EA003937B1 - Новые арилоксиалкилдиалкиламины - Google Patents
Новые арилоксиалкилдиалкиламины Download PDFInfo
- Publication number
- EA003937B1 EA003937B1 EA200000416A EA200000416A EA003937B1 EA 003937 B1 EA003937 B1 EA 003937B1 EA 200000416 A EA200000416 A EA 200000416A EA 200000416 A EA200000416 A EA 200000416A EA 003937 B1 EA003937 B1 EA 003937B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compound
- alcohol
- hydrochloride
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 38
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 37
- 150000002367 halogens Chemical class 0.000 claims abstract description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 230000009467 reduction Effects 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims abstract description 4
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 4
- 239000002168 alkylating agent Substances 0.000 claims abstract description 4
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003647 oxidation Effects 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 150000003457 sulfones Chemical class 0.000 claims abstract description 4
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 4
- YYSGCTYUSXXXBH-UHFFFAOYSA-N 1-chloro-2-[4-(chloromethyl)phenoxy]-2-ethylpiperidine Chemical compound ClCC1=CC=C(OC2(N(CCCC2)Cl)CC)C=C1 YYSGCTYUSXXXBH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 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 claims abstract description 3
- 230000002140 halogenating effect Effects 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003937 drug carrier Substances 0.000 claims abstract 2
- -1 4-chloromethylphenoxy Chemical group 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 230000029936 alkylation Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- IFOPGEYACSEATB-UHFFFAOYSA-N 2-[4-(chloromethyl)phenoxy]-1-ethylazepane Chemical compound ClCC1=CC=C(OC2N(CCCCC2)CC)C=C1 IFOPGEYACSEATB-UHFFFAOYSA-N 0.000 abstract 1
- VTFNKQHWKQUMRB-UHFFFAOYSA-N N-chloro-1-[4-(chloromethyl)phenoxy]-N-methylpropan-1-amine Chemical compound ClCC1=CC=C(OC(N(C)Cl)CC)C=C1 VTFNKQHWKQUMRB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 65
- 239000011541 reaction mixture Substances 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000000758 substrate Substances 0.000 description 26
- VOXZDWNPVJITMN-UHFFFAOYSA-N 13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2C3CCC(C)(C(CC4)O)C4C3CCC2=C1 VOXZDWNPVJITMN-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- 230000000694 effects Effects 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- 239000000262 estrogen Substances 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 235000002639 sodium chloride Nutrition 0.000 description 17
- 229940011871 estrogen Drugs 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 239000003814 drug Substances 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 14
- 108090000790 Enzymes Proteins 0.000 description 14
- 229940079593 drug Drugs 0.000 description 14
- 229940088598 enzyme Drugs 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 13
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 13
- 210000000988 bone and bone Anatomy 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 125000004951 trihalomethoxy group Chemical group 0.000 description 12
- 125000004953 trihalomethyl group Chemical group 0.000 description 12
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 10
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 10
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 108010026132 Gelatinases Proteins 0.000 description 8
- 102000013382 Gelatinases Human genes 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 7
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 7
- 229960002424 collagenase Drugs 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
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- 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 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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- 229920002307 Dextran Polymers 0.000 description 5
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 229960003454 tamoxifen citrate Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
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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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/32—Antioestrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Gynecology & Obstetrics (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Pregnancy & Childbirth (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Detergent Compositions (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95081897A | 1997-10-15 | 1997-10-15 | |
| US09/161,653 US6005102A (en) | 1997-10-15 | 1998-09-28 | Aryloxy-alkyl-dialkylamines |
| PCT/US1998/021609 WO1999019293A1 (en) | 1997-10-15 | 1998-10-14 | Novel aryloxy-alkyl-dialkylamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200000416A1 EA200000416A1 (ru) | 2000-10-30 |
| EA003937B1 true EA003937B1 (ru) | 2003-10-30 |
Family
ID=26858006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200000416A EA003937B1 (ru) | 1997-10-15 | 1998-10-14 | Новые арилоксиалкилдиалкиламины |
Country Status (26)
| Country | Link |
|---|---|
| EP (2) | EP1777214A3 (https=) |
| JP (1) | JP2001519410A (https=) |
| KR (1) | KR100669836B1 (https=) |
| CN (1) | CN1231458C (https=) |
| AR (1) | AR015183A1 (https=) |
| AT (1) | ATE355264T1 (https=) |
| AU (1) | AU757630C (https=) |
| BR (1) | BR9813069A (https=) |
| CA (1) | CA2306343C (https=) |
| CY (1) | CY1106497T1 (https=) |
| DE (1) | DE69837210T2 (https=) |
| DK (1) | DK1025077T3 (https=) |
| EA (1) | EA003937B1 (https=) |
| EE (1) | EE200000225A (https=) |
| ES (1) | ES2281937T3 (https=) |
| HU (1) | HUP0004419A3 (https=) |
| ID (1) | ID24417A (https=) |
| IL (2) | IL135343A0 (https=) |
| NO (1) | NO20001938L (https=) |
| NZ (1) | NZ503793A (https=) |
| PL (1) | PL198443B1 (https=) |
| PT (1) | PT1025077E (https=) |
| SI (1) | SI1025077T1 (https=) |
| SK (1) | SK286460B6 (https=) |
| TR (1) | TR200001012T2 (https=) |
| WO (1) | WO1999019293A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA005932B1 (ru) * | 1998-05-15 | 2005-08-25 | Уайт | 2-фенил-1-[4-(2-аминоэтокси)бензил]индол в комбинации с эстрогенами |
| US6479535B1 (en) | 1998-05-15 | 2002-11-12 | Wyeth | 2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations |
| CA2382683A1 (en) * | 1999-09-13 | 2001-03-22 | American Home Products Corporation | Glucopyranosides conjugates of 2-(4-hydroxy-phenyl)-1-¬4-(2-amin-1-yl-ethoxy)-benzyl|-1h-indol-5-ols |
| US6455568B2 (en) | 2000-07-06 | 2002-09-24 | Wyeth | Combination therapy for inhibiting sphincter incontinence |
| AR029538A1 (es) | 2000-07-06 | 2003-07-02 | Wyeth Corp | Composiciones farmaceuticas de agentes estrogenicos |
| AU2001273144A1 (en) | 2000-07-06 | 2002-01-21 | Wyeth | Use of substituted indole compounds for treating neuropeptide y-related conditions |
| MXPA03000170A (es) | 2000-07-06 | 2003-05-27 | Wyeth Corp | Combinaciones de un inhibidor de recaptacion de serotonina selectivo y agentes estrogenicos. |
| AR029539A1 (es) | 2000-07-06 | 2003-07-02 | Wyeth Corp | Combinaciones de estatinas y agentes estrogenicos |
| EP1656938A1 (en) | 2000-07-06 | 2006-05-17 | Wyeth | Combinations of SSRI and estrogenic agents |
| WO2002003990A2 (en) | 2000-07-06 | 2002-01-17 | Wyeth | Use of substituted insole compounds for treating excessive intraocular pressure |
| US6376486B1 (en) | 2000-07-06 | 2002-04-23 | American Home Products Corporation | Methods of inhibiting sphincter incontinence |
| US6369051B1 (en) | 2000-07-06 | 2002-04-09 | American Home Products Corporation | Combinations of SSRI and estrogenic agents |
| JP2004532834A (ja) * | 2001-03-23 | 2004-10-28 | イーライ・リリー・アンド・カンパニー | ヒスタミンｈ３受容体アンタゴニストである非イミダゾール系アリールアルキルアミン化合物、その製造および治療的使用 |
| JP2004531559A (ja) | 2001-05-22 | 2004-10-14 | イーライ・リリー・アンド・カンパニー | エストロゲン欠乏または内因性エストロゲンに対する異常な生理反応に関連する疾患を抑制するためのテトラヒドロキノリン誘導体 |
| EP1395563B1 (en) | 2001-05-22 | 2006-03-29 | Eli Lilly And Company | 2-substituted 1,2,3,4-tetrahydroquinolines and derivatives thereof, compositions and methods |
| US7314937B2 (en) | 2002-03-21 | 2008-01-01 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine H3 receptor antagonists, preparation and therapeutic uses |
| US7098241B2 (en) | 2002-12-16 | 2006-08-29 | Hoffmann-La Roche Inc. | Thiophene hydroxamic acid derivatives |
| WO2005100316A1 (en) | 2004-04-07 | 2005-10-27 | Wyeth | Crystalline polymorph of a bazedoxifene acetate |
| JP2007532548A (ja) | 2004-04-07 | 2007-11-15 | ワイス | バゼドキシフェンアセテートの結晶質多形体 |
| MXPA06011686A (es) | 2004-04-08 | 2006-12-14 | Wyeth Corp | Ascorbato de bazedoxifeno como modulador del receptor de estrogeno selectivo. |
| JP2008509148A (ja) * | 2004-08-05 | 2008-03-27 | ワイス | 塩酸ピピンドキシフェン一水和物の結晶多形 |
| EP1836155A2 (en) * | 2005-01-13 | 2007-09-26 | Wyeth, A Corporation of the State of Delaware | Processes for the preparation of aminoethoxybenzyl alcohols |
| US20100087661A1 (en) * | 2007-02-12 | 2010-04-08 | Josef Jirman | Method for the preparation of 5-benzyloxy-2-(4-benzyloxphenyl)-3-methyl-1h-indole |
| WO2009102771A1 (en) * | 2008-02-11 | 2009-08-20 | Wyeth | Methods of converting polymorphic form b of bazedoxifene acetate to polymorphic form a of bazedoxifene acetate |
| CA2758109A1 (en) * | 2009-04-13 | 2010-10-21 | Sandoz Ag | Processes for the synthesis of bazedoxifene acetate and intermediates thereof |
| US8569483B2 (en) | 2011-06-21 | 2013-10-29 | Divi's Laboratories, Ltd. | Process for the preparation of bazedoxifene acetate and intermediates thereof |
| CN104151265B (zh) * | 2013-05-13 | 2016-10-05 | 上海医药工业研究院 | 醋酸巴多昔芬中间体的制备方法 |
| US9751835B2 (en) | 2013-05-15 | 2017-09-05 | Indiana University Research And Technology Corporation | Processes and intermediates for preparing indole pharmaceuticals |
| IT201800006562A1 (it) * | 2018-06-21 | 2019-12-21 | Procedimento e intermedi utili per la preparazione di indoli | |
| IT201900001923A1 (it) | 2019-02-11 | 2020-08-11 | Erregierre Spa | Sali di bazedoxifene utili per la preparazione di bazedoxifene acetato |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CH448121A (de) | 1963-03-13 | 1967-12-15 | Hoffmann La Roche | Verfahren zur Herstellung substituierter Hydrazinverbindungen |
| WO1991007107A1 (en) * | 1989-11-13 | 1991-05-30 | Pfizer Inc. | Oxazolidinedione hypoglycemic agents |
| GB9326332D0 (en) | 1993-12-23 | 1994-02-23 | Karo Bio | Indole derivatives |
| CA2259487A1 (en) * | 1996-07-01 | 1998-01-08 | Margaret Mary Faul | Hypoglycemic and hypolipidemic compounds |
| YU40999A (sh) * | 1997-02-27 | 2002-06-19 | American Cyanamid Company | N-hidroksi-2-(alkil,aril ili heteroaril sulfanil,sulfinil ili sulfonil)-3-supstituisani alkil,aril ili heteroarilamidi, kao inhibitori za matrične metaloproteinaze |
| EP1011666A4 (en) * | 1997-04-30 | 2004-03-31 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
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1998
- 1998-10-14 PT PT98953459T patent/PT1025077E/pt unknown
- 1998-10-14 ES ES98953459T patent/ES2281937T3/es not_active Expired - Lifetime
- 1998-10-14 ID IDW20000680A patent/ID24417A/id unknown
- 1998-10-14 AU AU10831/99A patent/AU757630C/en not_active Ceased
- 1998-10-14 HU HU0004419A patent/HUP0004419A3/hu unknown
- 1998-10-14 SK SK537-2000A patent/SK286460B6/sk not_active IP Right Cessation
- 1998-10-14 SI SI9830877T patent/SI1025077T1/sl unknown
- 1998-10-14 EE EEP200000225A patent/EE200000225A/xx unknown
- 1998-10-14 EP EP07003195A patent/EP1777214A3/en not_active Withdrawn
- 1998-10-14 EA EA200000416A patent/EA003937B1/ru not_active IP Right Cessation
- 1998-10-14 EP EP98953459A patent/EP1025077B1/en not_active Expired - Lifetime
- 1998-10-14 PL PL339908A patent/PL198443B1/pl not_active IP Right Cessation
- 1998-10-14 KR KR1020007004031A patent/KR100669836B1/ko not_active Expired - Fee Related
- 1998-10-14 AR ARP980105112A patent/AR015183A1/es unknown
- 1998-10-14 WO PCT/US1998/021609 patent/WO1999019293A1/en not_active Ceased
- 1998-10-14 NZ NZ503793A patent/NZ503793A/xx unknown
- 1998-10-14 DK DK98953459T patent/DK1025077T3/da active
- 1998-10-14 CN CNB988121492A patent/CN1231458C/zh not_active Expired - Fee Related
- 1998-10-14 JP JP2000515866A patent/JP2001519410A/ja active Pending
- 1998-10-14 IL IL13534398A patent/IL135343A0/xx active IP Right Grant
- 1998-10-14 AT AT98953459T patent/ATE355264T1/de not_active IP Right Cessation
- 1998-10-14 BR BR9813069-2A patent/BR9813069A/pt not_active Application Discontinuation
- 1998-10-14 DE DE69837210T patent/DE69837210T2/de not_active Expired - Lifetime
- 1998-10-14 TR TR2000/01012T patent/TR200001012T2/xx unknown
- 1998-10-14 CA CA2306343A patent/CA2306343C/en not_active Expired - Fee Related
-
2000
- 2000-03-29 IL IL135343A patent/IL135343A/en not_active IP Right Cessation
- 2000-04-13 NO NO20001938A patent/NO20001938L/no not_active Application Discontinuation
-
2007
- 2007-04-05 CY CY20071100491T patent/CY1106497T1/el unknown
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
| EA003937B1 (ru) | Новые арилоксиалкилдиалкиламины | |
| US6005102A (en) | Aryloxy-alkyl-dialkylamines | |
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