RU2289587C2 - Стероидные соединения, способы их получения, фармацевтическая композиция, способы регуляции и совершенствования воспроизведения, промежуточные соединения - Google Patents
Стероидные соединения, способы их получения, фармацевтическая композиция, способы регуляции и совершенствования воспроизведения, промежуточные соединения Download PDFInfo
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- RU2289587C2 RU2289587C2 RU2003130228/04A RU2003130228A RU2289587C2 RU 2289587 C2 RU2289587 C2 RU 2289587C2 RU 2003130228/04 A RU2003130228/04 A RU 2003130228/04A RU 2003130228 A RU2003130228 A RU 2003130228A RU 2289587 C2 RU2289587 C2 RU 2289587C2
- Authority
- RU
- Russia
- Prior art keywords
- pregna
- methyl
- dimethyl
- dien
- compounds
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- -1 Steroid compounds Chemical class 0.000 title claims abstract description 163
- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 230000033228 biological regulation Effects 0.000 title claims description 8
- 210000000287 oocyte Anatomy 0.000 claims abstract description 59
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000003277 amino group Chemical group 0.000 claims abstract description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 239000012634 fragment Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 2
- 230000021121 meiosis Effects 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 62
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 230000001105 regulatory effect Effects 0.000 claims description 13
- 238000006268 reductive amination reaction Methods 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 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
- OTDOTSOSVDUYPU-VUVUMNNWSA-N (3s,5r,10s,13r,17r)-17-[(2s)-1-(3,3-dimethylpiperidin-1-yl)propan-2-yl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCCC(C)(C)C1 OTDOTSOSVDUYPU-VUVUMNNWSA-N 0.000 claims description 4
- WOTNUNXNDARBRO-LBLATDDSSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-(4-phenylpiperazin-1-yl)propan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N(CC1)CCN1C1=CC=CC=C1 WOTNUNXNDARBRO-LBLATDDSSA-N 0.000 claims description 4
- GKBHGYCSYJXRHT-NLUWZDHDSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-(4-pyrimidin-2-ylpiperazin-1-yl)propan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N(CC1)CCN1C1=NC=CC=N1 GKBHGYCSYJXRHT-NLUWZDHDSA-N 0.000 claims description 4
- FYPIHEPJWGYYNN-ACDJPIBPSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-morpholin-4-ylpropan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCOCC1 FYPIHEPJWGYYNN-ACDJPIBPSA-N 0.000 claims description 4
- ICXINXKOXHSQBO-PBJLWWPKSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-piperidin-1-ylpropan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCCCC1 ICXINXKOXHSQBO-PBJLWWPKSA-N 0.000 claims description 4
- IJNGCTNYTIGKDI-ACDJPIBPSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-pyrrolidin-1-ylpropan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCCC1 IJNGCTNYTIGKDI-ACDJPIBPSA-N 0.000 claims description 4
- QFPWLFITQPUXHV-KFAAVVAUSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-(4-methylpiperazin-1-yl)butan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN1CCN(C)CC1 QFPWLFITQPUXHV-KFAAVVAUSA-N 0.000 claims description 4
- WUWQKXKAYAZHIN-BYBMNWGSSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-(4-phenylpiperazin-1-yl)butan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN(CC1)CCN1C1=CC=CC=C1 WUWQKXKAYAZHIN-BYBMNWGSSA-N 0.000 claims description 4
- PKWNVYQEFUMSKR-ANKUBJOSSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-(4-pyridin-2-ylpiperazin-1-yl)butan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN(CC1)CCN1C1=CC=CC=N1 PKWNVYQEFUMSKR-ANKUBJOSSA-N 0.000 claims description 4
- DTTSEYLDUMDCLH-BQPBCQRUSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-morpholin-4-ylbutan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN1CCOCC1 DTTSEYLDUMDCLH-BQPBCQRUSA-N 0.000 claims description 4
- QRENNSDRNOUTTJ-KFAAVVAUSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-piperidin-1-ylbutan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN1CCCCC1 QRENNSDRNOUTTJ-KFAAVVAUSA-N 0.000 claims description 4
- JMUXKHOLEWUZTE-BQPBCQRUSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-4-pyrrolidin-1-ylbutan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)CN1CCCC1 JMUXKHOLEWUZTE-BQPBCQRUSA-N 0.000 claims description 4
- 125000003172 aldehyde group Chemical group 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 4
- ZNWOYQVXPIEQRC-HOFZUOGSSA-N (8s,9s,10r,13s,14s,17r)-17-[(2s)-1-hydroxypropan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CO)C)[C@@]1(C)CC2 ZNWOYQVXPIEQRC-HOFZUOGSSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 230000000269 nucleophilic effect Effects 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- JEPXCLDRHLFCEA-VUVUMNNWSA-N (3s,5r,10s,13r,17r)-17-[(2s)-1-(4,4-dimethylpiperidin-1-yl)propan-2-yl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCC(C)(C)CC1 JEPXCLDRHLFCEA-VUVUMNNWSA-N 0.000 claims description 2
- IZICFEGIZNHACS-PBJLWWPKSA-N (3s,5r,10s,13r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-(4-methylpiperazin-1-yl)propan-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCC3=C(CC[C@H]4C(C)(C)[C@@H](O)CC[C@@]43C)C2=CC1)C)N1CCN(C)CC1 IZICFEGIZNHACS-PBJLWWPKSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- QWUGXTUSOZVHEM-UZCUGSDUSA-N 3beta-Hydroxypregn-5-ene Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 QWUGXTUSOZVHEM-UZCUGSDUSA-N 0.000 claims 13
- MEJKEDTXBFUPAN-NMUSQOSSSA-N (3s,5r,10s,13r,17r)-17-[(2s)-1-hydroxypropan-2-yl]-4,4,10,13-tetramethyl-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@@H](CO)C)CC=C21 MEJKEDTXBFUPAN-NMUSQOSSSA-N 0.000 claims 1
- OSHHWCYAGNHCHJ-SRJXFZCCSA-N (3s,9s,10r,13r,14r,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-piperidin-1-ylpropan-2-yl]-1,2,3,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C(C)(C)C4=CC=C3[C@@H]2CC1)C)N1CCCCC1 OSHHWCYAGNHCHJ-SRJXFZCCSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000005012 migration Effects 0.000 claims 1
- 238000013508 migration Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000018046 regulation of meiosis Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 24
- 150000003431 steroids Chemical class 0.000 abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 16
- 241000282414 Homo sapiens Species 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- 230000001976 improved effect Effects 0.000 abstract description 5
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- 230000022866 positive regulation of meiosis Effects 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 2
- 125000006850 spacer group Chemical group 0.000 abstract description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
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- 230000002829 reductive effect Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
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- 239000012279 sodium borohydride Substances 0.000 description 15
- 229910000033 sodium borohydride Inorganic materials 0.000 description 15
- 235000003702 sterols Nutrition 0.000 description 15
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 14
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
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- RAVPVXLUNHXLHI-YOFBAJCKSA-N (3s,8s,9s,10r,13s,14s,17r)-4,4,10,13-tetramethyl-17-[(2s)-1-tri(propan-2-yl)silyloxypropan-2-yl]-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol Chemical compound C1C=C2C(C)(C)[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CO[Si](C(C)C)(C(C)C)C(C)C)C)[C@@]1(C)CC2 RAVPVXLUNHXLHI-YOFBAJCKSA-N 0.000 description 9
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- 238000001727 in vivo Methods 0.000 description 9
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
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- 230000003213 activating effect Effects 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 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 8
- 238000003776 cleavage reaction Methods 0.000 description 8
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 8
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- 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
-
- 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
-
- 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
-
- 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)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01250108A EP1245572A1 (en) | 2001-03-26 | 2001-03-26 | Aminosterol compounds, their use in the preparation of meiosis-regulating medicaments and method for their preparation |
| EP01250108.6 | 2001-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003130228A RU2003130228A (ru) | 2005-04-10 |
| RU2289587C2 true RU2289587C2 (ru) | 2006-12-20 |
Family
ID=8181575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003130228/04A RU2289587C2 (ru) | 2001-03-26 | 2002-03-20 | Стероидные соединения, способы их получения, фармацевтическая композиция, способы регуляции и совершенствования воспроизведения, промежуточные соединения |
Country Status (18)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1514874A1 (en) * | 2003-07-28 | 2005-03-16 | Schering Aktiengesellschaft | Thiomorpholino steroid compounds, the use thereof for the preparation of meiosis regulating medicaments and method for the preparation thereof |
| KR100689260B1 (ko) * | 2005-05-24 | 2007-03-02 | 삼원산업주식회사 | 항산화성 스틸벤계 형광증백제 및 이의 합성방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419661A (en) * | 1964-01-13 | 1968-12-31 | Univ Missouri | Oral contraceptive for birds |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1095167A (en) * | 1963-12-05 | 1967-12-13 | Shalom Sarel | Amino-steroids |
| DE1643004A1 (de) * | 1967-02-07 | 1971-04-08 | Schering Ag | Bisnorcholenderivate und Verfahren zu ihrer Herstellung |
| DE1930473A1 (de) * | 1969-06-14 | 1970-12-17 | Schering Ag | 22-N-substituierte (20R)-23,24-dinor-cholanderivate |
| US5716777A (en) | 1994-06-23 | 1998-02-10 | Novo Nordisk A/S | Regulation of meiosis using sterols |
| EP0813595A1 (en) * | 1995-03-06 | 1997-12-29 | Novo Nordisk A/S | Stimulation of meiosis |
| ATE254628T1 (de) | 1995-06-23 | 2003-12-15 | Novo Nordisk As | Meiose regulierende verbindungen. |
| EP0946584B1 (en) | 1996-12-20 | 2003-04-23 | Novo Nordisk A/S | Meiosis regulating compounds |
| JP2003522728A (ja) * | 1998-05-13 | 2003-07-29 | ノボ ノルディスク アクティーゼルスカブ | 減数分裂調節化合物 |
| KR20010043828A (ko) | 1998-05-26 | 2001-05-25 | 에바-마리아 시마-메이어, 얼설라 멜져, 마거, 하르트만 | ｃＡＭＰ-증강 화합물 단독 또는 감수분열-자극 화합물하나 이상과의 조합에 의한 불임 치료 방법 |
| EP1156821B1 (en) | 1999-02-24 | 2007-05-02 | Novo Nordisk A/S | Treatment of infertility |
| AU2794100A (en) | 1999-02-24 | 2000-09-14 | Novo Nordisk A/S | Treatment of infertility |
| CN1341147A (zh) | 1999-02-26 | 2002-03-20 | 诺沃挪第克公司 | 减数分裂活化甾醇增大着床率 |
| JP2003509365A (ja) | 1999-09-16 | 2003-03-11 | ノボ ノルディスク アクティーゼルスカブ | Ｉｖｆ用の組成物 |
| AU3376501A (en) | 2000-02-25 | 2001-09-03 | Novo Nordisk A/S | Improvement of implantation rate |
| US6988613B2 (en) * | 2001-02-06 | 2006-01-24 | Novo Nordisk A/S | Composition for IVF |
| ATE386495T1 (de) * | 2001-02-06 | 2008-03-15 | Novo Nordisk As | Behältnis mit niedrigem sauerstoffgehalt, das ff- mas enthält |
-
2001
- 2001-03-26 EP EP01250108A patent/EP1245572A1/en not_active Withdrawn
-
2002
- 2002-03-20 AU AU2002315260A patent/AU2002315260B2/en not_active Ceased
- 2002-03-20 UA UA2003109610A patent/UA75130C2/uk unknown
- 2002-03-20 MX MXPA03008199A patent/MXPA03008199A/es active IP Right Grant
- 2002-03-20 WO PCT/EP2002/003148 patent/WO2002079220A2/en not_active Ceased
- 2002-03-20 HU HU0303643A patent/HUP0303643A2/hu unknown
- 2002-03-20 IL IL15727202A patent/IL157272A0/xx unknown
- 2002-03-20 KR KR10-2003-7012456A patent/KR20030088043A/ko not_active Ceased
- 2002-03-20 BR BR0208381-7A patent/BR0208381A/pt not_active IP Right Cessation
- 2002-03-20 CN CNB028073673A patent/CN1332975C/zh not_active Expired - Fee Related
- 2002-03-20 RU RU2003130228/04A patent/RU2289587C2/ru not_active IP Right Cessation
- 2002-03-20 CZ CZ20032578A patent/CZ20032578A3/cs unknown
- 2002-03-20 CA CA002438210A patent/CA2438210A1/en not_active Abandoned
- 2002-03-20 PL PL02369576A patent/PL369576A1/xx not_active Application Discontinuation
- 2002-03-20 EP EP02740430A patent/EP1401856A2/en not_active Withdrawn
- 2002-03-20 JP JP2002577844A patent/JP2004534011A/ja active Pending
- 2002-03-26 US US10/105,939 patent/US6916921B2/en not_active Expired - Fee Related
-
2003
- 2003-09-25 NO NO20034273A patent/NO20034273L/no not_active Application Discontinuation
- 2003-10-23 ZA ZA200308271A patent/ZA200308271B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419661A (en) * | 1964-01-13 | 1968-12-31 | Univ Missouri | Oral contraceptive for birds |
Also Published As
| Publication number | Publication date |
|---|---|
| US6916921B2 (en) | 2005-07-12 |
| NO20034273L (no) | 2003-11-25 |
| CN1543473A (zh) | 2004-11-03 |
| BR0208381A (pt) | 2004-06-15 |
| IL157272A0 (en) | 2004-02-19 |
| JP2004534011A (ja) | 2004-11-11 |
| WO2002079220A2 (en) | 2002-10-10 |
| CN1332975C (zh) | 2007-08-22 |
| US20020188143A1 (en) | 2002-12-12 |
| ZA200308271B (en) | 2005-01-24 |
| UA75130C2 (en) | 2006-03-15 |
| MXPA03008199A (es) | 2004-01-29 |
| KR20030088043A (ko) | 2003-11-15 |
| HUP0303643A2 (hu) | 2004-03-01 |
| RU2003130228A (ru) | 2005-04-10 |
| WO2002079220A3 (en) | 2003-10-16 |
| AU2002315260B2 (en) | 2008-04-03 |
| CZ20032578A3 (cs) | 2003-12-17 |
| PL369576A1 (en) | 2005-05-02 |
| NO20034273D0 (no) | 2003-09-25 |
| EP1401856A2 (en) | 2004-03-31 |
| CA2438210A1 (en) | 2002-10-10 |
| EP1245572A1 (en) | 2002-10-02 |
| HK1070900A1 (en) | 2005-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20090321 |