CH576999A5 - Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes - Google Patents

Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes

Info

Publication number: CH576999A5
Authority: CH; Switzerland
Prior art keywords: formula; fluoro; treated; dependent; compound
Prior art date: 1973-02-28

Application number

CH295073A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1973-02-28

Filing date

1973-02-28

Publication date

1976-06-30

1973-02-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-02-28 Priority to CH295073A priority Critical patent/CH576999A5/de

1974-02-12 Priority to CA192,331A priority patent/CA1034113A/fr

1974-02-18 Priority to NL7402206A priority patent/NL7402206A/xx

1974-02-19 Priority to DE19742407813 priority patent/DE2407813A1/de

1974-02-26 Priority to AU66011/74A priority patent/AU479188B2/en

1974-02-26 Priority to GB861974A priority patent/GB1457802A/en

1974-02-26 Priority to FR7406452A priority patent/FR2218897B1/fr

1974-02-27 Priority to AT160974A priority patent/AT336812B/de

1974-02-27 Priority to BE141441A priority patent/BE811633A/fr

1974-02-28 Priority to JP2296274A priority patent/JPS49134667A/ja

1975-07-25 Priority to AT576675A priority patent/AT338446B/de

1975-07-25 Priority to AT576575A priority patent/AT337373B/de

1975-07-25 Priority to AT576475A priority patent/AT337372B/de

1975-09-25 Priority to US05/616,518 priority patent/US4002614A/en

1976-06-30 Publication of CH576999A5 publication Critical patent/CH576999A5/de

Links

-1 Halogenated 19-nor pregnane steroids Chemical class 0.000 title abstract description 32
150000000317 19-norpregnenes Chemical class 0.000 title 1
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims abstract description 6
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000000460 chlorine Chemical group 0.000 claims description 3
150000002084 enol ethers Chemical class 0.000 claims description 3
239000011737 fluorine Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
241001465754 Metazoa Species 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 3
230000016087 ovulation Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 2
230000003152 gestagenic effect Effects 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ALSXNTIVNJBNQE-ZWONNITHSA-N (8r,9r,10s,13r,14s,17s)-17-ethyl-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-hexadecahydrocyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC)[C@@]1(C)CC2 ALSXNTIVNJBNQE-ZWONNITHSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
USAYMJGCALIGIG-UHFFFAOYSA-N 2,3-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=C(Cl)C(=O)C=CC1=O USAYMJGCALIGIG-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
JWMFYGXQPXQEEM-NUNROCCHSA-N 5β-pregnane Chemical compound C([C@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](CC)[C@@]2(C)CC1 JWMFYGXQPXQEEM-NUNROCCHSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
239000000543 intermediate Substances 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
238000005907 ketalization reaction Methods 0.000 description 1
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
OEOFQABUOAWYMP-UHFFFAOYSA-N oxiren-2-ol Chemical compound OC1=CO1 OEOFQABUOAWYMP-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension 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
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH295073A 1973-02-28 1973-02-28 Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes CH576999A5 (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
CH295073A CH576999A5 (en)	1973-02-28	1973-02-28	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
CA192,331A CA1034113A (fr)	1973-02-28	1974-02-12	Norsteroides-19 halogenes
NL7402206A NL7402206A (fr)	1973-02-28	1974-02-18
DE19742407813 DE2407813A1 (de)	1973-02-28	1974-02-19	Halogenierte 19-norsteroide
AU66011/74A AU479188B2 (en)	1973-02-28	1974-02-26	Halogenated 19-norsteroids
GB861974A GB1457802A (fr)	1973-02-28	1974-02-26
FR7406452A FR2218897B1 (fr)	1973-02-28	1974-02-26
AT160974A AT336812B (de)	1973-02-28	1974-02-27	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
BE141441A BE811633A (fr)	1973-02-28	1974-02-27	19-norsteroides halogenes
JP2296274A JPS49134667A (fr)	1973-02-28	1974-02-28
AT576675A AT338446B (de)	1973-02-28	1975-07-25	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
AT576575A AT337373B (de)	1973-02-28	1975-07-25	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
AT576475A AT337372B (de)	1973-02-28	1975-07-25	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
US05/616,518 US4002614A (en)	1973-02-28	1975-09-25	Halogenated 19-norsteroids

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH295073A CH576999A5 (en)	1973-02-28	1973-02-28	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes

Publications (1)

Publication Number	Publication Date
CH576999A5 true CH576999A5 (en)	1976-06-30

Family

ID=4245283

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH295073A CH576999A5 (en)	1973-02-28	1973-02-28	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes

Country Status (2)

Country	Link
BE (1)	BE811633A (fr)
CH (1)	CH576999A5 (fr)

1973
- 1973-02-28 CH CH295073A patent/CH576999A5/de not_active IP Right Cessation
1974
- 1974-02-27 BE BE141441A patent/BE811633A/fr unknown

Also Published As

Publication number	Publication date
BE811633A (fr)	1974-08-27

Legal Events

Date	Code	Title	Description
1979-12-14	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH647532A5 (de)	1985-01-31	10-(1,2-propadienyl)-steroide und pharmazeutische zubereitungen, die diese verbindungen enthalten.
DE1443682C3 (de)	1973-12-20	7 alpha, 17 alpha-Dimethyl-östradiol und sein 3-Methyläther, Verfahren zu deren Herstellung und diese enthaltende pharma zeutische Präparate
DE1120446B (de)	1961-12-28	Verfahren zur Herstellung von 6-Methyl-3-oxo-í¸-steroiden
CH576999A5 (en)	1976-06-30	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
AT337372B (de)	1977-06-27	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
CH582716A5 (en)	1976-12-15	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
DE1188079B (de)	1965-03-04	Verfahren zur Herstellung von 17alpha, 21-Dioxysteroiden
CH577002A5 (en)	1976-06-30	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
CH577001A5 (en)	1976-06-30	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
DE1568502C3 (de)	1974-11-28	3-Cyanmethylen-androstene und -östrene und Verfahren zu ihrer Herstellung
CH577000A5 (en)	1976-06-30	Halogenated 19-nor pregnane steroids - prepd. by introduction of 6,7-double bond in corresp. 19-nor pregnenes
DE2055895A1 (de)	1971-05-27	Verfahren zur Herstellung von Steroiddenvaten
AT337373B (de)	1977-06-27	Verfahren zur herstellung von neuen 21-fluor-19-norpregnadienverbindungen
DE1267218B (de)	1968-05-02	Verfahren zur Herstellung von 19-Oxy-delta 4-3-keto-steroiden der Androstan- bzw. Pregnanreihe
AT282085B (de)	1970-06-10	Verfahren zur herstellung von neuen steroiden
DE1793676C2 (de)	1973-01-04	Verfahren zur Herstellung von Delta 4-bzw. Delta 5-ungesättigten Steroiden der Androstan-, Pregnan- und Sapogeninreihe mit einer Carboxylgruppe in 19-Stellung
AT233184B (de)	1964-04-25	Verfahren zur Herstellung von 3-Oxo-Δ<1,4>-steroiden
DE1493093C3 (fr)	1974-04-25
CH549001A (de)	1974-05-15	Verfahren zur herstellung neuer halogensteroide.
CH548992A (de)	1974-05-15	Verfahren zur herstellung neuer halogensteroide.
DE1177151B (de)	1964-09-03	Verfahren zur Herstellung von 16-Chlormethylen- bzw. 16-Brommethylen-steroiden
DE1224309B (de)	1966-09-08	Verfahren zur Herstellung von delta 4,6-3-Oxo-19-nor-steroiden
DE1134987B (de)	1962-08-23	Verfahren zur Herstellung von 17ª‡-Acyloxy-6-methyl-16-methylen-pregna-4, 6-dien-3, 20-dionen
CH513838A (de)	1971-10-15	Verfahren zur Herstellung von 17a-Propadiensteroiden
DE1136331B (de)	1962-09-13	Verfahren zur Herstellung von 4-Chlor- bzw. 4-Brom í¸-3-Ketonen der Androstan- oder Pregnanreihe