IL30547A - 6,9,11-trihalo-16alpha-methyl-pregna-1,4-diene-3,20-diones - Google Patents

6,9,11-trihalo-16alpha-methyl-pregna-1,4-diene-3,20-diones

Info

Publication number: IL30547A
Authority: IL; Israel
Prior art keywords: halogen; halogen atom; pregnadi; pharmaceutical preparation; yielding
Prior art date: 1967-08-16

Application number

IL30547A

Other languages

English (en)

Other versions

IL30547A0 (en

Original Assignee

Schering 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.)

1967-08-16

Filing date

1968-08-13

Publication date

1973-03-30

1967-08-16 Priority claimed from DE19671643036 external-priority patent/DE1643036C3/de

1968-08-13 Application filed by Schering Ag filed Critical Schering Ag

1968-10-24 Publication of IL30547A0 publication Critical patent/IL30547A0/xx

1973-03-30 Publication of IL30547A publication Critical patent/IL30547A/en

Links

150000001875 compounds Chemical class 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
150000003431 steroids Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
125000001309 chloro group Chemical group Cl* 0.000 claims 2
101150062190 sod1 gene Proteins 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
-1 hydrogen halides Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
239000013589 supplement Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
229920002527 Glycogen Polymers 0.000 description 1
DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000008350 Pruritus Vulvae Diseases 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
102000003929 Transaminases Human genes 0.000 description 1
108090000340 Transaminases Proteins 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
206010056530 Vulvovaginal pruritus Diseases 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000023852 carbohydrate metabolic process Effects 0.000 description 1
235000021256 carbohydrate metabolism Nutrition 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
229940096919 glycogen Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000037311 normal skin Effects 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229940020414 potassium triiodide Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide 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
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
ITQQKJGENXWHJK-UHFFFAOYSA-M sodium;hydrogen carbonate;sulfurous acid Chemical compound [Na+].OC(O)=O.OS([O-])=O ITQQKJGENXWHJK-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- 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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL30547A 1967-08-16 1968-08-13 6,9,11-trihalo-16alpha-methyl-pregna-1,4-diene-3,20-diones IL30547A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19671643036 DE1643036C3 (de)	1967-08-16	1967-08-16	Neue 11 beta-Halogensterolde, diese enthaltende Arzneimittel sowie Verfahren zu ihrer Herstellung

Publications (2)

Publication Number	Publication Date
IL30547A0 IL30547A0 (en)	1968-10-24
IL30547A true IL30547A (en)	1973-03-30

Family

ID=5684239

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30547A IL30547A (en)	1967-08-16	1968-08-13	6,9,11-trihalo-16alpha-methyl-pregna-1,4-diene-3,20-diones

Country Status (4)

Country	Link
CH (1)	CH512458A (pl)
IL (1)	IL30547A (pl)
NO (1)	NO128492B (pl)
PL (1)	PL71425B1 (pl)

1968
- 1968-07-22 CH CH1093268A patent/CH512458A/de not_active IP Right Cessation
- 1968-08-13 IL IL30547A patent/IL30547A/en unknown
- 1968-08-15 NO NO03203/68A patent/NO128492B/no unknown
- 1968-08-16 PL PL1968128659A patent/PL71425B1/pl unknown

Also Published As

Publication number	Publication date
IL30547A0 (en)	1968-10-24
CH512458A (de)	1971-09-15
NO128492B (pl)	1973-11-26
PL71425B1 (pl)	1974-06-29

Publication	Publication Date	Title
JPS61218595A (ja)	1986-09-29	新規スピロラクトン、その製法及びこれを含有する利尿剤
US2301811A (en)	1942-11-10	2-keto-levo-gulonic acid and process for the manufacture of same
SU664565A3 (ru)	1979-05-25	Способ получени пиридо (1,2а) пиримидинов или их оптических изомеров
US3609171A (en)	1971-09-28	11-halogen-substituted steroids
DE2007417A1 (de)	1970-09-03	Ein neues Oestratriol und ein Verfahren zu dessen Herstellung
Bowers et al.	1958	Steroids. XCV. 1 Synthesis of 6α-Methyl-21-desoxycortisone. A New Route to 6α-Methylcortisone
JPS5946292A (ja)	1984-03-15	２−置換セフエム誘導体の製造法
US3723484A (en)	1973-03-27	17-chloro steroids
IL30547A (en)	1973-03-30	6,9,11-trihalo-16alpha-methyl-pregna-1,4-diene-3,20-diones
SU730311A3 (ru)	1980-04-25	Способ получени кортикоидов
US3681405A (en)	1972-08-01	Novel 21,21-dichlorosteroids
SU890979A3 (ru)	1981-12-15	Способ получени кортикоидов
Gomer et al.	1944	Some glycol complexes of the light transition metals
US3718671A (en)	1973-02-27	21-halogen steroids
Bonner	1948	The Cleavage of Tetraacetyl-β-D-thioglucosides with Bromine in Acetic Acid1
US3474115A (en)	1969-10-21	Water soluble aldosterone like agents
US2824882A (en)	1958-02-25	16-cyano-7-oxopregnenolone and derivatives
US3001991A (en)	1961-09-26	16alpha,17alpha-isoalkylidenedioxy-4-pregnene-3,20-diones
IL34347A (en)	1973-10-25	New 2-chloro-delta1,4-steroids of the pregnane series
US2917510A (en)	1959-12-15	18-oxygenated-delta-3,20-dioxo-9alpha-halopregnenes
PL87291B1 (pl)	1976-06-30
US3300519A (en)	1967-01-24	6beta-thiocyanato pregnane derivatives
US3776946A (en)	1973-12-04	Chlorphenesin derivatives
US2892850A (en)	1959-06-30	21-chloro steroids
JPS5951941B2 (ja)	1984-12-17	カルボスチリル誘導体