CA2308773A1 - Oestra-1,3,5(10)-triene-7alpha-thioethers - Google Patents
Oestra-1,3,5(10)-triene-7alpha-thioethers Download PDFInfo
- Publication number
- CA2308773A1 CA2308773A1 CA002308773A CA2308773A CA2308773A1 CA 2308773 A1 CA2308773 A1 CA 2308773A1 CA 002308773 A CA002308773 A CA 002308773A CA 2308773 A CA2308773 A CA 2308773A CA 2308773 A1 CA2308773 A1 CA 2308773A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- alkyl
- formula
- pharmaceutically acceptable
- acceptable salt
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 172
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 108
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
- 239000000328 estrogen antagonist Substances 0.000 claims abstract description 21
- -1 -CHO Chemical group 0.000 claims abstract description 18
- 230000001833 anti-estrogenic effect Effects 0.000 claims abstract description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
- 229940046836 anti-estrogen Drugs 0.000 claims abstract description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 229910006069 SO3H Inorganic materials 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims description 146
- 238000000034 method Methods 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 230000001076 estrogenic effect Effects 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 206010030247 Oestrogen deficiency Diseases 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
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- 208000015114 central nervous system disease Diseases 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 230000018109 developmental process Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
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- 206010014561 Emphysema Diseases 0.000 claims 2
- 206010019755 Hepatitis chronic active Diseases 0.000 claims 2
- 206010019799 Hepatitis viral Diseases 0.000 claims 2
- 208000001738 Nervous System Trauma Diseases 0.000 claims 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010038687 Respiratory distress Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 238000009164 estrogen replacement therapy Methods 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
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- 230000002265 prevention Effects 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 201000008827 tuberculosis Diseases 0.000 claims 2
- 201000001862 viral hepatitis Diseases 0.000 claims 2
- GXJWTRXJYDUMOM-ULNWAEMLSA-N (8r,9s,13s,14s)-7-(4-bromophenyl)sulfanyl-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound C1([C@@H]2[C@@H](C3=CC=C(O)C=C3C1)CC[C@]1([C@H]2CCC1O)C)SC1=CC=C(Br)C=C1 GXJWTRXJYDUMOM-ULNWAEMLSA-N 0.000 claims 1
- UBWUVOKHOYGIJU-XJIYORDJSA-N (8r,9s,13s,14s)-7-(4-bromophenyl)sulfanyl-3,17-dihydroxy-13-methyl-8,9,11,12,14,15,16,17-octahydro-7h-cyclopenta[a]phenanthren-6-one Chemical compound C1([C@@H]2[C@@H](C3=CC=C(O)C=C3C1=O)CC[C@]1([C@H]2CCC1O)C)SC1=CC=C(Br)C=C1 UBWUVOKHOYGIJU-XJIYORDJSA-N 0.000 claims 1
- ORHXBOCSPIQMDH-ZMAGUPSESA-N (8r,9s,13s,14s)-7-(4-hydroxyphenyl)sulfanyl-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6,17-triol Chemical compound C1([C@@H]2[C@@H](C3=CC=C(O)C=C3C1O)CC[C@]1([C@H]2CCC1O)C)SC1=CC=C(O)C=C1 ORHXBOCSPIQMDH-ZMAGUPSESA-N 0.000 claims 1
- FROPUNBJULYSGP-PXMSTHCXSA-N (e)-3-[4-[[(8r,9s,13s,14s)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]sulfanyl]phenyl]-n,n-dimethylprop-2-enamide Chemical compound C1=CC(/C=C/C(=O)N(C)C)=CC=C1SC1[C@H]2[C@@H]3CCC(O)[C@@]3(C)CC[C@@H]2C2=CC=C(O)C=C2C1 FROPUNBJULYSGP-PXMSTHCXSA-N 0.000 claims 1
- XTTHLXBYZZLDHR-BNSMPPHFSA-N [(8r,9s,13s,14s)-3-methoxy-13-methyl-7-[4-(2-piperidin-1-ylethoxy)phenyl]sulfanyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1([C@H]2[C@@H]3CCC([C@@]3(C)CC[C@@H]2C2=CC=C(C=C2C1)OC)OC(C)=O)SC(C=C1)=CC=C1OCCN1CCCCC1 XTTHLXBYZZLDHR-BNSMPPHFSA-N 0.000 claims 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 claims 1
- 230000003262 anti-osteoporosis Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZESXPSUGWMXBGL-QRNYRMDWSA-N n-butyl-11-[[(8r,9s,13s,14s)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]sulfanyl]-n-methylundecanamide Chemical compound C1C[C@]2(C)C(O)CC[C@H]2[C@@H]2C(SCCCCCCCCCCC(=O)N(C)CCCC)CC3=CC(O)=CC=C3[C@H]21 ZESXPSUGWMXBGL-QRNYRMDWSA-N 0.000 claims 1
- QGAMWWULGQRYLA-WQJZBWLHSA-N n-butyl-11-[[(8r,9s,13s,14s)-3,17-dihydroxy-13-methyl-6-oxo-8,9,11,12,14,15,16,17-octahydro-7h-cyclopenta[a]phenanthren-7-yl]sulfanyl]-n-methylundecanamide Chemical compound C12=CC=C(O)C=C2C(=O)C(SCCCCCCCCCCC(=O)N(C)CCCC)[C@@H]2[C@@H]1CC[C@]1(C)C(O)CC[C@H]12 QGAMWWULGQRYLA-WQJZBWLHSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000262 estrogen Substances 0.000 abstract description 16
- 229940011871 estrogen Drugs 0.000 abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000010998 test method Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
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- 235000011152 sodium sulphate Nutrition 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000009806 oophorectomy Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 201000004240 prostatic hypertrophy Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 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
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
- 229960003454 tamoxifen citrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 201000007954 uterine fibroid Diseases 0.000 description 1
- 206010046811 uterine polyp Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0072—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the A ring of the steroid being aromatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Biotechnology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
L'invention concerne des oestrogènes et des anti-oestrogènes représentés par la formule (I) dont la structure est: (I), dans laquelle R est (II), (III), (IV) ou (V); R?1¿ et R?2¿ sont chacun indépendamment l'un de l'autre un alkyle comprenant 1-6 atomes de carbone ou des groupes alkyle qui forment ensemble un hétérocycle saturé comprenant 5-7 éléments; X est l'hydroxy, un alkoxy comprenant 1-6 atomes de carbone ou -OC(O)R?3¿; W est (VI), l'hydroxy, un alkyle comprenant 1-6 atomes de carbone, l'halogène, -CF¿3?, un alkoxy comprenant 1-6 atomes de carbones, -CHO, cyano, un alkylcarbonyle comprenant 2-7 atomes de carbone, un alkoxycarbonyle comprenant 2-7 atomes de carbone, amino, un alkylamino comprenant 1-6 atomes de carbone, un dialkylamino comprenant 1-6 atomes de carbone par groupe alkyle, trifluorométhoxy, un hydroxyalkyle comprenant 1-6 atomes de carbone, un alkoxyalkyle comprenant 2-12 atomes de carbone, -CN, -SO¿3?H, ou -CO¿2?H; R?3¿ est un alkyle comprenant 1-6 atomes de carbone; Z est (VII), (VIII), (IX) ou (X); Y est (XI), (XII), (XIII) ou (XIV); R?4¿ est l'hydrogène, un alkyle comprenant 1-6 atomes de carbone, un alcoyle comprenant 2-7 atomes de carbone ou un benzoyle; Q est l'hydrogène, -OR?5¿, ou NR?6¿R?7¿; R?5¿ est l'hydrogène ou un alkyle comprenant 1-6 atomes de carbone; R?6¿ et R?7¿ sont chacun indépendamment l'un de l'autre un alkyle comprenant 1-6 atomes de carbone ou R?6¿ et R?7¿ sont des groupes alkyle formant ensemble un hétérocycle saturé de 5-7 éléments; n = 4-12; et p = 2-6; ou un sel pharmaceutiquement acceptable de ce composé.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95650997A | 1997-10-23 | 1997-10-23 | |
| US08/956,509 | 1997-10-23 | ||
| PCT/US1998/022283 WO1999020646A1 (fr) | 1997-10-23 | 1998-10-21 | OESTRA-1,3,5(10)-TRIENE-7alpha-THIOETHERS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2308773A1 true CA2308773A1 (fr) | 1999-04-29 |
Family
ID=25498312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002308773A Abandoned CA2308773A1 (fr) | 1997-10-23 | 1998-10-21 | Oestra-1,3,5(10)-triene-7alpha-thioethers |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1025116A1 (fr) |
| JP (1) | JP2001520235A (fr) |
| AU (1) | AU1110699A (fr) |
| CA (1) | CA2308773A1 (fr) |
| WO (1) | WO1999020646A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6432643B1 (en) * | 1999-10-22 | 2002-08-13 | Duke University | Method of determining Alzheimer's disease risk using apolipoprotein E4 genotype analysis in combination with decreased estrogen levels |
| JP2007516009A (ja) | 2003-10-03 | 2007-06-21 | アカデミッシュ メディシュ セントラム | 基質の反射の画像処理のためのシステム及び方法。 |
| US9131861B2 (en) | 2004-11-30 | 2015-09-15 | Academisch Medisch Centrum | Pulsed lighting imaging systems and methods |
| US10112962B2 (en) * | 2014-07-02 | 2018-10-30 | Xavier University | Boron-based prodrug strategy for increased bioavailability and lower-dosage requirements for drug molecules containing at least one phenol (or aromatic hydroxyl) group |
| CN109415388A (zh) * | 2016-05-06 | 2019-03-01 | 路易斯安那泽维尔大学 | 选择性雌激素受体下调剂(serds) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2967188A (en) * | 1959-07-27 | 1961-01-03 | Searle & Co | 3, 17-bisoxygenated 7-acylthioestra-1, 3, 5(10)-trienes |
| GB8327256D0 (en) * | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
| FR2610933B1 (fr) * | 1987-02-18 | 1989-06-09 | Roussel Uclaf | Nouveaux 19-nor steroides substitues en position 7, leur preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant |
| DE4338316A1 (de) * | 1993-11-10 | 1995-05-11 | Jenapharm Gmbh | Neue Steroide mit radikophilen Substituenten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
-
1998
- 1998-10-21 EP EP98953837A patent/EP1025116A1/fr not_active Withdrawn
- 1998-10-21 WO PCT/US1998/022283 patent/WO1999020646A1/fr not_active Ceased
- 1998-10-21 CA CA002308773A patent/CA2308773A1/fr not_active Abandoned
- 1998-10-21 AU AU11106/99A patent/AU1110699A/en not_active Abandoned
- 1998-10-21 JP JP2000516987A patent/JP2001520235A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU1110699A (en) | 1999-05-10 |
| EP1025116A1 (fr) | 2000-08-09 |
| WO1999020646A1 (fr) | 1999-04-29 |
| JP2001520235A (ja) | 2001-10-30 |
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