DE1918291A1 - Verwendung von substituierten Aminen zum Stabilisieren von Oestrogensulfaten - Google Patents
Verwendung von substituierten Aminen zum Stabilisieren von OestrogensulfatenInfo
- Publication number
- DE1918291A1 DE1918291A1 DE19691918291 DE1918291A DE1918291A1 DE 1918291 A1 DE1918291 A1 DE 1918291A1 DE 19691918291 DE19691918291 DE 19691918291 DE 1918291 A DE1918291 A DE 1918291A DE 1918291 A1 DE1918291 A1 DE 1918291A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfate
- days
- sulfates
- stabilize
- substituted amines
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title claims description 7
- 229940011871 estrogen Drugs 0.000 title description 8
- 239000000262 estrogen Substances 0.000 title description 8
- 150000001412 amines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 5
- PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 claims description 5
- PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical compound OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 claims description 5
- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 claims description 5
- WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- WKRLQDKEXYKHJB-HFTRVMKXSA-N equilin Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 WKRLQDKEXYKHJB-HFTRVMKXSA-N 0.000 claims description 4
- 229960003399 estrone Drugs 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910000394 calcium triphosphate Inorganic materials 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- RFWLACFDYFIVMC-UHFFFAOYSA-D pentacalcium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O RFWLACFDYFIVMC-UHFFFAOYSA-D 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 8
- JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- JKKFKPJIXZFSSB-UHFFFAOYSA-N 1,3,5(10)-estratrien-17-one 3-sulfate Natural products OS(=O)(=O)OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 JKKFKPJIXZFSSB-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 2
- JYVKZELXZLJWPU-UHFFFAOYSA-N 2-(ethylamino)ethane-1,1,1-triol Chemical compound CCNCC(O)(O)O JYVKZELXZLJWPU-UHFFFAOYSA-N 0.000 description 2
- YKQVKNLXXNLCBR-UHFFFAOYSA-N 3-(methylamino)propane-1,1,1-triol Chemical compound CNCCC(O)(O)O YKQVKNLXXNLCBR-UHFFFAOYSA-N 0.000 description 2
- -1 Oestron Chemical compound 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
- YJBYRYVLFAUXBJ-HFTRVMKXSA-N [(9s,13s,14s)-13-methyl-17-oxo-9,11,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 YJBYRYVLFAUXBJ-HFTRVMKXSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- ZXIYZDSEASMXPI-UHFFFAOYSA-N 2-(methylamino)ethane-1,1,1-triol Chemical compound CNCC(O)(O)O ZXIYZDSEASMXPI-UHFFFAOYSA-N 0.000 description 1
- HOBGCONPBCCQHM-UHFFFAOYSA-N 2-(methylamino)ethane-1,1-diol Chemical compound CNCC(O)O HOBGCONPBCCQHM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-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 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 229940106582 estrogenic substances Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6805153A NL6805153A (enrdf_load_stackoverflow) | 1968-04-10 | 1968-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1918291A1 true DE1918291A1 (de) | 1969-10-23 |
Family
ID=19803313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691918291 Pending DE1918291A1 (de) | 1968-04-10 | 1969-04-10 | Verwendung von substituierten Aminen zum Stabilisieren von Oestrogensulfaten |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE731328A (enrdf_load_stackoverflow) |
| DE (1) | DE1918291A1 (enrdf_load_stackoverflow) |
| DK (1) | DK122260B (enrdf_load_stackoverflow) |
| FR (1) | FR2007431A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1262971A (enrdf_load_stackoverflow) |
| NL (1) | NL6805153A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0380021A3 (en) * | 1989-01-24 | 1991-01-09 | Abbott Laboratories | Stabilizing system for solid dosage forms |
| WO1993017036A1 (en) * | 1992-02-26 | 1993-09-02 | American Home Products Corporation | Alkali metal 8,9-dehydroestrone sulfate esters |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030158432A1 (en) * | 2002-01-08 | 2003-08-21 | Leonard Thomas W. | Synthesis of a mixture of sulfated estrogens using a sulfur trioxide complex |
| FR3112577B1 (fr) | 2020-07-15 | 2022-07-15 | Psa Automobiles Sa | Procede de determination de l’avance a l’allumage d’un moteur a combustion interne a allumage commande |
-
1968
- 1968-04-10 NL NL6805153A patent/NL6805153A/xx unknown
-
1969
- 1969-03-27 GB GB1619069A patent/GB1262971A/en not_active Expired
- 1969-04-01 DK DK183069A patent/DK122260B/da unknown
- 1969-04-10 FR FR6911112A patent/FR2007431A1/fr not_active Withdrawn
- 1969-04-10 DE DE19691918291 patent/DE1918291A1/de active Pending
- 1969-04-10 BE BE731328D patent/BE731328A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0380021A3 (en) * | 1989-01-24 | 1991-01-09 | Abbott Laboratories | Stabilizing system for solid dosage forms |
| WO1993017036A1 (en) * | 1992-02-26 | 1993-09-02 | American Home Products Corporation | Alkali metal 8,9-dehydroestrone sulfate esters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1262971A (en) | 1972-02-09 |
| DK122260B (da) | 1972-02-14 |
| FR2007431A1 (enrdf_load_stackoverflow) | 1970-01-09 |
| NL6805153A (enrdf_load_stackoverflow) | 1969-10-14 |
| BE731328A (enrdf_load_stackoverflow) | 1969-10-10 |
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