NZ508801A - Selective estrogen receptor modulator in combination with dehydroepiandrosterone (DHEA) or analogues - Google Patents
Selective estrogen receptor modulator in combination with dehydroepiandrosterone (DHEA) or analoguesInfo
- Publication number
- NZ508801A NZ508801A NZ508801A NZ50880199A NZ508801A NZ 508801 A NZ508801 A NZ 508801A NZ 508801 A NZ508801 A NZ 508801A NZ 50880199 A NZ50880199 A NZ 50880199A NZ 508801 A NZ508801 A NZ 508801A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- acid
- hydroxyl
- estrogen receptor
- receptor modulator
- Prior art date
Links
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 title claims abstract description 208
- 239000000333 selective estrogen receptor modulator Substances 0.000 title claims abstract description 121
- 229940095743 selective estrogen receptor modulator Drugs 0.000 title claims abstract description 102
- 239000002243 precursor Substances 0.000 claims abstract description 105
- 239000003163 gonadal steroid hormone Substances 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 31
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 claims abstract description 13
- 229960005471 androstenedione Drugs 0.000 claims abstract description 13
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims abstract description 13
- CZWCKYRVOZZJNM-USOAJAOKSA-N dehydroepiandrosterone sulfate Chemical compound C1[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 CZWCKYRVOZZJNM-USOAJAOKSA-N 0.000 claims abstract description 11
- CZWCKYRVOZZJNM-UHFFFAOYSA-N Prasterone sodium sulfate Natural products C1C(OS(O)(=O)=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 CZWCKYRVOZZJNM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229950009829 prasterone sulfate Drugs 0.000 claims abstract description 9
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 claims description 194
- 229960002847 prasterone Drugs 0.000 claims description 194
- 238000011282 treatment Methods 0.000 claims description 86
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- 241001070944 Mimosa Species 0.000 claims description 64
- -1 benzothiophene derivative compound Chemical class 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
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- 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 claims description 16
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
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- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 claims description 5
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 102000015694 estrogen receptors Human genes 0.000 claims description 4
- 108010038795 estrogen receptors Proteins 0.000 claims description 4
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 4
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 3
- 206010047791 Vulvovaginal dryness Diseases 0.000 claims description 2
- UCJGJABZCDBEDK-UHFFFAOYSA-N bazedoxifene Chemical group C=1C=C(OCCN2CCCCCC2)C=CC=1CN1C2=CC=C(O)C=C2C(C)=C1C1=CC=C(O)C=C1 UCJGJABZCDBEDK-UHFFFAOYSA-N 0.000 claims description 2
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- 210000003205 muscle Anatomy 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 45
- 150000002431 hydrogen Chemical class 0.000 claims 32
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 150000001562 benzopyrans Chemical class 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 6
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 6
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- 229930195733 hydrocarbon Natural products 0.000 claims 6
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 6
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims 6
- XZEUAXYWNKYKPL-URLMMPGGSA-N ormeloxifene Chemical class C1([C@@H]2[C@H](C3=CC=C(C=C3OC2(C)C)OC)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 XZEUAXYWNKYKPL-URLMMPGGSA-N 0.000 claims 6
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US09/096,284 US6465445B1 (en) | 1998-06-11 | 1998-06-11 | Medical uses of a selective estrogen receptor modulator in combination with sex steroid precursors |
PCT/CA1999/000538 WO1999063974A2 (en) | 1998-06-11 | 1999-06-10 | Selective estrogen receptor modulator in combination with denydroepiandrosterone (dhea) or analogues |
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NZ508801A NZ508801A (en) | 1998-06-11 | 1999-06-10 | Selective estrogen receptor modulator in combination with dehydroepiandrosterone (DHEA) or analogues |
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