CS209915B2 - Method of making the 4-halogenpregna-1,4-dien-3,20-dions - Google Patents

Method of making the 4-halogenpregna-1,4-dien-3,20-dions Download PDF

Info

Publication number: CS209915B2
Authority: CS; Czechoslovakia
Prior art keywords: diene; dione; hydroxy; methyl; chloro
Prior art date: 1978-04-05

Application number

CS792305A

Other languages

Czech (cs)

English (en)

Inventor

Francisco S Alvarez

Original Assignee

Syntex Inc

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.)

1978-04-05

Filing date

1979-04-04

Publication date

1981-12-31

1979-04-04 Application filed by Syntex Inc filed Critical Syntex Inc

1981-12-31 Publication of CS209915B2 publication Critical patent/CS209915B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 67
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 23
-1 bromo, hydroxy Chemical group 0.000 claims abstract description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 20
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims description 63
229910052731 fluorine Inorganic materials 0.000 claims description 51
229910052801 chlorine Inorganic materials 0.000 claims description 46
239000011737 fluorine Substances 0.000 claims description 46
239000000460 chlorine Substances 0.000 claims description 40
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 29
230000008569 process Effects 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
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 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
150000003431 steroids Chemical class 0.000 abstract description 20
230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
241000124008 Mammalia Species 0.000 abstract description 6
125000004432 carbon atom Chemical group C* 0.000 abstract description 6
239000007787 solid Substances 0.000 abstract description 5
230000000699 topical effect Effects 0.000 abstract description 2
125000001246 bromo group Chemical group Br* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 90
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 67
239000000203 mixture Substances 0.000 description 57
238000006243 chemical reaction Methods 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 28
239000000047 product Substances 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 20
239000002904 solvent Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
239000002244 precipitate Substances 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 11
235000011181 potassium carbonates Nutrition 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000002585 base Substances 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
239000002253 acid Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 6
239000010410 layer Substances 0.000 description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
ZKLFRQSZDUSMQE-UHFFFAOYSA-N 5,5-dichloroimidazolidine-2,4-dione Chemical compound ClC1(Cl)NC(=O)NC1=O ZKLFRQSZDUSMQE-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000002674 ointment Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
150000002081 enamines Chemical class 0.000 description 4
150000002191 fatty alcohols Chemical class 0.000 description 4
229960003469 flumetasone Drugs 0.000 description 4
WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 description 4
229940043075 fluocinolone Drugs 0.000 description 4
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000004264 Petrolatum Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
206010047139 Vasoconstriction Diseases 0.000 description 3
230000021736 acetylation Effects 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
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238000004587 chromatography analysis Methods 0.000 description 3
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230000008020 evaporation Effects 0.000 description 3
210000000245 forearm Anatomy 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
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239000003381 stabilizer Substances 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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CBYCRMIWATZBBW-RDQPJNLGSA-N (8r,9s,10s,13s,14s)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(CC)[C@@]1(C)CC2 CBYCRMIWATZBBW-RDQPJNLGSA-N 0.000 description 2
PGWDPYGLSQZOMQ-NMKBPFOZSA-N (8s,10s,13r,14s,17s)-17-ethyl-10,13-dimethyl-6,7,8,12,14,15,16,17-octahydro-3h-cyclopenta[a]phenanthrene Chemical class C1C=C[C@]2(C)C3=CC[C@]4(C)[C@@H](CC)CC[C@H]4[C@@H]3CCC2=C1 PGWDPYGLSQZOMQ-NMKBPFOZSA-N 0.000 description 2
FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
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 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
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WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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239000004480 active ingredient Substances 0.000 description 2
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238000004458 analytical method Methods 0.000 description 2
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
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GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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239000007929 subcutaneous injection Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
229960005294 triamcinolone Drugs 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
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ISBSSBGEYIBVTO-TYKWNDPBSA-N (20R,22R)-20,22-dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC2 ISBSSBGEYIBVTO-TYKWNDPBSA-N 0.000 description 1
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom
- 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
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Steroid Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS792305A 1978-04-05 1979-04-04 Method of making the 4-halogenpregna-1,4-dien-3,20-dions CS209915B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US89364178A	1978-04-05	1978-04-05

Publications (1)

Publication Number	Publication Date
CS209915B2 true CS209915B2 (en)	1981-12-31

Family

ID=25401847

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS792305A CS209915B2 (en)	1978-04-05	1979-04-04	Method of making the 4-halogenpregna-1,4-dien-3,20-dions

Country Status (16)

Country	Link
EP (1)	EP0004766A3 (de)
JP (1)	JPS54135762A (de)
AR (1)	AR224124A1 (de)
AT (1)	ATA251679A (de)
AU (1)	AU4575379A (de)
CS (1)	CS209915B2 (de)
DK (1)	DK136379A (de)
ES (1)	ES479269A1 (de)
FI (1)	FI791080A7 (de)
GR (1)	GR66483B (de)
IL (1)	IL56989A0 (de)
IT (1)	IT7967708A0 (de)
NO (1)	NO791143L (de)
PL (1)	PL214677A1 (de)
PT (1)	PT69410A (de)
ZA (1)	ZA791637B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4340538A (en) *	1980-07-21	1982-07-20	The Upjohn Company	Process for producing 6α-fluoro-Δ1,4 -3-keto steroids
CN103391945B (zh) *	2011-03-15	2016-11-09	奇斯药制品公司	异噁唑烷衍生物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3125591A (en) *		1964-03-17		Derivatives thereof
FR1273890A (fr) *	1960-05-14	1961-10-20	Chimiotherapie Lab Franc	Procédé de préparation de stéroïdes 21-bromés
US3169131A (en) *	1963-03-29	1965-02-09	Upjohn Co	Process for the preparation of 4-fluorohydrocortisone, 21-acylates and 16-substituted derivatives thereof, and intermediates produced in the preparation thereof

1979
- 1979-03-30 AR AR276017A patent/AR224124A1/es active
- 1979-03-30 PT PT69410A patent/PT69410A/pt unknown
- 1979-03-31 GR GR58745A patent/GR66483B/el unknown
- 1979-04-02 EP EP79300542A patent/EP0004766A3/de not_active Withdrawn
- 1979-04-02 FI FI791080A patent/FI791080A7/fi not_active Application Discontinuation
- 1979-04-02 IL IL56989A patent/IL56989A0/xx unknown
- 1979-04-03 DK DK136379A patent/DK136379A/da unknown
- 1979-04-03 AU AU45753/79A patent/AU4575379A/en not_active Abandoned
- 1979-04-04 ES ES479269A patent/ES479269A1/es not_active Expired
- 1979-04-04 AT AT0251679A patent/ATA251679A/de unknown
- 1979-04-04 PL PL21467779A patent/PL214677A1/xx unknown
- 1979-04-04 NO NO791143A patent/NO791143L/no unknown
- 1979-04-04 IT IT7967708A patent/IT7967708A0/it unknown
- 1979-04-04 CS CS792305A patent/CS209915B2/cs unknown
- 1979-04-05 ZA ZA791637A patent/ZA791637B/xx unknown
- 1979-04-05 JP JP4041179A patent/JPS54135762A/ja active Pending

Also Published As

Publication number	Publication date
AR224124A1 (es)	1981-10-30
EP0004766A3 (de)	1979-10-31
ZA791637B (en)	1980-11-26
AU4575379A (en)	1979-10-11
JPS54135762A (en)	1979-10-22
DK136379A (da)	1979-10-06
ES479269A1 (es)	1980-01-16
ATA251679A (de)	1982-04-15
IL56989A0 (en)	1979-07-25
EP0004766A2 (de)	1979-10-17
NO791143L (no)	1979-10-08
FI791080A7 (fi)	1981-01-01
IT7967708A0 (it)	1979-04-04
PL214677A1 (de)	1980-01-02
PT69410A (fr)	1979-04-01
GR66483B (de)	1981-03-24

Publication	Publication Date	Title
EP0004773B1 (de)	1981-04-29	4-Halo-3-oxo-androst-4-en-17beta-thiocarbonsäureester, ihre pharmazeutische Anwendung und Verfahren zu ihrer Herstellung
EP0004741B1 (de)	1981-01-28	Thioetiansäurederivate, ihre Herstellung und ihre pharmazeutische Anwendung
US4267173A (en)	1981-05-12	Use of 6β-fluoro-7α-halogenocorticoids as topical anti-inflammatories and pharmaceutical formulations useful therefor
US4187301A (en)	1980-02-05	17 Beta-thiocarboxylic acid esters of 6 alpha, 6 beta-difluoro-3-oxoandrost-4-enes
US4172132A (en)	1979-10-23	1,3,5(10),6,8,14-19-Nor-pregnahexaenes, their use as anti-psoriatic agents, and pharmaceutical formulations useful therefor
US4261984A (en)	1981-04-14	17β-thiocarboxylic acid esters of 3-oxo-4-halo-16β-methylandrost-4-enes
US4226862A (en)	1980-10-07	Steroids and process for preparing the same
US4336200A (en)	1982-06-22	17α-Acyloxy-5β-corticoids
EP0029151B1 (de)	1985-09-25	6-Alpha-fluor-9-alpha-chlor-prednisolon-17,21-Diester, pharmazeutische Zusammensetzungen, die sie enthalten, und Zwischenprodukte
JPS596880B2 (ja)	1984-02-15	Ｄ−ホモステロイドの製造方法
US4318853A (en)	1982-03-09	9β,11β-Epoxy-5β-corticoids
US4024131A (en)	1977-05-17	16-Methyl-9α-halo steroid esters, ethers and preparation thereof
US4655971A (en)	1987-04-07	Novel process for the preparation of steroidal esters
EP0001864A1 (de)	1979-05-16	In 6-Stellung durch Sauerstoff substituierte 3,20-Dioxo-pregnanderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DK146017B (da)	1983-05-24	Analogifremgangsmaade til fremstilling af 17alfa-acyloxy-9alfa,21-dihalogen-11beta-hydroxy-6alfa-fluor-16beta-methyl-pregna-1,4-dien-3,20-dion-forbindelser
CS209915B2 (en)	1981-12-31	Method of making the 4-halogenpregna-1,4-dien-3,20-dions
US4427591A (en)	1984-01-24	Reduced A ring-Δ9(11) -corticoids
US4273770A (en)	1981-06-16	4-Halo steroids
US4232013A (en)	1980-11-04	16,17-Pyrazolino- and 16,17-isopyrazolino-1,4-pregnadiene derivatives
CA1129407A (en)	1982-08-10	Antiinflammatory steroid of the androstane series
US4261986A (en)	1981-04-14	4-Halo etianic acids and derivatives thereof
US4185101A (en)	1980-01-22	1,3,5(10),6,8-19-Nor-pregnapentaenes, their use as anti-psoriatic agents, and pharmaceutical formulations useful therefor
US4278669A (en)	1981-07-14	3-Oxo-4-halo-16β-methylandrost-4-ene 17β-carboxylic acids and esters
IE43979B1 (en)	1981-07-15	21-acetals and mixed acetals of steroidal 21-aldehydes,intermediates and methods of preparation
CS208494B2 (en)	1981-09-15	Method of making the alcylesters of the 4-halogen-3-oxoandrosta-1,4-dien-17 beta-cyrboxyl acid