EP0000300A1 - Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden - Google Patents

Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden Download PDF

Info

Publication number: EP0000300A1
Authority: EP; European Patent Office
Prior art keywords: methoxy; estra; diol; agent; trien
Prior art date: 1977-06-27
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.): Granted

Application number

EP78400016A

Other languages

English (en)

French (fr)

Other versions

EP0000300B1 (de

Inventor

Alain Jouquey

Jean-Pierre Raynaud

Jean Salmon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

Priority date (The priority date 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 date listed.)

1977-06-27

Filing date

1978-06-12

Publication date

1979-01-10

1978-06-12 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1979-01-10 Publication of EP0000300A1 publication Critical patent/EP0000300A1/de

1982-01-06 Application granted granted Critical

1982-01-06 Publication of EP0000300B1 publication Critical patent/EP0000300B1/de

Status Expired legal-status Critical Current

Links

YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 title claims abstract description 9
229910052722 tritium Inorganic materials 0.000 title claims abstract description 9
150000003431 steroids Chemical class 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims abstract description 7
230000015572 biosynthetic process Effects 0.000 title claims description 7
238000003786 synthesis reaction Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title abstract description 4
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims abstract description 6
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 6
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
239000000047 product Substances 0.000 claims description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
239000003795 chemical substances by application Substances 0.000 claims description 23
HLCRYAZDZCJZFG-BDXSIMOUSA-N (8s,9s,13s,14s)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene Chemical compound C1CC2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HLCRYAZDZCJZFG-BDXSIMOUSA-N 0.000 claims description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
-1 acyl radical Chemical class 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 7
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229960004719 nandrolone Drugs 0.000 claims description 6
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 claims description 5
238000006266 etherification reaction Methods 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
229960001124 trientine Drugs 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 4
238000005886 esterification reaction Methods 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical group O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
230000000903 blocking effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
125000002252 acyl group Chemical group 0.000 abstract 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 4
230000000694 effects Effects 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000005672 tetraenes Chemical class 0.000 description 2
VBAFPUVFQZWOJM-MHJRRCNVSA-N (8r,9r,10s,13r,14s)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C1CCC[C@@H]2[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 VBAFPUVFQZWOJM-MHJRRCNVSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QGSLALDVLLRLGA-XLMAVXFVSA-N [(8r,9s,13r,14s)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-13-yl]methanediol Chemical compound C1CC2=CC=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C(O)O)CC2 QGSLALDVLLRLGA-XLMAVXFVSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
239000003098 androgen Substances 0.000 description 1
229940030486 androgens Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012374 esterification agent Substances 0.000 description 1
150000002163 estratetraenes Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000003862 glucocorticoid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
AVTYONGGKAJVTE-UHFFFAOYSA-L potassium tartrate Chemical class [K+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O AVTYONGGKAJVTE-UHFFFAOYSA-L 0.000 description 1
239000001472 potassium tartrate Substances 0.000 description 1
235000011005 potassium tartrates Nutrition 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
102000003998 progesterone receptors Human genes 0.000 description 1
108090000468 progesterone receptors Proteins 0.000 description 1
229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
150000005671 trienes Chemical class 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- 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
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified

Definitions

the present invention relates to new steroids from the series of substituted estratetraene, their preparation process and their application to the synthesis of derivatives of the series of astradiols labeled with tritium.
the subject of the invention is the steroids of general formula I in which R represents hydrogen or R ', R' being an acyl radical having from 1 to 5 carbon atoms, the benzoyl radical substituted or not, or a tetrahydropyranyl, trityl or trimethylsilyl radical, and R 1 represents an acyl radical having from 1 to 5 carbon atoms, the substituted or unsubstituted benzoyl radical or a tetrahydropyranyl, trityl or trimethylsilyl radical.
R and / or R 1 represents. an acyl radical having from 1 to 5 carbon carbon, it may be for example the residue of formic acid, acetic acid, p ropionique, butyric or valeric acids.
R and / or R 1 represents a substituted benzoyl radical, it can be substituted for example by a halogen such as chlorine or Bromine, by an alkyl radical having from 1 to 5 carbon atoms, by the trifluoromethoxy radical, or by an alkyloxy radical having from 1 to 5 carbon atoms.
a halogen such as chlorine or Bromine
the subject of the invention is also a process for preparing the products corresponding to the general formula above.
tissues of other classes of steroid hormones glucocorticoids, mineral corticosteroids, androgens or progestogens.
Stage B Acetoxy-17 ⁇ dibromo-2, 6 methoxy-11 ⁇ estrene 4 one-3
the reaction mixture consisting of 45.2 mg of methoxy-11 ⁇ diacetate estra-1, 3, 5 (10), 6 tetraene diol-3, 17 ⁇ , 10 mg of palladium black and 0.3 cc is cooled with liquid nitrogen. redistilled ethyl acetate, then introduced under vacuum 3.87 cm3 of tritium, measured at 0 ° C. and at normal pressure with a total activity of 10 Ci.
reaction mixture is allowed to return to ambient temperature, maintained under stirring for 3 hours, collects the excess of tritium, filters, distills the solvent under reduced pressure and, after removal of the labile tritium, obtains 46 mg of diacetate / 6,7- 3 H / methoxy- 11 ⁇ estra-1, 3, 5 (10) triene diol-3, 17 ⁇ sought for a specific activity of 54.03 Ci / mM.
Stage B / 6. 7- 3 H / methoxy-11 ⁇ estra-1, 3, 5 (10) triene diol-3.17 ⁇

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Investigating Or Analysing Biological Materials (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

EP78400016A 1977-06-27 1978-06-12 Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden Expired EP0000300B1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7719613		1977-06-27
FR7719613A FR2401173A1 (fr)	1977-06-27	1977-06-27	Nouveaux steroides, leur procede de preparation et leur application dans la synthese de steroides marques au tritium

Publications (2)

Publication Number	Publication Date
EP0000300A1 true EP0000300A1 (de)	1979-01-10
EP0000300B1 EP0000300B1 (de)	1982-01-06

Family

ID=9192607

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP78400016A Expired EP0000300B1 (de)	1977-06-27	1978-06-12	Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden

Country Status (7)

Country	Link
US (1)	US4191697A (de)
EP (1)	EP0000300B1 (de)
JP (2)	JPS5412362A (de)
CA (1)	CA1130277A (de)
DE (1)	DE2861501D1 (de)
FR (1)	FR2401173A1 (de)
IT (1)	IT1105060B (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0431327A1 (de) *	1989-11-10	1991-06-12	Hoechst Aktiengesellschaft	Synthetische Vakzine zur spezifischen Induktion zytotoxischer T-Lymphozyten
DE102017119621A1 (de)	2016-12-01	2018-06-07	Pouya Molana	Mayonnaise-Pulver-Zusammensetzung und Verfahren zur Herstellung eines Lebensmittelprodukts unter Verwendung eines solchen
EP3587369A1 (de)	2009-04-03	2020-01-01	Verescence France	Herstellungsverfahren eines glasbehälters

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3414508A1 (de) *	1984-04-13	1985-10-24	Schering AG, 1000 Berlin und 4709 Bergkamen	Mehrfach tritiierte steroid-20.17-spirolactone und ihre verwendung als tracersubstanzen
US4757062A (en) *	1985-11-01	1988-07-12	E. I. Du Pont De Nemours And Company	Substituted benzoate ester prodrugs of estrogens
AU1924701A (en)	1999-12-15	2001-06-25	Dow Global Technologies Inc.	Multi-component articles prepared from hydrogenated block copolymers

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3020294A (en) *	1950-03-28	1962-02-06	Syntex Sa	Production of ring a aromatic steroids
GB1151404A (en) *	1966-06-07	1969-05-07	Roussel Uclaf	Novel Gona-1,3,5(10)-Trienes, Processes for their Preparation, and Compositions incorporating them

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2115033B1 (de) *	1970-11-24	1974-03-22	Roussel Uclaf

1977
- 1977-06-27 FR FR7719613A patent/FR2401173A1/fr active Granted
1978
- 1978-06-12 EP EP78400016A patent/EP0000300B1/de not_active Expired
- 1978-06-12 DE DE7878400016T patent/DE2861501D1/de not_active Expired
- 1978-06-15 US US05/915,601 patent/US4191697A/en not_active Expired - Lifetime
- 1978-06-23 CA CA306,095A patent/CA1130277A/fr not_active Expired
- 1978-06-26 JP JP7660378A patent/JPS5412362A/ja active Granted
- 1978-06-26 IT IT50022/78A patent/IT1105060B/it active
1986
- 1986-11-28 JP JP61282211A patent/JPS62142196A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3020294A (en) *	1950-03-28	1962-02-06	Syntex Sa	Production of ring a aromatic steroids
GB1151404A (en) *	1966-06-07	1969-05-07	Roussel Uclaf	Novel Gona-1,3,5(10)-Trienes, Processes for their Preparation, and Compositions incorporating them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 82 (1975) 43644y & YAKUGAKU ZASSHI, 1974 94(11) 1484-8. *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0431327A1 (de) *	1989-11-10	1991-06-12	Hoechst Aktiengesellschaft	Synthetische Vakzine zur spezifischen Induktion zytotoxischer T-Lymphozyten
EP3587369A1 (de)	2009-04-03	2020-01-01	Verescence France	Herstellungsverfahren eines glasbehälters
DE102017119621A1 (de)	2016-12-01	2018-06-07	Pouya Molana	Mayonnaise-Pulver-Zusammensetzung und Verfahren zur Herstellung eines Lebensmittelprodukts unter Verwendung eines solchen

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Publication number	Publication date
JPS62142196A (ja)	1987-06-25
JPS6220196B2 (de)	1987-05-06
JPS6360035B2 (de)	1988-11-22
DE2861501D1 (en)	1982-02-25
IT1105060B (it)	1985-10-28
FR2401173B1 (de)	1980-04-04
EP0000300B1 (de)	1982-01-06
JPS5412362A (en)	1979-01-30
IT7850022A0 (it)	1978-06-26
FR2401173A1 (fr)	1979-03-23
US4191697A (en)	1980-03-04
CA1130277A (fr)	1982-08-24

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Publication	Publication Date	Title
CH633811A5 (fr)	1982-12-31	Derives steroides 4,9-dieniques 11beta-substitues, procede de preparation et compositions pharmaceutiques.
EP0313960B1 (de)	1992-07-29	In Position-10 durch ein Radikal mit Doppel- bzw. Dreifachbindung substituierte Steroide und Verfahren zu ihrer Herstellung
EP0000300B1 (de)	1982-01-06	Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden
EP0024983B1 (de)	1984-07-25	Amino-14-steroidderivate und Verfahren zu ihrer Herstellung
CH652726A5 (fr)	1985-11-29	Derives steroides 17-oxazolines, leur procede de preparation et leur utilisation a la preparation de corticosteroides.
EP0443957B1 (de)	1995-05-10	Neue 17-spiro substituierte Steroide, Verfahren zu deren Herstellung und Zwischenprodukten davon, ihre Verwendung als Arzneimittel sowie pharmazeutische Präparate davon
CA1140110A (fr)	1983-01-25	Procede de preparation de nouveaux derives de l'androst-4-ene
CA1146531A (fr)	1983-05-17	Procede de preparation de nouveaux derives 2,2- dimethyl 19-nor steroides
CA1096857A (fr)	1981-03-03	PROCEDE DE PREPARATION DE NOUVEAUX DERIVES 17- SPIROSULTINES ET DES.gamma.-HYDROXY ACIDES
EP0275728B1 (de)	1991-05-29	Steroide, die in Stellung 23 eine Sulfinylgruppe tragen, Verfahren zu deren Herstellung, deren Verwendung zur Herstellung von Verbindungen der 20-Ketopregnanreihe sowie Zwischenprodukte zu dieser Verwendung
EP0058097B1 (de)	1984-07-25	Verfahren zur Herstellung von 17-alpha-Hydroxy-17beta-hydroxyacetyl-Steroiden und die erhaltenen entsprechenden Zwischenprodukte
EP0157842A1 (de)	1985-10-16	Verfahren zur herstellung von derivaten der 17 alpha-hydroxy-19-nor-progesteron-reihe.
CA1096372A (fr)	1981-02-24	Procede de preparation de nouveaux 2,2-dimethyl 19- nor steroides
EP0059146B1 (de)	1985-09-25	Arzneimittel, abgeleitet von 3-Hydroxy-dodecahydro-benz(e)inden-7-on, Produkte, abgeleitet von 3-Hydroxy-dodecahydro-benz(e)inden-7-on und Verfahren zu ihrer Herstellung
EP0013844B1 (de)	1981-11-04	Substituierte Penten-2-yl-Derivate von Malonsäure; Verfahren zu ihrer Herstellung und ihre Verwendung bei der Synthese eines Zwischenproduktes der Chrysanthemsäure
CA1122590A (fr)	1982-04-27	Steroides, leur procede de preparation et leur application dans la synthese de steroides marques au tritium
CH626378A5 (de)	1981-11-13
EP0184573A1 (de)	1986-06-11	Verfahren zur Herstellung von alpha-Hydroxyalkancarbonsäuren
CA1326235C (fr)	1994-01-18	Composes steroides utiles pour la preparation de produits de la serie 20-ceto pregnane
EP0595990A1 (de)	1994-05-11	Neue 6-substituierte steroide, verfahren zu deren herstellung sowie pharmazeutische präparate davon
CH629504A5 (en)	1982-04-30	19-Norpregnatetraene derivatives
CH410890A (fr)	1966-04-15	Procédé de préparation d'un nouveau réactif utile notamment pour l'obtention de certaines lactones de composés stéroïdes
FR2465748A1 (fr)	1981-03-27	A-nor-, a-nor-18-homo-steroides et leur procede de preparation
BE556145A (de)
FR2477146A1 (fr)	1981-09-04	Procede pour la preparation d'acide calcitroique et de ses esters, et composes ainsi obtenus

EP0000300A1 - Substituierte Estra-1,3,5(10),6-tetraene, Verfahren zur Herstellung und Verwendung in der Synthese von Tritium markierten Steroiden - Google Patents

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