DK167534B1 - 19-substituerede progesteronderivater - Google Patents

19-substituerede progesteronderivater Download PDF

Info

Publication number: DK167534B1
Authority: DK; Denmark
Prior art keywords: hydroxy; solution; ether; propynyl; compound
Prior art date: 1988-06-28

Application number

DK318589A

Other languages

Danish (da)

English (en)

Other versions

DK318589D0 (da

DK318589A (da

Inventor

Gene Warwick Holbert

John O'neal Johnston

Original Assignee

Merrell Dow Pharma

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.)

1988-06-28

Filing date

1989-06-27

Publication date

1993-11-15

1989-06-27 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1989-06-27 Publication of DK318589D0 publication Critical patent/DK318589D0/da

1989-12-29 Publication of DK318589A publication Critical patent/DK318589A/da

1993-11-15 Application granted granted Critical

1993-11-15 Publication of DK167534B1 publication Critical patent/DK167534B1/da

Links

239000000758 substrate Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 46
150000003145 progesterone derivatives Chemical class 0.000 claims abstract description 4
FRJMUTSJHOCODZ-ACXQXYJUSA-N (8s,9s,10s,13s,14s,17s)-17-(2-hydroxyacetyl)-13-methyl-10-prop-2-ynyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical group O=C1CC[C@]2(CC#C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 FRJMUTSJHOCODZ-ACXQXYJUSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000003112 inhibitor Substances 0.000 abstract description 5
229940030600 antihypertensive agent Drugs 0.000 abstract description 3
239000002220 antihypertensive agent Substances 0.000 abstract description 3
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Natural products C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract 1
230000037361 pathway Effects 0.000 abstract 1
229960003387 progesterone Drugs 0.000 abstract 1
239000000186 progesterone Substances 0.000 abstract 1
150000003146 progesterones Chemical class 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 23
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
229910052943 magnesium sulfate Inorganic materials 0.000 description 18
235000019341 magnesium sulphate Nutrition 0.000 description 18
239000012267 brine Substances 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000013078 crystal Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
241000700159 Rattus Species 0.000 description 12
150000003431 steroids Chemical class 0.000 description 11
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
238000000034 method Methods 0.000 description 9
ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 8
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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238000003556 assay Methods 0.000 description 6
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230000005764 inhibitory process Effects 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
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ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 5
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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YLERVAXAQFOFRI-UHFFFAOYSA-M magnesium;propa-1,2-diene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C#C YLERVAXAQFOFRI-UHFFFAOYSA-M 0.000 description 3
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
238000006036 Oppenauer oxidation reaction Methods 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000002202 Polyethylene glycol Substances 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241000282887 Suidae Species 0.000 description 1
MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
229960002478 aldosterone Drugs 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000003886 aromatase inhibitor Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
AQRHTGSVDQECPZ-UHFFFAOYSA-N azane;lithium Chemical compound [Li].N AQRHTGSVDQECPZ-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229920002988 biodegradable polymer Polymers 0.000 description 1
239000004621 biodegradable polymer Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001844 chromium Chemical class 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000000981 epithelium Anatomy 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000013299 hypertensive rat model Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000002438 mitochondrial effect Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000006225 natural substrate Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920000260 silastic Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
239000008399 tap water Substances 0.000 description 1
150000003515 testosterones Chemical class 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
238000012549 training Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- 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
- C07J5/0007—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 not substituted in position 17 alfa
- C07J5/0015—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 not substituted in position 17 alfa not substituted in position 16
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
- 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
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
- 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
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
- C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DK318589A 1988-06-28 1989-06-27 19-substituerede progesteronderivater DK167534B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US21240988		1988-06-28
US07/212,409 US4910191A (en)	1988-06-28	1988-06-28	19-substituted progesterone derivatives useful as 19-hydroxylase inhibitors

Publications (3)

Publication Number	Publication Date
DK318589D0 DK318589D0 (da)	1989-06-27
DK318589A DK318589A (da)	1989-12-29
DK167534B1 true DK167534B1 (da)	1993-11-15

Family

ID=22790892

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK318589A DK167534B1 (da)	1988-06-28	1989-06-27	19-substituerede progesteronderivater

Country Status (20)

Country	Link
US (1)	US4910191A (no)
EP (1)	EP0348910B1 (no)
JP (1)	JP2729320B2 (no)
KR (1)	KR0160280B1 (no)
CN (1)	CN1033032C (no)
AT (1)	ATE122681T1 (no)
AU (1)	AU610473B2 (no)
CA (1)	CA1321578C (no)
DE (1)	DE68922660T2 (no)
DK (1)	DK167534B1 (no)
ES (1)	ES2075014T3 (no)
FI (1)	FI92706C (no)
HU (1)	HU204066B (no)
IE (1)	IE66338B1 (no)
IL (1)	IL90727A (no)
NO (1)	NO174511B (no)
NZ (1)	NZ229696A (no)
PH (1)	PH25714A (no)
PT (1)	PT90988B (no)
ZA (1)	ZA894754B (no)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4433374A1 (de) *	1994-09-20	1996-03-21	Hoechst Ag	17-Desoxi-corticosteroid-21-/O/-Carbonsäure- ester, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
US7053228B2 (en)	2000-09-18	2006-05-30	Applied Research Systems Ars Holding N.V.	Sulfur analogues of 21-hydroxy-6,19-oxidoprogesterone (21OH-6OP) for treating excess of glucocorticoids
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)
EP2061440A2 (en) *	2007-04-04	2009-05-27	Sigmoid Pharma Limited	A pharmaceutical composition of tacrolimus
JP5640079B2 (ja)	2009-05-18	2014-12-10	シグモイド・ファーマ・リミテッドＳｉｇｍｏｉｄＰｈａｒｍａＬｉｍｉｔｅｄ	油滴含有組成物
GB201020032D0 (en)	2010-11-25	2011-01-12	Sigmoid Pharma Ltd	Composition
CN102268058B (zh) *	2011-05-24	2012-10-10	湖南诺凯生物医药有限公司	制备17α-羟基孕酮或其类似物的方法
GB201212010D0 (en)	2012-07-05	2012-08-22	Sigmoid Pharma Ltd	Formulations
GB201319791D0 (en)	2013-11-08	2013-12-25	Sigmoid Pharma Ltd	Formulations
EP3215127B1 (en)	2014-11-07	2020-10-28	Sublimity Therapeutics Limited	Compositions comprising cyclosporin

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1051693A (no) *	1962-07-09
US3275622A (en) *	1963-12-18	1966-09-27	Syntex Corp	19-alkylidene-delta4-3, 20-keto pregnanes
US3275621A (en) *	1963-12-18	1966-09-27	Syntex Corp	19-amino-delta4-pregnenes and-10alpha-pregnenes and process for their preparation
US3558673A (en) *	1966-10-29	1971-01-26	Ormonoterapia Richter Spa	10beta-amino-19-nor-pregnanes and method for the preparation thereof
US3849402A (en) *	1971-01-06	1974-11-19	Steele Chem Co Ltd	19-oxygenated and 19-nor delta8(14)-steroid compounds
US4041055A (en) *	1975-11-17	1977-08-09	The Upjohn Company	Process for the preparation of 17α-hydroxyprogesterones and corticoids from androstenes
FR2462445A1 (fr) *	1979-07-31	1981-02-13	Roussel Uclaf	Nouveaux derives 17-/(hydroxymethyl) (formamido) methylene/steroides, leur procede de preparation et leur application a l'introduction de la chaine laterale hydroxyacetyle
US4322416A (en) *	1980-06-27	1982-03-30	Merrell Dow Pharmaceuticals Inc.	10-Alkynyl steroids
US4289762A (en) *	1980-06-27	1981-09-15	Merrell Dow Pharmaceuticals Inc.	10-(1,2-Propadienyl) steroids as irreversible aromatase inhibitors
US4293548A (en) *	1980-09-02	1981-10-06	Merrell Dow Pharmaceuticals Inc.	18-Substituted pregn-4-ene-3,20-diones
FR2498607A1 (fr) *	1981-01-29	1982-07-30	Roussel Uclaf	Nouveau procede de preparation de 17a-hydroxy 17b-hydroxyacetyle steroides, produits intermediaires correspondants et produits finals obtenus
US4495102A (en) *	1982-09-03	1985-01-22	G. D. Searle & Co.	Aminoalkyl steroids
US4473564A (en) *	1983-07-12	1984-09-25	Akzo N.V.	19-Thio-androstane derivatives
FR2576025B1 (fr) *	1985-01-14	1987-01-23	Roussel Uclaf	Nouveaux steroides substitues en position 10, leur procede et les intermediaires de preparation, leur application comme medicaments, les compositions pharmaceutiques les contenant
GB8531745D0 (en) *	1985-12-24	1986-02-05	Erba Farmitalia	10beta-alkynyl-4-9(11)-estradiene derivatives

1988
- 1988-06-28 US US07/212,409 patent/US4910191A/en not_active Expired - Lifetime
1989
- 1989-06-22 ZA ZA894754A patent/ZA894754B/xx unknown
- 1989-06-23 IL IL90727A patent/IL90727A/xx not_active IP Right Cessation
- 1989-06-23 NZ NZ229696A patent/NZ229696A/en unknown
- 1989-06-27 AT AT89111698T patent/ATE122681T1/de not_active IP Right Cessation
- 1989-06-27 DK DK318589A patent/DK167534B1/da not_active IP Right Cessation
- 1989-06-27 IE IE208689A patent/IE66338B1/en not_active IP Right Cessation
- 1989-06-27 KR KR1019890008839A patent/KR0160280B1/ko not_active Expired - Fee Related
- 1989-06-27 ES ES89111698T patent/ES2075014T3/es not_active Expired - Lifetime
- 1989-06-27 NO NO892678A patent/NO174511B/no not_active IP Right Cessation
- 1989-06-27 PT PT90988A patent/PT90988B/pt not_active IP Right Cessation
- 1989-06-27 CA CA000604023A patent/CA1321578C/en not_active Expired - Lifetime
- 1989-06-27 JP JP1162846A patent/JP2729320B2/ja not_active Expired - Lifetime
- 1989-06-27 EP EP89111698A patent/EP0348910B1/en not_active Expired - Lifetime
- 1989-06-27 PH PH38860A patent/PH25714A/en unknown
- 1989-06-27 DE DE68922660T patent/DE68922660T2/de not_active Expired - Lifetime
- 1989-06-27 HU HU893241A patent/HU204066B/hu not_active IP Right Cessation
- 1989-06-28 AU AU37127/89A patent/AU610473B2/en not_active Ceased
- 1989-06-28 CN CN89104356A patent/CN1033032C/zh not_active Expired - Fee Related
- 1989-06-28 FI FI893163A patent/FI92706C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK318589D0 (da)	1989-06-27
PT90988B (pt)	1994-11-30
DE68922660D1 (de)	1995-06-22
ES2075014T3 (es)	1995-10-01
IL90727A (en)	1993-05-13
HU204066B (en)	1991-11-28
AU610473B2 (en)	1991-05-16
DK318589A (da)	1989-12-29
NO892678D0 (no)	1989-06-27
NZ229696A (en)	1992-03-26
IE66338B1 (en)	1995-12-27
EP0348910A3 (en)	1990-03-21
PT90988A (pt)	1989-12-29
CN1039593A (zh)	1990-02-14
ATE122681T1 (de)	1995-06-15
KR910000588A (ko)	1991-01-29
FI92706C (fi)	1994-12-27
FI92706B (fi)	1994-09-15
DE68922660T2 (de)	1996-01-18
CA1321578C (en)	1993-08-24
CN1033032C (zh)	1996-10-16
NO174511B (no)	1994-02-07
FI893163L (fi)	1989-12-29
EP0348910B1 (en)	1995-05-17
AU3712789A (en)	1990-01-04
NO892678L (no)	1989-12-29
NO174511C (no)	1994-05-18
JPH0248598A (ja)	1990-02-19
HUT51288A (en)	1990-04-28
IE892086L (en)	1989-12-28
PH25714A (en)	1991-09-18
EP0348910A2 (en)	1990-01-03
JP2729320B2 (ja)	1998-03-18
KR0160280B1 (ko)	1998-11-16
IL90727A0 (en)	1990-01-18
US4910191A (en)	1990-03-20
ZA894754B (en)	1990-05-30
FI893163A0 (fi)	1989-06-28

Publication	Publication Date	Title
EP0097572B1 (fr)	1986-11-05	Nouveaux 19-nor stéroides substitués en 11 et éventuellement en 2,leur préparation, leur application comme médicaments, les compositions les renfermant et les nouveaux intermédiaires obtenus
US4322416A (en)	1982-03-30	10-Alkynyl steroids
FR2497807A1 (fr)	1982-07-16	Nouveaux derives steroides substitues en 11b, leur proc ede de preparation et leur application comme medicament
NO178264B (no)	1995-11-13
DK167534B1 (da)	1993-11-15	19-substituerede progesteronderivater
US4081537A (en)	1978-03-28	Δ15 -Steroids and pharmaceutical compositions thereof
CH647532A5 (de)	1985-01-31	10-(1,2-propadienyl)-steroide und pharmazeutische zubereitungen, die diese verbindungen enthalten.
US5166201A (en)	1992-11-24	2β,19-ethylene bridged steroids as aromatase inhibitors
US4920114A (en)	1990-04-24	19-fluoro- or cyano-21-hydroxyprogesterone derivatives useful as 19-hydroxylase inhibitors
Klimstra et al.	1965	Anabolic Agents. A-Ring Conjugated Enone Androstane Derivatives1a
US4293548A (en)	1981-10-06	18-Substituted pregn-4-ene-3,20-diones

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