BE714282A - - Google Patents

Info

Publication number: BE714282A
Authority: BE; Belgium
Prior art keywords: group; dione; acetate; diol; ester
Prior art date: 1968-04-26

Application number

Other languages

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.)

1968-04-26

Filing date

1968-04-26

Publication date

1968-09-16

1968-04-26 Application filed filed Critical

1968-09-16 Publication of BE714282A publication Critical patent/BE714282A/fr

Links

150000001875 compounds Chemical class 0.000 claims description 13
230000003647 oxidation Effects 0.000 claims description 13
238000007254 oxidation reaction Methods 0.000 claims description 13
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 9
230000035935 pregnancy Effects 0.000 claims description 8
-1 4 -Pregnene-6,20-diol-3-one Chemical compound 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
230000002175 menstrual effect Effects 0.000 claims description 6
229910019142 PO4 Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
239000010452 phosphate Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
238000003745 diagnosis Methods 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 6
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 5
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 5
238000006243 chemical reaction Methods 0.000 claims 3
241000575946 Ione Species 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
101100241859 Mus musculus Oacyl gene Proteins 0.000 claims 1
102100029781 NEDD8-activating enzyme E1 regulatory subunit Human genes 0.000 claims 1
101100539459 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uba5 gene Proteins 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
229910052782 aluminium Inorganic materials 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
239000011435 rock Substances 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
238000009835 boiling Methods 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
230000017105 transposition Effects 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
201000000736 Amenorrhea Diseases 0.000 description 3
206010001928 Amenorrhoea Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
231100000540 amenorrhea Toxicity 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound 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 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000009471 action Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000002405 diagnostic procedure Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000000762 glandular Effects 0.000 description 2
206010020718 hyperplasia Diseases 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000000203 mixture 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
238000001953 recrystallisation Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
241000269350 Anura Species 0.000 description 1
241000283074 Equus asinus Species 0.000 description 1
101150050733 Gnas gene Proteins 0.000 description 1
241000332699 Moneses Species 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical group [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000005842 biochemical reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
238000013399 early diagnosis Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000000366 juvenile effect Effects 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
230000005906 menstruation Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000002320 montanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
239000000583 progesterone congener Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

BE714282D 1968-04-26 1968-04-26 BE714282A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE714282		1968-04-26

Publications (1)

Publication Number	Publication Date
BE714282A true BE714282A (de)	1968-09-16

Family

ID=3852812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE714282D BE714282A (de)	1968-04-26	1968-04-26

Country Status (1)

Country	Link
BE (1)	BE714282A (de)

1968
- 1968-04-26 BE BE714282D patent/BE714282A/fr unknown

Publication	Publication Date	Title
FR2459248A1 (fr)	1981-01-09	Hemi-esters du cholesterol utilisables en medecine et leur procede de fabrication
EP0012639B1 (de)	1983-09-07	3-Quinoleincarbonsäure-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament und diese enthaltende Arzneimittel
CH627648A5 (fr)	1982-01-29	Nouveaux derives de 20,21-dinoreburnamenine, procede de preparation et compositions pharmaceutiques.
EP0012640B1 (de)	1982-05-05	Verfahren zur Reinigung von Chenodesoxycholsäure und nach diesem Verfahren erhaltene Produkte
EP0101383B1 (de)	1986-11-12	14-Aminosteroidderivate, ihre therapeutische Anwendung und Verfahren zu ihrer Herstellung
FR2499981A1 (fr)	1982-08-20	Acides amino-2 halogenobenzoyl-3 methylphenylacetiques et leurs esters et sels utiles comme medicaments anti-inflammatoires et analgesiques
BE1000157A5 (fr)	1988-06-28	Procede de preparation de derives de la moranoline.
EP0012641B1 (de)	1982-05-12	Substituierte-19-nor-pregn-4-en-3,20-dion-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
CA1096372A (fr)	1981-02-24	Procede de preparation de nouveaux 2,2-dimethyl 19- nor steroides
JPH02279696A (ja)	1990-11-15	高純度の３―α―７―β―ジヒドロキシコラン酸の調整方法
BE594849A (de)
US3873699A (en)	1975-03-25	Pharmacologically active substances isolated from {8 cadia ellisiana {b
CH622251A5 (de)	1981-03-31
CH619969A5 (en)	1980-10-31	Process for the preparation of new halogenated derivatives of the 16alpha-methylpregnane series
BE639708A (de)
BE632212A (de)
CH640233A5 (fr)	1983-12-30	Acides (4h) 1,3-benzodioxine 2-carboxyliques substitues et leurs esters, procedes pour leur preparation et compositions pharmaceutiques les renfermant.
BE503509A (de)
BE697967A (de)	1967-11-03
BE636257A (de)
BE571503A (de)
BE636675A (de)
BE887147A (fr)	1981-07-20	Nouveaux composes heterocycliques utiles comme agents antiallergiques
BE701544A (de)	1968-01-19
BE709614A (de)	1968-05-30