CA2215647A1 - Naphthyl compounds, compositions, and methods - Google Patents
Naphthyl compounds, compositions, and methods Download PDFInfo
- Publication number
- CA2215647A1 CA2215647A1 CA002215647A CA2215647A CA2215647A1 CA 2215647 A1 CA2215647 A1 CA 2215647A1 CA 002215647 A CA002215647 A CA 002215647A CA 2215647 A CA2215647 A CA 2215647A CA 2215647 A1 CA2215647 A1 CA 2215647A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- symptoms
- alleviating
- alkyl
- 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 Substances 0.000 title abstract description 25
- 238000000034 method Methods 0.000 title abstract description 19
- 125000001624 naphthyl group Chemical group 0.000 title abstract description 3
- 239000000262 estrogen Substances 0.000 claims abstract description 27
- 229940011871 estrogen Drugs 0.000 claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 20
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 11
- 230000001419 dependent effect Effects 0.000 claims abstract description 10
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- 230000001575 pathological effect Effects 0.000 claims abstract description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 methyl-1-pyrrolidinyl Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 208000024891 symptom Diseases 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 206010027304 Menopausal symptoms Diseases 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 239000000583 progesterone congener Substances 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 206010046766 uterine cancer Diseases 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000010260 leiomyoma Diseases 0.000 claims 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims 1
- 208000010579 uterine corpus leiomyoma Diseases 0.000 claims 1
- 201000007954 uterine fibroid Diseases 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 18
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 208000006386 Bone Resorption Diseases 0.000 abstract description 4
- 230000024279 bone resorption Effects 0.000 abstract description 4
- 206010065687 Bone loss Diseases 0.000 abstract description 3
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 28
- 238000011282 treatment Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000007832 Na2SO4 Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 239000000843 powder Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 210000000988 bone and bone Anatomy 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 229960002568 ethinylestradiol Drugs 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 210000004291 uterus Anatomy 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 208000001685 postmenopausal osteoporosis Diseases 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- WIJNYNBSPQMJGO-UHFFFAOYSA-N (3-phenylmethoxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 WIJNYNBSPQMJGO-UHFFFAOYSA-N 0.000 description 4
- OGNAYZYHKOZIJZ-UHFFFAOYSA-N 1-[3-[3-[6-methoxy-2-(4-methoxyphenyl)naphthalen-1-yl]phenoxy]propyl]piperidine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1C1=CC=CC(OCCCN2CCCCC2)=C1 OGNAYZYHKOZIJZ-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- FPUBKDOMTWBPIH-UHFFFAOYSA-N 3-[6-methoxy-2-(4-methoxyphenyl)naphthalen-1-yl]phenol Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1C1=CC=CC(O)=C1 FPUBKDOMTWBPIH-UHFFFAOYSA-N 0.000 description 4
- IURMDCHGRBRRDL-UHFFFAOYSA-N 6-(4-hydroxyphenyl)-5-[3-(3-piperidin-1-ylpropoxy)phenyl]naphthalen-2-ol Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1C1=CC=CC(OCCCN2CCCCC2)=C1 IURMDCHGRBRRDL-UHFFFAOYSA-N 0.000 description 4
- 229910015845 BBr3 Inorganic materials 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 229920002472 Starch Polymers 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 239000012911 assay medium Substances 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 210000003979 eosinophil Anatomy 0.000 description 4
- 239000012091 fetal bovine serum Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000009806 oophorectomy Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
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- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000000689 upper leg Anatomy 0.000 description 4
- XWESVFWQTLDAGE-UHFFFAOYSA-N 1-[2-[3-[6-methoxy-2-(4-methoxyphenyl)naphthalen-1-yl]phenoxy]ethyl]piperidine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1C1=CC=CC(OCCN2CCCCC2)=C1 XWESVFWQTLDAGE-UHFFFAOYSA-N 0.000 description 3
- WYRATTOTTSTNMK-UHFFFAOYSA-N 1-[4-[3-[6-methoxy-2-(4-methoxyphenyl)naphthalen-1-yl]phenoxy]butyl]piperidine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1C1=CC=CC(OCCCCN2CCCCC2)=C1 WYRATTOTTSTNMK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 108010092408 Eosinophil Peroxidase Proteins 0.000 description 3
- 102000044708 Eosinophil peroxidases Human genes 0.000 description 3
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 235000012222 talc Nutrition 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
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- 241000220479 Acacia Species 0.000 description 2
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- 206010003497 Asphyxia Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 208000010392 Bone Fractures Diseases 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
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- 206010017076 Fracture Diseases 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2948496P | 1996-10-24 | 1996-10-24 | |
| US60/029,484 | 1996-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2215647A1 true CA2215647A1 (en) | 1998-04-24 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002215647A Abandoned CA2215647A1 (en) | 1996-10-24 | 1997-09-11 | Naphthyl compounds, compositions, and methods |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5952350A (enExample) |
| EP (1) | EP0838459B1 (enExample) |
| JP (1) | JPH10130212A (enExample) |
| AT (1) | ATE277026T1 (enExample) |
| CA (1) | CA2215647A1 (enExample) |
| DE (1) | DE69730796T2 (enExample) |
| ES (1) | ES2227654T3 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL120266A (en) | 1996-02-28 | 2005-05-17 | Pfizer | Use of estrogen antagonists and estrogen agonists in the preparation of medicaments for inhibiting pathological conditions |
| SI0826679T1 (en) * | 1996-08-29 | 2002-04-30 | Eli Lilly And Company | Naphthyl compounds and compositions |
| ID19392A (id) | 1996-08-29 | 1998-07-09 | Lilly Co Eli | Senyawa naftil dan bahan pertengahan serta komposisi dan metode penggunaan |
| EP1004306A3 (en) * | 1998-08-06 | 2000-06-07 | Pfizer Products Inc. | Estrogen agonists/antagonists |
| US7001926B2 (en) * | 2000-03-10 | 2006-02-21 | Oxigene, Inc. | Tubulin binding agents and corresponding prodrug constructs |
| US7091240B2 (en) * | 2000-03-10 | 2006-08-15 | Oxigene, Inc. | Tubulin binding ligands and corresponding prodrug constructs |
| US6610705B1 (en) * | 2000-03-31 | 2003-08-26 | Council Of Scientific And Industrial Research | Process for the preparation of diaryl naphthyl methanes |
| US20050245489A1 (en) * | 2004-05-03 | 2005-11-03 | Pinney Kevin G | Chromene-containing compounds with anti-tubulin and vascular targeting activity |
| US7456214B2 (en) * | 2004-05-03 | 2008-11-25 | Baylor University | Chromene-containing compounds with anti-tubulin and vascular targeting activity |
| FR2899895B1 (fr) * | 2006-04-12 | 2010-09-17 | Servier Lab | Nouveaux sels de strontium d'acides sulfoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN114133336B (zh) * | 2020-09-03 | 2024-04-02 | 沈阳药科大学 | 4-甲氧基萘取代的苯胺类化合物及其制备方法和应用 |
| CN113620788A (zh) * | 2021-08-11 | 2021-11-09 | 苏州求索生物科技有限公司 | 一种3-甲氧基苯乙基溴的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274213A (en) * | 1961-09-05 | 1966-09-20 | Upjohn Co | Alkoxy-substituted 2-phenyl-1-(tertiary-aminoalkoxy)phenyl-3, 4-dihydronaphthalenes |
| DE1300575B (de) * | 1965-05-21 | 1969-08-07 | Bristol Myers Co | Benzo[b]thiophene |
| US3394125A (en) * | 1965-10-23 | 1968-07-23 | Bristol Myers Co | 2-phenyl-3-tertiary-aminoalkoxy phenyl-and corresponding tertiaryaminoalkyl thio benzfurans substituted in the benzo nucleus with an alkoxy or tertiaryamino alkoxy or alkylthio group |
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| US4230862A (en) * | 1975-10-28 | 1980-10-28 | Eli Lilly And Company | Antifertility compounds |
| US4358593A (en) * | 1981-04-03 | 1982-11-09 | Eli Lilly And Company | Process for preparing 3-(4-aminoethoxybenzoyl)benzo[b]thiophenes |
| US4380635A (en) * | 1981-04-03 | 1983-04-19 | Eli Lilly And Company | Synthesis of acylated benzothiophenes |
| US4418068A (en) * | 1981-04-03 | 1983-11-29 | Eli Lilly And Company | Antiestrogenic and antiandrugenic benzothiophenes |
| GB2097788B (en) * | 1981-04-03 | 1985-04-24 | Lilly Co Eli | Benzothiophene compounds and process for preparing them |
| JPH02501301A (ja) * | 1987-09-25 | 1990-05-10 | チバ‐ガイギー アクチェンゲゼルシャフト | ４‐（トリアルキルベンジル）‐ピペラジニル化合物のジアシル誘導体 |
| US5395842A (en) * | 1988-10-31 | 1995-03-07 | Endorecherche Inc. | Anti-estrogenic compounds and compositions |
| DE4117512A1 (de) * | 1991-05-25 | 1992-11-26 | Schering Ag | 2-phenylbenzo(b)furane und -thiophene, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| US5147880A (en) * | 1991-07-22 | 1992-09-15 | Eli Lilly And Company | Benzo[a]fluorene compounds |
| JP3157882B2 (ja) * | 1991-11-15 | 2001-04-16 | 帝国臓器製薬株式会社 | 新規なベンゾチオフエン誘導体 |
| US6756388B1 (en) * | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| US7501441B1 (en) * | 1994-09-20 | 2009-03-10 | Eli Lilly And Company | Naphthyl compounds, intermediates, processes, compositions, and methods |
| US5552412A (en) * | 1995-01-09 | 1996-09-03 | Pfizer Inc | 5-substitued-6-cyclic-5,6,7,8-tetrahydronaphthalen2-ol compounds which are useful for treating osteoporosis |
| US6451817B1 (en) * | 1995-03-10 | 2002-09-17 | Eli Lilly And Company | Alpha-substituted-1-benzyl-napthyls |
-
1997
- 1997-09-11 CA CA002215647A patent/CA2215647A1/en not_active Abandoned
- 1997-10-22 AT AT97308375T patent/ATE277026T1/de not_active IP Right Cessation
- 1997-10-22 ES ES97308375T patent/ES2227654T3/es not_active Expired - Lifetime
- 1997-10-22 EP EP97308375A patent/EP0838459B1/en not_active Expired - Lifetime
- 1997-10-22 DE DE69730796T patent/DE69730796T2/de not_active Expired - Fee Related
- 1997-10-22 JP JP9289614A patent/JPH10130212A/ja active Pending
- 1997-10-23 US US08/956,678 patent/US5952350A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5952350A (en) | 1999-09-14 |
| EP0838459A1 (en) | 1998-04-29 |
| ES2227654T3 (es) | 2005-04-01 |
| DE69730796T2 (de) | 2005-09-29 |
| JPH10130212A (ja) | 1998-05-19 |
| EP0838459B1 (en) | 2004-09-22 |
| ATE277026T1 (de) | 2004-10-15 |
| DE69730796D1 (de) | 2004-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |