BE564226A - - Google Patents

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Publication number: BE564226A
Authority: BE; Belgium
Prior art keywords: ether; hydroxy; pregn; alkyl; derivative
Prior art date

Application number

Other languages

Publication of BE564226A publication Critical patent/BE564226A/fr

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RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 118
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 33
238000000034 method Methods 0.000 claims description 31
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
BUDQDWGNQVEFAC-UHFFFAOYSA-N 3,4-dihydro-2H-pyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
-1 alkyl sulfate halide Chemical class 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 13
235000006408 oxalic acid Nutrition 0.000 claims description 11
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
230000008929 regeneration Effects 0.000 claims description 5
238000011069 regeneration method Methods 0.000 claims description 5
239000012445 acidic reagent Substances 0.000 claims description 4
125000004432 carbon atoms Chemical group C* 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
QYKIQEUNHZKYBP-UHFFFAOYSA-N vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
230000002152 alkylating Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 39
238000002844 melting Methods 0.000 description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
239000000203 mixture Substances 0.000 description 31
150000001875 compounds Chemical class 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 26
229910001868 water Inorganic materials 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 15
XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
229910052744 lithium Inorganic materials 0.000 description 11
238000010992 reflux Methods 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000008079 hexane Substances 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
235000019270 ammonium chloride Nutrition 0.000 description 8
229920000591 gum Polymers 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
239000008101 lactose Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
239000008107 starch Substances 0.000 description 6
HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000010790 dilution Methods 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000001072 progestational Effects 0.000 description 5
238000000746 purification Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
AFRJJFRNGGLMDW-UHFFFAOYSA-N Lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000005712 crystallization Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
PVWOIHVRPOBWPI-UHFFFAOYSA-N N-Propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000004072 triols Chemical class 0.000 description 3
OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
LVGKNOAMLMIIKO-QXMHVHEDSA-N Ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229940093471 ethyl oleate Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
230000004927 fusion Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
229940094025 potassium bicarbonate Drugs 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
238000005303 weighing Methods 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
229940063655 Aluminum stearate Drugs 0.000 description 1
206010001928 Amenorrhoea Diseases 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
CHNXZKVNWQUJIB-CEGNMAFCSA-N Ethisterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 CHNXZKVNWQUJIB-CEGNMAFCSA-N 0.000 description 1
229960000445 Ethisterone Drugs 0.000 description 1
208000007106 Menorrhagia Diseases 0.000 description 1
210000001331 Nose Anatomy 0.000 description 1
FEMRXDWBWXQOGV-UHFFFAOYSA-N Potassium amide Chemical compound [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 description 1
206010036618 Premenstrual syndrome Diseases 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
210000004291 Uterus Anatomy 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
201000000736 amenorrhea Diseases 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drugs Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 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
238000001914 filtration Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
230000002085 persistent Effects 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
201000000484 premenstrual tension Diseases 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001172 regenerating Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
201000010874 syndrome Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

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Steroid Compounds (AREA)

BE564226D BE564226A (ja)

Publications (1)

Publication Number	Publication Date
BE564226A true BE564226A (ja)

Family

ID=185171

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE564226D BE564226A (ja)

Country Status (1)

Country	Link
BE (1)	BE564226A (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2002160A1 (ja) *	1968-02-19	1969-10-17	Sandoz Sa

0
- BE BE564226D patent/BE564226A/fr unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2002160A1 (ja) *	1968-02-19	1969-10-17	Sandoz Sa

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