16 | 1972-05-09 | Parke Davis & Co | 4,4'-(2-cycloalkyl-alkylidene) diphenols and ethers and esters thereof |
| BE793686A (fr) * | 1972-01-07 | 1973-07-04 | Beecham Group Ltd | Composes di-aryliques biologiquement actifs |
| GB2108486B (en) * | 1981-10-26 | 1986-01-29 | Farmos Group Ltd | Alkane and alkene derivatives and their preparation and use |
-
1981
- 1981-10-26 GB GB08132240A patent/GB2108486B/en not_active Expired
-
1982
- 1982-10-12 FI FI823465A patent/FI77842C/fi not_active IP Right Cessation
- 1982-10-18 SU SU823503159A patent/SU1329615A3/ru active
- 1982-10-21 EP EP82305612A patent/EP0078158B1/en not_active Expired
- 1982-10-21 DE DE8282305612T patent/DE3273219D1/de not_active Expired
- 1982-10-21 AT AT82305612T patent/ATE22065T1/de not_active IP Right Cessation
- 1982-10-22 ZA ZA827742A patent/ZA827742B/xx unknown
- 1982-10-22 NZ NZ202269A patent/NZ202269A/en unknown
- 1982-10-22 IL IL67049A patent/IL67049A/xx not_active IP Right Cessation
- 1982-10-22 AU AU89702/82A patent/AU555477B2/en not_active Ceased
- 1982-10-22 IE IE2551/82A patent/IE54586B1/en not_active IP Right Cessation
- 1982-10-23 JP JP57186650A patent/JPS5879934A/ja active Granted
- 1982-10-25 DK DK472082A patent/DK472082A/da not_active Application Discontinuation
- 1982-10-25 HU HU823395A patent/HU193268B/hu not_active IP Right Cessation
- 1982-10-25 CA CA000414128A patent/CA1310974C/en not_active Expired - Fee Related
- 1982-10-25 DD DD82244246A patent/DD211548A1/de not_active IP Right Cessation
- 1982-10-25 NO NO823537A patent/NO159079C/no unknown
- 1982-10-26 US US06/436,805 patent/US4556677A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IE54586B1 (en) | 1989-12-06 |
| ZA827742B (en) | 1983-08-31 |
| GB2108486B (en) | 1986-01-29 |
| FI823465A0 (fi) | 1982-10-12 |
| AU555477B2 (en) | 1986-09-25 |
| NO159079B (no) | 1988-08-22 |
| AU8970282A (en) | 1983-05-12 |
| EP0078158A3 (en) | 1984-01-18 |
| GB2108486A (en) | 1983-05-18 |
| CA1310974C (en) | 1992-12-01 |
| DD211548A1 (de) | 1984-07-18 |
| NZ202269A (en) | 1985-05-31 |
| EP0078158A2 (en) | 1983-05-04 |
| DE3273219D1 (en) | 1986-10-16 |
| ATE22065T1 (de) | 1986-09-15 |
| FI823465L (fi) | 1983-04-27 |
| NO159079C (no) | 1988-11-30 |
| DK472082A (da) | 1983-04-27 |
| SU1329615A3 (ru) | 1987-08-07 |
| IL67049A (en) | 1987-07-31 |
| JPS5879934A (ja) | 1983-05-13 |
| IE822551L (en) | 1983-04-26 |
| FI77842B (fi) | 1989-01-31 |
| JPH0239492B2 (esLanguage) | 1990-09-05 |
| US4556677A (en) | 1985-12-03 |
| EP0078158B1 (en) | 1986-09-10 |
| NO823537L (no) | 1983-04-27 |
| FI77842C (fi) | 1989-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |