DE10056676A1 - Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximen - Google Patents
Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximenInfo
- Publication number
- DE10056676A1 DE10056676A1 DE10056676A DE10056676A DE10056676A1 DE 10056676 A1 DE10056676 A1 DE 10056676A1 DE 10056676 A DE10056676 A DE 10056676A DE 10056676 A DE10056676 A DE 10056676A DE 10056676 A1 DE10056676 A1 DE 10056676A1
- Authority
- DE
- Germany
- Prior art keywords
- benzaldehyde
- group
- oxoestra
- oxime
- formula
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 15
- YIKRUHLWWPEUCP-QXIQIYTISA-N N-[[2-[[(8R,9R,10S,13S)-1,2,3,4,5,6,7,8,9,10,11,12-dodecahydrocyclopenta[a]phenanthren-13-yl]methyl]phenyl]methylidene]hydroxylamine Chemical class C([C@@]12C=CC=C1[C@@H]1CCC3CCCC[C@@H]3[C@H]1CC2)C1=C(C=NO)C=CC=C1 YIKRUHLWWPEUCP-QXIQIYTISA-N 0.000 title abstract 2
- 238000003747 Grignard reaction Methods 0.000 title description 3
- 201000009273 Endometriosis Diseases 0.000 title description 2
- -1 methylene compound Chemical class 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 150000002923 oximes Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract description 11
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 claims abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 239000011777 magnesium Substances 0.000 claims abstract description 7
- 239000002585 base Substances 0.000 claims abstract description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 4
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 4
- 230000007017 scission Effects 0.000 claims abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 3
- 125000006239 protecting group Chemical group 0.000 claims abstract description 3
- 230000000707 stereoselective effect Effects 0.000 claims abstract description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
- 150000001299 aldehydes Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 3
- VTWKXBJHBHYJBI-VURMDHGXSA-N (nz)-n-benzylidenehydroxylamine Chemical class O\N=C/C1=CC=CC=C1 VTWKXBJHBHYJBI-VURMDHGXSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- VTWKXBJHBHYJBI-UHFFFAOYSA-N n-benzylidenehydroxylamine Chemical class ON=CC1=CC=CC=C1 VTWKXBJHBHYJBI-UHFFFAOYSA-N 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 24
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 11
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 3
- 150000001340 alkali metals Chemical class 0.000 abstract description 3
- 150000003935 benzaldehydes Chemical class 0.000 abstract description 2
- 229940045803 cuprous chloride Drugs 0.000 abstract 2
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 2
- 238000007142 ring opening reaction Methods 0.000 abstract 2
- UTACOMXUXXSZHE-XKJLRJJASA-N (8s,10s,13s,14s)-13-methyl-2,3,4,5,6,7,8,10,12,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-one Chemical compound C1CCC[C@@H]2C3=CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 UTACOMXUXXSZHE-XKJLRJJASA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000003544 oxime group Chemical group 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
- TWFNGPDYMFEHOB-UHFFFAOYSA-N 1-bromo-4-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=C(Br)C=C1 TWFNGPDYMFEHOB-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 1
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000000380 anti-gestagenic effect Effects 0.000 description 1
- 230000002800 anti-glucocorticoid effect Effects 0.000 description 1
- 239000003418 antiprogestin Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003152 gestagenic effect Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical class [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0085—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Studio Devices (AREA)
Priority Applications (29)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10056676A DE10056676A1 (de) | 2000-11-10 | 2000-11-10 | Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximen |
| YU34303A YU34303A (sh) | 2000-11-10 | 2001-11-09 | Postupak za proizvodnju 4-(17alfa-supstituisani-3-oksoestra -4,9-dien-11beta-il)benzaldehid-(1e ili 1z)-oksima |
| EP01993608A EP1339734B1 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl) benzaldehyd-(1e oder 1z)-oximen |
| DE50110829T DE50110829D1 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl) benzaldehyd-(1e oder 1z)-oximen |
| EEP200300222A EE200300222A (et) | 2000-11-10 | 2001-11-09 | 4-(17a-asendatud-3-oksoöstra-4,9-dieen-11ß-üül)-bensaldehüüd-(1E või 1Z)-oksiimide valmistamismeetod |
| JP2002541114A JP4263478B2 (ja) | 2000-11-10 | 2001-11-09 | ４−（１７α−置換−３−オキソエストラ−４，９−ジエン−１１β−イル）ベンズアルデヒド−（１Ｅまたは１Ｚ）−オキシムの製造法 |
| HU0301765A HUP0301765A2 (hu) | 2000-11-10 | 2001-11-09 | Eljárás 4-(17alfa-szubtituált-3-oxoösztra-4,9-dién-11béta-il)-benzaldehid-(1E vagy 1Z)-oximok elżállítására |
| CNB018186785A CN100368427C (zh) | 2000-11-10 | 2001-11-09 | 制备4-(17α-取代的-3-氧代雌-4,9-二烯-11β-基)苯甲醛-(1E或1Z)-肟的方法 |
| EA200300506A EA005530B1 (ru) | 2000-11-10 | 2001-11-09 | СПОСОБ ПОЛУЧЕНИЯ 4-(17α-ЗАМЕЩЕННЫХ-3-ОКСОЭСТРА-4,9-ДИЕН-11β-ИЛ)БЕНЗАЛЬДЕГИД-(1E ИЛИ 1Z)ОКСИМОВ |
| AU1691102A AU1691102A (en) | 2000-11-10 | 2001-11-09 | Method for the production of 4-(17alpha substituted 3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1e or 1z)-oximes |
| HK04105980.7A HK1063187B (en) | 2000-11-10 | 2001-11-09 | PROCESS FOR THE PRODUCTION OF 4-(17α-SUBSTITUTED-3-OXOESTRA-4, 9-DIEN-11β-YL)BENZALDEHYDE-(1E OR 1Z)-OXIMES |
| CZ20031282A CZ301425B6 (cs) | 2000-11-10 | 2001-11-09 | Zpusob prípravy 4-(17alfa-substituovaných-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E ci 1Z)-oximu |
| HR20030458A HRP20030458A2 (en) | 2000-11-10 | 2001-11-09 | METHOD FOR THE PRODUCTION OF 4-(17α-SUBSTITUTED-3-OXOESTRA-4,9-DIEN-11?-IL)BENZALDEHYD-(1E OR 1Z)-OXIMES |
| IL15568001A IL155680A0 (en) | 2000-11-10 | 2001-11-09 | Method for the production of 4-alph-(17alpha substituted 3-oxoestra-4,9-dien-11-yl) enzaldehyde-(1e or 1z)-oximes |
| CA2427632A CA2427632C (en) | 2000-11-10 | 2001-11-09 | Process for the production of 4-(17.alpha.-substituted-3-oxoestra-4,9-dien-11.beta.-yl)benzaldehyde-(1e or 1z)-oximes |
| MXPA03004109A MXPA03004109A (es) | 2000-11-10 | 2001-11-09 | Metodo para la produccion de 4-(17alfa substituidas 3-oxoestra-4,9-dien-11-il) benzaldehid- (1e o 1z)-oximas. |
| AU2002216911A AU2002216911B2 (en) | 2000-11-10 | 2001-11-09 | Method for the production of 4-(17alpha substituted 3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E or 1Z)-oximes |
| US10/416,029 US7214808B2 (en) | 2000-11-10 | 2001-11-09 | Method for the production of 4-(17α-substituted-3-oxoestra-4,9-dien-11β-yl)benzaldehyde-(1E)-oximes |
| AT01993608T ATE337328T1 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha- substituierten-3-oxoestra-4,9-dien-11beta-yl) benzaldehyd-(1e oder 1z)-oximen |
| PL361399A PL205091B1 (pl) | 2000-11-10 | 2001-11-09 | Sposób otrzymywania 4-(17α-podstawionych-3-oksoestra-4,9-dien-11β-ylo)benzaldehydo-(1E lub 1Z)-oksymów |
| SK551-2003A SK286601B6 (sk) | 2000-11-10 | 2001-11-09 | Spôsob prípravy 4-(17alfa-substituovaných-3-oxoestra-4,9-dien- 11beta-yl)benzaldehyd-(1E alebo 1Z) oxímov |
| BR0115249-1A BR0115249A (pt) | 2000-11-10 | 2001-11-09 | Processo para a produção de 4-(3-oxoestra-4,9-dien-11beta-il-17alfa-substituìda)be nzaldeìdo-(1e ou 1z)-oximas |
| PCT/DE2001/004218 WO2002038582A2 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha-(substituierten-methyl)-3-oxoestra-4,9 dien-11-yl)benzaldehyd-(1e oder 1z)-oximen |
| NZ525962A NZ525962A (en) | 2000-11-10 | 2001-11-09 | Method for the production of 4-(17alpha substituted 3-oxoestra-4,9-dien-11beta-YL)benzaldehyd-(1E or 1Z)-oximes |
| KR1020037006317A KR100836323B1 (ko) | 2000-11-10 | 2001-11-09 | 4-(17α-치환된-3-옥소에스트라-4,9-디엔-11β-일)벤즈알데히드-(1Ｅ 또는 1Ｚ)-옥심의 제조 방법 |
| IL155680A IL155680A (en) | 2000-11-10 | 2003-04-30 | Method to generate 4- (17 alpha-converted 3 - oxoester - 4,9 - diane - 11 - il) benzaldehyde - (1 E or 1Z) - oximes |
| NO20032080A NO20032080D0 (no) | 2000-11-10 | 2003-05-09 | Fremgangsmåte for fremstilling av 4-(17<alfa>-substituerte-3- oksoöstra-4,9-dien-11-yl)benzaldehyd-(1E eller 1Z)-oksimer |
| BG107886A BG107886A (bg) | 2000-11-10 | 2003-06-06 | Метод за получаване на 4-(17алфа-заместени-3-оксоестра-4,9-диен-11бета-ил)бензалдехид-(1е или 1z) оксими |
| ZA200304480A ZA200304480B (en) | 2000-11-10 | 2003-06-09 | Method for the production of 4-(17Alpha substituted 3-oxoestra-4,9-dien-11-yl)benzaldehyd-(1E or 1Z)-oximes. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10056676A DE10056676A1 (de) | 2000-11-10 | 2000-11-10 | Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10056676A1 true DE10056676A1 (de) | 2002-05-16 |
Family
ID=7663441
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10056676A Withdrawn DE10056676A1 (de) | 2000-11-10 | 2000-11-10 | Verfahren zur Herstellung von 4-/17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl)benzaldehyd-(1E oder 1Z)-oximen |
| DE50110829T Expired - Lifetime DE50110829D1 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl) benzaldehyd-(1e oder 1z)-oximen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50110829T Expired - Lifetime DE50110829D1 (de) | 2000-11-10 | 2001-11-09 | Verfahren zur herstellung von 4-(17alpha-substituierten-3-oxoestra-4,9-dien-11beta-yl) benzaldehyd-(1e oder 1z)-oximen |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7214808B2 (https=) |
| EP (1) | EP1339734B1 (https=) |
| JP (1) | JP4263478B2 (https=) |
| KR (1) | KR100836323B1 (https=) |
| CN (1) | CN100368427C (https=) |
| AT (1) | ATE337328T1 (https=) |
| AU (2) | AU2002216911B2 (https=) |
| BG (1) | BG107886A (https=) |
| BR (1) | BR0115249A (https=) |
| CA (1) | CA2427632C (https=) |
| CZ (1) | CZ301425B6 (https=) |
| DE (2) | DE10056676A1 (https=) |
| EA (1) | EA005530B1 (https=) |
| EE (1) | EE200300222A (https=) |
| HR (1) | HRP20030458A2 (https=) |
| HU (1) | HUP0301765A2 (https=) |
| IL (2) | IL155680A0 (https=) |
| MX (1) | MXPA03004109A (https=) |
| NO (1) | NO20032080D0 (https=) |
| NZ (1) | NZ525962A (https=) |
| PL (1) | PL205091B1 (https=) |
| SK (1) | SK286601B6 (https=) |
| WO (1) | WO2002038582A2 (https=) |
| YU (1) | YU34303A (https=) |
| ZA (1) | ZA200304480B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006018888A1 (de) * | 2006-04-18 | 2007-10-25 | Bayer Schering Pharma Ag | Verfahren zur Herstellung von 4-[17beta-Methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-dien-11beta-yl]benzaldehyd-(E)-oxims (Asoprisnil) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4843372B2 (ja) * | 2006-05-09 | 2011-12-21 | 株式会社リコー | 画像処理装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4332284C2 (de) * | 1993-09-20 | 1997-05-28 | Jenapharm Gmbh | 11-Benzaldoxim-17beta-methoxy-17alpha-methoxymethyl-estradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE4332283A1 (de) * | 1993-09-20 | 1995-04-13 | Jenapharm Gmbh | Neue 11-Benzaldoximestradien-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5576310A (en) * | 1994-09-20 | 1996-11-19 | Jenapharm Gmbh | 11-benzaldoxime-17β-methoxy-17α-methoxymethyl-estrasdiene derivatives, methods for their production and pharmaceuticals containing such compounds |
-
2000
- 2000-11-10 DE DE10056676A patent/DE10056676A1/de not_active Withdrawn
-
2001
- 2001-11-09 HU HU0301765A patent/HUP0301765A2/hu unknown
- 2001-11-09 MX MXPA03004109A patent/MXPA03004109A/es active IP Right Grant
- 2001-11-09 AU AU2002216911A patent/AU2002216911B2/en not_active Ceased
- 2001-11-09 DE DE50110829T patent/DE50110829D1/de not_active Expired - Lifetime
- 2001-11-09 AT AT01993608T patent/ATE337328T1/de not_active IP Right Cessation
- 2001-11-09 KR KR1020037006317A patent/KR100836323B1/ko not_active Expired - Fee Related
- 2001-11-09 YU YU34303A patent/YU34303A/sh unknown
- 2001-11-09 CZ CZ20031282A patent/CZ301425B6/cs not_active IP Right Cessation
- 2001-11-09 IL IL15568001A patent/IL155680A0/xx unknown
- 2001-11-09 BR BR0115249-1A patent/BR0115249A/pt not_active IP Right Cessation
- 2001-11-09 AU AU1691102A patent/AU1691102A/xx active Pending
- 2001-11-09 HR HR20030458A patent/HRP20030458A2/hr not_active Application Discontinuation
- 2001-11-09 EA EA200300506A patent/EA005530B1/ru not_active IP Right Cessation
- 2001-11-09 PL PL361399A patent/PL205091B1/pl not_active IP Right Cessation
- 2001-11-09 JP JP2002541114A patent/JP4263478B2/ja not_active Expired - Fee Related
- 2001-11-09 NZ NZ525962A patent/NZ525962A/en unknown
- 2001-11-09 SK SK551-2003A patent/SK286601B6/sk not_active IP Right Cessation
- 2001-11-09 CA CA2427632A patent/CA2427632C/en not_active Expired - Lifetime
- 2001-11-09 CN CNB018186785A patent/CN100368427C/zh not_active Expired - Fee Related
- 2001-11-09 US US10/416,029 patent/US7214808B2/en not_active Expired - Lifetime
- 2001-11-09 EP EP01993608A patent/EP1339734B1/de not_active Expired - Lifetime
- 2001-11-09 EE EEP200300222A patent/EE200300222A/xx unknown
- 2001-11-09 WO PCT/DE2001/004218 patent/WO2002038582A2/de not_active Ceased
-
2003
- 2003-04-30 IL IL155680A patent/IL155680A/en not_active IP Right Cessation
- 2003-05-09 NO NO20032080A patent/NO20032080D0/no unknown
- 2003-06-06 BG BG107886A patent/BG107886A/bg unknown
- 2003-06-09 ZA ZA200304480A patent/ZA200304480B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006018888A1 (de) * | 2006-04-18 | 2007-10-25 | Bayer Schering Pharma Ag | Verfahren zur Herstellung von 4-[17beta-Methoxy-17alpha-methoxymethyl-3-oxoestra-4,9-dien-11beta-yl]benzaldehyd-(E)-oxims (Asoprisnil) |
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| Date | Code | Title | Description |
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| 8127 | New person/name/address of the applicant |
Owner name: SCHERING AG, 13353 BERLIN, DE |
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| 8127 | New person/name/address of the applicant |
Owner name: BAYER SCHERING PHARMA AG, 13353 BERLIN, DE |
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| 8139 | Disposal/non-payment of the annual fee |